diff --git a/apps/client/src/menus/tree_context_menu.ts b/apps/client/src/menus/tree_context_menu.ts
index 901a16559..51f9912b3 100644
--- a/apps/client/src/menus/tree_context_menu.ts
+++ b/apps/client/src/menus/tree_context_menu.ts
@@ -140,7 +140,13 @@ export default class TreeContextMenu implements SelectMenuItemEventListener<Tree
                         uiIcon: "bx bx-rename",
                         enabled: isNotRoot && parentNotSearch && notOptionsOrHelp
                     },
-                    { title: t("tree-context-menu.convert-to-attachment"), command: "convertNoteToAttachment", uiIcon: "bx bx-paperclip", enabled: isNotRoot && !isHoisted && notOptionsOrHelp },
+                    {
+                        title:
+                        t("tree-context-menu.convert-to-attachment"),
+                        command: "convertNoteToAttachment",
+                        uiIcon: "bx bx-paperclip",
+                        enabled: isNotRoot && !isHoisted && notOptionsOrHelp && selectedNotes.some(note => note.isEligibleForConversionToAttachment())
+                    },
 
                     { kind: "separator" },