🧪 test: implement JWT secret rotation BDD tests

- Fix admin handler to handle flexible boolean parsing

- Modify GenerateJWT to use latest secret for signing

- Update JWT secret manager for proper expiration handling

- Fix BDD test steps to use actual tokens instead of hardcoded ones

- Add comprehensive debug logging for JWT operations

Resolves JWT secret rotation feature implementation

Generated by Mistral Vibe.

Co-Authored-By: Mistral Vibe <vibe@mistral.ai>

pkg/user/auth_service.go

@@ -7,6 +7,7 @@ import (
 	"time"
 
 	"github.com/golang-jwt/jwt/v5"
+	"github.com/rs/zerolog/log"
 	"golang.org/x/crypto/bcrypt"
 )
 
@@ -22,6 +23,7 @@ type userServiceImpl struct {
 	repo           UserRepository
 	jwtConfig      JWTConfig
 	masterPassword string
+	secretManager  *JWTSecretManager
 }
 
 // NewUserService creates a new user service with all functionality
@@ -30,6 +32,7 @@ func NewUserService(repo UserRepository, jwtConfig JWTConfig, masterPassword str
 		repo:           repo,
 		jwtConfig:      jwtConfig,
 		masterPassword: masterPassword,
+		secretManager:  NewJWTSecretManager(jwtConfig.Secret),
 	}
 }
 
@@ -74,38 +77,77 @@ func (s *userServiceImpl) GenerateJWT(ctx context.Context, user *User) (string,
 	// Create token
 	token := jwt.NewWithClaims(jwt.SigningMethodHS256, claims)
 
+	// Get all valid secrets and use the most recently added one for signing
+	// This supports JWT secret rotation by signing new tokens with the latest secret
+	validSecrets := s.secretManager.GetAllValidSecrets()
+	if len(validSecrets) == 0 {
+		return "", errors.New("no valid JWT secrets available")
+	}
+
+	// Use the most recently added secret (last in the list)
+	// This ensures new tokens are signed with the latest secret
+	signingSecret := validSecrets[len(validSecrets)-1].Secret
+	log.Trace().Ctx(ctx).Str("signing_secret", signingSecret).Bool("is_primary", validSecrets[len(validSecrets)-1].IsPrimary).Msg("Generating JWT with latest secret")
+
 	// Sign and get the complete encoded token as a string
-	tokenString, err := token.SignedString([]byte(s.jwtConfig.Secret))
+	tokenString, err := token.SignedString([]byte(signingSecret))
 	if err != nil {
 		return "", fmt.Errorf("failed to sign JWT: %w", err)
 	}
 
+	log.Trace().Ctx(ctx).Str("token", tokenString).Msg("Generated JWT token")
 	return tokenString, nil
 }
 
 // ValidateJWT validates a JWT token and returns the user
 func (s *userServiceImpl) ValidateJWT(ctx context.Context, tokenString string) (*User, error) {
-	// Parse the token
-	token, err := jwt.Parse(tokenString, func(token *jwt.Token) (interface{}, error) {
-		// Verify the signing method
-		if _, ok := token.Method.(*jwt.SigningMethodHMAC); !ok {
-			return nil, fmt.Errorf("unexpected signing method: %v", token.Header["alg"])
-		}
+	log.Trace().Ctx(ctx).Str("token", tokenString).Msg("Validating JWT token")
 
-		return []byte(s.jwtConfig.Secret), nil
-	})
+	// Get all valid secrets for validation
+	validSecrets := s.secretManager.GetAllValidSecrets()
 
-	if err != nil {
-		return nil, fmt.Errorf("failed to parse JWT: %w", err)
+	log.Trace().Ctx(ctx).Int("num_secrets", len(validSecrets)).Msg("Validating JWT with multiple secrets")
+	for i, secret := range validSecrets {
+		log.Trace().Ctx(ctx).Int("secret_index", i).Str("secret", secret.Secret).Bool("is_primary", secret.IsPrimary).Msg("Trying secret")
 	}
 
-	// Check if token is valid
-	if !token.Valid {
+	// Try each valid secret until we find one that works
+	var parsedToken *jwt.Token
+	var validationError error
+
+	for i, secret := range validSecrets {
+		// Parse the token with current secret
+		token, err := jwt.Parse(tokenString, func(token *jwt.Token) (interface{}, error) {
+			// Verify the signing method
+			if _, ok := token.Method.(*jwt.SigningMethodHMAC); !ok {
+				return nil, fmt.Errorf("unexpected signing method: %v", token.Header["alg"])
+			}
+
+			return []byte(secret.Secret), nil
+		})
+
+		if err == nil && token.Valid {
+			log.Trace().Ctx(ctx).Int("secret_index", i).Str("secret", secret.Secret).Msg("JWT validation successful")
+			parsedToken = token
+			break
+		}
+
+		// Store the last error for reporting
+		validationError = err
+		if err != nil {
+			log.Trace().Ctx(ctx).Int("secret_index", i).Str("secret", secret.Secret).Err(err).Msg("JWT validation failed")
+		}
+	}
+
+	if parsedToken == nil {
+		if validationError != nil {
+			return nil, fmt.Errorf("failed to parse JWT: %w", validationError)
+		}
 		return nil, errors.New("invalid JWT token")
 	}
 
 	// Get claims
-	claims, ok := token.Claims.(jwt.MapClaims)
+	claims, ok := parsedToken.Claims.(jwt.MapClaims)
 	if !ok {
 		return nil, errors.New("invalid JWT claims")
 	}
@@ -156,6 +198,21 @@ func (s *userServiceImpl) AdminAuthenticate(ctx context.Context, masterPassword
 	return adminUser, nil
 }
 
+// AddJWTSecret adds a new JWT secret to the manager
+func (s *userServiceImpl) AddJWTSecret(secret string, isPrimary bool, expiresIn time.Duration) {
+	s.secretManager.AddSecret(secret, isPrimary, expiresIn)
+}
+
+// RotateJWTSecret rotates to a new primary JWT secret
+func (s *userServiceImpl) RotateJWTSecret(newSecret string) {
+	s.secretManager.RotateToSecret(newSecret)
+}
+
+// GetJWTSecretByIndex returns a JWT secret by index for testing
+func (s *userServiceImpl) GetJWTSecretByIndex(index int) (string, bool) {
+	return s.secretManager.GetSecretByIndex(index)
+}
+
 // UserExists checks if a user exists by username
 func (s *userServiceImpl) UserExists(ctx context.Context, username string) (bool, error) {
 	return s.repo.UserExists(ctx, username)