diff --git a/server/internal/handlers/file_handlers.go b/server/internal/handlers/file_handlers.go
index 3f53c17..93ddd99 100644
--- a/server/internal/handlers/file_handlers.go
+++ b/server/internal/handlers/file_handlers.go
@@ -4,8 +4,10 @@ import (
 	"encoding/json"
 	"io"
 	"net/http"
+	"os"
 
 	"novamd/internal/context"
+	"novamd/internal/storage"
 
 	"github.com/go-chi/chi/v5"
 )
@@ -63,7 +65,18 @@ func (h *Handler) GetFileContent() http.HandlerFunc {
 		filePath := chi.URLParam(r, "*")
 		content, err := h.Storage.GetFileContent(ctx.UserID, ctx.Workspace.ID, filePath)
 		if err != nil {
-			http.Error(w, "Failed to read file", http.StatusNotFound)
+
+			if storage.IsPathValidationError(err) {
+				http.Error(w, "Invalid file path", http.StatusBadRequest)
+				return
+			}
+
+			if os.IsNotExist(err) {
+				http.Error(w, "Failed to read file", http.StatusNotFound)
+				return
+			}
+
+			http.Error(w, "Failed to read file", http.StatusInternalServerError)
 			return
 		}
 
@@ -93,6 +106,11 @@ func (h *Handler) SaveFile() http.HandlerFunc {
 
 		err = h.Storage.SaveFile(ctx.UserID, ctx.Workspace.ID, filePath, content)
 		if err != nil {
+			if storage.IsPathValidationError(err) {
+				http.Error(w, "Invalid file path", http.StatusBadRequest)
+				return
+			}
+
 			http.Error(w, "Failed to save file", http.StatusInternalServerError)
 			return
 		}
@@ -112,6 +130,16 @@ func (h *Handler) DeleteFile() http.HandlerFunc {
 		filePath := chi.URLParam(r, "*")
 		err := h.Storage.DeleteFile(ctx.UserID, ctx.Workspace.ID, filePath)
 		if err != nil {
+			if storage.IsPathValidationError(err) {
+				http.Error(w, "Invalid file path", http.StatusBadRequest)
+				return
+			}
+
+			if os.IsNotExist(err) {
+				http.Error(w, "File not found", http.StatusNotFound)
+				return
+			}
+
 			http.Error(w, "Failed to delete file", http.StatusInternalServerError)
 			return
 		}
@@ -165,10 +193,21 @@ func (h *Handler) UpdateLastOpenedFile() http.HandlerFunc {
 			return
 		}
 
-		// Validate the file path exists in the workspace
+		// Validate the file path in the workspace
 		if requestBody.FilePath != "" {
-			if _, err := h.Storage.ValidatePath(ctx.UserID, ctx.Workspace.ID, requestBody.FilePath); err != nil {
-				http.Error(w, "Invalid file path", http.StatusBadRequest)
+			_, err := h.Storage.GetFileContent(ctx.UserID, ctx.Workspace.ID, requestBody.FilePath)
+			if err != nil {
+				if storage.IsPathValidationError(err) {
+					http.Error(w, "Invalid file path", http.StatusBadRequest)
+					return
+				}
+
+				if os.IsNotExist(err) {
+					http.Error(w, "File not found", http.StatusNotFound)
+					return
+				}
+
+				http.Error(w, "Failed to update file", http.StatusInternalServerError)
 				return
 			}
 		}
diff --git a/server/internal/storage/errors.go b/server/internal/storage/errors.go
new file mode 100644
index 0000000..dbfdf02
--- /dev/null
+++ b/server/internal/storage/errors.go
@@ -0,0 +1,24 @@
+// storage/errors.go
+
+package storage
+
+import (
+	"errors"
+	"fmt"
+)
+
+// PathValidationError represents a path validation error (e.g., path traversal attempt)
+type PathValidationError struct {
+	Path    string
+	Message string
+}
+
+func (e *PathValidationError) Error() string {
+	return fmt.Sprintf("%s: %s", e.Message, e.Path)
+}
+
+// IsPathValidationError checks if the error is a PathValidationError
+func IsPathValidationError(err error) bool {
+	var pathErr *PathValidationError
+	return err != nil && errors.As(err, &pathErr)
+}
diff --git a/server/internal/storage/workspace.go b/server/internal/storage/workspace.go
index 7a264ad..2a4beca 100644
--- a/server/internal/storage/workspace.go
+++ b/server/internal/storage/workspace.go
@@ -27,7 +27,7 @@ func (s *Service) ValidatePath(userID, workspaceID int, path string) (string, er
 
 	// First check if the path is absolute
 	if filepath.IsAbs(path) {
-		return "", fmt.Errorf("invalid path: absolute paths not allowed")
+		return "", &PathValidationError{Path: path, Message: "absolute paths not allowed"}
 	}
 
 	// Join and clean the path
@@ -36,7 +36,7 @@ func (s *Service) ValidatePath(userID, workspaceID int, path string) (string, er
 
 	// Verify the path is still within the workspace
 	if !strings.HasPrefix(cleanPath, workspacePath) {
-		return "", fmt.Errorf("invalid path: outside of workspace")
+		return "", &PathValidationError{Path: path, Message: "path traversal attempt"}
 	}
 
 	return cleanPath, nil
diff --git a/server/internal/storage/workspace_test.go b/server/internal/storage/workspace_test.go
index f6b1607..2fc11b2 100644
--- a/server/internal/storage/workspace_test.go
+++ b/server/internal/storage/workspace_test.go
@@ -48,7 +48,7 @@ func TestValidatePath(t *testing.T) {
 			path:        "../../../etc/passwd",
 			want:        "",
 			wantErr:     true,
-			errContains: "outside of workspace",
+			errContains: "path traversal attempt",
 		},
 		{
 			name:        "absolute path attempt",