diff --git a/scripts/startup/bl_ui/space_view3d.py b/scripts/startup/bl_ui/space_view3d.py
index 40ce95d0dd4..b151c72a5a6 100644
--- a/scripts/startup/bl_ui/space_view3d.py
+++ b/scripts/startup/bl_ui/space_view3d.py
@@ -2772,7 +2772,7 @@ class VIEW3D_MT_object_animation(Menu):
         layout = self.layout
 
         layout.operator("anim.keyframe_insert", text="Insert Keyframe")
-        layout.operator("anim.keyframe_insert_menu", text="Insert Keyframe with Keying Set")
+        layout.operator("anim.keyframe_insert_menu", text="Insert Keyframe with Keying Set").always_prompt = True
         layout.operator("anim.keyframe_delete_v3d", text="Delete Keyframes...")
         layout.operator("anim.keyframe_clear_v3d", text="Clear Keyframes...")
         layout.operator("anim.keying_set_active_set", text="Change Keying Set...")
@@ -3037,7 +3037,7 @@ class VIEW3D_MT_object_context_menu(Menu):
         layout.separator()
 
         layout.operator("anim.keyframe_insert", text="Insert Keyframe")
-        layout.operator("anim.keyframe_insert_menu", text="Insert Keyframe with Keying Set")
+        layout.operator("anim.keyframe_insert_menu", text="Insert Keyframe with Keying Set").always_prompt = True
 
         layout.separator()
 
@@ -4155,7 +4155,7 @@ class VIEW3D_MT_pose_context_menu(Menu):
         layout.operator_context = 'INVOKE_REGION_WIN'
 
         layout.operator("anim.keyframe_insert", text="Insert Keyframe")
-        layout.operator("anim.keyframe_insert_menu", text="Insert Keyframe with Keying Set")
+        layout.operator("anim.keyframe_insert_menu", text="Insert Keyframe with Keying Set").always_prompt = True
 
         layout.separator()