My ~4 yr old MacBook restarts whenever I tell it to shut down and won't properly go to sleep.

It will only shut down if I hold the power button. Late 2009 MacBook running 10.6.8. It does this in Safe Mode, I've done an SMC reset, the extended hardware test (no problems), and it doesn't seem to be connected to any particular application being opened or amount of time the computer was in use. Has anyone been able to fix this problem? I've seen a lot of forum posts with no solution.

Take the machine into your local Apple Store or an AASP and have them fix it.
I had a similar issue when I was syncing a friend's iPhone (I don't own one) in that the machine shut down when the iPhone was plugged in. But I was able to reboot. A lot of people seems to have the problem that you describe, however.
Clinton

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