diff --git a/go_cloud/internal/errors/errors.go b/go_cloud/internal/errors/errors.go
index 02289a3..6531473 100644
--- a/go_cloud/internal/errors/errors.go
+++ b/go_cloud/internal/errors/errors.go
@@ -6,7 +6,7 @@ import (
 	"net/http"
 	"os"
 
-	"github.com/go-chi/chi/v5/middleware"
+	chimiddleware "github.com/go-chi/chi/v5/middleware"
 	"github.com/google/uuid"
 )
 
@@ -40,7 +40,7 @@ func WriteError(w http.ResponseWriter, code ErrorCode, message string, status in
 
 // GetRequestID extracts the request ID from the request context
 func GetRequestID(r *http.Request) string {
-	if reqID := middleware.GetReqID(r.Context()); reqID != "" {
+	if reqID := chimiddleware.GetReqID(r.Context()); reqID != "" {
 		return reqID
 	}
 	return "unknown"
@@ -48,10 +48,10 @@ func GetRequestID(r *http.Request) string {
 
 // GetUserID extracts user ID from context if available
 func GetUserID(r *http.Request) string {
-	if userID := r.Context().Value("user"); userID != nil {
-		if uid, ok := userID.(string); ok {
-			return uid
-		}
+	// Use type contextKey matching middleware package
+	type contextKey string
+	if userID, ok := r.Context().Value(contextKey("user")).(string); ok && userID != "" {
+		return userID
 	}
 	return ""
 }
diff --git a/go_cloud/internal/http/routes.go b/go_cloud/internal/http/routes.go
index 4b92e3c..d12da6f 100644
--- a/go_cloud/internal/http/routes.go
+++ b/go_cloud/internal/http/routes.go
@@ -351,7 +351,7 @@ func listFilesHandler(w http.ResponseWriter, r *http.Request, db *database.DB) {
 }
 
 func viewerHandler(w http.ResponseWriter, r *http.Request, db *database.DB, auditLogger *audit.Logger) {
-	userIDStr := r.Context().Value("user").(string)
+	userIDStr, _ := middleware.GetUserID(r.Context())
 	userID, _ := uuid.Parse(userIDStr)
 	orgID := r.Context().Value("org").(uuid.UUID)
 	fileId := chi.URLParam(r, "fileId")
@@ -382,7 +382,7 @@ func viewerHandler(w http.ResponseWriter, r *http.Request, db *database.DB, audi
 }
 
 func editorHandler(w http.ResponseWriter, r *http.Request, db *database.DB, auditLogger *audit.Logger) {
-	userIDStr := r.Context().Value("user").(string)
+	userIDStr, _ := middleware.GetUserID(r.Context())
 	userID, _ := uuid.Parse(userIDStr)
 	orgID := r.Context().Value("org").(uuid.UUID)
 	fileId := chi.URLParam(r, "fileId")
@@ -405,7 +405,7 @@ func editorHandler(w http.ResponseWriter, r *http.Request, db *database.DB, audi
 }
 
 func annotationsHandler(w http.ResponseWriter, r *http.Request, db *database.DB, auditLogger *audit.Logger) {
-	userIDStr := r.Context().Value("user").(string)
+	userIDStr, _ := middleware.GetUserID(r.Context())
 	userID, _ := uuid.Parse(userIDStr)
 	orgID := r.Context().Value("org").(uuid.UUID)
 	fileId := chi.URLParam(r, "fileId")
@@ -848,7 +848,7 @@ func passwordLoginHandler(w http.ResponseWriter, r *http.Request, db *database.D
 
 // userFilesHandler returns files for the authenticated user's personal workspace.
 func userFilesHandler(w http.ResponseWriter, r *http.Request, db *database.DB) {
-	userIDStr, ok := r.Context().Value("user").(string)
+	userIDStr, ok := middleware.GetUserID(r.Context())
 	if !ok || userIDStr == "" {
 		errors.WriteError(w, errors.CodeUnauthenticated, "Unauthorized", http.StatusUnauthorized)
 		return
@@ -899,7 +899,7 @@ func userFilesHandler(w http.ResponseWriter, r *http.Request, db *database.DB) {
 // createOrgFileHandler creates a file or folder record for an org workspace.
 func createOrgFileHandler(w http.ResponseWriter, r *http.Request, db *database.DB, auditLogger *audit.Logger, storageClient *storage.WebDAVClient) {
 	orgID := r.Context().Value("org").(uuid.UUID)
-	userIDStr, _ := r.Context().Value("user").(string)
+	userIDStr, _ := middleware.GetUserID(r.Context())
 	userID, _ := uuid.Parse(userIDStr)
 	var f *database.File
 	var err error
@@ -1039,7 +1039,7 @@ func createOrgFileHandler(w http.ResponseWriter, r *http.Request, db *database.D
 // deleteOrgFileHandler deletes a file/folder in org workspace by path
 func deleteOrgFileHandler(w http.ResponseWriter, r *http.Request, db *database.DB, auditLogger *audit.Logger, storageClient *storage.WebDAVClient) {
 	orgID := r.Context().Value("org").(uuid.UUID)
-	userIDStr, _ := r.Context().Value("user").(string)
+	userIDStr, _ := middleware.GetUserID(r.Context())
 	userID, _ := uuid.Parse(userIDStr)
 
 	var req struct {
@@ -1084,7 +1084,7 @@ func deleteOrgFilePostHandler(w http.ResponseWriter, r *http.Request, db *databa
 
 // createUserFileHandler creates a file or folder record for the authenticated user's personal workspace.
 func createUserFileHandler(w http.ResponseWriter, r *http.Request, db *database.DB, auditLogger *audit.Logger, storageClient *storage.WebDAVClient) {
-	userIDStr, ok := r.Context().Value("user").(string)
+	userIDStr, ok := middleware.GetUserID(r.Context())
 	if !ok || userIDStr == "" {
 		errors.WriteError(w, errors.CodeUnauthenticated, "Unauthorized", http.StatusUnauthorized)
 		return
@@ -1216,7 +1216,7 @@ func deleteUserFilePostHandler(w http.ResponseWriter, r *http.Request, db *datab
 
 // deleteUserFileHandler deletes a file/folder in user's personal workspace by path
 func deleteUserFileHandler(w http.ResponseWriter, r *http.Request, db *database.DB, auditLogger *audit.Logger, storageClient *storage.WebDAVClient) {
-	userIDStr, ok := r.Context().Value("user").(string)
+	userIDStr, ok := middleware.GetUserID(r.Context())
 	if !ok || userIDStr == "" {
 		errors.WriteError(w, errors.CodeUnauthenticated, "Unauthorized", http.StatusUnauthorized)
 		return
@@ -1298,7 +1298,7 @@ func downloadOrgFileHandler(w http.ResponseWriter, r *http.Request, db *database
 
 // downloadUserFileHandler downloads a file from user's personal workspace
 func downloadUserFileHandler(w http.ResponseWriter, r *http.Request, db *database.DB, storageClient *storage.WebDAVClient) {
-	userIDStr, ok := r.Context().Value("user").(string)
+	userIDStr, ok := middleware.GetUserID(r.Context())
 	if !ok || userIDStr == "" {
 		errors.WriteError(w, errors.CodeUnauthenticated, "Unauthorized", http.StatusUnauthorized)
 		return
diff --git a/go_cloud/internal/middleware/middleware.go b/go_cloud/internal/middleware/middleware.go
index 91dcbb2..215a18c 100644
--- a/go_cloud/internal/middleware/middleware.go
+++ b/go_cloud/internal/middleware/middleware.go
@@ -54,6 +54,18 @@ const (
 	orgKey     contextKey = "org"
 )
 
+// GetUserID retrieves the user ID from the request context
+func GetUserID(ctx context.Context) (string, bool) {
+	userID, ok := ctx.Value(userKey).(string)
+	return userID, ok
+}
+
+// GetSession retrieves the session from the request context
+func GetSession(ctx context.Context) (*database.Session, bool) {
+	session, ok := ctx.Value(sessionKey).(*database.Session)
+	return session, ok
+}
+
 // Auth middleware
 func Auth(jwtManager *jwt.Manager, db *database.DB) func(http.Handler) http.Handler {
 	return func(next http.Handler) http.Handler {