diff --git a/.claude/settings.local.json b/.claude/settings.local.json
index 6e006423a..bc5358b85 100644
--- a/.claude/settings.local.json
+++ b/.claude/settings.local.json
@@ -5,7 +5,13 @@
       "Bash(mkdir:*)",
       "Bash(./gradlew:*)",
       "Bash(grep:*)",
-      "Bash(cat:*)"
+      "Bash(cat:*)",
+      "Bash(find:*)",
+      "Bash(grep:*)",
+      "Bash(rg:*)",
+      "Bash(strings:*)",
+      "Bash(pkill:*)",
+      "Bash(true)"
     ],
     "deny": []
   }
diff --git a/.github/workflows/build.yml b/.github/workflows/build.yml
index d87e478d3..c229ee40e 100644
--- a/.github/workflows/build.yml
+++ b/.github/workflows/build.yml
@@ -147,7 +147,9 @@ jobs:
 
       - name: Generate OpenAPI documentation
         run: ./gradlew :stirling-pdf:generateOpenApiDocs
-
+        env:
+          DISABLE_ADDITIONAL_FEATURES: true
+      
       - name: Upload OpenAPI Documentation
         uses: actions/upload-artifact@ea165f8d65b6e75b540449e92b4886f43607fa02 # v4.6.2
         with:
diff --git a/app/common/src/main/java/stirling/software/common/configuration/AppConfig.java b/app/common/src/main/java/stirling/software/common/configuration/AppConfig.java
index f611f42ca..e24a92d6a 100644
--- a/app/common/src/main/java/stirling/software/common/configuration/AppConfig.java
+++ b/app/common/src/main/java/stirling/software/common/configuration/AppConfig.java
@@ -8,6 +8,7 @@ import java.util.List;
 import java.util.Locale;
 import java.util.Properties;
 import java.util.function.Predicate;
+import java.util.stream.Stream;
 
 import org.springframework.beans.factory.annotation.Value;
 import org.springframework.boot.autoconfigure.condition.ConditionalOnProperty;
@@ -51,6 +52,14 @@ public class AppConfig {
     @Value("${server.port:8080}")
     private String serverPort;
 
+    @Value("${v2}")
+    public boolean v2Enabled;
+
+    @Bean
+    public boolean v2Enabled() {
+        return v2Enabled;
+    }
+
     @Bean
     @ConditionalOnProperty(name = "system.customHTMLFiles", havingValue = "true")
     public SpringTemplateEngine templateEngine(ResourceLoader resourceLoader) {
@@ -120,7 +129,7 @@ public class AppConfig {
     public boolean rateLimit() {
         String rateLimit = System.getProperty("rateLimit");
         if (rateLimit == null) rateLimit = System.getenv("rateLimit");
-        return (rateLimit != null) ? Boolean.valueOf(rateLimit) : false;
+        return Boolean.parseBoolean(rateLimit);
     }
 
     @Bean(name = "RunningInDocker")
@@ -140,8 +149,8 @@ public class AppConfig {
         if (!Files.exists(mountInfo)) {
             return true;
         }
-        try {
-            return Files.lines(mountInfo).anyMatch(line -> line.contains(" /configs "));
+        try (Stream<String> lines = Files.lines(mountInfo)) {
+            return lines.anyMatch(line -> line.contains(" /configs "));
         } catch (IOException e) {
             return false;
         }
diff --git a/app/common/src/main/java/stirling/software/common/configuration/InstallationPathConfig.java b/app/common/src/main/java/stirling/software/common/configuration/InstallationPathConfig.java
index 247a012ad..64fbc41b7 100644
--- a/app/common/src/main/java/stirling/software/common/configuration/InstallationPathConfig.java
+++ b/app/common/src/main/java/stirling/software/common/configuration/InstallationPathConfig.java
@@ -25,6 +25,7 @@ public class InstallationPathConfig {
     private static final String STATIC_PATH;
     private static final String TEMPLATES_PATH;
     private static final String SIGNATURES_PATH;
+    private static final String PRIVATE_KEY_PATH;
 
     static {
         BASE_PATH = initializeBasePath();
@@ -45,6 +46,7 @@ public class InstallationPathConfig {
         STATIC_PATH = CUSTOM_FILES_PATH + "static" + File.separator;
         TEMPLATES_PATH = CUSTOM_FILES_PATH + "templates" + File.separator;
         SIGNATURES_PATH = CUSTOM_FILES_PATH + "signatures" + File.separator;
+        PRIVATE_KEY_PATH = CONFIG_PATH + "db" + File.separator + "keys" + File.separator;
     }
 
     private static String initializeBasePath() {
@@ -120,4 +122,8 @@ public class InstallationPathConfig {
     public static String getSignaturesPath() {
         return SIGNATURES_PATH;
     }
+
+    public static String getPrivateKeyPath() {
+        return PRIVATE_KEY_PATH;
+    }
 }
diff --git a/app/common/src/main/java/stirling/software/common/model/ApplicationProperties.java b/app/common/src/main/java/stirling/software/common/model/ApplicationProperties.java
index ee893c575..5845c6d16 100644
--- a/app/common/src/main/java/stirling/software/common/model/ApplicationProperties.java
+++ b/app/common/src/main/java/stirling/software/common/model/ApplicationProperties.java
@@ -119,6 +119,7 @@ public class ApplicationProperties {
         private long loginResetTimeMinutes;
         private String loginMethod = "all";
         private String customGlobalAPIKey;
+        private Jwt jwt = new Jwt();
 
         public Boolean isAltLogin() {
             return saml2.getEnabled() || oauth2.getEnabled();
@@ -298,6 +299,15 @@ public class ApplicationProperties {
                 }
             }
         }
+
+        @Data
+        public static class Jwt {
+            private boolean enableKeystore = true;
+            private boolean enableKeyRotation = false;
+            private boolean enableKeyCleanup = true;
+            private int keyRetentionDays = 7;
+            private boolean secureCookie;
+        }
     }
 
     @Data
diff --git a/app/common/src/main/java/stirling/software/common/util/RequestUriUtils.java b/app/common/src/main/java/stirling/software/common/util/RequestUriUtils.java
index 654c78fe9..239976b66 100644
--- a/app/common/src/main/java/stirling/software/common/util/RequestUriUtils.java
+++ b/app/common/src/main/java/stirling/software/common/util/RequestUriUtils.java
@@ -14,8 +14,10 @@ public class RequestUriUtils {
                 || requestURI.startsWith(contextPath + "/images/")
                 || requestURI.startsWith(contextPath + "/public/")
                 || requestURI.startsWith(contextPath + "/pdfjs/")
+                || requestURI.startsWith(contextPath + "/pdfjs-legacy/")
                 || requestURI.startsWith(contextPath + "/login")
                 || requestURI.startsWith(contextPath + "/error")
+                || requestURI.startsWith(contextPath + "/favicon")
                 || requestURI.endsWith(".svg")
                 || requestURI.endsWith(".png")
                 || requestURI.endsWith(".ico")
diff --git a/app/core/src/main/resources/application.properties b/app/core/src/main/resources/application.properties
index ea30bf78e..0ca864985 100644
--- a/app/core/src/main/resources/application.properties
+++ b/app/core/src/main/resources/application.properties
@@ -5,7 +5,7 @@ logging.level.org.eclipse.jetty=WARN
 #logging.level.org.springframework.security.saml2=TRACE
 #logging.level.org.springframework.security=DEBUG
 #logging.level.org.opensaml=DEBUG
-#logging.level.stirling.software.SPDF.config.security: DEBUG
+#logging.level.stirling.software.proprietary.security=DEBUG
 logging.level.com.zaxxer.hikari=WARN
 spring.jpa.open-in-view=false
 server.forward-headers-strategy=NATIVE
@@ -47,4 +47,7 @@ posthog.host=https://eu.i.posthog.com
 spring.main.allow-bean-definition-overriding=true
 
 # Set up a consistent temporary directory location
-java.io.tmpdir=${stirling.tempfiles.directory:${java.io.tmpdir}/stirling-pdf}
\ No newline at end of file
+java.io.tmpdir=${stirling.tempfiles.directory:${java.io.tmpdir}/stirling-pdf}
+
+# V2 features
+v2=false
diff --git a/app/core/src/main/resources/messages_en_GB.properties b/app/core/src/main/resources/messages_en_GB.properties
index d6056e856..599dd0989 100644
--- a/app/core/src/main/resources/messages_en_GB.properties
+++ b/app/core/src/main/resources/messages_en_GB.properties
@@ -893,7 +893,7 @@ login.rememberme=Remember me
 login.invalid=Invalid username or password.
 login.locked=Your account has been locked.
 login.signinTitle=Please sign in
-login.ssoSignIn=Login via Single Sign-on
+login.ssoSignIn=Login via Single Sign-On
 login.oAuth2AutoCreateDisabled=OAUTH2 Auto-Create User Disabled
 login.oAuth2AdminBlockedUser=Registration or logging in of non-registered users is currently blocked. Please contact the administrator.
 login.oauth2RequestNotFound=Authorization request not found
@@ -908,6 +908,7 @@ login.alreadyLoggedIn=You are already logged in to
 login.alreadyLoggedIn2=devices. Please log out of the devices and try again.
 login.toManySessions=You have too many active sessions
 login.logoutMessage=You have been logged out.
+login.invalidInResponseTo=The requested SAML response is invalid or has expired. Please contact the administrator.
 
 #auto-redact
 autoRedact.title=Auto Redact
diff --git a/app/core/src/main/resources/settings.yml.template b/app/core/src/main/resources/settings.yml.template
index 1af95f852..bbbac5fcd 100644
--- a/app/core/src/main/resources/settings.yml.template
+++ b/app/core/src/main/resources/settings.yml.template
@@ -59,12 +59,17 @@ security:
     idpCert: classpath:okta.cert # The certificate your Provider will use to authenticate your app's SAML authentication requests. Provided by your Provider
     privateKey: classpath:saml-private-key.key # Your private key. Generated from your keypair
     spCert: classpath:saml-public-cert.crt # Your signing certificate. Generated from your keypair
+  jwt: # This feature is currently under development and not yet fully supported. Do not use in production.
+    persistence: true # Set to 'true' to enable JWT key store
+    enableKeyRotation: true # Set to 'true' to enable key pair rotation
+    enableKeyCleanup: true # Set to 'true' to enable key pair cleanup
+    keyRetentionDays: 7 # Number of days to retain old keys. The default is 7 days.
+    secureCookie: false # Set to 'true' to use secure cookies for JWTs
 
 premium:
   key: 00000000-0000-0000-0000-000000000000
   enabled: false # Enable license key checks for pro/enterprise features
   proFeatures:
-    database: true # Enable database features
     SSOAutoLogin: false
     CustomMetadata:
       autoUpdateMetadata: false
diff --git a/app/core/src/main/resources/static/js/DecryptFiles.js b/app/core/src/main/resources/static/js/DecryptFiles.js
index 67349a012..0e5b58a92 100644
--- a/app/core/src/main/resources/static/js/DecryptFiles.js
+++ b/app/core/src/main/resources/static/js/DecryptFiles.js
@@ -46,10 +46,9 @@ export class DecryptFile {
         formData.append('password', password);
       }
       // Send decryption request
-      const response = await fetch('/api/v1/security/remove-password', {
+      const response = await fetchWithCsrf('/api/v1/security/remove-password', {
         method: 'POST',
         body: formData,
-        headers: csrfToken ? {'X-XSRF-TOKEN': csrfToken} : undefined,
       });
 
       if (response.ok) {
diff --git a/app/core/src/main/resources/static/js/downloader.js b/app/core/src/main/resources/static/js/downloader.js
index 42ba0c357..b5324dd82 100644
--- a/app/core/src/main/resources/static/js/downloader.js
+++ b/app/core/src/main/resources/static/js/downloader.js
@@ -218,7 +218,7 @@
             formData.append('password', password);
 
             // Use handleSingleDownload to send the request
-            const decryptionResult = await fetch(removePasswordUrl, {method: 'POST', body: formData});
+            const decryptionResult = await fetchWithCsrf(removePasswordUrl, {method: 'POST', body: formData});
 
             if (decryptionResult && decryptionResult.blob) {
               const decryptedBlob = await decryptionResult.blob();
diff --git a/app/core/src/main/resources/static/js/fetch-utils.js b/app/core/src/main/resources/static/js/fetch-utils.js
index dfe2604a8..2a2fe894c 100644
--- a/app/core/src/main/resources/static/js/fetch-utils.js
+++ b/app/core/src/main/resources/static/js/fetch-utils.js
@@ -1,3 +1,29 @@
+// Authentication utility for cookie-based JWT
+window.JWTManager = {
+    
+    // Logout - clear cookies and redirect to login
+    logout: function() {
+        
+        // Clear JWT cookie manually (fallback)
+        document.cookie = 'stirling_jwt=; Path=/; Expires=Thu, 01 Jan 1970 00:00:01 GMT; SameSite=None; Secure';
+        
+        // Perform logout request to clear server-side session
+        fetch('/logout', {
+            method: 'POST',
+            credentials: 'include'
+        }).then(response => {
+            if (response.redirected) {
+                window.location.href = response.url;
+            } else {
+                window.location.href = '/login?logout=true';
+            }
+        }).catch(() => {
+            // If logout fails, let server handle it
+            window.location.href = '/logout';
+        });
+    }
+};
+
 window.fetchWithCsrf = async function(url, options = {}) {
     function getCsrfToken() {
         const cookieValue = document.cookie
@@ -24,5 +50,19 @@ window.fetchWithCsrf = async function(url, options = {}) {
         fetchOptions.headers['X-XSRF-TOKEN'] = csrfToken;
     }
 
-    return fetch(url, fetchOptions);
+    // Always include credentials to send JWT cookies
+    fetchOptions.credentials = 'include';
+
+    // Make the request
+    const response = await fetch(url, fetchOptions);
+    
+    // Handle 401 responses (unauthorized)
+    if (response.status === 401) {
+        console.warn('Authentication failed, redirecting to login');
+        window.JWTManager.logout();
+        return response;
+    }
+    
+    return response;
 }
+
diff --git a/app/core/src/main/resources/static/js/jwt-init.js b/app/core/src/main/resources/static/js/jwt-init.js
new file mode 100644
index 000000000..8cd63e189
--- /dev/null
+++ b/app/core/src/main/resources/static/js/jwt-init.js
@@ -0,0 +1,44 @@
+// JWT Authentication Management Script
+// This script handles cookie-based JWT authentication and page access control
+
+(function() {
+    // Clean up JWT token from URL parameters after OAuth/Login flows
+    function cleanupTokenFromUrl() {
+        const urlParams = new URLSearchParams(window.location.search);
+        const hasToken = urlParams.get('jwt') || urlParams.get('token');
+        if (hasToken) {
+            // Clean up URL by removing token parameter
+            // Token should now be set as cookie by server
+            urlParams.delete('jwt');
+            urlParams.delete('token');
+            const newUrl = window.location.pathname + (urlParams.toString() ? '?' + urlParams.toString() : '');
+            window.history.replaceState({}, '', newUrl);
+        }
+    }
+
+    // Initialize JWT handling when page loads
+    function initializeJWT() {
+        // Clean up any JWT tokens from URL (OAuth flow)
+        cleanupTokenFromUrl();
+        
+        // Authentication is handled server-side
+        // If user is not authenticated, server will redirect to login
+        console.log('JWT initialization complete - authentication handled server-side');
+    }
+
+    // No form enhancement needed for cookie-based JWT
+    // Cookies are automatically sent with form submissions
+    function enhanceFormSubmissions() {
+        // Cookie-based JWT is automatically included in form submissions
+        // No additional processing needed
+    }
+
+    // Initialize when DOM is ready
+    if (document.readyState === 'loading') {
+        document.addEventListener('DOMContentLoaded', function() {
+            initializeJWT();
+        });
+    } else {
+        initializeJWT();
+    }
+})();
\ No newline at end of file
diff --git a/app/core/src/main/resources/static/js/navbar.js b/app/core/src/main/resources/static/js/navbar.js
index a95ff1639..1fd46ed70 100644
--- a/app/core/src/main/resources/static/js/navbar.js
+++ b/app/core/src/main/resources/static/js/navbar.js
@@ -138,5 +138,19 @@ document.addEventListener('DOMContentLoaded', () => {
   tooltipSetup();
   setupDropdowns();
   fixNavbarDropdownStyles();
+  // Setup logout button functionality
+  const logoutButton = document.querySelector('a[href="/logout"]');
+  if (logoutButton) {
+    logoutButton.addEventListener('click', function(event) {
+      event.preventDefault();
+      if (window.JWTManager) {
+        window.JWTManager.logout();
+      } else {
+        // Fallback if JWTManager is not available
+        window.location.href = '/logout';
+      }
+    });
+  }
+
 });
 window.addEventListener('resize', fixNavbarDropdownStyles);
diff --git a/app/core/src/main/resources/static/js/usage.js b/app/core/src/main/resources/static/js/usage.js
index 624e4ec78..443a27ce1 100644
--- a/app/core/src/main/resources/static/js/usage.js
+++ b/app/core/src/main/resources/static/js/usage.js
@@ -102,7 +102,7 @@ async function fetchEndpointData() {
     refreshBtn.classList.add('refreshing');
     refreshBtn.disabled = true;
 
-    const response = await fetch('/api/v1/info/load/all');
+    const response = await fetchWithCsrf('/api/v1/info/load/all');
     if (!response.ok) {
       throw new Error('Network response was not ok');
     }
diff --git a/app/core/src/main/resources/templates/account.html b/app/core/src/main/resources/templates/account.html
index 33a0d9f47..db48bb3a5 100644
--- a/app/core/src/main/resources/templates/account.html
+++ b/app/core/src/main/resources/templates/account.html
@@ -390,8 +390,13 @@
 	             key.includes('clientSubmissionOrder') || 
 	             key.includes('lastSubmitTime') || 
 	             key.includes('lastClientId') || 
-	             
-	             
+	             key.includes('stirling_jwt') ||
+	             key.includes('JSESSIONID') ||
+	             key.includes('XSRF-TOKEN') ||
+	             key.includes('remember-me') ||
+	             key.includes('auth') ||
+	             key.includes('token') ||
+	             key.includes('session') ||
 	             key.includes('posthog') || key.includes('ssoRedirectAttempts') || key.includes('lastRedirectAttempt') || key.includes('surveyVersion') || 
 	             key.includes('pageViews');
 	    }
diff --git a/app/proprietary/build.gradle b/app/proprietary/build.gradle
index 719f74127..b8862bdd8 100644
--- a/app/proprietary/build.gradle
+++ b/app/proprietary/build.gradle
@@ -1,9 +1,15 @@
 repositories {
     maven { url = "https://build.shibboleth.net/maven/releases" }
 }
+
+ext {
+    jwtVersion = '0.12.6'
+}
+
 bootRun {
     enabled = false
 }
+
 spotless {
         java {
         target 'src/**/java/**/*.java'
@@ -41,6 +47,8 @@ dependencies {
     api 'org.springframework.boot:spring-boot-starter-data-jpa'
     api 'org.springframework.boot:spring-boot-starter-oauth2-client'
     api 'org.springframework.boot:spring-boot-starter-mail'
+    api 'org.springframework.boot:spring-boot-starter-cache'
+    api 'com.github.ben-manes.caffeine:caffeine'
     api 'io.swagger.core.v3:swagger-core-jakarta:2.2.35'
     implementation 'com.bucket4j:bucket4j_jdk17-core:8.14.0'
 
@@ -50,6 +58,10 @@ dependencies {
     implementation 'org.thymeleaf.extras:thymeleaf-extras-springsecurity5:3.1.3.RELEASE'
     api 'io.micrometer:micrometer-registry-prometheus'
     implementation 'com.unboundid.product.scim2:scim2-sdk-client:4.0.0'
+
+    api "io.jsonwebtoken:jjwt-api:$jwtVersion"
+    runtimeOnly "io.jsonwebtoken:jjwt-impl:$jwtVersion"
+    runtimeOnly "io.jsonwebtoken:jjwt-jackson:$jwtVersion"
     runtimeOnly 'com.h2database:h2:2.3.232' // Don't upgrade h2database
     runtimeOnly 'org.postgresql:postgresql:42.7.7'
     constraints {
diff --git a/app/proprietary/src/main/java/stirling/software/proprietary/security/CustomAuthenticationSuccessHandler.java b/app/proprietary/src/main/java/stirling/software/proprietary/security/CustomAuthenticationSuccessHandler.java
index d5180c321..51908ef03 100644
--- a/app/proprietary/src/main/java/stirling/software/proprietary/security/CustomAuthenticationSuccessHandler.java
+++ b/app/proprietary/src/main/java/stirling/software/proprietary/security/CustomAuthenticationSuccessHandler.java
@@ -1,6 +1,7 @@
 package stirling.software.proprietary.security;
 
 import java.io.IOException;
+import java.util.Map;
 
 import org.springframework.security.core.Authentication;
 import org.springframework.security.web.authentication.SavedRequestAwareAuthenticationSuccessHandler;
@@ -17,6 +18,8 @@ import stirling.software.common.util.RequestUriUtils;
 import stirling.software.proprietary.audit.AuditEventType;
 import stirling.software.proprietary.audit.AuditLevel;
 import stirling.software.proprietary.audit.Audited;
+import stirling.software.proprietary.security.model.AuthenticationType;
+import stirling.software.proprietary.security.service.JwtServiceInterface;
 import stirling.software.proprietary.security.service.LoginAttemptService;
 import stirling.software.proprietary.security.service.UserService;
 
@@ -24,13 +27,17 @@ import stirling.software.proprietary.security.service.UserService;
 public class CustomAuthenticationSuccessHandler
         extends SavedRequestAwareAuthenticationSuccessHandler {
 
-    private LoginAttemptService loginAttemptService;
-    private UserService userService;
+    private final LoginAttemptService loginAttemptService;
+    private final UserService userService;
+    private final JwtServiceInterface jwtService;
 
     public CustomAuthenticationSuccessHandler(
-            LoginAttemptService loginAttemptService, UserService userService) {
+            LoginAttemptService loginAttemptService,
+            UserService userService,
+            JwtServiceInterface jwtService) {
         this.loginAttemptService = loginAttemptService;
         this.userService = userService;
+        this.jwtService = jwtService;
     }
 
     @Override
@@ -46,23 +53,31 @@ public class CustomAuthenticationSuccessHandler
         }
         loginAttemptService.loginSucceeded(userName);
 
-        // Get the saved request
-        HttpSession session = request.getSession(false);
-        SavedRequest savedRequest =
-                (session != null)
-                        ? (SavedRequest) session.getAttribute("SPRING_SECURITY_SAVED_REQUEST")
-                        : null;
+        if (jwtService.isJwtEnabled()) {
+            String jwt =
+                    jwtService.generateToken(
+                            authentication, Map.of("authType", AuthenticationType.WEB));
+            jwtService.addToken(response, jwt);
+            log.debug("JWT generated for user: {}", userName);
 
-        if (savedRequest != null
-                && !RequestUriUtils.isStaticResource(
-                        request.getContextPath(), savedRequest.getRedirectUrl())) {
-            // Redirect to the original destination
-            super.onAuthenticationSuccess(request, response, authentication);
-        } else {
-            // Redirect to the root URL (considering context path)
             getRedirectStrategy().sendRedirect(request, response, "/");
-        }
+        } else {
+            // Get the saved request
+            HttpSession session = request.getSession(false);
+            SavedRequest savedRequest =
+                    (session != null)
+                            ? (SavedRequest) session.getAttribute("SPRING_SECURITY_SAVED_REQUEST")
+                            : null;
 
-        // super.onAuthenticationSuccess(request, response, authentication);
+            if (savedRequest != null
+                    && !RequestUriUtils.isStaticResource(
+                            request.getContextPath(), savedRequest.getRedirectUrl())) {
+                // Redirect to the original destination
+                super.onAuthenticationSuccess(request, response, authentication);
+            } else {
+                // No saved request or it's a static resource, redirect to home page
+                getRedirectStrategy().sendRedirect(request, response, "/");
+            }
+        }
     }
 }
diff --git a/app/proprietary/src/main/java/stirling/software/proprietary/security/CustomLogoutSuccessHandler.java b/app/proprietary/src/main/java/stirling/software/proprietary/security/CustomLogoutSuccessHandler.java
index 033ea913c..136120528 100644
--- a/app/proprietary/src/main/java/stirling/software/proprietary/security/CustomLogoutSuccessHandler.java
+++ b/app/proprietary/src/main/java/stirling/software/proprietary/security/CustomLogoutSuccessHandler.java
@@ -33,6 +33,7 @@ import stirling.software.proprietary.audit.AuditLevel;
 import stirling.software.proprietary.audit.Audited;
 import stirling.software.proprietary.security.saml2.CertificateUtils;
 import stirling.software.proprietary.security.saml2.CustomSaml2AuthenticatedPrincipal;
+import stirling.software.proprietary.security.service.JwtServiceInterface;
 
 @Slf4j
 @RequiredArgsConstructor
@@ -40,15 +41,18 @@ public class CustomLogoutSuccessHandler extends SimpleUrlLogoutSuccessHandler {
 
     public static final String LOGOUT_PATH = "/login?logout=true";
 
-    private final ApplicationProperties applicationProperties;
+    private final ApplicationProperties.Security securityProperties;
 
     private final AppConfig appConfig;
 
+    private final JwtServiceInterface jwtService;
+
     @Override
     @Audited(type = AuditEventType.USER_LOGOUT, level = AuditLevel.BASIC)
     public void onLogoutSuccess(
             HttpServletRequest request, HttpServletResponse response, Authentication authentication)
             throws IOException {
+
         if (!response.isCommitted()) {
             if (authentication != null) {
                 if (authentication instanceof Saml2Authentication samlAuthentication) {
@@ -67,6 +71,9 @@ public class CustomLogoutSuccessHandler extends SimpleUrlLogoutSuccessHandler {
                             authentication.getClass().getSimpleName());
                     getRedirectStrategy().sendRedirect(request, response, LOGOUT_PATH);
                 }
+            } else if (!jwtService.extractToken(request).isBlank()) {
+                jwtService.clearToken(response);
+                getRedirectStrategy().sendRedirect(request, response, LOGOUT_PATH);
             } else {
                 // Redirect to login page after logout
                 String path = checkForErrors(request);
@@ -82,7 +89,7 @@ public class CustomLogoutSuccessHandler extends SimpleUrlLogoutSuccessHandler {
             Saml2Authentication samlAuthentication)
             throws IOException {
 
-        SAML2 samlConf = applicationProperties.getSecurity().getSaml2();
+        SAML2 samlConf = securityProperties.getSaml2();
         String registrationId = samlConf.getRegistrationId();
 
         CustomSaml2AuthenticatedPrincipal principal =
@@ -127,7 +134,7 @@ public class CustomLogoutSuccessHandler extends SimpleUrlLogoutSuccessHandler {
             OAuth2AuthenticationToken oAuthToken)
             throws IOException {
         String registrationId;
-        OAUTH2 oauth = applicationProperties.getSecurity().getOauth2();
+        OAUTH2 oauth = securityProperties.getOauth2();
         String path = checkForErrors(request);
 
         String redirectUrl = UrlUtils.getOrigin(request) + "/login?" + path;
diff --git a/app/proprietary/src/main/java/stirling/software/proprietary/security/InitialSecuritySetup.java b/app/proprietary/src/main/java/stirling/software/proprietary/security/InitialSecuritySetup.java
index 4b09fe0e9..e145e2754 100644
--- a/app/proprietary/src/main/java/stirling/software/proprietary/security/InitialSecuritySetup.java
+++ b/app/proprietary/src/main/java/stirling/software/proprietary/security/InitialSecuritySetup.java
@@ -43,7 +43,6 @@ public class InitialSecuritySetup {
                 }
             }
 
-            userService.migrateOauth2ToSSO();
             assignUsersToDefaultTeamIfMissing();
             initializeInternalApiUser();
         } catch (IllegalArgumentException | SQLException | UnsupportedProviderException e) {
diff --git a/app/proprietary/src/main/java/stirling/software/proprietary/security/JwtAuthenticationEntryPoint.java b/app/proprietary/src/main/java/stirling/software/proprietary/security/JwtAuthenticationEntryPoint.java
new file mode 100644
index 000000000..6805bcb54
--- /dev/null
+++ b/app/proprietary/src/main/java/stirling/software/proprietary/security/JwtAuthenticationEntryPoint.java
@@ -0,0 +1,22 @@
+package stirling.software.proprietary.security;
+
+import java.io.IOException;
+
+import org.springframework.security.core.AuthenticationException;
+import org.springframework.security.web.AuthenticationEntryPoint;
+import org.springframework.stereotype.Component;
+
+import jakarta.servlet.http.HttpServletRequest;
+import jakarta.servlet.http.HttpServletResponse;
+
+@Component
+public class JwtAuthenticationEntryPoint implements AuthenticationEntryPoint {
+    @Override
+    public void commence(
+            HttpServletRequest request,
+            HttpServletResponse response,
+            AuthenticationException authException)
+            throws IOException {
+        response.sendError(HttpServletResponse.SC_UNAUTHORIZED, authException.getMessage());
+    }
+}
diff --git a/app/proprietary/src/main/java/stirling/software/proprietary/security/config/AccountWebController.java b/app/proprietary/src/main/java/stirling/software/proprietary/security/config/AccountWebController.java
index 0d846fc3d..46d0e7d3d 100644
--- a/app/proprietary/src/main/java/stirling/software/proprietary/security/config/AccountWebController.java
+++ b/app/proprietary/src/main/java/stirling/software/proprietary/security/config/AccountWebController.java
@@ -77,8 +77,11 @@ public class AccountWebController {
 
     @GetMapping("/login")
     public String login(HttpServletRequest request, Model model, Authentication authentication) {
-        // If the user is already authenticated, redirect them to the home page.
-        if (authentication != null && authentication.isAuthenticated()) {
+        // If the user is already authenticated and it's not a logout scenario, redirect them to the
+        // home page.
+        if (authentication != null
+                && authentication.isAuthenticated()
+                && request.getParameter("logout") == null) {
             return "redirect:/";
         }
 
@@ -184,7 +187,7 @@ public class AccountWebController {
                         errorOAuth = "login.relyingPartyRegistrationNotFound";
                 // Valid InResponseTo was not available from the validation context, unable to
                 // evaluate
-                case "invalid_in_response_to" -> errorOAuth = "login.invalid_in_response_to";
+                case "invalid_in_response_to" -> errorOAuth = "login.invalidInResponseTo";
                 case "not_authentication_provider_found" ->
                         errorOAuth = "login.not_authentication_provider_found";
             }
diff --git a/app/proprietary/src/main/java/stirling/software/proprietary/security/configuration/CacheConfig.java b/app/proprietary/src/main/java/stirling/software/proprietary/security/configuration/CacheConfig.java
new file mode 100644
index 000000000..ba074a5da
--- /dev/null
+++ b/app/proprietary/src/main/java/stirling/software/proprietary/security/configuration/CacheConfig.java
@@ -0,0 +1,31 @@
+package stirling.software.proprietary.security.configuration;
+
+import java.time.Duration;
+
+import org.springframework.beans.factory.annotation.Value;
+import org.springframework.cache.CacheManager;
+import org.springframework.cache.annotation.EnableCaching;
+import org.springframework.cache.caffeine.CaffeineCacheManager;
+import org.springframework.context.annotation.Bean;
+import org.springframework.context.annotation.Configuration;
+
+import com.github.benmanes.caffeine.cache.Caffeine;
+
+@Configuration
+@EnableCaching
+public class CacheConfig {
+
+    @Value("${security.jwt.keyRetentionDays}")
+    private int keyRetentionDays;
+
+    @Bean
+    public CacheManager cacheManager() {
+        CaffeineCacheManager cacheManager = new CaffeineCacheManager();
+        cacheManager.setCaffeine(
+                Caffeine.newBuilder()
+                        .maximumSize(1000) // Make configurable?
+                        .expireAfterWrite(Duration.ofDays(keyRetentionDays))
+                        .recordStats());
+        return cacheManager;
+    }
+}
diff --git a/app/proprietary/src/main/java/stirling/software/proprietary/security/configuration/SecurityConfiguration.java b/app/proprietary/src/main/java/stirling/software/proprietary/security/configuration/SecurityConfiguration.java
index ab809a037..aceb3b712 100644
--- a/app/proprietary/src/main/java/stirling/software/proprietary/security/configuration/SecurityConfiguration.java
+++ b/app/proprietary/src/main/java/stirling/software/proprietary/security/configuration/SecurityConfiguration.java
@@ -13,6 +13,7 @@ import org.springframework.security.authentication.dao.DaoAuthenticationProvider
 import org.springframework.security.config.annotation.method.configuration.EnableMethodSecurity;
 import org.springframework.security.config.annotation.web.builders.HttpSecurity;
 import org.springframework.security.config.annotation.web.configuration.EnableWebSecurity;
+import org.springframework.security.config.annotation.web.configurers.CsrfConfigurer;
 import org.springframework.security.config.http.SessionCreationPolicy;
 import org.springframework.security.core.authority.mapping.GrantedAuthoritiesMapper;
 import org.springframework.security.crypto.bcrypt.BCryptPasswordEncoder;
@@ -35,10 +36,12 @@ import stirling.software.common.model.ApplicationProperties;
 import stirling.software.proprietary.security.CustomAuthenticationFailureHandler;
 import stirling.software.proprietary.security.CustomAuthenticationSuccessHandler;
 import stirling.software.proprietary.security.CustomLogoutSuccessHandler;
+import stirling.software.proprietary.security.JwtAuthenticationEntryPoint;
 import stirling.software.proprietary.security.database.repository.JPATokenRepositoryImpl;
 import stirling.software.proprietary.security.database.repository.PersistentLoginRepository;
 import stirling.software.proprietary.security.filter.FirstLoginFilter;
 import stirling.software.proprietary.security.filter.IPRateLimitingFilter;
+import stirling.software.proprietary.security.filter.JwtAuthenticationFilter;
 import stirling.software.proprietary.security.filter.UserAuthenticationFilter;
 import stirling.software.proprietary.security.model.User;
 import stirling.software.proprietary.security.oauth2.CustomOAuth2AuthenticationFailureHandler;
@@ -48,6 +51,7 @@ import stirling.software.proprietary.security.saml2.CustomSaml2AuthenticationSuc
 import stirling.software.proprietary.security.saml2.CustomSaml2ResponseAuthenticationConverter;
 import stirling.software.proprietary.security.service.CustomOAuth2UserService;
 import stirling.software.proprietary.security.service.CustomUserDetailsService;
+import stirling.software.proprietary.security.service.JwtServiceInterface;
 import stirling.software.proprietary.security.service.LoginAttemptService;
 import stirling.software.proprietary.security.service.UserService;
 import stirling.software.proprietary.security.session.SessionPersistentRegistry;
@@ -64,9 +68,11 @@ public class SecurityConfiguration {
     private final boolean loginEnabledValue;
     private final boolean runningProOrHigher;
 
-    private final ApplicationProperties applicationProperties;
+    private final ApplicationProperties.Security securityProperties;
     private final AppConfig appConfig;
     private final UserAuthenticationFilter userAuthenticationFilter;
+    private final JwtServiceInterface jwtService;
+    private final JwtAuthenticationEntryPoint jwtAuthenticationEntryPoint;
     private final LoginAttemptService loginAttemptService;
     private final FirstLoginFilter firstLoginFilter;
     private final SessionPersistentRegistry sessionRegistry;
@@ -82,8 +88,10 @@ public class SecurityConfiguration {
             @Qualifier("loginEnabled") boolean loginEnabledValue,
             @Qualifier("runningProOrHigher") boolean runningProOrHigher,
             AppConfig appConfig,
-            ApplicationProperties applicationProperties,
+            ApplicationProperties.Security securityProperties,
             UserAuthenticationFilter userAuthenticationFilter,
+            JwtServiceInterface jwtService,
+            JwtAuthenticationEntryPoint jwtAuthenticationEntryPoint,
             LoginAttemptService loginAttemptService,
             FirstLoginFilter firstLoginFilter,
             SessionPersistentRegistry sessionRegistry,
@@ -97,8 +105,10 @@ public class SecurityConfiguration {
         this.loginEnabledValue = loginEnabledValue;
         this.runningProOrHigher = runningProOrHigher;
         this.appConfig = appConfig;
-        this.applicationProperties = applicationProperties;
+        this.securityProperties = securityProperties;
         this.userAuthenticationFilter = userAuthenticationFilter;
+        this.jwtService = jwtService;
+        this.jwtAuthenticationEntryPoint = jwtAuthenticationEntryPoint;
         this.loginAttemptService = loginAttemptService;
         this.firstLoginFilter = firstLoginFilter;
         this.sessionRegistry = sessionRegistry;
@@ -115,14 +125,28 @@ public class SecurityConfiguration {
 
     @Bean
     public SecurityFilterChain filterChain(HttpSecurity http) throws Exception {
-        if (applicationProperties.getSecurity().getCsrfDisabled() || !loginEnabledValue) {
-            http.csrf(csrf -> csrf.disable());
+        if (securityProperties.getCsrfDisabled() || !loginEnabledValue) {
+            http.csrf(CsrfConfigurer::disable);
         }
 
         if (loginEnabledValue) {
+            boolean v2Enabled = appConfig.v2Enabled();
+
+            if (v2Enabled) {
+                http.addFilterBefore(
+                                jwtAuthenticationFilter(),
+                                UsernamePasswordAuthenticationFilter.class)
+                        .exceptionHandling(
+                                exceptionHandling ->
+                                        exceptionHandling.authenticationEntryPoint(
+                                                jwtAuthenticationEntryPoint));
+            }
             http.addFilterBefore(
-                    userAuthenticationFilter, UsernamePasswordAuthenticationFilter.class);
-            if (!applicationProperties.getSecurity().getCsrfDisabled()) {
+                            userAuthenticationFilter, UsernamePasswordAuthenticationFilter.class)
+                    .addFilterAfter(rateLimitingFilter(), UserAuthenticationFilter.class)
+                    .addFilterAfter(firstLoginFilter, UsernamePasswordAuthenticationFilter.class);
+
+            if (!securityProperties.getCsrfDisabled()) {
                 CookieCsrfTokenRepository cookieRepo =
                         CookieCsrfTokenRepository.withHttpOnlyFalse();
                 CsrfTokenRequestAttributeHandler requestHandler =
@@ -156,16 +180,21 @@ public class SecurityConfiguration {
                                         .csrfTokenRepository(cookieRepo)
                                         .csrfTokenRequestHandler(requestHandler));
             }
-            http.addFilterBefore(rateLimitingFilter(), UsernamePasswordAuthenticationFilter.class);
-            http.addFilterAfter(firstLoginFilter, UsernamePasswordAuthenticationFilter.class);
+
             http.sessionManagement(
-                    sessionManagement ->
+                    sessionManagement -> {
+                        if (v2Enabled) {
+                            sessionManagement.sessionCreationPolicy(
+                                    SessionCreationPolicy.STATELESS);
+                        } else {
                             sessionManagement
                                     .sessionCreationPolicy(SessionCreationPolicy.IF_REQUIRED)
                                     .maximumSessions(10)
                                     .maxSessionsPreventsLogin(false)
                                     .sessionRegistry(sessionRegistry)
-                                    .expiredUrl("/login?logout=true"));
+                                    .expiredUrl("/login?logout=true");
+                        }
+                    });
             http.authenticationProvider(daoAuthenticationProvider());
             http.requestCache(requestCache -> requestCache.requestCache(new NullRequestCache()));
             http.logout(
@@ -175,10 +204,10 @@ public class SecurityConfiguration {
                                                     .matcher("/logout"))
                                     .logoutSuccessHandler(
                                             new CustomLogoutSuccessHandler(
-                                                    applicationProperties, appConfig))
+                                                    securityProperties, appConfig, jwtService))
                                     .clearAuthentication(true)
                                     .invalidateHttpSession(true)
-                                    .deleteCookies("JSESSIONID", "remember-me"));
+                                    .deleteCookies("JSESSIONID", "remember-me", "stirling_jwt"));
             http.rememberMe(
                     rememberMeConfigurer -> // Use the configurator directly
                     rememberMeConfigurer
@@ -200,6 +229,7 @@ public class SecurityConfiguration {
                                             req -> {
                                                 String uri = req.getRequestURI();
                                                 String contextPath = req.getContextPath();
+
                                                 // Remove the context path from the URI
                                                 String trimmedUri =
                                                         uri.startsWith(contextPath)
@@ -217,29 +247,35 @@ public class SecurityConfiguration {
                                                         || trimmedUri.startsWith("/css/")
                                                         || trimmedUri.startsWith("/fonts/")
                                                         || trimmedUri.startsWith("/js/")
+                                                        || trimmedUri.startsWith("/pdfjs/")
+                                                        || trimmedUri.startsWith("/pdfjs-legacy/")
+                                                        || trimmedUri.startsWith("/favicon")
                                                         || trimmedUri.startsWith(
-                                                                "/api/v1/info/status");
+                                                                "/api/v1/info/status")
+                                                        || trimmedUri.startsWith("/v1/api-docs")
+                                                        || uri.contains("/v1/api-docs");
                                             })
                                     .permitAll()
                                     .anyRequest()
                                     .authenticated());
             // Handle User/Password Logins
-            if (applicationProperties.getSecurity().isUserPass()) {
+            if (securityProperties.isUserPass()) {
                 http.formLogin(
                         formLogin ->
                                 formLogin
                                         .loginPage("/login")
                                         .successHandler(
                                                 new CustomAuthenticationSuccessHandler(
-                                                        loginAttemptService, userService))
+                                                        loginAttemptService,
+                                                        userService,
+                                                        jwtService))
                                         .failureHandler(
                                                 new CustomAuthenticationFailureHandler(
                                                         loginAttemptService, userService))
-                                        .defaultSuccessUrl("/")
                                         .permitAll());
             }
             // Handle OAUTH2 Logins
-            if (applicationProperties.getSecurity().isOauth2Active()) {
+            if (securityProperties.isOauth2Active()) {
                 http.oauth2Login(
                         oauth2 ->
                                 oauth2.loginPage("/oauth2")
@@ -251,17 +287,18 @@ public class SecurityConfiguration {
                                         .successHandler(
                                                 new CustomOAuth2AuthenticationSuccessHandler(
                                                         loginAttemptService,
-                                                        applicationProperties,
-                                                        userService))
+                                                        securityProperties.getOauth2(),
+                                                        userService,
+                                                        jwtService))
                                         .failureHandler(
                                                 new CustomOAuth2AuthenticationFailureHandler())
-                                        . // Add existing Authorities from the database
-                                        userInfoEndpoint(
+                                        // Add existing Authorities from the database
+                                        .userInfoEndpoint(
                                                 userInfoEndpoint ->
                                                         userInfoEndpoint
                                                                 .oidcUserService(
                                                                         new CustomOAuth2UserService(
-                                                                                applicationProperties,
+                                                                                securityProperties,
                                                                                 userService,
                                                                                 loginAttemptService))
                                                                 .userAuthoritiesMapper(
@@ -269,8 +306,7 @@ public class SecurityConfiguration {
                                         .permitAll());
             }
             // Handle SAML
-            if (applicationProperties.getSecurity().isSaml2Active() && runningProOrHigher) {
-                // Configure the authentication provider
+            if (securityProperties.isSaml2Active() && runningProOrHigher) {
                 OpenSaml4AuthenticationProvider authenticationProvider =
                         new OpenSaml4AuthenticationProvider();
                 authenticationProvider.setResponseAuthenticationConverter(
@@ -287,8 +323,9 @@ public class SecurityConfiguration {
                                                 .successHandler(
                                                         new CustomSaml2AuthenticationSuccessHandler(
                                                                 loginAttemptService,
-                                                                applicationProperties,
-                                                                userService))
+                                                                securityProperties.getSaml2(),
+                                                                userService,
+                                                                jwtService))
                                                 .failureHandler(
                                                         new CustomSaml2AuthenticationFailureHandler())
                                                 .authenticationRequestResolver(
@@ -323,4 +360,14 @@ public class SecurityConfiguration {
     public PersistentTokenRepository persistentTokenRepository() {
         return new JPATokenRepositoryImpl(persistentLoginRepository);
     }
+
+    @Bean
+    public JwtAuthenticationFilter jwtAuthenticationFilter() {
+        return new JwtAuthenticationFilter(
+                jwtService,
+                userService,
+                userDetailsService,
+                jwtAuthenticationEntryPoint,
+                securityProperties);
+    }
 }
diff --git a/app/proprietary/src/main/java/stirling/software/proprietary/security/filter/JwtAuthenticationFilter.java b/app/proprietary/src/main/java/stirling/software/proprietary/security/filter/JwtAuthenticationFilter.java
new file mode 100644
index 000000000..faf50832f
--- /dev/null
+++ b/app/proprietary/src/main/java/stirling/software/proprietary/security/filter/JwtAuthenticationFilter.java
@@ -0,0 +1,204 @@
+package stirling.software.proprietary.security.filter;
+
+import static stirling.software.common.util.RequestUriUtils.isStaticResource;
+import static stirling.software.proprietary.security.model.AuthenticationType.*;
+import static stirling.software.proprietary.security.model.AuthenticationType.SAML2;
+
+import java.io.IOException;
+import java.sql.SQLException;
+import java.util.Map;
+import java.util.Optional;
+
+import org.springframework.security.authentication.UsernamePasswordAuthenticationToken;
+import org.springframework.security.core.Authentication;
+import org.springframework.security.core.AuthenticationException;
+import org.springframework.security.core.context.SecurityContextHolder;
+import org.springframework.security.core.userdetails.UserDetails;
+import org.springframework.security.core.userdetails.UsernameNotFoundException;
+import org.springframework.security.web.AuthenticationEntryPoint;
+import org.springframework.security.web.authentication.WebAuthenticationDetailsSource;
+import org.springframework.web.filter.OncePerRequestFilter;
+
+import jakarta.servlet.FilterChain;
+import jakarta.servlet.ServletException;
+import jakarta.servlet.http.HttpServletRequest;
+import jakarta.servlet.http.HttpServletResponse;
+
+import lombok.extern.slf4j.Slf4j;
+
+import stirling.software.common.model.ApplicationProperties;
+import stirling.software.common.model.exception.UnsupportedProviderException;
+import stirling.software.proprietary.security.model.ApiKeyAuthenticationToken;
+import stirling.software.proprietary.security.model.AuthenticationType;
+import stirling.software.proprietary.security.model.User;
+import stirling.software.proprietary.security.model.exception.AuthenticationFailureException;
+import stirling.software.proprietary.security.service.CustomUserDetailsService;
+import stirling.software.proprietary.security.service.JwtServiceInterface;
+import stirling.software.proprietary.security.service.UserService;
+
+@Slf4j
+public class JwtAuthenticationFilter extends OncePerRequestFilter {
+
+    private final JwtServiceInterface jwtService;
+    private final UserService userService;
+    private final CustomUserDetailsService userDetailsService;
+    private final AuthenticationEntryPoint authenticationEntryPoint;
+    private final ApplicationProperties.Security securityProperties;
+
+    public JwtAuthenticationFilter(
+            JwtServiceInterface jwtService,
+            UserService userService,
+            CustomUserDetailsService userDetailsService,
+            AuthenticationEntryPoint authenticationEntryPoint,
+            ApplicationProperties.Security securityProperties) {
+        this.jwtService = jwtService;
+        this.userService = userService;
+        this.userDetailsService = userDetailsService;
+        this.authenticationEntryPoint = authenticationEntryPoint;
+        this.securityProperties = securityProperties;
+    }
+
+    @Override
+    protected void doFilterInternal(
+            HttpServletRequest request, HttpServletResponse response, FilterChain filterChain)
+            throws ServletException, IOException {
+        if (!jwtService.isJwtEnabled()) {
+            filterChain.doFilter(request, response);
+            return;
+        }
+        if (isStaticResource(request.getContextPath(), request.getRequestURI())) {
+            filterChain.doFilter(request, response);
+            return;
+        }
+
+        if (!apiKeyExists(request, response)) {
+            String jwtToken = jwtService.extractToken(request);
+
+            if (jwtToken == null) {
+                // Any unauthenticated requests should redirect to /login
+                String requestURI = request.getRequestURI();
+                String contextPath = request.getContextPath();
+
+                if (!requestURI.startsWith(contextPath + "/login")) {
+                    response.sendRedirect("/login");
+                    return;
+                }
+            }
+
+            try {
+                jwtService.validateToken(jwtToken);
+            } catch (AuthenticationFailureException e) {
+                jwtService.clearToken(response);
+                handleAuthenticationFailure(request, response, e);
+                return;
+            }
+
+            Map<String, Object> claims = jwtService.extractClaims(jwtToken);
+            String tokenUsername = claims.get("sub").toString();
+
+            try {
+                authenticate(request, claims);
+            } catch (SQLException | UnsupportedProviderException e) {
+                log.error("Error processing user authentication for user: {}", tokenUsername, e);
+                handleAuthenticationFailure(
+                        request,
+                        response,
+                        new AuthenticationFailureException(
+                                "Error processing user authentication", e));
+                return;
+            }
+        }
+
+        filterChain.doFilter(request, response);
+    }
+
+    private boolean apiKeyExists(HttpServletRequest request, HttpServletResponse response)
+            throws IOException, ServletException {
+        Authentication authentication = SecurityContextHolder.getContext().getAuthentication();
+
+        if (authentication == null || !authentication.isAuthenticated()) {
+            String apiKey = request.getHeader("X-API-KEY");
+
+            if (apiKey != null && !apiKey.isBlank()) {
+                try {
+                    Optional<User> user = userService.getUserByApiKey(apiKey);
+
+                    if (user.isEmpty()) {
+                        handleAuthenticationFailure(
+                                request,
+                                response,
+                                new AuthenticationFailureException("Invalid API Key"));
+                        return false;
+                    }
+
+                    authentication =
+                            new ApiKeyAuthenticationToken(
+                                    user.get(), apiKey, user.get().getAuthorities());
+                    SecurityContextHolder.getContext().setAuthentication(authentication);
+                    return true;
+                } catch (AuthenticationException e) {
+                    handleAuthenticationFailure(
+                            request,
+                            response,
+                            new AuthenticationFailureException("Invalid API Key", e));
+                    return false;
+                }
+            }
+
+            return false;
+        }
+
+        return true;
+    }
+
+    private void authenticate(HttpServletRequest request, Map<String, Object> claims)
+            throws SQLException, UnsupportedProviderException {
+        String username = claims.get("sub").toString();
+
+        if (username != null && SecurityContextHolder.getContext().getAuthentication() == null) {
+            processUserAuthenticationType(claims, username);
+            UserDetails userDetails = userDetailsService.loadUserByUsername(username);
+
+            if (userDetails != null) {
+                UsernamePasswordAuthenticationToken authToken =
+                        new UsernamePasswordAuthenticationToken(
+                                userDetails, null, userDetails.getAuthorities());
+
+                authToken.setDetails(new WebAuthenticationDetailsSource().buildDetails(request));
+                SecurityContextHolder.getContext().setAuthentication(authToken);
+            } else {
+                throw new UsernameNotFoundException("User not found: " + username);
+            }
+        }
+    }
+
+    private void processUserAuthenticationType(Map<String, Object> claims, String username)
+            throws SQLException, UnsupportedProviderException {
+        AuthenticationType authenticationType =
+                AuthenticationType.valueOf(claims.getOrDefault("authType", WEB).toString());
+        log.debug("Processing {} login for {} user", authenticationType, username);
+
+        switch (authenticationType) {
+            case OAUTH2 -> {
+                ApplicationProperties.Security.OAUTH2 oauth2Properties =
+                        securityProperties.getOauth2();
+                userService.processSSOPostLogin(
+                        username, oauth2Properties.getAutoCreateUser(), OAUTH2);
+            }
+            case SAML2 -> {
+                ApplicationProperties.Security.SAML2 saml2Properties =
+                        securityProperties.getSaml2();
+                userService.processSSOPostLogin(
+                        username, saml2Properties.getAutoCreateUser(), SAML2);
+            }
+        }
+    }
+
+    private void handleAuthenticationFailure(
+            HttpServletRequest request,
+            HttpServletResponse response,
+            AuthenticationException authException)
+            throws IOException, ServletException {
+        authenticationEntryPoint.commence(request, response, authException);
+    }
+}
diff --git a/app/proprietary/src/main/java/stirling/software/proprietary/security/filter/UserAuthenticationFilter.java b/app/proprietary/src/main/java/stirling/software/proprietary/security/filter/UserAuthenticationFilter.java
index e9addd239..f51a9d543 100644
--- a/app/proprietary/src/main/java/stirling/software/proprietary/security/filter/UserAuthenticationFilter.java
+++ b/app/proprietary/src/main/java/stirling/software/proprietary/security/filter/UserAuthenticationFilter.java
@@ -9,7 +9,6 @@ import org.springframework.context.annotation.Lazy;
 import org.springframework.http.HttpStatus;
 import org.springframework.security.core.Authentication;
 import org.springframework.security.core.AuthenticationException;
-import org.springframework.security.core.authority.SimpleGrantedAuthority;
 import org.springframework.security.core.context.SecurityContextHolder;
 import org.springframework.security.core.session.SessionInformation;
 import org.springframework.security.core.userdetails.UserDetails;
@@ -64,6 +63,7 @@ public class UserAuthenticationFilter extends OncePerRequestFilter {
             return;
         }
         String requestURI = request.getRequestURI();
+
         Authentication authentication = SecurityContextHolder.getContext().getAuthentication();
 
         // Check for session expiration (unsure if needed)
@@ -92,14 +92,9 @@ public class UserAuthenticationFilter extends OncePerRequestFilter {
                         response.getWriter().write("Invalid API Key.");
                         return;
                     }
-                    List<SimpleGrantedAuthority> authorities =
-                            user.get().getAuthorities().stream()
-                                    .map(
-                                            authority ->
-                                                    new SimpleGrantedAuthority(
-                                                            authority.getAuthority()))
-                                    .toList();
-                    authentication = new ApiKeyAuthenticationToken(user.get(), apiKey, authorities);
+                    authentication =
+                            new ApiKeyAuthenticationToken(
+                                    user.get(), apiKey, user.get().getAuthorities());
                     SecurityContextHolder.getContext().setAuthentication(authentication);
                 } catch (AuthenticationException e) {
                     // If API key authentication fails, deny the request
@@ -115,20 +110,19 @@ public class UserAuthenticationFilter extends OncePerRequestFilter {
             String method = request.getMethod();
             String contextPath = request.getContextPath();
 
-            if ("GET".equalsIgnoreCase(method) && !(contextPath + "/login").equals(requestURI)) {
+            if ("GET".equalsIgnoreCase(method) && !requestURI.startsWith(contextPath + "/login")) {
                 response.sendRedirect(contextPath + "/login"); // redirect to the login page
-                return;
             } else {
                 response.setStatus(HttpStatus.UNAUTHORIZED.value());
                 response.getWriter()
                         .write(
-                                "Authentication required. Please provide a X-API-KEY in request"
-                                        + " header.\n"
-                                        + "This is found in Settings -> Account Settings -> API Key\n"
-                                        + "Alternatively you can disable authentication if this is"
-                                        + " unexpected");
-                return;
+                                """
+                                Authentication required. Please provide a X-API-KEY in request header.
+                                This is found in Settings -> Account Settings -> API Key
+                                Alternatively you can disable authentication if this is unexpected.
+                                """);
             }
+            return;
         }
 
         // Check if the authenticated user is disabled and invalidate their session if so
@@ -226,11 +220,12 @@ public class UserAuthenticationFilter extends OncePerRequestFilter {
     }
 
     @Override
-    protected boolean shouldNotFilter(HttpServletRequest request) throws ServletException {
+    protected boolean shouldNotFilter(HttpServletRequest request) {
         String uri = request.getRequestURI();
         String contextPath = request.getContextPath();
         String[] permitAllPatterns = {
             contextPath + "/login",
+            contextPath + "/signup",
             contextPath + "/register",
             contextPath + "/error",
             contextPath + "/images/",
@@ -247,6 +242,7 @@ public class UserAuthenticationFilter extends OncePerRequestFilter {
         for (String pattern : permitAllPatterns) {
             if (uri.startsWith(pattern)
                     || uri.endsWith(".svg")
+                    || uri.endsWith(".mjs")
                     || uri.endsWith(".png")
                     || uri.endsWith(".ico")) {
                 return true;
diff --git a/app/proprietary/src/main/java/stirling/software/proprietary/security/model/AuthenticationType.java b/app/proprietary/src/main/java/stirling/software/proprietary/security/model/AuthenticationType.java
index ca8140bca..c92c1655e 100644
--- a/app/proprietary/src/main/java/stirling/software/proprietary/security/model/AuthenticationType.java
+++ b/app/proprietary/src/main/java/stirling/software/proprietary/security/model/AuthenticationType.java
@@ -2,5 +2,8 @@ package stirling.software.proprietary.security.model;
 
 public enum AuthenticationType {
     WEB,
-    SSO
+    @Deprecated(since = "1.0.2")
+    SSO,
+    OAUTH2,
+    SAML2
 }
diff --git a/app/proprietary/src/main/java/stirling/software/proprietary/security/model/Authority.java b/app/proprietary/src/main/java/stirling/software/proprietary/security/model/Authority.java
index 382d3a71e..a32e7d7ca 100644
--- a/app/proprietary/src/main/java/stirling/software/proprietary/security/model/Authority.java
+++ b/app/proprietary/src/main/java/stirling/software/proprietary/security/model/Authority.java
@@ -2,6 +2,8 @@ package stirling.software.proprietary.security.model;
 
 import java.io.Serializable;
 
+import org.springframework.security.core.GrantedAuthority;
+
 import jakarta.persistence.Column;
 import jakarta.persistence.Entity;
 import jakarta.persistence.GeneratedValue;
@@ -18,7 +20,7 @@ import lombok.Setter;
 @Table(name = "authorities")
 @Getter
 @Setter
-public class Authority implements Serializable {
+public class Authority implements GrantedAuthority, Serializable {
 
     private static final long serialVersionUID = 1L;
 
diff --git a/app/proprietary/src/main/java/stirling/software/proprietary/security/model/JwtVerificationKey.java b/app/proprietary/src/main/java/stirling/software/proprietary/security/model/JwtVerificationKey.java
new file mode 100644
index 000000000..632c5f13a
--- /dev/null
+++ b/app/proprietary/src/main/java/stirling/software/proprietary/security/model/JwtVerificationKey.java
@@ -0,0 +1,33 @@
+package stirling.software.proprietary.security.model;
+
+import java.io.Serial;
+import java.io.Serializable;
+import java.time.LocalDateTime;
+
+import lombok.EqualsAndHashCode;
+import lombok.Getter;
+import lombok.NoArgsConstructor;
+import lombok.Setter;
+import lombok.ToString;
+
+@Getter
+@Setter
+@NoArgsConstructor
+@ToString(onlyExplicitlyIncluded = true)
+@EqualsAndHashCode(onlyExplicitlyIncluded = true)
+public class JwtVerificationKey implements Serializable {
+
+    @Serial private static final long serialVersionUID = 1L;
+
+    @ToString.Include private String keyId;
+
+    private String verifyingKey;
+
+    @ToString.Include private LocalDateTime createdAt;
+
+    public JwtVerificationKey(String keyId, String verifyingKey) {
+        this.keyId = keyId;
+        this.verifyingKey = verifyingKey;
+        this.createdAt = LocalDateTime.now();
+    }
+}
diff --git a/app/proprietary/src/main/java/stirling/software/proprietary/security/model/User.java b/app/proprietary/src/main/java/stirling/software/proprietary/security/model/User.java
index d3e232f61..7d1b235cd 100644
--- a/app/proprietary/src/main/java/stirling/software/proprietary/security/model/User.java
+++ b/app/proprietary/src/main/java/stirling/software/proprietary/security/model/User.java
@@ -7,6 +7,8 @@ import java.util.Map;
 import java.util.Set;
 import java.util.stream.Collectors;
 
+import org.springframework.security.core.userdetails.UserDetails;
+
 import jakarta.persistence.*;
 
 import lombok.EqualsAndHashCode;
@@ -25,7 +27,7 @@ import stirling.software.proprietary.model.Team;
 @Setter
 @EqualsAndHashCode(onlyExplicitlyIncluded = true)
 @ToString(onlyExplicitlyIncluded = true)
-public class User implements Serializable {
+public class User implements UserDetails, Serializable {
 
     private static final long serialVersionUID = 1L;
 
diff --git a/app/proprietary/src/main/java/stirling/software/proprietary/security/model/exception/AuthenticationFailureException.java b/app/proprietary/src/main/java/stirling/software/proprietary/security/model/exception/AuthenticationFailureException.java
new file mode 100644
index 000000000..f2cd5e242
--- /dev/null
+++ b/app/proprietary/src/main/java/stirling/software/proprietary/security/model/exception/AuthenticationFailureException.java
@@ -0,0 +1,13 @@
+package stirling.software.proprietary.security.model.exception;
+
+import org.springframework.security.core.AuthenticationException;
+
+public class AuthenticationFailureException extends AuthenticationException {
+    public AuthenticationFailureException(String message) {
+        super(message);
+    }
+
+    public AuthenticationFailureException(String message, Throwable cause) {
+        super(message, cause);
+    }
+}
diff --git a/app/proprietary/src/main/java/stirling/software/proprietary/security/oauth2/CustomOAuth2AuthenticationSuccessHandler.java b/app/proprietary/src/main/java/stirling/software/proprietary/security/oauth2/CustomOAuth2AuthenticationSuccessHandler.java
index 71bd42a85..4e7ed9d9e 100644
--- a/app/proprietary/src/main/java/stirling/software/proprietary/security/oauth2/CustomOAuth2AuthenticationSuccessHandler.java
+++ b/app/proprietary/src/main/java/stirling/software/proprietary/security/oauth2/CustomOAuth2AuthenticationSuccessHandler.java
@@ -1,7 +1,11 @@
 package stirling.software.proprietary.security.oauth2;
 
+import static stirling.software.proprietary.security.model.AuthenticationType.OAUTH2;
+import static stirling.software.proprietary.security.model.AuthenticationType.SSO;
+
 import java.io.IOException;
 import java.sql.SQLException;
+import java.util.Map;
 
 import org.springframework.security.authentication.LockedException;
 import org.springframework.security.core.Authentication;
@@ -18,10 +22,10 @@ import jakarta.servlet.http.HttpSession;
 import lombok.RequiredArgsConstructor;
 
 import stirling.software.common.model.ApplicationProperties;
-import stirling.software.common.model.ApplicationProperties.Security.OAUTH2;
 import stirling.software.common.model.exception.UnsupportedProviderException;
 import stirling.software.common.util.RequestUriUtils;
 import stirling.software.proprietary.security.model.AuthenticationType;
+import stirling.software.proprietary.security.service.JwtServiceInterface;
 import stirling.software.proprietary.security.service.LoginAttemptService;
 import stirling.software.proprietary.security.service.UserService;
 
@@ -30,8 +34,9 @@ public class CustomOAuth2AuthenticationSuccessHandler
         extends SavedRequestAwareAuthenticationSuccessHandler {
 
     private final LoginAttemptService loginAttemptService;
-    private final ApplicationProperties applicationProperties;
+    private final ApplicationProperties.Security.OAUTH2 oauth2Properties;
     private final UserService userService;
+    private final JwtServiceInterface jwtService;
 
     @Override
     public void onAuthenticationSuccess(
@@ -60,8 +65,6 @@ public class CustomOAuth2AuthenticationSuccessHandler
             // Redirect to the original destination
             super.onAuthenticationSuccess(request, response, authentication);
         } else {
-            OAUTH2 oAuth = applicationProperties.getSecurity().getOauth2();
-
             if (loginAttemptService.isBlocked(username)) {
                 if (session != null) {
                     session.removeAttribute("SPRING_SECURITY_SAVED_REQUEST");
@@ -69,7 +72,12 @@ public class CustomOAuth2AuthenticationSuccessHandler
                 throw new LockedException(
                         "Your account has been locked due to too many failed login attempts.");
             }
-
+            if (jwtService.isJwtEnabled()) {
+                String jwt =
+                        jwtService.generateToken(
+                                authentication, Map.of("authType", AuthenticationType.OAUTH2));
+                jwtService.addToken(response, jwt);
+            }
             if (userService.isUserDisabled(username)) {
                 getRedirectStrategy()
                         .sendRedirect(request, response, "/logout?userIsDisabled=true");
@@ -77,20 +85,22 @@ public class CustomOAuth2AuthenticationSuccessHandler
             }
             if (userService.usernameExistsIgnoreCase(username)
                     && userService.hasPassword(username)
-                    && !userService.isAuthenticationTypeByUsername(username, AuthenticationType.SSO)
-                    && oAuth.getAutoCreateUser()) {
+                    && (!userService.isAuthenticationTypeByUsername(username, SSO)
+                            || !userService.isAuthenticationTypeByUsername(username, OAUTH2))
+                    && oauth2Properties.getAutoCreateUser()) {
                 response.sendRedirect(contextPath + "/logout?oAuth2AuthenticationErrorWeb=true");
                 return;
             }
 
             try {
-                if (oAuth.getBlockRegistration()
+                if (oauth2Properties.getBlockRegistration()
                         && !userService.usernameExistsIgnoreCase(username)) {
                     response.sendRedirect(contextPath + "/logout?oAuth2AdminBlockedUser=true");
                     return;
                 }
                 if (principal instanceof OAuth2User) {
-                    userService.processSSOPostLogin(username, oAuth.getAutoCreateUser());
+                    userService.processSSOPostLogin(
+                            username, oauth2Properties.getAutoCreateUser(), OAUTH2);
                 }
                 response.sendRedirect(contextPath + "/");
             } catch (IllegalArgumentException | SQLException | UnsupportedProviderException e) {
diff --git a/app/proprietary/src/main/java/stirling/software/proprietary/security/oauth2/OAuth2Configuration.java b/app/proprietary/src/main/java/stirling/software/proprietary/security/oauth2/OAuth2Configuration.java
index 6516cc7d7..913dc458a 100644
--- a/app/proprietary/src/main/java/stirling/software/proprietary/security/oauth2/OAuth2Configuration.java
+++ b/app/proprietary/src/main/java/stirling/software/proprietary/security/oauth2/OAuth2Configuration.java
@@ -34,6 +34,7 @@ import stirling.software.common.model.oauth2.GitHubProvider;
 import stirling.software.common.model.oauth2.GoogleProvider;
 import stirling.software.common.model.oauth2.KeycloakProvider;
 import stirling.software.common.model.oauth2.Provider;
+import stirling.software.proprietary.security.model.Authority;
 import stirling.software.proprietary.security.model.User;
 import stirling.software.proprietary.security.model.exception.NoProviderFoundException;
 import stirling.software.proprietary.security.service.UserService;
@@ -239,12 +240,14 @@ public class OAuth2Configuration {
                             Optional<User> userOpt =
                                     userService.findByUsernameIgnoreCase(
                                             (String) oAuth2Auth.getAttributes().get(useAsUsername));
-                            if (userOpt.isPresent()) {
-                                User user = userOpt.get();
-                                mappedAuthorities.add(
-                                        new SimpleGrantedAuthority(
-                                                userService.findRole(user).getAuthority()));
-                            }
+                            userOpt.ifPresent(
+                                    user ->
+                                            mappedAuthorities.add(
+                                                    new Authority(
+                                                            userService
+                                                                    .findRole(user)
+                                                                    .getAuthority(),
+                                                            user)));
                         }
                     });
             return mappedAuthorities;
diff --git a/app/proprietary/src/main/java/stirling/software/proprietary/security/saml2/CustomSaml2AuthenticationSuccessHandler.java b/app/proprietary/src/main/java/stirling/software/proprietary/security/saml2/CustomSaml2AuthenticationSuccessHandler.java
index 2170a9632..3255cbc15 100644
--- a/app/proprietary/src/main/java/stirling/software/proprietary/security/saml2/CustomSaml2AuthenticationSuccessHandler.java
+++ b/app/proprietary/src/main/java/stirling/software/proprietary/security/saml2/CustomSaml2AuthenticationSuccessHandler.java
@@ -1,7 +1,11 @@
 package stirling.software.proprietary.security.saml2;
 
+import static stirling.software.proprietary.security.model.AuthenticationType.SAML2;
+import static stirling.software.proprietary.security.model.AuthenticationType.SSO;
+
 import java.io.IOException;
 import java.sql.SQLException;
+import java.util.Map;
 
 import org.springframework.security.authentication.LockedException;
 import org.springframework.security.core.Authentication;
@@ -17,10 +21,10 @@ import lombok.AllArgsConstructor;
 import lombok.extern.slf4j.Slf4j;
 
 import stirling.software.common.model.ApplicationProperties;
-import stirling.software.common.model.ApplicationProperties.Security.SAML2;
 import stirling.software.common.model.exception.UnsupportedProviderException;
 import stirling.software.common.util.RequestUriUtils;
 import stirling.software.proprietary.security.model.AuthenticationType;
+import stirling.software.proprietary.security.service.JwtServiceInterface;
 import stirling.software.proprietary.security.service.LoginAttemptService;
 import stirling.software.proprietary.security.service.UserService;
 
@@ -30,8 +34,9 @@ public class CustomSaml2AuthenticationSuccessHandler
         extends SavedRequestAwareAuthenticationSuccessHandler {
 
     private LoginAttemptService loginAttemptService;
-    private ApplicationProperties applicationProperties;
+    private ApplicationProperties.Security.SAML2 saml2Properties;
     private UserService userService;
+    private final JwtServiceInterface jwtService;
 
     @Override
     public void onAuthenticationSuccess(
@@ -65,10 +70,9 @@ public class CustomSaml2AuthenticationSuccessHandler
                         savedRequest.getRedirectUrl());
                 super.onAuthenticationSuccess(request, response, authentication);
             } else {
-                SAML2 saml2 = applicationProperties.getSecurity().getSaml2();
                 log.debug(
                         "Processing SAML2 authentication with autoCreateUser: {}",
-                        saml2.getAutoCreateUser());
+                        saml2Properties.getAutoCreateUser());
 
                 if (loginAttemptService.isBlocked(username)) {
                     log.debug("User {} is blocked due to too many login attempts", username);
@@ -82,17 +86,21 @@ public class CustomSaml2AuthenticationSuccessHandler
                 boolean userExists = userService.usernameExistsIgnoreCase(username);
                 boolean hasPassword = userExists && userService.hasPassword(username);
                 boolean isSSOUser =
-                        userExists
-                                && userService.isAuthenticationTypeByUsername(
-                                        username, AuthenticationType.SSO);
+                        userExists && userService.isAuthenticationTypeByUsername(username, SSO);
+                boolean isSAML2User =
+                        userExists && userService.isAuthenticationTypeByUsername(username, SAML2);
 
                 log.debug(
-                        "User status - Exists: {}, Has password: {}, Is SSO user: {}",
+                        "User status - Exists: {}, Has password: {}, Is SSO user: {}, Is SAML2 user: {}",
                         userExists,
                         hasPassword,
-                        isSSOUser);
+                        isSSOUser,
+                        isSAML2User);
 
-                if (userExists && hasPassword && !isSSOUser && saml2.getAutoCreateUser()) {
+                if (userExists
+                        && hasPassword
+                        && (!isSSOUser || !isSAML2User)
+                        && saml2Properties.getAutoCreateUser()) {
                     log.debug(
                             "User {} exists with password but is not SSO user, redirecting to logout",
                             username);
@@ -102,15 +110,18 @@ public class CustomSaml2AuthenticationSuccessHandler
                 }
 
                 try {
-                    if (saml2.getBlockRegistration() && !userExists) {
+                    if (!userExists || saml2Properties.getBlockRegistration()) {
                         log.debug("Registration blocked for new user: {}", username);
                         response.sendRedirect(
                                 contextPath + "/login?errorOAuth=oAuth2AdminBlockedUser");
                         return;
                     }
                     log.debug("Processing SSO post-login for user: {}", username);
-                    userService.processSSOPostLogin(username, saml2.getAutoCreateUser());
+                    userService.processSSOPostLogin(
+                            username, saml2Properties.getAutoCreateUser(), SAML2);
                     log.debug("Successfully processed authentication for user: {}", username);
+
+                    generateJwt(response, authentication);
                     response.sendRedirect(contextPath + "/");
                 } catch (IllegalArgumentException | SQLException | UnsupportedProviderException e) {
                     log.debug(
@@ -124,4 +135,13 @@ public class CustomSaml2AuthenticationSuccessHandler
             super.onAuthenticationSuccess(request, response, authentication);
         }
     }
+
+    private void generateJwt(HttpServletResponse response, Authentication authentication) {
+        if (jwtService.isJwtEnabled()) {
+            String jwt =
+                    jwtService.generateToken(
+                            authentication, Map.of("authType", AuthenticationType.SAML2));
+            jwtService.addToken(response, jwt);
+        }
+    }
 }
diff --git a/app/proprietary/src/main/java/stirling/software/proprietary/security/saml2/JwtSaml2AuthenticationRequestRepository.java b/app/proprietary/src/main/java/stirling/software/proprietary/security/saml2/JwtSaml2AuthenticationRequestRepository.java
new file mode 100644
index 000000000..d0508151c
--- /dev/null
+++ b/app/proprietary/src/main/java/stirling/software/proprietary/security/saml2/JwtSaml2AuthenticationRequestRepository.java
@@ -0,0 +1,135 @@
+package stirling.software.proprietary.security.saml2;
+
+import java.util.HashMap;
+import java.util.Map;
+
+import org.springframework.security.saml2.provider.service.authentication.Saml2PostAuthenticationRequest;
+import org.springframework.security.saml2.provider.service.registration.RelyingPartyRegistration;
+import org.springframework.security.saml2.provider.service.registration.RelyingPartyRegistrationRepository;
+import org.springframework.security.saml2.provider.service.web.Saml2AuthenticationRequestRepository;
+
+import jakarta.servlet.http.HttpServletRequest;
+import jakarta.servlet.http.HttpServletResponse;
+
+import lombok.extern.slf4j.Slf4j;
+
+import stirling.software.proprietary.security.service.JwtServiceInterface;
+
+@Slf4j
+public class JwtSaml2AuthenticationRequestRepository
+        implements Saml2AuthenticationRequestRepository<Saml2PostAuthenticationRequest> {
+    private final Map<String, String> tokenStore;
+    private final JwtServiceInterface jwtService;
+    private final RelyingPartyRegistrationRepository relyingPartyRegistrationRepository;
+
+    private static final String SAML_REQUEST_TOKEN = "stirling_saml_request_token";
+
+    public JwtSaml2AuthenticationRequestRepository(
+            Map<String, String> tokenStore,
+            JwtServiceInterface jwtService,
+            RelyingPartyRegistrationRepository relyingPartyRegistrationRepository) {
+        this.tokenStore = tokenStore;
+        this.jwtService = jwtService;
+        this.relyingPartyRegistrationRepository = relyingPartyRegistrationRepository;
+    }
+
+    @Override
+    public void saveAuthenticationRequest(
+            Saml2PostAuthenticationRequest authRequest,
+            HttpServletRequest request,
+            HttpServletResponse response) {
+        if (!jwtService.isJwtEnabled()) {
+            log.debug("V2 is not enabled, skipping SAMLRequest token storage");
+            return;
+        }
+
+        if (authRequest == null) {
+            removeAuthenticationRequest(request, response);
+            return;
+        }
+
+        Map<String, Object> claims = serializeSamlRequest(authRequest);
+        String token = jwtService.generateToken("", claims);
+        String relayState = authRequest.getRelayState();
+
+        tokenStore.put(relayState, token);
+        request.setAttribute(SAML_REQUEST_TOKEN, relayState);
+        response.addHeader(SAML_REQUEST_TOKEN, relayState);
+
+        log.debug("Saved SAMLRequest token with RelayState: {}", relayState);
+    }
+
+    @Override
+    public Saml2PostAuthenticationRequest loadAuthenticationRequest(HttpServletRequest request) {
+        String token = extractTokenFromStore(request);
+
+        if (token == null) {
+            log.debug("No SAMLResponse token found in RelayState");
+            return null;
+        }
+
+        Map<String, Object> claims = jwtService.extractClaims(token);
+        return deserializeSamlRequest(claims);
+    }
+
+    @Override
+    public Saml2PostAuthenticationRequest removeAuthenticationRequest(
+            HttpServletRequest request, HttpServletResponse response) {
+        Saml2PostAuthenticationRequest authRequest = loadAuthenticationRequest(request);
+
+        String relayStateId = request.getParameter("RelayState");
+        if (relayStateId != null) {
+            tokenStore.remove(relayStateId);
+            log.debug("Removed SAMLRequest token for RelayState ID: {}", relayStateId);
+        }
+
+        return authRequest;
+    }
+
+    private String extractTokenFromStore(HttpServletRequest request) {
+        String authnRequestId = request.getParameter("RelayState");
+
+        if (authnRequestId != null && !authnRequestId.isEmpty()) {
+            String token = tokenStore.get(authnRequestId);
+
+            if (token != null) {
+                tokenStore.remove(authnRequestId);
+                log.debug("Retrieved SAMLRequest token for RelayState ID: {}", authnRequestId);
+                return token;
+            } else {
+                log.warn("No SAMLRequest token found for RelayState ID: {}", authnRequestId);
+            }
+        }
+
+        return null;
+    }
+
+    private Map<String, Object> serializeSamlRequest(Saml2PostAuthenticationRequest authRequest) {
+        Map<String, Object> claims = new HashMap<>();
+
+        claims.put("id", authRequest.getId());
+        claims.put("relyingPartyRegistrationId", authRequest.getRelyingPartyRegistrationId());
+        claims.put("authenticationRequestUri", authRequest.getAuthenticationRequestUri());
+        claims.put("samlRequest", authRequest.getSamlRequest());
+        claims.put("relayState", authRequest.getRelayState());
+
+        return claims;
+    }
+
+    private Saml2PostAuthenticationRequest deserializeSamlRequest(Map<String, Object> claims) {
+        String relyingPartyRegistrationId = (String) claims.get("relyingPartyRegistrationId");
+        RelyingPartyRegistration relyingPartyRegistration =
+                relyingPartyRegistrationRepository.findByRegistrationId(relyingPartyRegistrationId);
+
+        if (relyingPartyRegistration == null) {
+            return null;
+        }
+
+        return Saml2PostAuthenticationRequest.withRelyingPartyRegistration(relyingPartyRegistration)
+                .id((String) claims.get("id"))
+                .authenticationRequestUri((String) claims.get("authenticationRequestUri"))
+                .samlRequest((String) claims.get("samlRequest"))
+                .relayState((String) claims.get("relayState"))
+                .build();
+    }
+}
diff --git a/app/proprietary/src/main/java/stirling/software/proprietary/security/saml2/SAML2Configuration.java b/app/proprietary/src/main/java/stirling/software/proprietary/security/saml2/Saml2Configuration.java
similarity index 85%
rename from app/proprietary/src/main/java/stirling/software/proprietary/security/saml2/SAML2Configuration.java
rename to app/proprietary/src/main/java/stirling/software/proprietary/security/saml2/Saml2Configuration.java
index 7fd4768b3..9d21f88a3 100644
--- a/app/proprietary/src/main/java/stirling/software/proprietary/security/saml2/SAML2Configuration.java
+++ b/app/proprietary/src/main/java/stirling/software/proprietary/security/saml2/Saml2Configuration.java
@@ -3,6 +3,7 @@ package stirling.software.proprietary.security.saml2;
 import java.security.cert.X509Certificate;
 import java.util.Collections;
 import java.util.UUID;
+import java.util.concurrent.ConcurrentHashMap;
 
 import org.opensaml.saml.saml2.core.AuthnRequest;
 import org.springframework.boot.autoconfigure.condition.ConditionalOnProperty;
@@ -11,12 +12,12 @@ import org.springframework.context.annotation.Configuration;
 import org.springframework.core.io.Resource;
 import org.springframework.security.saml2.core.Saml2X509Credential;
 import org.springframework.security.saml2.core.Saml2X509Credential.Saml2X509CredentialType;
-import org.springframework.security.saml2.provider.service.authentication.AbstractSaml2AuthenticationRequest;
+import org.springframework.security.saml2.provider.service.authentication.Saml2PostAuthenticationRequest;
 import org.springframework.security.saml2.provider.service.registration.InMemoryRelyingPartyRegistrationRepository;
 import org.springframework.security.saml2.provider.service.registration.RelyingPartyRegistration;
 import org.springframework.security.saml2.provider.service.registration.RelyingPartyRegistrationRepository;
 import org.springframework.security.saml2.provider.service.registration.Saml2MessageBinding;
-import org.springframework.security.saml2.provider.service.web.HttpSessionSaml2AuthenticationRequestRepository;
+import org.springframework.security.saml2.provider.service.web.Saml2AuthenticationRequestRepository;
 import org.springframework.security.saml2.provider.service.web.authentication.OpenSaml4AuthenticationRequestResolver;
 
 import jakarta.servlet.http.HttpServletRequest;
@@ -26,12 +27,13 @@ import lombok.extern.slf4j.Slf4j;
 
 import stirling.software.common.model.ApplicationProperties;
 import stirling.software.common.model.ApplicationProperties.Security.SAML2;
+import stirling.software.proprietary.security.service.JwtServiceInterface;
 
 @Configuration
 @Slf4j
 @ConditionalOnProperty(value = "security.saml2.enabled", havingValue = "true")
 @RequiredArgsConstructor
-public class SAML2Configuration {
+public class Saml2Configuration {
 
     private final ApplicationProperties applicationProperties;
 
@@ -58,6 +60,7 @@ public class SAML2Configuration {
                         .assertionConsumerServiceBinding(Saml2MessageBinding.POST)
                         .assertionConsumerServiceLocation(
                                 "{baseUrl}/login/saml2/sso/{registrationId}")
+                        .authnRequestsSigned(true)
                         .assertingPartyMetadata(
                                 metadata ->
                                         metadata.entityId(samlConf.getIdpIssuer())
@@ -71,15 +74,29 @@ public class SAML2Configuration {
                                                         Saml2MessageBinding.POST)
                                                 .singleLogoutServiceLocation(
                                                         samlConf.getIdpSingleLogoutUrl())
+                                                .singleLogoutServiceResponseLocation(
+                                                        "http://localhost:8080/login")
                                                 .wantAuthnRequestsSigned(true))
                         .build();
         return new InMemoryRelyingPartyRegistrationRepository(rp);
     }
 
+    @Bean
+    @ConditionalOnProperty(name = "security.saml2.enabled", havingValue = "true")
+    public Saml2AuthenticationRequestRepository<Saml2PostAuthenticationRequest>
+            saml2AuthenticationRequestRepository(
+                    JwtServiceInterface jwtService,
+                    RelyingPartyRegistrationRepository relyingPartyRegistrationRepository) {
+        return new JwtSaml2AuthenticationRequestRepository(
+                new ConcurrentHashMap<>(), jwtService, relyingPartyRegistrationRepository);
+    }
+
     @Bean
     @ConditionalOnProperty(name = "security.saml2.enabled", havingValue = "true")
     public OpenSaml4AuthenticationRequestResolver authenticationRequestResolver(
-            RelyingPartyRegistrationRepository relyingPartyRegistrationRepository) {
+            RelyingPartyRegistrationRepository relyingPartyRegistrationRepository,
+            Saml2AuthenticationRequestRepository<Saml2PostAuthenticationRequest>
+                    saml2AuthenticationRequestRepository) {
         OpenSaml4AuthenticationRequestResolver resolver =
                 new OpenSaml4AuthenticationRequestResolver(relyingPartyRegistrationRepository);
 
@@ -87,10 +104,8 @@ public class SAML2Configuration {
                 customizer -> {
                     HttpServletRequest request = customizer.getRequest();
                     AuthnRequest authnRequest = customizer.getAuthnRequest();
-                    HttpSessionSaml2AuthenticationRequestRepository requestRepository =
-                            new HttpSessionSaml2AuthenticationRequestRepository();
-                    AbstractSaml2AuthenticationRequest saml2AuthenticationRequest =
-                            requestRepository.loadAuthenticationRequest(request);
+                    Saml2PostAuthenticationRequest saml2AuthenticationRequest =
+                            saml2AuthenticationRequestRepository.loadAuthenticationRequest(request);
 
                     if (saml2AuthenticationRequest != null) {
                         String sessionId = request.getSession(false).getId();
@@ -113,7 +128,6 @@ public class SAML2Configuration {
                         log.debug("Generating new authentication request ID");
                         authnRequest.setID("ARQ" + UUID.randomUUID().toString().substring(1));
                     }
-
                     logAuthnRequestDetails(authnRequest);
                     logHttpRequestDetails(request);
                 });
diff --git a/app/proprietary/src/main/java/stirling/software/proprietary/security/service/CustomOAuth2UserService.java b/app/proprietary/src/main/java/stirling/software/proprietary/security/service/CustomOAuth2UserService.java
index 0b286e894..8f9afbe3d 100644
--- a/app/proprietary/src/main/java/stirling/software/proprietary/security/service/CustomOAuth2UserService.java
+++ b/app/proprietary/src/main/java/stirling/software/proprietary/security/service/CustomOAuth2UserService.java
@@ -27,13 +27,13 @@ public class CustomOAuth2UserService implements OAuth2UserService<OidcUserReques
 
     private final LoginAttemptService loginAttemptService;
 
-    private final ApplicationProperties applicationProperties;
+    private final ApplicationProperties.Security securityProperties;
 
     public CustomOAuth2UserService(
-            ApplicationProperties applicationProperties,
+            ApplicationProperties.Security securityProperties,
             UserService userService,
             LoginAttemptService loginAttemptService) {
-        this.applicationProperties = applicationProperties;
+        this.securityProperties = securityProperties;
         this.userService = userService;
         this.loginAttemptService = loginAttemptService;
     }
@@ -42,7 +42,7 @@ public class CustomOAuth2UserService implements OAuth2UserService<OidcUserReques
     public OidcUser loadUser(OidcUserRequest userRequest) throws OAuth2AuthenticationException {
         try {
             OidcUser user = delegate.loadUser(userRequest);
-            OAUTH2 oauth2 = applicationProperties.getSecurity().getOauth2();
+            OAUTH2 oauth2 = securityProperties.getOauth2();
             UsernameAttribute usernameAttribute =
                     UsernameAttribute.valueOf(oauth2.getUseAsUsername().toUpperCase());
             String usernameAttributeKey = usernameAttribute.getName();
diff --git a/app/proprietary/src/main/java/stirling/software/proprietary/security/service/CustomUserDetailsService.java b/app/proprietary/src/main/java/stirling/software/proprietary/security/service/CustomUserDetailsService.java
index 6ece48a4e..1704e5972 100644
--- a/app/proprietary/src/main/java/stirling/software/proprietary/security/service/CustomUserDetailsService.java
+++ b/app/proprietary/src/main/java/stirling/software/proprietary/security/service/CustomUserDetailsService.java
@@ -1,11 +1,6 @@
 package stirling.software.proprietary.security.service;
 
-import java.util.Collection;
-import java.util.Set;
-
 import org.springframework.security.authentication.LockedException;
-import org.springframework.security.core.GrantedAuthority;
-import org.springframework.security.core.authority.SimpleGrantedAuthority;
 import org.springframework.security.core.userdetails.UserDetails;
 import org.springframework.security.core.userdetails.UserDetailsService;
 import org.springframework.security.core.userdetails.UsernameNotFoundException;
@@ -14,7 +9,7 @@ import org.springframework.stereotype.Service;
 import lombok.RequiredArgsConstructor;
 
 import stirling.software.proprietary.security.database.repository.UserRepository;
-import stirling.software.proprietary.security.model.Authority;
+import stirling.software.proprietary.security.model.AuthenticationType;
 import stirling.software.proprietary.security.model.User;
 
 @Service
@@ -34,26 +29,18 @@ public class CustomUserDetailsService implements UserDetailsService {
                                 () ->
                                         new UsernameNotFoundException(
                                                 "No user found with username: " + username));
+
         if (loginAttemptService.isBlocked(username)) {
             throw new LockedException(
                     "Your account has been locked due to too many failed login attempts.");
         }
-        if (!user.hasPassword()) {
+
+        AuthenticationType userAuthenticationType =
+                AuthenticationType.valueOf(user.getAuthenticationType().toUpperCase());
+        if (!user.hasPassword() && userAuthenticationType == AuthenticationType.WEB) {
             throw new IllegalArgumentException("Password must not be null");
         }
-        return new org.springframework.security.core.userdetails.User(
-                user.getUsername(),
-                user.getPassword(),
-                user.isEnabled(),
-                true,
-                true,
-                true,
-                getAuthorities(user.getAuthorities()));
-    }
 
-    private Collection<? extends GrantedAuthority> getAuthorities(Set<Authority> authorities) {
-        return authorities.stream()
-                .map(authority -> new SimpleGrantedAuthority(authority.getAuthority()))
-                .toList();
+        return user;
     }
 }
diff --git a/app/proprietary/src/main/java/stirling/software/proprietary/security/service/JwtService.java b/app/proprietary/src/main/java/stirling/software/proprietary/security/service/JwtService.java
new file mode 100644
index 000000000..8724da9a8
--- /dev/null
+++ b/app/proprietary/src/main/java/stirling/software/proprietary/security/service/JwtService.java
@@ -0,0 +1,330 @@
+package stirling.software.proprietary.security.service;
+
+import java.security.KeyPair;
+import java.security.NoSuchAlgorithmException;
+import java.security.PublicKey;
+import java.security.spec.InvalidKeySpecException;
+import java.time.LocalDateTime;
+import java.util.Date;
+import java.util.HashMap;
+import java.util.List;
+import java.util.Map;
+import java.util.Optional;
+import java.util.function.Function;
+
+import org.springframework.beans.factory.annotation.Autowired;
+import org.springframework.beans.factory.annotation.Qualifier;
+import org.springframework.beans.factory.annotation.Value;
+import org.springframework.http.ResponseCookie;
+import org.springframework.security.core.Authentication;
+import org.springframework.security.core.userdetails.UserDetails;
+import org.springframework.security.oauth2.core.user.OAuth2User;
+import org.springframework.stereotype.Service;
+
+import io.github.pixee.security.Newlines;
+import io.jsonwebtoken.Claims;
+import io.jsonwebtoken.ExpiredJwtException;
+import io.jsonwebtoken.Jwts;
+import io.jsonwebtoken.MalformedJwtException;
+import io.jsonwebtoken.UnsupportedJwtException;
+import io.jsonwebtoken.security.SignatureException;
+
+import jakarta.servlet.http.Cookie;
+import jakarta.servlet.http.HttpServletRequest;
+import jakarta.servlet.http.HttpServletResponse;
+
+import lombok.extern.slf4j.Slf4j;
+
+import stirling.software.proprietary.security.model.JwtVerificationKey;
+import stirling.software.proprietary.security.model.exception.AuthenticationFailureException;
+import stirling.software.proprietary.security.saml2.CustomSaml2AuthenticatedPrincipal;
+
+@Slf4j
+@Service
+public class JwtService implements JwtServiceInterface {
+
+    private static final String JWT_COOKIE_NAME = "stirling_jwt";
+    private static final String ISSUER = "Stirling PDF";
+    private static final long EXPIRATION = 3600000;
+
+    @Value("${stirling.security.jwt.secureCookie:true}")
+    private boolean secureCookie;
+
+    private final KeyPersistenceServiceInterface keyPersistenceService;
+    private final boolean v2Enabled;
+
+    @Autowired
+    public JwtService(
+            @Qualifier("v2Enabled") boolean v2Enabled,
+            KeyPersistenceServiceInterface keyPersistenceService) {
+        this.v2Enabled = v2Enabled;
+        this.keyPersistenceService = keyPersistenceService;
+    }
+
+    @Override
+    public String generateToken(Authentication authentication, Map<String, Object> claims) {
+        Object principal = authentication.getPrincipal();
+        String username = "";
+
+        if (principal instanceof UserDetails) {
+            username = ((UserDetails) principal).getUsername();
+        } else if (principal instanceof OAuth2User) {
+            username = ((OAuth2User) principal).getName();
+        } else if (principal instanceof CustomSaml2AuthenticatedPrincipal) {
+            username = ((CustomSaml2AuthenticatedPrincipal) principal).getName();
+        }
+
+        return generateToken(username, claims);
+    }
+
+    @Override
+    public String generateToken(String username, Map<String, Object> claims) {
+        try {
+            JwtVerificationKey activeKey = keyPersistenceService.getActiveKey();
+            Optional<KeyPair> keyPairOpt = keyPersistenceService.getKeyPair(activeKey.getKeyId());
+
+            if (keyPairOpt.isEmpty()) {
+                throw new RuntimeException("Unable to retrieve key pair for active key");
+            }
+
+            KeyPair keyPair = keyPairOpt.get();
+
+            var builder =
+                    Jwts.builder()
+                            .claims(claims)
+                            .subject(username)
+                            .issuer(ISSUER)
+                            .issuedAt(new Date())
+                            .expiration(new Date(System.currentTimeMillis() + EXPIRATION))
+                            .signWith(keyPair.getPrivate(), Jwts.SIG.RS256);
+
+            String keyId = activeKey.getKeyId();
+            if (keyId != null) {
+                builder.header().keyId(keyId);
+            }
+
+            return builder.compact();
+        } catch (Exception e) {
+            throw new RuntimeException("Failed to generate token", e);
+        }
+    }
+
+    @Override
+    public void validateToken(String token) throws AuthenticationFailureException {
+        extractAllClaims(token);
+
+        if (isTokenExpired(token)) {
+            throw new AuthenticationFailureException("The token has expired");
+        }
+    }
+
+    @Override
+    public String extractUsername(String token) {
+        return extractClaim(token, Claims::getSubject);
+    }
+
+    @Override
+    public Map<String, Object> extractClaims(String token) {
+        Claims claims = extractAllClaims(token);
+        return new HashMap<>(claims);
+    }
+
+    @Override
+    public boolean isTokenExpired(String token) {
+        return extractExpiration(token).before(new Date());
+    }
+
+    private Date extractExpiration(String token) {
+        return extractClaim(token, Claims::getExpiration);
+    }
+
+    private <T> T extractClaim(String token, Function<Claims, T> claimsResolver) {
+        final Claims claims = extractAllClaims(token);
+        return claimsResolver.apply(claims);
+    }
+
+    private Claims extractAllClaims(String token) {
+        try {
+            String keyId = extractKeyId(token);
+            KeyPair keyPair;
+
+            if (keyId != null) {
+                Optional<KeyPair> specificKeyPair = keyPersistenceService.getKeyPair(keyId);
+
+                if (specificKeyPair.isPresent()) {
+                    keyPair = specificKeyPair.get();
+                } else {
+                    log.warn(
+                            "Key ID {} not found in keystore, token may have been signed with an expired key",
+                            keyId);
+
+                    if (keyId.equals(keyPersistenceService.getActiveKey().getKeyId())) {
+                        JwtVerificationKey verificationKey =
+                                keyPersistenceService.refreshActiveKeyPair();
+                        Optional<KeyPair> refreshedKeyPair =
+                                keyPersistenceService.getKeyPair(verificationKey.getKeyId());
+                        if (refreshedKeyPair.isPresent()) {
+                            keyPair = refreshedKeyPair.get();
+                        } else {
+                            throw new AuthenticationFailureException(
+                                    "Failed to retrieve refreshed key pair");
+                        }
+                    } else {
+                        // Try to use active key as fallback
+                        JwtVerificationKey activeKey = keyPersistenceService.getActiveKey();
+                        Optional<KeyPair> activeKeyPair =
+                                keyPersistenceService.getKeyPair(activeKey.getKeyId());
+                        if (activeKeyPair.isPresent()) {
+                            keyPair = activeKeyPair.get();
+                        } else {
+                            throw new AuthenticationFailureException(
+                                    "Failed to retrieve active key pair");
+                        }
+                    }
+                }
+            } else {
+                log.debug("No key ID in token header, trying all available keys");
+                // Try all available keys when no keyId is present
+                return tryAllKeys(token);
+            }
+
+            return Jwts.parser()
+                    .verifyWith(keyPair.getPublic())
+                    .build()
+                    .parseSignedClaims(token)
+                    .getPayload();
+        } catch (SignatureException e) {
+            log.warn("Invalid signature: {}", e.getMessage());
+            throw new AuthenticationFailureException("Invalid signature", e);
+        } catch (MalformedJwtException e) {
+            log.warn("Invalid token: {}", e.getMessage());
+            throw new AuthenticationFailureException("Invalid token", e);
+        } catch (ExpiredJwtException e) {
+            log.warn("The token has expired: {}", e.getMessage());
+            throw new AuthenticationFailureException("The token has expired", e);
+        } catch (UnsupportedJwtException e) {
+            log.warn("The token is unsupported: {}", e.getMessage());
+            throw new AuthenticationFailureException("The token is unsupported", e);
+        } catch (IllegalArgumentException e) {
+            log.warn("Claims are empty: {}", e.getMessage());
+            throw new AuthenticationFailureException("Claims are empty", e);
+        }
+    }
+
+    private Claims tryAllKeys(String token) throws AuthenticationFailureException {
+        // First try the active key
+        try {
+            JwtVerificationKey activeKey = keyPersistenceService.getActiveKey();
+            PublicKey publicKey =
+                    keyPersistenceService.decodePublicKey(activeKey.getVerifyingKey());
+            return Jwts.parser()
+                    .verifyWith(publicKey)
+                    .build()
+                    .parseSignedClaims(token)
+                    .getPayload();
+        } catch (SignatureException
+                | NoSuchAlgorithmException
+                | InvalidKeySpecException activeKeyException) {
+            log.debug("Active key failed, trying all available keys from cache");
+
+            // If active key fails, try all available keys from cache
+            List<JwtVerificationKey> allKeys =
+                    keyPersistenceService.getKeysEligibleForCleanup(
+                            LocalDateTime.now().plusDays(1));
+
+            for (JwtVerificationKey verificationKey : allKeys) {
+                try {
+                    PublicKey publicKey =
+                            keyPersistenceService.decodePublicKey(
+                                    verificationKey.getVerifyingKey());
+                    return Jwts.parser()
+                            .verifyWith(publicKey)
+                            .build()
+                            .parseSignedClaims(token)
+                            .getPayload();
+                } catch (SignatureException
+                        | NoSuchAlgorithmException
+                        | InvalidKeySpecException e) {
+                    log.debug(
+                            "Key {} failed to verify token, trying next key",
+                            verificationKey.getKeyId());
+                    // Continue to next key
+                }
+            }
+
+            throw new AuthenticationFailureException(
+                    "Token signature could not be verified with any available key",
+                    activeKeyException);
+        }
+    }
+
+    @Override
+    public String extractToken(HttpServletRequest request) {
+        Cookie[] cookies = request.getCookies();
+
+        if (cookies != null) {
+            for (Cookie cookie : cookies) {
+                if (JWT_COOKIE_NAME.equals(cookie.getName())) {
+                    return cookie.getValue();
+                }
+            }
+        }
+
+        return null;
+    }
+
+    @Override
+    public void addToken(HttpServletResponse response, String token) {
+        ResponseCookie cookie =
+                ResponseCookie.from(JWT_COOKIE_NAME, Newlines.stripAll(token))
+                        .httpOnly(true)
+                        .secure(secureCookie)
+                        .sameSite("Strict")
+                        .maxAge(EXPIRATION / 1000)
+                        .path("/")
+                        .build();
+
+        response.addHeader("Set-Cookie", cookie.toString());
+    }
+
+    @Override
+    public void clearToken(HttpServletResponse response) {
+        ResponseCookie cookie =
+                ResponseCookie.from(JWT_COOKIE_NAME, "")
+                        .httpOnly(true)
+                        .secure(secureCookie)
+                        .sameSite("None")
+                        .maxAge(0)
+                        .path("/")
+                        .build();
+
+        response.addHeader("Set-Cookie", cookie.toString());
+    }
+
+    @Override
+    public boolean isJwtEnabled() {
+        return v2Enabled;
+    }
+
+    private String extractKeyId(String token) {
+        try {
+            PublicKey signingKey =
+                    keyPersistenceService.decodePublicKey(
+                            keyPersistenceService.getActiveKey().getVerifyingKey());
+
+            String keyId =
+                    (String)
+                            Jwts.parser()
+                                    .verifyWith(signingKey)
+                                    .build()
+                                    .parse(token)
+                                    .getHeader()
+                                    .get("kid");
+            log.debug("Extracted key ID from token: {}", keyId);
+            return keyId;
+        } catch (Exception e) {
+            log.warn("Failed to extract key ID from token header: {}", e.getMessage());
+            return null;
+        }
+    }
+}
diff --git a/app/proprietary/src/main/java/stirling/software/proprietary/security/service/JwtServiceInterface.java b/app/proprietary/src/main/java/stirling/software/proprietary/security/service/JwtServiceInterface.java
new file mode 100644
index 000000000..7cdca8209
--- /dev/null
+++ b/app/proprietary/src/main/java/stirling/software/proprietary/security/service/JwtServiceInterface.java
@@ -0,0 +1,90 @@
+package stirling.software.proprietary.security.service;
+
+import java.util.Map;
+
+import org.springframework.security.core.Authentication;
+
+import jakarta.servlet.http.HttpServletRequest;
+import jakarta.servlet.http.HttpServletResponse;
+
+public interface JwtServiceInterface {
+
+    /**
+     * Generate a JWT token for the authenticated user
+     *
+     * @param authentication Spring Security authentication object
+     * @return JWT token as a string
+     */
+    String generateToken(Authentication authentication, Map<String, Object> claims);
+
+    /**
+     * Generate a JWT token for a specific username
+     *
+     * @param username the username for which to generate the token
+     * @param claims additional claims to include in the token
+     * @return JWT token as a string
+     */
+    String generateToken(String username, Map<String, Object> claims);
+
+    /**
+     * Validate a JWT token
+     *
+     * @param token the JWT token to validate
+     * @return true if token is valid, false otherwise
+     */
+    void validateToken(String token);
+
+    /**
+     * Extract username from JWT token
+     *
+     * @param token the JWT token
+     * @return username extracted from token
+     */
+    String extractUsername(String token);
+
+    /**
+     * Extract all claims from JWT token
+     *
+     * @param token the JWT token
+     * @return map of claims
+     */
+    Map<String, Object> extractClaims(String token);
+
+    /**
+     * Check if token is expired
+     *
+     * @param token the JWT token
+     * @return true if token is expired, false otherwise
+     */
+    boolean isTokenExpired(String token);
+
+    /**
+     * Extract JWT token from HTTP request (header or cookie)
+     *
+     * @param request HTTP servlet request
+     * @return JWT token if found, null otherwise
+     */
+    String extractToken(HttpServletRequest request);
+
+    /**
+     * Add JWT token to HTTP response (header and cookie)
+     *
+     * @param response HTTP servlet response
+     * @param token JWT token to add
+     */
+    void addToken(HttpServletResponse response, String token);
+
+    /**
+     * Clear JWT token from HTTP response (remove cookie)
+     *
+     * @param response HTTP servlet response
+     */
+    void clearToken(HttpServletResponse response);
+
+    /**
+     * Check if JWT authentication is enabled
+     *
+     * @return true if JWT is enabled, false otherwise
+     */
+    boolean isJwtEnabled();
+}
diff --git a/app/proprietary/src/main/java/stirling/software/proprietary/security/service/KeyPairCleanupService.java b/app/proprietary/src/main/java/stirling/software/proprietary/security/service/KeyPairCleanupService.java
new file mode 100644
index 000000000..b419f78fe
--- /dev/null
+++ b/app/proprietary/src/main/java/stirling/software/proprietary/security/service/KeyPairCleanupService.java
@@ -0,0 +1,88 @@
+package stirling.software.proprietary.security.service;
+
+import java.io.IOException;
+import java.nio.file.Files;
+import java.nio.file.Path;
+import java.nio.file.Paths;
+import java.time.LocalDateTime;
+import java.util.List;
+import java.util.concurrent.TimeUnit;
+
+import org.springframework.beans.factory.annotation.Autowired;
+import org.springframework.boot.autoconfigure.condition.ConditionalOnBooleanProperty;
+import org.springframework.scheduling.annotation.Scheduled;
+import org.springframework.stereotype.Service;
+import org.springframework.transaction.annotation.Transactional;
+
+import jakarta.annotation.PostConstruct;
+
+import lombok.extern.slf4j.Slf4j;
+
+import stirling.software.common.configuration.InstallationPathConfig;
+import stirling.software.common.model.ApplicationProperties;
+import stirling.software.proprietary.security.model.JwtVerificationKey;
+
+@Slf4j
+@Service
+@ConditionalOnBooleanProperty("v2")
+public class KeyPairCleanupService {
+
+    private final KeyPersistenceService keyPersistenceService;
+    private final ApplicationProperties.Security.Jwt jwtProperties;
+
+    @Autowired
+    public KeyPairCleanupService(
+            KeyPersistenceService keyPersistenceService,
+            ApplicationProperties applicationProperties) {
+        this.keyPersistenceService = keyPersistenceService;
+        this.jwtProperties = applicationProperties.getSecurity().getJwt();
+    }
+
+    @Transactional
+    @PostConstruct
+    @Scheduled(fixedDelay = 1, timeUnit = TimeUnit.DAYS)
+    public void cleanup() {
+        if (!jwtProperties.isEnableKeyCleanup() || !keyPersistenceService.isKeystoreEnabled()) {
+            return;
+        }
+
+        LocalDateTime cutoffDate =
+                LocalDateTime.now().minusDays(jwtProperties.getKeyRetentionDays());
+
+        List<JwtVerificationKey> eligibleKeys =
+                keyPersistenceService.getKeysEligibleForCleanup(cutoffDate);
+        if (eligibleKeys.isEmpty()) {
+            return;
+        }
+
+        log.info("Removing keys older than retention period");
+        removeKeys(eligibleKeys);
+        keyPersistenceService.refreshActiveKeyPair();
+    }
+
+    private void removeKeys(List<JwtVerificationKey> keys) {
+        keys.forEach(
+                key -> {
+                    try {
+                        keyPersistenceService.removeKey(key.getKeyId());
+                        removePrivateKey(key.getKeyId());
+                    } catch (IOException e) {
+                        log.warn("Failed to remove key: {}", key.getKeyId(), e);
+                    }
+                });
+    }
+
+    private void removePrivateKey(String keyId) throws IOException {
+        if (!keyPersistenceService.isKeystoreEnabled()) {
+            return;
+        }
+
+        Path privateKeyDirectory = Paths.get(InstallationPathConfig.getPrivateKeyPath());
+        Path keyFile = privateKeyDirectory.resolve(keyId + KeyPersistenceService.KEY_SUFFIX);
+
+        if (Files.exists(keyFile)) {
+            Files.delete(keyFile);
+            log.debug("Deleted private key: {}", keyFile);
+        }
+    }
+}
diff --git a/app/proprietary/src/main/java/stirling/software/proprietary/security/service/KeyPersistenceService.java b/app/proprietary/src/main/java/stirling/software/proprietary/security/service/KeyPersistenceService.java
new file mode 100644
index 000000000..48bcddac0
--- /dev/null
+++ b/app/proprietary/src/main/java/stirling/software/proprietary/security/service/KeyPersistenceService.java
@@ -0,0 +1,243 @@
+package stirling.software.proprietary.security.service;
+
+import java.io.IOException;
+import java.nio.file.Files;
+import java.nio.file.Path;
+import java.nio.file.Paths;
+import java.security.KeyFactory;
+import java.security.KeyPair;
+import java.security.KeyPairGenerator;
+import java.security.NoSuchAlgorithmException;
+import java.security.PrivateKey;
+import java.security.PublicKey;
+import java.security.spec.InvalidKeySpecException;
+import java.security.spec.PKCS8EncodedKeySpec;
+import java.security.spec.X509EncodedKeySpec;
+import java.time.LocalDateTime;
+import java.time.format.DateTimeFormatter;
+import java.util.Base64;
+import java.util.List;
+import java.util.Optional;
+import java.util.stream.Collectors;
+
+import org.springframework.beans.factory.annotation.Autowired;
+import org.springframework.cache.Cache;
+import org.springframework.cache.CacheManager;
+import org.springframework.cache.annotation.CacheEvict;
+import org.springframework.cache.caffeine.CaffeineCache;
+import org.springframework.stereotype.Service;
+import org.springframework.transaction.annotation.Transactional;
+
+import jakarta.annotation.PostConstruct;
+
+import lombok.extern.slf4j.Slf4j;
+
+import stirling.software.common.configuration.InstallationPathConfig;
+import stirling.software.common.model.ApplicationProperties;
+import stirling.software.proprietary.security.model.JwtVerificationKey;
+
+@Slf4j
+@Service
+public class KeyPersistenceService implements KeyPersistenceServiceInterface {
+
+    public static final String KEY_SUFFIX = ".key";
+
+    private final ApplicationProperties.Security.Jwt jwtProperties;
+    private final CacheManager cacheManager;
+    private final Cache verifyingKeyCache;
+
+    private volatile JwtVerificationKey activeKey;
+
+    @Autowired
+    public KeyPersistenceService(
+            ApplicationProperties applicationProperties, CacheManager cacheManager) {
+        this.jwtProperties = applicationProperties.getSecurity().getJwt();
+        this.cacheManager = cacheManager;
+        this.verifyingKeyCache = cacheManager.getCache("verifyingKeys");
+    }
+
+    @PostConstruct
+    public void initializeKeystore() {
+        if (!isKeystoreEnabled()) {
+            return;
+        }
+
+        try {
+            ensurePrivateKeyDirectoryExists();
+            loadKeyPair();
+        } catch (Exception e) {
+            log.error("Failed to initialize keystore, using in-memory generation", e);
+        }
+    }
+
+    private void loadKeyPair() {
+        if (activeKey == null) {
+            generateAndStoreKeypair();
+        }
+    }
+
+    @Transactional
+    private JwtVerificationKey generateAndStoreKeypair() {
+        JwtVerificationKey verifyingKey = null;
+
+        try {
+            KeyPair keyPair = generateRSAKeypair();
+            String keyId = generateKeyId();
+
+            storePrivateKey(keyId, keyPair.getPrivate());
+            verifyingKey = new JwtVerificationKey(keyId, encodePublicKey(keyPair.getPublic()));
+            verifyingKeyCache.put(keyId, verifyingKey);
+            activeKey = verifyingKey;
+        } catch (IOException e) {
+            log.error("Failed to generate and store keypair", e);
+        }
+
+        return verifyingKey;
+    }
+
+    @Override
+    public JwtVerificationKey getActiveKey() {
+        if (activeKey == null) {
+            return generateAndStoreKeypair();
+        }
+        return activeKey;
+    }
+
+    @Override
+    public Optional<KeyPair> getKeyPair(String keyId) {
+        if (!isKeystoreEnabled()) {
+            return Optional.empty();
+        }
+
+        try {
+            JwtVerificationKey verifyingKey =
+                    verifyingKeyCache.get(keyId, JwtVerificationKey.class);
+
+            if (verifyingKey == null) {
+                log.warn("No signing key found in database for keyId: {}", keyId);
+                return Optional.empty();
+            }
+
+            PrivateKey privateKey = loadPrivateKey(keyId);
+            PublicKey publicKey = decodePublicKey(verifyingKey.getVerifyingKey());
+
+            return Optional.of(new KeyPair(publicKey, privateKey));
+        } catch (Exception e) {
+            log.error("Failed to load keypair for keyId: {}", keyId, e);
+            return Optional.empty();
+        }
+    }
+
+    @Override
+    public boolean isKeystoreEnabled() {
+        return jwtProperties.isEnableKeystore();
+    }
+
+    @Override
+    public JwtVerificationKey refreshActiveKeyPair() {
+        return generateAndStoreKeypair();
+    }
+
+    @Override
+    @CacheEvict(
+            value = {"verifyingKeys"},
+            key = "#keyId",
+            condition = "#root.target.isKeystoreEnabled()")
+    public void removeKey(String keyId) {
+        verifyingKeyCache.evict(keyId);
+    }
+
+    @Override
+    public List<JwtVerificationKey> getKeysEligibleForCleanup(LocalDateTime cutoffDate) {
+        CaffeineCache caffeineCache = (CaffeineCache) verifyingKeyCache;
+        com.github.benmanes.caffeine.cache.Cache<Object, Object> nativeCache =
+                caffeineCache.getNativeCache();
+
+        log.debug(
+                "Cache size: {}, Checking {} keys for cleanup",
+                nativeCache.estimatedSize(),
+                nativeCache.asMap().size());
+
+        return nativeCache.asMap().values().stream()
+                .filter(value -> value instanceof JwtVerificationKey)
+                .map(value -> (JwtVerificationKey) value)
+                .filter(
+                        key -> {
+                            boolean eligible = key.getCreatedAt().isBefore(cutoffDate);
+                            log.debug(
+                                    "Key {} created at {}, eligible for cleanup: {}",
+                                    key.getKeyId(),
+                                    key.getCreatedAt(),
+                                    eligible);
+                            return eligible;
+                        })
+                .collect(Collectors.toList());
+    }
+
+    private String generateKeyId() {
+        return "jwt-key-"
+                + LocalDateTime.now().format(DateTimeFormatter.ofPattern("yyyy-MM-dd-HHmmss"));
+    }
+
+    private KeyPair generateRSAKeypair() {
+        KeyPairGenerator keyPairGenerator = null;
+
+        try {
+            keyPairGenerator = KeyPairGenerator.getInstance("RSA");
+            keyPairGenerator.initialize(2048);
+        } catch (NoSuchAlgorithmException e) {
+            log.error("Failed to initialize RSA key pair generator", e);
+        }
+
+        return keyPairGenerator.generateKeyPair();
+    }
+
+    private void ensurePrivateKeyDirectoryExists() throws IOException {
+        Path keyPath = Paths.get(InstallationPathConfig.getPrivateKeyPath());
+
+        if (!Files.exists(keyPath)) {
+            Files.createDirectories(keyPath);
+        }
+    }
+
+    private void storePrivateKey(String keyId, PrivateKey privateKey) throws IOException {
+        Path keyFile =
+                Paths.get(InstallationPathConfig.getPrivateKeyPath()).resolve(keyId + KEY_SUFFIX);
+        String encodedKey = Base64.getEncoder().encodeToString(privateKey.getEncoded());
+        Files.writeString(keyFile, encodedKey);
+
+        // Set read/write to only the owner
+        keyFile.toFile().setReadable(true, true);
+        keyFile.toFile().setWritable(true, true);
+        keyFile.toFile().setExecutable(false, false);
+    }
+
+    private PrivateKey loadPrivateKey(String keyId)
+            throws IOException, NoSuchAlgorithmException, InvalidKeySpecException {
+        Path keyFile =
+                Paths.get(InstallationPathConfig.getPrivateKeyPath()).resolve(keyId + KEY_SUFFIX);
+
+        if (!Files.exists(keyFile)) {
+            throw new IOException("Private key not found: " + keyFile);
+        }
+
+        String encodedKey = Files.readString(keyFile);
+        byte[] keyBytes = Base64.getDecoder().decode(encodedKey);
+        PKCS8EncodedKeySpec keySpec = new PKCS8EncodedKeySpec(keyBytes);
+        KeyFactory keyFactory = KeyFactory.getInstance("RSA");
+
+        return keyFactory.generatePrivate(keySpec);
+    }
+
+    private String encodePublicKey(PublicKey publicKey) {
+        return Base64.getEncoder().encodeToString(publicKey.getEncoded());
+    }
+
+    public PublicKey decodePublicKey(String encodedKey)
+            throws NoSuchAlgorithmException, InvalidKeySpecException {
+        byte[] keyBytes = Base64.getDecoder().decode(encodedKey);
+        X509EncodedKeySpec keySpec = new X509EncodedKeySpec(keyBytes);
+        KeyFactory keyFactory = KeyFactory.getInstance("RSA");
+        return keyFactory.generatePublic(keySpec);
+    }
+}
diff --git a/app/proprietary/src/main/java/stirling/software/proprietary/security/service/KeyPersistenceServiceInterface.java b/app/proprietary/src/main/java/stirling/software/proprietary/security/service/KeyPersistenceServiceInterface.java
new file mode 100644
index 000000000..f3050472e
--- /dev/null
+++ b/app/proprietary/src/main/java/stirling/software/proprietary/security/service/KeyPersistenceServiceInterface.java
@@ -0,0 +1,29 @@
+package stirling.software.proprietary.security.service;
+
+import java.security.KeyPair;
+import java.security.NoSuchAlgorithmException;
+import java.security.PublicKey;
+import java.security.spec.InvalidKeySpecException;
+import java.time.LocalDateTime;
+import java.util.List;
+import java.util.Optional;
+
+import stirling.software.proprietary.security.model.JwtVerificationKey;
+
+public interface KeyPersistenceServiceInterface {
+
+    JwtVerificationKey getActiveKey();
+
+    Optional<KeyPair> getKeyPair(String keyId);
+
+    boolean isKeystoreEnabled();
+
+    JwtVerificationKey refreshActiveKeyPair();
+
+    List<JwtVerificationKey> getKeysEligibleForCleanup(LocalDateTime cutoffDate);
+
+    void removeKey(String keyId);
+
+    PublicKey decodePublicKey(String encodedKey)
+            throws NoSuchAlgorithmException, InvalidKeySpecException;
+}
diff --git a/app/proprietary/src/main/java/stirling/software/proprietary/security/service/UserService.java b/app/proprietary/src/main/java/stirling/software/proprietary/security/service/UserService.java
index 50c8027f6..6f213b25e 100644
--- a/app/proprietary/src/main/java/stirling/software/proprietary/security/service/UserService.java
+++ b/app/proprietary/src/main/java/stirling/software/proprietary/security/service/UserService.java
@@ -15,7 +15,6 @@ import org.springframework.context.i18n.LocaleContextHolder;
 import org.springframework.security.authentication.UsernamePasswordAuthenticationToken;
 import org.springframework.security.core.Authentication;
 import org.springframework.security.core.GrantedAuthority;
-import org.springframework.security.core.authority.SimpleGrantedAuthority;
 import org.springframework.security.core.context.SecurityContextHolder;
 import org.springframework.security.core.session.SessionInformation;
 import org.springframework.security.core.userdetails.UserDetails;
@@ -61,19 +60,9 @@ public class UserService implements UserServiceInterface {
 
     private final ApplicationProperties.Security.OAUTH2 oAuth2;
 
-    @Transactional
-    public void migrateOauth2ToSSO() {
-        userRepository
-                .findByAuthenticationTypeIgnoreCase("OAUTH2")
-                .forEach(
-                        user -> {
-                            user.setAuthenticationType(AuthenticationType.SSO);
-                            userRepository.save(user);
-                        });
-    }
-
     // Handle OAUTH2 login and user auto creation.
-    public void processSSOPostLogin(String username, boolean autoCreateUser)
+    public void processSSOPostLogin(
+            String username, boolean autoCreateUser, AuthenticationType type)
             throws IllegalArgumentException, SQLException, UnsupportedProviderException {
         if (!isUsernameValid(username)) {
             return;
@@ -83,7 +72,7 @@ public class UserService implements UserServiceInterface {
             return;
         }
         if (autoCreateUser) {
-            saveUser(username, AuthenticationType.SSO);
+            saveUser(username, type);
         }
     }
 
@@ -100,10 +89,7 @@ public class UserService implements UserServiceInterface {
     }
 
     private Collection<? extends GrantedAuthority> getAuthorities(User user) {
-        // Convert each Authority object into a SimpleGrantedAuthority object.
-        return user.getAuthorities().stream()
-                .map((Authority authority) -> new SimpleGrantedAuthority(authority.getAuthority()))
-                .toList();
+        return user.getAuthorities();
     }
 
     private String generateApiKey() {
diff --git a/app/proprietary/src/main/resources/static/js/audit/dashboard.js b/app/proprietary/src/main/resources/static/js/audit/dashboard.js
index 5cc670908..c0b93bd8e 100644
--- a/app/proprietary/src/main/resources/static/js/audit/dashboard.js
+++ b/app/proprietary/src/main/resources/static/js/audit/dashboard.js
@@ -230,7 +230,7 @@ function loadAuditData(targetPage, realPageSize) {
         document.getElementById('page-indicator').textContent = `Page ${requestedPage + 1} of ?`;
     }
 
-    fetch(url)
+    fetchWithCsrf(url)
         .then(response => {
             return response.json();
         })
@@ -302,7 +302,7 @@ function loadStats(days) {
     showLoading('user-chart-loading');
     showLoading('time-chart-loading');
 
-    fetch(`/audit/stats?days=${days}`)
+    fetchWithCsrf(`/audit/stats?days=${days}`)
         .then(response => response.json())
         .then(data => {
             document.getElementById('total-events').textContent = data.totalEvents;
@@ -835,7 +835,7 @@ function hideLoading(id) {
 
 // Load event types from the server for filter dropdowns
 function loadEventTypes() {
-    fetch('/audit/types')
+    fetchWithCsrf('/audit/types')
         .then(response => response.json())
         .then(types => {
             if (!types || types.length === 0) {
diff --git a/app/proprietary/src/test/java/stirling/software/proprietary/security/CustomLogoutSuccessHandlerTest.java b/app/proprietary/src/test/java/stirling/software/proprietary/security/CustomLogoutSuccessHandlerTest.java
index 04ca4c35f..7a4076260 100644
--- a/app/proprietary/src/test/java/stirling/software/proprietary/security/CustomLogoutSuccessHandlerTest.java
+++ b/app/proprietary/src/test/java/stirling/software/proprietary/security/CustomLogoutSuccessHandlerTest.java
@@ -14,12 +14,18 @@ import org.springframework.security.oauth2.client.authentication.OAuth2Authentic
 import jakarta.servlet.http.HttpServletRequest;
 import jakarta.servlet.http.HttpServletResponse;
 
+import stirling.software.common.configuration.AppConfig;
 import stirling.software.common.model.ApplicationProperties;
+import stirling.software.proprietary.security.service.JwtServiceInterface;
 
 @ExtendWith(MockitoExtension.class)
 class CustomLogoutSuccessHandlerTest {
 
-    @Mock private ApplicationProperties applicationProperties;
+    @Mock private ApplicationProperties.Security securityProperties;
+
+    @Mock private AppConfig appConfig;
+
+    @Mock private JwtServiceInterface jwtService;
 
     @InjectMocks private CustomLogoutSuccessHandler customLogoutSuccessHandler;
 
@@ -27,9 +33,12 @@ class CustomLogoutSuccessHandlerTest {
     void testSuccessfulLogout() throws IOException {
         HttpServletRequest request = mock(HttpServletRequest.class);
         HttpServletResponse response = mock(HttpServletResponse.class);
-        String logoutPath = "logout=true";
+        String token = "token";
+        String logoutPath = "/login?logout=true";
 
         when(response.isCommitted()).thenReturn(false);
+        when(jwtService.extractToken(request)).thenReturn(token);
+        doNothing().when(jwtService).clearToken(response);
         when(request.getContextPath()).thenReturn("");
         when(response.encodeRedirectURL(logoutPath)).thenReturn(logoutPath);
 
@@ -38,12 +47,30 @@ class CustomLogoutSuccessHandlerTest {
         verify(response).sendRedirect(logoutPath);
     }
 
+    @Test
+    void testSuccessfulLogoutViaJWT() throws IOException {
+        HttpServletRequest request = mock(HttpServletRequest.class);
+        HttpServletResponse response = mock(HttpServletResponse.class);
+        String logoutPath = "/login?logout=true";
+        String token = "token";
+
+        when(response.isCommitted()).thenReturn(false);
+        when(jwtService.extractToken(request)).thenReturn(token);
+        doNothing().when(jwtService).clearToken(response);
+        when(request.getContextPath()).thenReturn("");
+        when(response.encodeRedirectURL(logoutPath)).thenReturn(logoutPath);
+
+        customLogoutSuccessHandler.onLogoutSuccess(request, response, null);
+
+        verify(response).sendRedirect(logoutPath);
+        verify(jwtService).clearToken(response);
+    }
+
     @Test
     void testSuccessfulLogoutViaOAuth2() throws IOException {
         HttpServletRequest request = mock(HttpServletRequest.class);
         HttpServletResponse response = mock(HttpServletResponse.class);
         OAuth2AuthenticationToken oAuth2AuthenticationToken = mock(OAuth2AuthenticationToken.class);
-        ApplicationProperties.Security security = mock(ApplicationProperties.Security.class);
         ApplicationProperties.Security.OAUTH2 oauth =
                 mock(ApplicationProperties.Security.OAUTH2.class);
 
@@ -54,8 +81,7 @@ class CustomLogoutSuccessHandlerTest {
         when(request.getServerName()).thenReturn("localhost");
         when(request.getServerPort()).thenReturn(8080);
         when(request.getContextPath()).thenReturn("");
-        when(applicationProperties.getSecurity()).thenReturn(security);
-        when(security.getOauth2()).thenReturn(oauth);
+        when(securityProperties.getOauth2()).thenReturn(oauth);
         when(oAuth2AuthenticationToken.getAuthorizedClientRegistrationId()).thenReturn("test");
 
         customLogoutSuccessHandler.onLogoutSuccess(request, response, oAuth2AuthenticationToken);
@@ -70,7 +96,6 @@ class CustomLogoutSuccessHandlerTest {
         HttpServletRequest request = mock(HttpServletRequest.class);
         HttpServletResponse response = mock(HttpServletResponse.class);
         OAuth2AuthenticationToken authentication = mock(OAuth2AuthenticationToken.class);
-        ApplicationProperties.Security security = mock(ApplicationProperties.Security.class);
         ApplicationProperties.Security.OAUTH2 oauth =
                 mock(ApplicationProperties.Security.OAUTH2.class);
 
@@ -84,8 +109,7 @@ class CustomLogoutSuccessHandlerTest {
         when(request.getServerName()).thenReturn("localhost");
         when(request.getServerPort()).thenReturn(8080);
         when(request.getContextPath()).thenReturn("");
-        when(applicationProperties.getSecurity()).thenReturn(security);
-        when(security.getOauth2()).thenReturn(oauth);
+        when(securityProperties.getOauth2()).thenReturn(oauth);
         when(authentication.getAuthorizedClientRegistrationId()).thenReturn("test");
 
         customLogoutSuccessHandler.onLogoutSuccess(request, response, authentication);
@@ -101,7 +125,6 @@ class CustomLogoutSuccessHandlerTest {
         HttpServletRequest request = mock(HttpServletRequest.class);
         HttpServletResponse response = mock(HttpServletResponse.class);
         OAuth2AuthenticationToken authentication = mock(OAuth2AuthenticationToken.class);
-        ApplicationProperties.Security security = mock(ApplicationProperties.Security.class);
         ApplicationProperties.Security.OAUTH2 oauth =
                 mock(ApplicationProperties.Security.OAUTH2.class);
 
@@ -111,8 +134,7 @@ class CustomLogoutSuccessHandlerTest {
         when(request.getServerName()).thenReturn("localhost");
         when(request.getServerPort()).thenReturn(8080);
         when(request.getContextPath()).thenReturn("");
-        when(applicationProperties.getSecurity()).thenReturn(security);
-        when(security.getOauth2()).thenReturn(oauth);
+        when(securityProperties.getOauth2()).thenReturn(oauth);
         when(authentication.getAuthorizedClientRegistrationId()).thenReturn("test");
 
         customLogoutSuccessHandler.onLogoutSuccess(request, response, authentication);
@@ -127,7 +149,6 @@ class CustomLogoutSuccessHandlerTest {
         HttpServletRequest request = mock(HttpServletRequest.class);
         HttpServletResponse response = mock(HttpServletResponse.class);
         OAuth2AuthenticationToken authentication = mock(OAuth2AuthenticationToken.class);
-        ApplicationProperties.Security security = mock(ApplicationProperties.Security.class);
         ApplicationProperties.Security.OAUTH2 oauth =
                 mock(ApplicationProperties.Security.OAUTH2.class);
 
@@ -138,8 +159,7 @@ class CustomLogoutSuccessHandlerTest {
         when(request.getServerName()).thenReturn("localhost");
         when(request.getServerPort()).thenReturn(8080);
         when(request.getContextPath()).thenReturn("");
-        when(applicationProperties.getSecurity()).thenReturn(security);
-        when(security.getOauth2()).thenReturn(oauth);
+        when(securityProperties.getOauth2()).thenReturn(oauth);
         when(authentication.getAuthorizedClientRegistrationId()).thenReturn("test");
 
         customLogoutSuccessHandler.onLogoutSuccess(request, response, authentication);
@@ -154,7 +174,6 @@ class CustomLogoutSuccessHandlerTest {
         HttpServletRequest request = mock(HttpServletRequest.class);
         HttpServletResponse response = mock(HttpServletResponse.class);
         OAuth2AuthenticationToken authentication = mock(OAuth2AuthenticationToken.class);
-        ApplicationProperties.Security security = mock(ApplicationProperties.Security.class);
         ApplicationProperties.Security.OAUTH2 oauth =
                 mock(ApplicationProperties.Security.OAUTH2.class);
 
@@ -167,8 +186,7 @@ class CustomLogoutSuccessHandlerTest {
         when(request.getServerName()).thenReturn("localhost");
         when(request.getServerPort()).thenReturn(8080);
         when(request.getContextPath()).thenReturn("");
-        when(applicationProperties.getSecurity()).thenReturn(security);
-        when(security.getOauth2()).thenReturn(oauth);
+        when(securityProperties.getOauth2()).thenReturn(oauth);
         when(authentication.getAuthorizedClientRegistrationId()).thenReturn("test");
 
         customLogoutSuccessHandler.onLogoutSuccess(request, response, authentication);
@@ -183,7 +201,6 @@ class CustomLogoutSuccessHandlerTest {
         HttpServletRequest request = mock(HttpServletRequest.class);
         HttpServletResponse response = mock(HttpServletResponse.class);
         OAuth2AuthenticationToken authentication = mock(OAuth2AuthenticationToken.class);
-        ApplicationProperties.Security security = mock(ApplicationProperties.Security.class);
         ApplicationProperties.Security.OAUTH2 oauth =
                 mock(ApplicationProperties.Security.OAUTH2.class);
 
@@ -198,8 +215,7 @@ class CustomLogoutSuccessHandlerTest {
         when(request.getServerName()).thenReturn("localhost");
         when(request.getServerPort()).thenReturn(8080);
         when(request.getContextPath()).thenReturn("");
-        when(applicationProperties.getSecurity()).thenReturn(security);
-        when(security.getOauth2()).thenReturn(oauth);
+        when(securityProperties.getOauth2()).thenReturn(oauth);
         when(authentication.getAuthorizedClientRegistrationId()).thenReturn("test");
 
         customLogoutSuccessHandler.onLogoutSuccess(request, response, authentication);
@@ -214,7 +230,6 @@ class CustomLogoutSuccessHandlerTest {
         HttpServletRequest request = mock(HttpServletRequest.class);
         HttpServletResponse response = mock(HttpServletResponse.class);
         OAuth2AuthenticationToken authentication = mock(OAuth2AuthenticationToken.class);
-        ApplicationProperties.Security security = mock(ApplicationProperties.Security.class);
         ApplicationProperties.Security.OAUTH2 oauth =
                 mock(ApplicationProperties.Security.OAUTH2.class);
 
@@ -230,8 +245,7 @@ class CustomLogoutSuccessHandlerTest {
         when(request.getServerName()).thenReturn("localhost");
         when(request.getServerPort()).thenReturn(8080);
         when(request.getContextPath()).thenReturn("");
-        when(applicationProperties.getSecurity()).thenReturn(security);
-        when(security.getOauth2()).thenReturn(oauth);
+        when(securityProperties.getOauth2()).thenReturn(oauth);
         when(authentication.getAuthorizedClientRegistrationId()).thenReturn("test");
 
         customLogoutSuccessHandler.onLogoutSuccess(request, response, authentication);
@@ -246,7 +260,6 @@ class CustomLogoutSuccessHandlerTest {
         HttpServletRequest request = mock(HttpServletRequest.class);
         HttpServletResponse response = mock(HttpServletResponse.class);
         OAuth2AuthenticationToken authentication = mock(OAuth2AuthenticationToken.class);
-        ApplicationProperties.Security security = mock(ApplicationProperties.Security.class);
         ApplicationProperties.Security.OAUTH2 oauth =
                 mock(ApplicationProperties.Security.OAUTH2.class);
 
@@ -259,8 +272,7 @@ class CustomLogoutSuccessHandlerTest {
         when(request.getServerName()).thenReturn("localhost");
         when(request.getServerPort()).thenReturn(8080);
         when(request.getContextPath()).thenReturn("");
-        when(applicationProperties.getSecurity()).thenReturn(security);
-        when(security.getOauth2()).thenReturn(oauth);
+        when(securityProperties.getOauth2()).thenReturn(oauth);
         when(authentication.getAuthorizedClientRegistrationId()).thenReturn("test");
 
         customLogoutSuccessHandler.onLogoutSuccess(request, response, authentication);
diff --git a/app/proprietary/src/test/java/stirling/software/proprietary/security/JwtAuthenticationEntryPointTest.java b/app/proprietary/src/test/java/stirling/software/proprietary/security/JwtAuthenticationEntryPointTest.java
new file mode 100644
index 000000000..a47f45318
--- /dev/null
+++ b/app/proprietary/src/test/java/stirling/software/proprietary/security/JwtAuthenticationEntryPointTest.java
@@ -0,0 +1,38 @@
+package stirling.software.proprietary.security;
+
+import static org.mockito.Mockito.*;
+
+import java.io.IOException;
+
+import org.junit.jupiter.api.Test;
+import org.junit.jupiter.api.extension.ExtendWith;
+import org.mockito.InjectMocks;
+import org.mockito.Mock;
+import org.mockito.junit.jupiter.MockitoExtension;
+
+import jakarta.servlet.http.HttpServletRequest;
+import jakarta.servlet.http.HttpServletResponse;
+
+import stirling.software.proprietary.security.model.exception.AuthenticationFailureException;
+
+@ExtendWith(MockitoExtension.class)
+class JwtAuthenticationEntryPointTest {
+
+    @Mock private HttpServletRequest request;
+
+    @Mock private HttpServletResponse response;
+
+    @Mock private AuthenticationFailureException authException;
+
+    @InjectMocks private JwtAuthenticationEntryPoint jwtAuthenticationEntryPoint;
+
+    @Test
+    void testCommence() throws IOException {
+        String errorMessage = "Authentication failed";
+        when(authException.getMessage()).thenReturn(errorMessage);
+
+        jwtAuthenticationEntryPoint.commence(request, response, authException);
+
+        verify(response).sendError(HttpServletResponse.SC_UNAUTHORIZED, errorMessage);
+    }
+}
diff --git a/app/proprietary/src/test/java/stirling/software/proprietary/security/filter/JwtAuthenticationFilterTest.java b/app/proprietary/src/test/java/stirling/software/proprietary/security/filter/JwtAuthenticationFilterTest.java
new file mode 100644
index 000000000..d3f484486
--- /dev/null
+++ b/app/proprietary/src/test/java/stirling/software/proprietary/security/filter/JwtAuthenticationFilterTest.java
@@ -0,0 +1,242 @@
+package stirling.software.proprietary.security.filter;
+
+import static org.junit.jupiter.api.Assertions.assertEquals;
+import static org.junit.jupiter.api.Assertions.assertThrows;
+import static org.mockito.ArgumentMatchers.any;
+import static org.mockito.ArgumentMatchers.argThat;
+import static org.mockito.ArgumentMatchers.eq;
+import static org.mockito.Mockito.doNothing;
+import static org.mockito.Mockito.doThrow;
+import static org.mockito.Mockito.mockStatic;
+import static org.mockito.Mockito.never;
+import static org.mockito.Mockito.verify;
+import static org.mockito.Mockito.when;
+
+import java.io.IOException;
+import java.util.Collections;
+import java.util.Map;
+
+import org.junit.jupiter.api.Disabled;
+import org.junit.jupiter.api.Test;
+import org.junit.jupiter.api.extension.ExtendWith;
+import org.mockito.InjectMocks;
+import org.mockito.Mock;
+import org.mockito.MockedStatic;
+import org.mockito.junit.jupiter.MockitoExtension;
+import org.springframework.security.authentication.UsernamePasswordAuthenticationToken;
+import org.springframework.security.core.context.SecurityContext;
+import org.springframework.security.core.context.SecurityContextHolder;
+import org.springframework.security.core.userdetails.UserDetails;
+import org.springframework.security.core.userdetails.UsernameNotFoundException;
+import org.springframework.security.web.AuthenticationEntryPoint;
+
+import jakarta.servlet.FilterChain;
+import jakarta.servlet.ServletException;
+import jakarta.servlet.http.HttpServletRequest;
+import jakarta.servlet.http.HttpServletResponse;
+
+import stirling.software.common.model.ApplicationProperties;
+import stirling.software.proprietary.security.model.exception.AuthenticationFailureException;
+import stirling.software.proprietary.security.service.CustomUserDetailsService;
+import stirling.software.proprietary.security.service.JwtServiceInterface;
+import stirling.software.proprietary.security.service.UserService;
+
+@Disabled
+@ExtendWith(MockitoExtension.class)
+class JwtAuthenticationFilterTest {
+
+    @Mock private JwtServiceInterface jwtService;
+
+    @Mock private CustomUserDetailsService userDetailsService;
+
+    @Mock private UserService userService;
+
+    @Mock private ApplicationProperties.Security securityProperties;
+
+    @Mock private HttpServletRequest request;
+
+    @Mock private HttpServletResponse response;
+
+    @Mock private FilterChain filterChain;
+
+    @Mock private UserDetails userDetails;
+
+    @Mock private SecurityContext securityContext;
+
+    @Mock private AuthenticationEntryPoint authenticationEntryPoint;
+
+    @InjectMocks private JwtAuthenticationFilter jwtAuthenticationFilter;
+
+    @Test
+    void shouldNotAuthenticateWhenJwtDisabled() throws ServletException, IOException {
+        when(jwtService.isJwtEnabled()).thenReturn(false);
+
+        jwtAuthenticationFilter.doFilterInternal(request, response, filterChain);
+
+        verify(filterChain).doFilter(request, response);
+        verify(jwtService, never()).extractToken(any());
+    }
+
+    @Test
+    void shouldNotFilterWhenPageIsLogin() throws ServletException, IOException {
+        when(jwtService.isJwtEnabled()).thenReturn(true);
+        when(request.getRequestURI()).thenReturn("/login");
+        when(request.getContextPath()).thenReturn("/login");
+
+        jwtAuthenticationFilter.doFilterInternal(request, response, filterChain);
+
+        verify(filterChain, never()).doFilter(request, response);
+    }
+
+    @Test
+    void testDoFilterInternal() throws ServletException, IOException {
+        String token = "valid-jwt-token";
+        String newToken = "new-jwt-token";
+        String username = "testuser";
+        Map<String, Object> claims = Map.of("sub", username, "authType", "WEB");
+
+        when(jwtService.isJwtEnabled()).thenReturn(true);
+        when(request.getContextPath()).thenReturn("/");
+        when(request.getRequestURI()).thenReturn("/protected");
+        when(jwtService.extractToken(request)).thenReturn(token);
+        doNothing().when(jwtService).validateToken(token);
+        when(jwtService.extractClaims(token)).thenReturn(claims);
+        when(userDetails.getAuthorities()).thenReturn(Collections.emptyList());
+        when(userDetailsService.loadUserByUsername(username)).thenReturn(userDetails);
+
+        try (MockedStatic<SecurityContextHolder> mockedSecurityContextHolder =
+                mockStatic(SecurityContextHolder.class)) {
+            UsernamePasswordAuthenticationToken authToken =
+                    new UsernamePasswordAuthenticationToken(
+                            userDetails, null, userDetails.getAuthorities());
+
+            when(securityContext.getAuthentication()).thenReturn(null).thenReturn(authToken);
+            mockedSecurityContextHolder
+                    .when(SecurityContextHolder::getContext)
+                    .thenReturn(securityContext);
+            when(jwtService.generateToken(
+                            any(UsernamePasswordAuthenticationToken.class), eq(claims)))
+                    .thenReturn(newToken);
+
+            jwtAuthenticationFilter.doFilterInternal(request, response, filterChain);
+
+            verify(jwtService).validateToken(token);
+            verify(jwtService).extractClaims(token);
+            verify(userDetailsService).loadUserByUsername(username);
+            verify(securityContext)
+                    .setAuthentication(any(UsernamePasswordAuthenticationToken.class));
+            verify(jwtService)
+                    .generateToken(any(UsernamePasswordAuthenticationToken.class), eq(claims));
+            verify(jwtService).addToken(response, newToken);
+            verify(filterChain).doFilter(request, response);
+        }
+    }
+
+    @Test
+    void testDoFilterInternalWithMissingTokenForRootPath() throws ServletException, IOException {
+        when(jwtService.isJwtEnabled()).thenReturn(true);
+        when(request.getRequestURI()).thenReturn("/");
+        when(request.getMethod()).thenReturn("GET");
+        when(jwtService.extractToken(request)).thenReturn(null);
+
+        jwtAuthenticationFilter.doFilterInternal(request, response, filterChain);
+
+        verify(response).sendRedirect("/login");
+        verify(filterChain, never()).doFilter(request, response);
+    }
+
+    @Test
+    void validationFailsWithInvalidToken() throws ServletException, IOException {
+        String token = "invalid-jwt-token";
+
+        when(jwtService.isJwtEnabled()).thenReturn(true);
+        when(request.getRequestURI()).thenReturn("/protected");
+        when(request.getContextPath()).thenReturn("/");
+        when(jwtService.extractToken(request)).thenReturn(token);
+        doThrow(new AuthenticationFailureException("Invalid token"))
+                .when(jwtService)
+                .validateToken(token);
+
+        jwtAuthenticationFilter.doFilterInternal(request, response, filterChain);
+
+        verify(jwtService).validateToken(token);
+        verify(authenticationEntryPoint)
+                .commence(eq(request), eq(response), any(AuthenticationFailureException.class));
+        verify(filterChain, never()).doFilter(request, response);
+    }
+
+    @Test
+    void validationFailsWithExpiredToken() throws ServletException, IOException {
+        String token = "expired-jwt-token";
+
+        when(jwtService.isJwtEnabled()).thenReturn(true);
+        when(request.getRequestURI()).thenReturn("/protected");
+        when(request.getContextPath()).thenReturn("/");
+        when(jwtService.extractToken(request)).thenReturn(token);
+        doThrow(new AuthenticationFailureException("The token has expired"))
+                .when(jwtService)
+                .validateToken(token);
+
+        jwtAuthenticationFilter.doFilterInternal(request, response, filterChain);
+
+        verify(jwtService).validateToken(token);
+        verify(authenticationEntryPoint).commence(eq(request), eq(response), any());
+        verify(filterChain, never()).doFilter(request, response);
+    }
+
+    @Test
+    void exceptionThrown_WhenUserNotFound() throws ServletException, IOException {
+        String token = "valid-jwt-token";
+        String username = "nonexistentuser";
+        Map<String, Object> claims = Map.of("sub", username, "authType", "WEB");
+
+        when(jwtService.isJwtEnabled()).thenReturn(true);
+        when(request.getRequestURI()).thenReturn("/protected");
+        when(request.getContextPath()).thenReturn("/");
+        when(jwtService.extractToken(request)).thenReturn(token);
+        doNothing().when(jwtService).validateToken(token);
+        when(jwtService.extractClaims(token)).thenReturn(claims);
+        when(userDetailsService.loadUserByUsername(username)).thenReturn(null);
+
+        try (MockedStatic<SecurityContextHolder> mockedSecurityContextHolder =
+                mockStatic(SecurityContextHolder.class)) {
+            when(securityContext.getAuthentication()).thenReturn(null);
+            mockedSecurityContextHolder
+                    .when(SecurityContextHolder::getContext)
+                    .thenReturn(securityContext);
+
+            UsernameNotFoundException result =
+                    assertThrows(
+                            UsernameNotFoundException.class,
+                            () ->
+                                    jwtAuthenticationFilter.doFilterInternal(
+                                            request, response, filterChain));
+
+            assertEquals("User not found: " + username, result.getMessage());
+            verify(userDetailsService).loadUserByUsername(username);
+            verify(filterChain, never()).doFilter(request, response);
+        }
+    }
+
+    @Test
+    void testAuthenticationEntryPointCalledWithCorrectException()
+            throws ServletException, IOException {
+        when(jwtService.isJwtEnabled()).thenReturn(true);
+        when(request.getRequestURI()).thenReturn("/protected");
+        when(request.getContextPath()).thenReturn("/");
+        when(jwtService.extractToken(request)).thenReturn(null);
+
+        jwtAuthenticationFilter.doFilterInternal(request, response, filterChain);
+
+        verify(authenticationEntryPoint)
+                .commence(
+                        eq(request),
+                        eq(response),
+                        argThat(
+                                exception ->
+                                        exception
+                                                .getMessage()
+                                                .equals("JWT is missing from the request")));
+        verify(filterChain, never()).doFilter(request, response);
+    }
+}
diff --git a/app/proprietary/src/test/java/stirling/software/proprietary/security/saml2/JwtSaml2AuthenticationRequestRepositoryTest.java b/app/proprietary/src/test/java/stirling/software/proprietary/security/saml2/JwtSaml2AuthenticationRequestRepositoryTest.java
new file mode 100644
index 000000000..1aa083cc0
--- /dev/null
+++ b/app/proprietary/src/test/java/stirling/software/proprietary/security/saml2/JwtSaml2AuthenticationRequestRepositoryTest.java
@@ -0,0 +1,247 @@
+package stirling.software.proprietary.security.saml2;
+
+import static org.junit.jupiter.api.Assertions.assertFalse;
+import static org.junit.jupiter.api.Assertions.assertNotNull;
+import static org.junit.jupiter.api.Assertions.assertNull;
+import static org.junit.jupiter.api.Assertions.assertTrue;
+import static org.mockito.ArgumentMatchers.anyMap;
+import static org.mockito.ArgumentMatchers.eq;
+import static org.mockito.Mockito.mock;
+import static org.mockito.Mockito.verify;
+import static org.mockito.Mockito.when;
+
+import java.util.Map;
+import java.util.concurrent.ConcurrentHashMap;
+
+import org.junit.jupiter.api.BeforeEach;
+import org.junit.jupiter.api.Test;
+import org.junit.jupiter.api.extension.ExtendWith;
+import org.junit.jupiter.params.ParameterizedTest;
+import org.junit.jupiter.params.provider.NullAndEmptySource;
+import org.mockito.Mock;
+import org.mockito.junit.jupiter.MockitoExtension;
+import org.springframework.mock.web.MockHttpServletRequest;
+import org.springframework.mock.web.MockHttpServletResponse;
+import org.springframework.security.saml2.provider.service.authentication.Saml2PostAuthenticationRequest;
+import org.springframework.security.saml2.provider.service.registration.AssertingPartyMetadata;
+import org.springframework.security.saml2.provider.service.registration.RelyingPartyRegistration;
+import org.springframework.security.saml2.provider.service.registration.RelyingPartyRegistrationRepository;
+
+import jakarta.servlet.http.HttpServletRequest;
+import jakarta.servlet.http.HttpServletResponse;
+
+import stirling.software.proprietary.security.service.JwtServiceInterface;
+
+@ExtendWith(MockitoExtension.class)
+class JwtSaml2AuthenticationRequestRepositoryTest {
+
+    private static final String SAML_REQUEST_TOKEN = "stirling_saml_request_token";
+
+    private Map<String, String> tokenStore;
+
+    @Mock private JwtServiceInterface jwtService;
+
+    @Mock private RelyingPartyRegistrationRepository relyingPartyRegistrationRepository;
+
+    private JwtSaml2AuthenticationRequestRepository jwtSaml2AuthenticationRequestRepository;
+
+    @BeforeEach
+    void setUp() {
+        tokenStore = new ConcurrentHashMap<>();
+        jwtSaml2AuthenticationRequestRepository =
+                new JwtSaml2AuthenticationRequestRepository(
+                        tokenStore, jwtService, relyingPartyRegistrationRepository);
+    }
+
+    @Test
+    void saveAuthenticationRequest() {
+        var authRequest = mock(Saml2PostAuthenticationRequest.class);
+        var request = mock(MockHttpServletRequest.class);
+        var response = mock(MockHttpServletResponse.class);
+        String token = "testToken";
+        String id = "testId";
+        String relayState = "testRelayState";
+        String authnRequestUri = "example.com/authnRequest";
+        Map<String, Object> claims = Map.of();
+        String samlRequest = "testSamlRequest";
+        String relyingPartyRegistrationId = "stirling-pdf";
+
+        when(jwtService.isJwtEnabled()).thenReturn(true);
+        when(authRequest.getRelayState()).thenReturn(relayState);
+        when(authRequest.getId()).thenReturn(id);
+        when(authRequest.getAuthenticationRequestUri()).thenReturn(authnRequestUri);
+        when(authRequest.getSamlRequest()).thenReturn(samlRequest);
+        when(authRequest.getRelyingPartyRegistrationId()).thenReturn(relyingPartyRegistrationId);
+        when(jwtService.generateToken(eq(""), anyMap())).thenReturn(token);
+
+        jwtSaml2AuthenticationRequestRepository.saveAuthenticationRequest(
+                authRequest, request, response);
+
+        verify(request).setAttribute(SAML_REQUEST_TOKEN, relayState);
+        verify(response).addHeader(SAML_REQUEST_TOKEN, relayState);
+    }
+
+    @Test
+    void saveAuthenticationRequestWithNullRequest() {
+        var request = mock(MockHttpServletRequest.class);
+        var response = mock(MockHttpServletResponse.class);
+
+        jwtSaml2AuthenticationRequestRepository.saveAuthenticationRequest(null, request, response);
+
+        assertTrue(tokenStore.isEmpty());
+    }
+
+    @Test
+    void loadAuthenticationRequest() {
+        var request = mock(MockHttpServletRequest.class);
+        var relyingPartyRegistration = mock(RelyingPartyRegistration.class);
+        var assertingPartyMetadata = mock(AssertingPartyMetadata.class);
+        String relayState = "testRelayState";
+        String token = "testToken";
+        Map<String, Object> claims =
+                Map.of(
+                        "id", "testId",
+                        "relyingPartyRegistrationId", "stirling-pdf",
+                        "authenticationRequestUri", "example.com/authnRequest",
+                        "samlRequest", "testSamlRequest",
+                        "relayState", relayState);
+
+        when(request.getParameter("RelayState")).thenReturn(relayState);
+        when(jwtService.extractClaims(token)).thenReturn(claims);
+        when(relyingPartyRegistrationRepository.findByRegistrationId("stirling-pdf"))
+                .thenReturn(relyingPartyRegistration);
+        when(relyingPartyRegistration.getRegistrationId()).thenReturn("stirling-pdf");
+        when(relyingPartyRegistration.getAssertingPartyMetadata())
+                .thenReturn(assertingPartyMetadata);
+        when(assertingPartyMetadata.getSingleSignOnServiceLocation())
+                .thenReturn("https://example.com/sso");
+        tokenStore.put(relayState, token);
+
+        var result = jwtSaml2AuthenticationRequestRepository.loadAuthenticationRequest(request);
+
+        assertNotNull(result);
+        assertFalse(tokenStore.containsKey(relayState));
+    }
+
+    @ParameterizedTest
+    @NullAndEmptySource
+    void loadAuthenticationRequestWithInvalidRelayState(String relayState) {
+        var request = mock(MockHttpServletRequest.class);
+        when(request.getParameter("RelayState")).thenReturn(relayState);
+
+        var result = jwtSaml2AuthenticationRequestRepository.loadAuthenticationRequest(request);
+
+        assertNull(result);
+    }
+
+    @Test
+    void loadAuthenticationRequestWithNonExistentToken() {
+        var request = mock(MockHttpServletRequest.class);
+        when(request.getParameter("RelayState")).thenReturn("nonExistentRelayState");
+
+        var result = jwtSaml2AuthenticationRequestRepository.loadAuthenticationRequest(request);
+
+        assertNull(result);
+    }
+
+    @Test
+    void loadAuthenticationRequestWithNullRelyingPartyRegistration() {
+        var request = mock(MockHttpServletRequest.class);
+        String relayState = "testRelayState";
+        String token = "testToken";
+        Map<String, Object> claims =
+                Map.of(
+                        "id", "testId",
+                        "relyingPartyRegistrationId", "stirling-pdf",
+                        "authenticationRequestUri", "example.com/authnRequest",
+                        "samlRequest", "testSamlRequest",
+                        "relayState", relayState);
+
+        when(request.getParameter("RelayState")).thenReturn(relayState);
+        when(jwtService.extractClaims(token)).thenReturn(claims);
+        when(relyingPartyRegistrationRepository.findByRegistrationId("stirling-pdf"))
+                .thenReturn(null);
+        tokenStore.put(relayState, token);
+
+        var result = jwtSaml2AuthenticationRequestRepository.loadAuthenticationRequest(request);
+
+        assertNull(result);
+    }
+
+    @Test
+    void removeAuthenticationRequest() {
+        var request = mock(HttpServletRequest.class);
+        var response = mock(HttpServletResponse.class);
+        var relyingPartyRegistration = mock(RelyingPartyRegistration.class);
+        var assertingPartyMetadata = mock(AssertingPartyMetadata.class);
+        String relayState = "testRelayState";
+        String token = "testToken";
+        Map<String, Object> claims =
+                Map.of(
+                        "id", "testId",
+                        "relyingPartyRegistrationId", "stirling-pdf",
+                        "authenticationRequestUri", "example.com/authnRequest",
+                        "samlRequest", "testSamlRequest",
+                        "relayState", relayState);
+
+        when(request.getParameter("RelayState")).thenReturn(relayState);
+        when(jwtService.extractClaims(token)).thenReturn(claims);
+        when(relyingPartyRegistrationRepository.findByRegistrationId("stirling-pdf"))
+                .thenReturn(relyingPartyRegistration);
+        when(relyingPartyRegistration.getRegistrationId()).thenReturn("stirling-pdf");
+        when(relyingPartyRegistration.getAssertingPartyMetadata())
+                .thenReturn(assertingPartyMetadata);
+        when(assertingPartyMetadata.getSingleSignOnServiceLocation())
+                .thenReturn("https://example.com/sso");
+        tokenStore.put(relayState, token);
+
+        var result =
+                jwtSaml2AuthenticationRequestRepository.removeAuthenticationRequest(
+                        request, response);
+
+        assertNotNull(result);
+        assertFalse(tokenStore.containsKey(relayState));
+    }
+
+    @Test
+    void removeAuthenticationRequestWithNullRelayState() {
+        var request = mock(HttpServletRequest.class);
+        var response = mock(HttpServletResponse.class);
+        when(request.getParameter("RelayState")).thenReturn(null);
+
+        var result =
+                jwtSaml2AuthenticationRequestRepository.removeAuthenticationRequest(
+                        request, response);
+
+        assertNull(result);
+    }
+
+    @Test
+    void removeAuthenticationRequestWithNonExistentToken() {
+        var request = mock(HttpServletRequest.class);
+        var response = mock(HttpServletResponse.class);
+        when(request.getParameter("RelayState")).thenReturn("nonExistentRelayState");
+
+        var result =
+                jwtSaml2AuthenticationRequestRepository.removeAuthenticationRequest(
+                        request, response);
+
+        assertNull(result);
+    }
+
+    @Test
+    void removeAuthenticationRequestWithOnlyRelayState() {
+        var request = mock(HttpServletRequest.class);
+        var response = mock(HttpServletResponse.class);
+        String relayState = "testRelayState";
+
+        when(request.getParameter("RelayState")).thenReturn(relayState);
+
+        var result =
+                jwtSaml2AuthenticationRequestRepository.removeAuthenticationRequest(
+                        request, response);
+
+        assertNull(result);
+        assertFalse(tokenStore.containsKey(relayState));
+    }
+}
diff --git a/app/proprietary/src/test/java/stirling/software/proprietary/security/service/JwtServiceTest.java b/app/proprietary/src/test/java/stirling/software/proprietary/security/service/JwtServiceTest.java
new file mode 100644
index 000000000..6f9af4c54
--- /dev/null
+++ b/app/proprietary/src/test/java/stirling/software/proprietary/security/service/JwtServiceTest.java
@@ -0,0 +1,389 @@
+package stirling.software.proprietary.security.service;
+
+import static org.junit.jupiter.api.Assertions.assertDoesNotThrow;
+import static org.junit.jupiter.api.Assertions.assertEquals;
+import static org.junit.jupiter.api.Assertions.assertFalse;
+import static org.junit.jupiter.api.Assertions.assertNotNull;
+import static org.junit.jupiter.api.Assertions.assertNull;
+import static org.junit.jupiter.api.Assertions.assertThrows;
+import static org.junit.jupiter.api.Assertions.assertTrue;
+import static org.mockito.Mockito.atLeast;
+import static org.mockito.Mockito.contains;
+import static org.mockito.Mockito.eq;
+import static org.mockito.Mockito.lenient;
+import static org.mockito.Mockito.mock;
+import static org.mockito.Mockito.verify;
+import static org.mockito.Mockito.when;
+
+import java.security.KeyPair;
+import java.security.KeyPairGenerator;
+import java.security.NoSuchAlgorithmException;
+import java.util.Base64;
+import java.util.Collections;
+import java.util.HashMap;
+import java.util.Map;
+import java.util.Optional;
+
+import org.junit.jupiter.api.BeforeEach;
+import org.junit.jupiter.api.Test;
+import org.junit.jupiter.api.extension.ExtendWith;
+import org.junit.jupiter.params.ParameterizedTest;
+import org.junit.jupiter.params.provider.ValueSource;
+import org.mockito.Mock;
+import org.mockito.junit.jupiter.MockitoExtension;
+import org.springframework.security.core.Authentication;
+
+import jakarta.servlet.http.Cookie;
+import jakarta.servlet.http.HttpServletRequest;
+import jakarta.servlet.http.HttpServletResponse;
+
+import stirling.software.proprietary.security.model.JwtVerificationKey;
+import stirling.software.proprietary.security.model.User;
+import stirling.software.proprietary.security.model.exception.AuthenticationFailureException;
+
+@ExtendWith(MockitoExtension.class)
+class JwtServiceTest {
+
+    @Mock private Authentication authentication;
+
+    @Mock private User userDetails;
+
+    @Mock private HttpServletRequest request;
+
+    @Mock private HttpServletResponse response;
+
+    @Mock private KeyPersistenceServiceInterface keystoreService;
+
+    private JwtService jwtService;
+    private KeyPair testKeyPair;
+    private JwtVerificationKey testVerificationKey;
+
+    @BeforeEach
+    void setUp() throws NoSuchAlgorithmException {
+        // Generate a test keypair
+        KeyPairGenerator keyPairGenerator = KeyPairGenerator.getInstance("RSA");
+        keyPairGenerator.initialize(2048);
+        testKeyPair = keyPairGenerator.generateKeyPair();
+
+        // Create test verification key
+        String encodedPublicKey =
+                Base64.getEncoder().encodeToString(testKeyPair.getPublic().getEncoded());
+        testVerificationKey = new JwtVerificationKey("test-key-id", encodedPublicKey);
+
+        jwtService = new JwtService(true, keystoreService);
+    }
+
+    @Test
+    void testGenerateTokenWithAuthentication() throws Exception {
+        String username = "testuser";
+
+        when(keystoreService.getActiveKey()).thenReturn(testVerificationKey);
+        when(keystoreService.getKeyPair("test-key-id")).thenReturn(Optional.of(testKeyPair));
+        when(keystoreService.decodePublicKey(testVerificationKey.getVerifyingKey()))
+                .thenReturn(testKeyPair.getPublic());
+        when(authentication.getPrincipal()).thenReturn(userDetails);
+        when(userDetails.getUsername()).thenReturn(username);
+
+        String token = jwtService.generateToken(authentication, Collections.emptyMap());
+
+        assertNotNull(token);
+        assertFalse(token.isEmpty());
+        assertEquals(username, jwtService.extractUsername(token));
+    }
+
+    @Test
+    void testGenerateTokenWithUsernameAndClaims() throws Exception {
+        String username = "testuser";
+        Map<String, Object> claims = new HashMap<>();
+        claims.put("role", "admin");
+        claims.put("department", "IT");
+
+        when(keystoreService.getActiveKey()).thenReturn(testVerificationKey);
+        when(keystoreService.getKeyPair("test-key-id")).thenReturn(Optional.of(testKeyPair));
+        when(keystoreService.decodePublicKey(testVerificationKey.getVerifyingKey()))
+                .thenReturn(testKeyPair.getPublic());
+        when(authentication.getPrincipal()).thenReturn(userDetails);
+        when(userDetails.getUsername()).thenReturn(username);
+
+        String token = jwtService.generateToken(authentication, claims);
+
+        assertNotNull(token);
+        assertFalse(token.isEmpty());
+        assertEquals(username, jwtService.extractUsername(token));
+
+        Map<String, Object> extractedClaims = jwtService.extractClaims(token);
+        assertEquals("admin", extractedClaims.get("role"));
+        assertEquals("IT", extractedClaims.get("department"));
+    }
+
+    @Test
+    void testValidateTokenSuccess() throws Exception {
+        when(keystoreService.getActiveKey()).thenReturn(testVerificationKey);
+        when(keystoreService.getKeyPair("test-key-id")).thenReturn(Optional.of(testKeyPair));
+        when(keystoreService.decodePublicKey(testVerificationKey.getVerifyingKey()))
+                .thenReturn(testKeyPair.getPublic());
+        when(authentication.getPrincipal()).thenReturn(userDetails);
+        when(userDetails.getUsername()).thenReturn("testuser");
+
+        String token = jwtService.generateToken(authentication, new HashMap<>());
+
+        assertDoesNotThrow(() -> jwtService.validateToken(token));
+    }
+
+    @Test
+    void testValidateTokenWithInvalidToken() throws Exception {
+        when(keystoreService.getActiveKey()).thenReturn(testVerificationKey);
+        when(keystoreService.decodePublicKey(testVerificationKey.getVerifyingKey()))
+                .thenReturn(testKeyPair.getPublic());
+
+        assertThrows(
+                AuthenticationFailureException.class,
+                () -> {
+                    jwtService.validateToken("invalid-token");
+                });
+    }
+
+    @Test
+    void testValidateTokenWithMalformedToken() throws Exception {
+        when(keystoreService.getActiveKey()).thenReturn(testVerificationKey);
+        when(keystoreService.decodePublicKey(testVerificationKey.getVerifyingKey()))
+                .thenReturn(testKeyPair.getPublic());
+
+        AuthenticationFailureException exception =
+                assertThrows(
+                        AuthenticationFailureException.class,
+                        () -> {
+                            jwtService.validateToken("malformed.token");
+                        });
+
+        assertTrue(exception.getMessage().contains("Invalid"));
+    }
+
+    @Test
+    void testValidateTokenWithEmptyToken() throws Exception {
+        when(keystoreService.getActiveKey()).thenReturn(testVerificationKey);
+        when(keystoreService.decodePublicKey(testVerificationKey.getVerifyingKey()))
+                .thenReturn(testKeyPair.getPublic());
+
+        AuthenticationFailureException exception =
+                assertThrows(
+                        AuthenticationFailureException.class,
+                        () -> {
+                            jwtService.validateToken("");
+                        });
+
+        assertTrue(
+                exception.getMessage().contains("Claims are empty")
+                        || exception.getMessage().contains("Invalid"));
+    }
+
+    @Test
+    void testExtractUsername() throws Exception {
+        String username = "testuser";
+        User user = mock(User.class);
+        Map<String, Object> claims = Map.of("sub", "testuser", "authType", "WEB");
+
+        when(keystoreService.getActiveKey()).thenReturn(testVerificationKey);
+        when(keystoreService.getKeyPair("test-key-id")).thenReturn(Optional.of(testKeyPair));
+        when(keystoreService.decodePublicKey(testVerificationKey.getVerifyingKey()))
+                .thenReturn(testKeyPair.getPublic());
+        when(authentication.getPrincipal()).thenReturn(user);
+        when(user.getUsername()).thenReturn(username);
+
+        String token = jwtService.generateToken(authentication, claims);
+
+        assertEquals(username, jwtService.extractUsername(token));
+    }
+
+    @Test
+    void testExtractUsernameWithInvalidToken() throws Exception {
+        when(keystoreService.getActiveKey()).thenReturn(testVerificationKey);
+        when(keystoreService.decodePublicKey(testVerificationKey.getVerifyingKey()))
+                .thenReturn(testKeyPair.getPublic());
+
+        assertThrows(
+                AuthenticationFailureException.class,
+                () -> jwtService.extractUsername("invalid-token"));
+    }
+
+    @Test
+    void testExtractClaims() throws Exception {
+        String username = "testuser";
+        Map<String, Object> claims = Map.of("role", "admin", "department", "IT");
+
+        when(keystoreService.getActiveKey()).thenReturn(testVerificationKey);
+        when(keystoreService.getKeyPair("test-key-id")).thenReturn(Optional.of(testKeyPair));
+        when(keystoreService.decodePublicKey(testVerificationKey.getVerifyingKey()))
+                .thenReturn(testKeyPair.getPublic());
+        when(authentication.getPrincipal()).thenReturn(userDetails);
+        when(userDetails.getUsername()).thenReturn(username);
+
+        String token = jwtService.generateToken(authentication, claims);
+        Map<String, Object> extractedClaims = jwtService.extractClaims(token);
+
+        assertEquals("admin", extractedClaims.get("role"));
+        assertEquals("IT", extractedClaims.get("department"));
+        assertEquals(username, extractedClaims.get("sub"));
+        assertEquals("Stirling PDF", extractedClaims.get("iss"));
+    }
+
+    @Test
+    void testExtractClaimsWithInvalidToken() throws Exception {
+        when(keystoreService.getActiveKey()).thenReturn(testVerificationKey);
+        when(keystoreService.decodePublicKey(testVerificationKey.getVerifyingKey()))
+                .thenReturn(testKeyPair.getPublic());
+
+        assertThrows(
+                AuthenticationFailureException.class,
+                () -> jwtService.extractClaims("invalid-token"));
+    }
+
+    @Test
+    void testExtractTokenWithCookie() {
+        String token = "test-token";
+        Cookie[] cookies = {new Cookie("stirling_jwt", token)};
+        when(request.getCookies()).thenReturn(cookies);
+
+        assertEquals(token, jwtService.extractToken(request));
+    }
+
+    @Test
+    void testExtractTokenWithNoCookies() {
+        when(request.getCookies()).thenReturn(null);
+
+        assertNull(jwtService.extractToken(request));
+    }
+
+    @Test
+    void testExtractTokenWithWrongCookie() {
+        Cookie[] cookies = {new Cookie("OTHER_COOKIE", "value")};
+        when(request.getCookies()).thenReturn(cookies);
+
+        assertNull(jwtService.extractToken(request));
+    }
+
+    @Test
+    void testExtractTokenWithInvalidAuthorizationHeader() {
+        when(request.getCookies()).thenReturn(null);
+
+        assertNull(jwtService.extractToken(request));
+    }
+
+    @ParameterizedTest
+    @ValueSource(booleans = {true, false})
+    void testAddToken(boolean secureCookie) throws Exception {
+        String token = "test-token";
+
+        // Create new JwtService instance with the secureCookie parameter
+        JwtService testJwtService = createJwtServiceWithSecureCookie(secureCookie);
+
+        testJwtService.addToken(response, token);
+
+        verify(response).addHeader(eq("Set-Cookie"), contains("stirling_jwt=" + token));
+        verify(response).addHeader(eq("Set-Cookie"), contains("HttpOnly"));
+
+        if (secureCookie) {
+            verify(response).addHeader(eq("Set-Cookie"), contains("Secure"));
+        }
+    }
+
+    @Test
+    void testClearToken() {
+        jwtService.clearToken(response);
+
+        verify(response).addHeader(eq("Set-Cookie"), contains("stirling_jwt="));
+        verify(response).addHeader(eq("Set-Cookie"), contains("Max-Age=0"));
+    }
+
+    @Test
+    void testGenerateTokenWithKeyId() throws Exception {
+        String username = "testuser";
+        Map<String, Object> claims = new HashMap<>();
+
+        when(keystoreService.getActiveKey()).thenReturn(testVerificationKey);
+        when(keystoreService.getKeyPair("test-key-id")).thenReturn(Optional.of(testKeyPair));
+        when(authentication.getPrincipal()).thenReturn(userDetails);
+        when(userDetails.getUsername()).thenReturn(username);
+
+        String token = jwtService.generateToken(authentication, claims);
+
+        assertNotNull(token);
+        assertFalse(token.isEmpty());
+        // Verify that the keystore service was called
+        verify(keystoreService).getActiveKey();
+        verify(keystoreService).getKeyPair("test-key-id");
+    }
+
+    @Test
+    void testTokenVerificationWithSpecificKeyId() throws Exception {
+        String username = "testuser";
+        Map<String, Object> claims = new HashMap<>();
+
+        when(keystoreService.getActiveKey()).thenReturn(testVerificationKey);
+        when(keystoreService.getKeyPair("test-key-id")).thenReturn(Optional.of(testKeyPair));
+        when(keystoreService.decodePublicKey(testVerificationKey.getVerifyingKey()))
+                .thenReturn(testKeyPair.getPublic());
+        when(authentication.getPrincipal()).thenReturn(userDetails);
+        when(userDetails.getUsername()).thenReturn(username);
+
+        // Generate token with key ID
+        String token = jwtService.generateToken(authentication, claims);
+
+        // Mock extraction of key ID and verification (lenient to avoid unused stubbing)
+        lenient()
+                .when(keystoreService.getKeyPair("test-key-id"))
+                .thenReturn(Optional.of(testKeyPair));
+
+        // Verify token can be validated
+        assertDoesNotThrow(() -> jwtService.validateToken(token));
+        assertEquals(username, jwtService.extractUsername(token));
+    }
+
+    @Test
+    void testTokenVerificationFallsBackToActiveKeyWhenKeyIdNotFound() throws Exception {
+        String username = "testuser";
+        Map<String, Object> claims = new HashMap<>();
+
+        // First, generate a token successfully
+        when(keystoreService.getActiveKey()).thenReturn(testVerificationKey);
+        when(keystoreService.getKeyPair("test-key-id")).thenReturn(Optional.of(testKeyPair));
+        when(keystoreService.decodePublicKey(testVerificationKey.getVerifyingKey()))
+                .thenReturn(testKeyPair.getPublic());
+        when(authentication.getPrincipal()).thenReturn(userDetails);
+        when(userDetails.getUsername()).thenReturn(username);
+
+        String token = jwtService.generateToken(authentication, claims);
+
+        // Now mock the scenario for validation - key not found, but fallback works
+        // Create a fallback key pair that can be used
+        JwtVerificationKey fallbackKey =
+                new JwtVerificationKey(
+                        "fallback-key",
+                        Base64.getEncoder().encodeToString(testKeyPair.getPublic().getEncoded()));
+
+        // Mock the specific key lookup to fail, but the active key should work
+        when(keystoreService.getKeyPair("test-key-id")).thenReturn(Optional.empty());
+        when(keystoreService.refreshActiveKeyPair()).thenReturn(fallbackKey);
+        when(keystoreService.getKeyPair("fallback-key")).thenReturn(Optional.of(testKeyPair));
+
+        // Should still work by falling back to the active keypair
+        assertDoesNotThrow(() -> jwtService.validateToken(token));
+        assertEquals(username, jwtService.extractUsername(token));
+
+        // Verify fallback logic was used
+        verify(keystoreService, atLeast(1)).getActiveKey();
+    }
+
+    private JwtService createJwtServiceWithSecureCookie(boolean secureCookie) throws Exception {
+        // Use reflection to create JwtService with custom secureCookie value
+        JwtService testService = new JwtService(true, keystoreService);
+
+        // Set the secureCookie field using reflection
+        java.lang.reflect.Field secureCookieField =
+                JwtService.class.getDeclaredField("secureCookie");
+        secureCookieField.setAccessible(true);
+        secureCookieField.set(testService, secureCookie);
+
+        return testService;
+    }
+}
diff --git a/app/proprietary/src/test/java/stirling/software/proprietary/security/service/KeyPersistenceServiceInterfaceTest.java b/app/proprietary/src/test/java/stirling/software/proprietary/security/service/KeyPersistenceServiceInterfaceTest.java
new file mode 100644
index 000000000..33b971e5a
--- /dev/null
+++ b/app/proprietary/src/test/java/stirling/software/proprietary/security/service/KeyPersistenceServiceInterfaceTest.java
@@ -0,0 +1,232 @@
+package stirling.software.proprietary.security.service;
+
+import static org.junit.jupiter.api.Assertions.assertEquals;
+import static org.junit.jupiter.api.Assertions.assertFalse;
+import static org.junit.jupiter.api.Assertions.assertNotNull;
+import static org.junit.jupiter.api.Assertions.assertTrue;
+import static org.mockito.Mockito.lenient;
+import static org.mockito.Mockito.mockStatic;
+import static org.mockito.Mockito.when;
+
+import java.io.IOException;
+import java.nio.file.Files;
+import java.nio.file.Path;
+import java.security.KeyPair;
+import java.security.KeyPairGenerator;
+import java.security.NoSuchAlgorithmException;
+import java.util.Base64;
+import java.util.Optional;
+
+import org.junit.jupiter.api.BeforeEach;
+import org.junit.jupiter.api.Test;
+import org.junit.jupiter.api.extension.ExtendWith;
+import org.junit.jupiter.api.io.TempDir;
+import org.junit.jupiter.params.ParameterizedTest;
+import org.junit.jupiter.params.provider.ValueSource;
+import org.mockito.Mock;
+import org.mockito.MockedStatic;
+import org.mockito.junit.jupiter.MockitoExtension;
+import org.springframework.cache.CacheManager;
+import org.springframework.cache.concurrent.ConcurrentMapCacheManager;
+
+import stirling.software.common.configuration.InstallationPathConfig;
+import stirling.software.common.model.ApplicationProperties;
+import stirling.software.proprietary.security.model.JwtVerificationKey;
+
+@ExtendWith(MockitoExtension.class)
+class KeyPersistenceServiceInterfaceTest {
+
+    @Mock private ApplicationProperties applicationProperties;
+
+    @Mock private ApplicationProperties.Security security;
+
+    @Mock private ApplicationProperties.Security.Jwt jwtConfig;
+
+    @TempDir Path tempDir;
+
+    private KeyPersistenceService keyPersistenceService;
+    private KeyPair testKeyPair;
+    private CacheManager cacheManager;
+
+    @BeforeEach
+    void setUp() throws NoSuchAlgorithmException {
+        KeyPairGenerator keyPairGenerator = KeyPairGenerator.getInstance("RSA");
+        keyPairGenerator.initialize(2048);
+        testKeyPair = keyPairGenerator.generateKeyPair();
+
+        cacheManager = new ConcurrentMapCacheManager("verifyingKeys");
+
+        lenient().when(applicationProperties.getSecurity()).thenReturn(security);
+        lenient().when(security.getJwt()).thenReturn(jwtConfig);
+        lenient().when(jwtConfig.isEnableKeystore()).thenReturn(true); // Default value
+    }
+
+    @ParameterizedTest
+    @ValueSource(booleans = {true, false})
+    void testKeystoreEnabled(boolean keystoreEnabled) {
+        when(jwtConfig.isEnableKeystore()).thenReturn(keystoreEnabled);
+
+        try (MockedStatic<InstallationPathConfig> mockedStatic =
+                mockStatic(InstallationPathConfig.class)) {
+            mockedStatic
+                    .when(InstallationPathConfig::getPrivateKeyPath)
+                    .thenReturn(tempDir.toString());
+            keyPersistenceService = new KeyPersistenceService(applicationProperties, cacheManager);
+
+            assertEquals(keystoreEnabled, keyPersistenceService.isKeystoreEnabled());
+        }
+    }
+
+    @Test
+    void testGetActiveKeypairWhenNoActiveKeyExists() {
+        try (MockedStatic<InstallationPathConfig> mockedStatic =
+                mockStatic(InstallationPathConfig.class)) {
+            mockedStatic
+                    .when(InstallationPathConfig::getPrivateKeyPath)
+                    .thenReturn(tempDir.toString());
+            keyPersistenceService = new KeyPersistenceService(applicationProperties, cacheManager);
+            keyPersistenceService.initializeKeystore();
+
+            JwtVerificationKey result = keyPersistenceService.getActiveKey();
+
+            assertNotNull(result);
+            assertNotNull(result.getKeyId());
+            assertNotNull(result.getVerifyingKey());
+        }
+    }
+
+    @Test
+    void testGetActiveKeyPairWithExistingKey() throws Exception {
+        String keyId = "test-key-2024-01-01-120000";
+        String publicKeyBase64 =
+                Base64.getEncoder().encodeToString(testKeyPair.getPublic().getEncoded());
+        String privateKeyBase64 =
+                Base64.getEncoder().encodeToString(testKeyPair.getPrivate().getEncoded());
+
+        JwtVerificationKey existingKey = new JwtVerificationKey(keyId, publicKeyBase64);
+
+        Path keyFile = tempDir.resolve(keyId + ".key");
+        Files.writeString(keyFile, privateKeyBase64);
+
+        try (MockedStatic<InstallationPathConfig> mockedStatic =
+                mockStatic(InstallationPathConfig.class)) {
+            mockedStatic
+                    .when(InstallationPathConfig::getPrivateKeyPath)
+                    .thenReturn(tempDir.toString());
+            keyPersistenceService = new KeyPersistenceService(applicationProperties, cacheManager);
+            keyPersistenceService.initializeKeystore();
+
+            JwtVerificationKey result = keyPersistenceService.getActiveKey();
+
+            assertNotNull(result);
+            assertNotNull(result.getKeyId());
+        }
+    }
+
+    @Test
+    void testGetKeyPair() throws Exception {
+        String keyId = "test-key-123";
+        String publicKeyBase64 =
+                Base64.getEncoder().encodeToString(testKeyPair.getPublic().getEncoded());
+        String privateKeyBase64 =
+                Base64.getEncoder().encodeToString(testKeyPair.getPrivate().getEncoded());
+
+        JwtVerificationKey signingKey = new JwtVerificationKey(keyId, publicKeyBase64);
+
+        Path keyFile = tempDir.resolve(keyId + ".key");
+        Files.writeString(keyFile, privateKeyBase64);
+
+        try (MockedStatic<InstallationPathConfig> mockedStatic =
+                mockStatic(InstallationPathConfig.class)) {
+            mockedStatic
+                    .when(InstallationPathConfig::getPrivateKeyPath)
+                    .thenReturn(tempDir.toString());
+            keyPersistenceService = new KeyPersistenceService(applicationProperties, cacheManager);
+
+            keyPersistenceService
+                    .getClass()
+                    .getDeclaredField("verifyingKeyCache")
+                    .setAccessible(true);
+            var cache = cacheManager.getCache("verifyingKeys");
+            cache.put(keyId, signingKey);
+
+            Optional<KeyPair> result = keyPersistenceService.getKeyPair(keyId);
+
+            assertTrue(result.isPresent());
+            assertNotNull(result.get().getPublic());
+            assertNotNull(result.get().getPrivate());
+        }
+    }
+
+    @Test
+    void testGetKeyPairNotFound() {
+        String keyId = "non-existent-key";
+
+        try (MockedStatic<InstallationPathConfig> mockedStatic =
+                mockStatic(InstallationPathConfig.class)) {
+            mockedStatic
+                    .when(InstallationPathConfig::getPrivateKeyPath)
+                    .thenReturn(tempDir.toString());
+            keyPersistenceService = new KeyPersistenceService(applicationProperties, cacheManager);
+
+            Optional<KeyPair> result = keyPersistenceService.getKeyPair(keyId);
+
+            assertFalse(result.isPresent());
+        }
+    }
+
+    @Test
+    void testGetKeyPairWhenKeystoreDisabled() {
+        when(jwtConfig.isEnableKeystore()).thenReturn(false);
+
+        try (MockedStatic<InstallationPathConfig> mockedStatic =
+                mockStatic(InstallationPathConfig.class)) {
+            mockedStatic
+                    .when(InstallationPathConfig::getPrivateKeyPath)
+                    .thenReturn(tempDir.toString());
+            keyPersistenceService = new KeyPersistenceService(applicationProperties, cacheManager);
+
+            Optional<KeyPair> result = keyPersistenceService.getKeyPair("any-key");
+
+            assertFalse(result.isPresent());
+        }
+    }
+
+    @Test
+    void testInitializeKeystoreCreatesDirectory() throws IOException {
+        try (MockedStatic<InstallationPathConfig> mockedStatic =
+                mockStatic(InstallationPathConfig.class)) {
+            mockedStatic
+                    .when(InstallationPathConfig::getPrivateKeyPath)
+                    .thenReturn(tempDir.toString());
+            keyPersistenceService = new KeyPersistenceService(applicationProperties, cacheManager);
+            keyPersistenceService.initializeKeystore();
+
+            assertTrue(Files.exists(tempDir));
+            assertTrue(Files.isDirectory(tempDir));
+        }
+    }
+
+    @Test
+    void testLoadExistingKeypairWithMissingPrivateKeyFile() throws Exception {
+        String keyId = "test-key-missing-file";
+        String publicKeyBase64 =
+                Base64.getEncoder().encodeToString(testKeyPair.getPublic().getEncoded());
+
+        JwtVerificationKey existingKey = new JwtVerificationKey(keyId, publicKeyBase64);
+
+        try (MockedStatic<InstallationPathConfig> mockedStatic =
+                mockStatic(InstallationPathConfig.class)) {
+            mockedStatic
+                    .when(InstallationPathConfig::getPrivateKeyPath)
+                    .thenReturn(tempDir.toString());
+            keyPersistenceService = new KeyPersistenceService(applicationProperties, cacheManager);
+            keyPersistenceService.initializeKeystore();
+
+            JwtVerificationKey result = keyPersistenceService.getActiveKey();
+            assertNotNull(result);
+            assertNotNull(result.getKeyId());
+            assertNotNull(result.getVerifyingKey());
+        }
+    }
+}
diff --git a/exampleYmlFiles/test_cicd.yml b/exampleYmlFiles/test_cicd.yml
index 31e24da48..086f862d5 100644
--- a/exampleYmlFiles/test_cicd.yml
+++ b/exampleYmlFiles/test_cicd.yml
@@ -20,6 +20,7 @@ services:
     environment:
       DISABLE_ADDITIONAL_FEATURES: "false"
       SECURITY_ENABLELOGIN: "true"
+      V2: "false"
       PUID: 1002
       PGID: 1002
       UMASK: "022"