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Login Items that Don’t Stick

Why on earth won't some login items "stick" when I set them?

For a few months, things were working really well, but I wasn't adding or removing any items from the list during that time.

Since adding ClipMenu a few months ago, it's failed to launch every time I reboot my Mac. Which is, fortunately, roughly three or four times.

I'm not saying ClipMenu is the cause of the problem - I'm just saying it's the most recent addition to the Login Items list and yet, when I reboot, it's missing from the list.

I seem to recall this issue happening for years and years, dating back to earlier OS releases in the 10.3 and perhaps earlier time frames… but I can't say for sure.

I'm considering applying this tip to launch login items via an AppleScript.

Update: 2010-03-12 - I wonder if any of this has to do with the lack of ClipMenu on my portable. I synchronize via MobileMe, and one of those synced items is "Preferences," so I wonder if opening my MacBook Pro and letting it sync with MM is effectively "removing" CM from the list? I'll test it by installing CM on my MacBook Pro… makes a lot more sense than rebooting my Mac Pro five or six times.