We discovered in bug 508727 that the lovely Spotlight field in the Help menu on 10.5 somehow disables any tooltips we try to set on other items in that menu. This bug covers trying to figure out if there's any way to make the tooltip display through additional hackery (and filing rdar:// as necessary).
I just tested, and this works correctly in Snow Leopard. Given that it's been fixed in the OS and it's not clear how we could work around this on 10.5, pushing out.
8 years ago