The recently landed PR #115798has made it so the hotkey `K` would call `anim.keyframe_insert_menu` with the property `always_prompt` set to `True`. This property still defaulted to `False` when called from the menu leading to inconsistent behavior when a keying set is active. Fix it by setting `always_prompt` to `True` for the menu entries. Pull Request: https://projects.blender.org/blender/blender/pulls/117511