diff --git a/frontend/src/components/panels/editor/FileEditor.tsx b/frontend/src/components/panels/editor/FileEditor.tsx
index 02acdc1d..864a4993 100644
--- a/frontend/src/components/panels/editor/FileEditor.tsx
+++ b/frontend/src/components/panels/editor/FileEditor.tsx
@@ -312,15 +312,14 @@ function HeadlessFileTree({
     setContextMenu(null);
   }, [contextMenu, sessionId]);
 
-  // Delete handler
-  const handleDelete = useCallback(async (file: FileItem) => {
+  const handleDelete = useCallback(async (file: FileItem, options: { skipConfirm?: boolean } = {}) => {
     const files = getSelectedFilesForAction(file);
     const confirmMessage = files.length > 1
       ? `Move ${files.length} items to trash?`
       : files[0]?.isDirectory
         ? `Move folder "${files[0].name}" and all its contents to trash?`
         : `Move file "${files[0]?.name}" to trash?`;
-    if (!confirm(confirmMessage)) return;
+    if (!options.skipConfirm && !confirm(confirmMessage)) return;
 
     try {
       for (const target of files) {
@@ -328,6 +327,7 @@ function HeadlessFileTree({
           sessionId,
           filePath: target.path,
           useTrash: true,
+          allowPermanentFallback: !options.skipConfirm,
         });
 
         if (!result.success) {
@@ -725,7 +725,7 @@ function HeadlessFileTree({
         const item = tree.getItemInstance(selectedItems[0])?.getItemData();
         if (item) {
           e.preventDefault();
-          handleDelete(item);
+          handleDelete(item, { skipConfirm: isMac() && e.metaKey });
         }
       }
       if ((e.metaKey || e.ctrlKey) && e.key.toLowerCase() === 'c' && selectedItems.length > 0) {
diff --git a/main/src/ipc/file.ts b/main/src/ipc/file.ts
index bb3d746e..54130afb 100644
--- a/main/src/ipc/file.ts
+++ b/main/src/ipc/file.ts
@@ -55,6 +55,7 @@ interface FileDeleteRequest {
   sessionId: string;
   filePath: string;
   useTrash?: boolean;
+  allowPermanentFallback?: boolean;
 }
 
 interface FileRenameRequest {
@@ -722,6 +723,12 @@ export function registerFileHandlers(ipcMain: IpcMain, services: AppServices): v
           await shell.trashItem(fullPath);
           return { success: true };
         } catch (trashError) {
+          if (request.allowPermanentFallback === false) {
+            return {
+              success: false,
+              error: trashError instanceof Error ? trashError.message : 'Failed to move item to trash'
+            };
+          }
           console.warn('Failed to move item to trash, permanently deleting instead:', trashError);
         }
       }