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I've got three 10.6 computers that won't install OS X updates. Checking for new software will show about a dozen updates (Security updates, Safari, iPhoto, printers, etc) and if choose install it downloads them. After downloading and then clicking restart the computer sits at the purplish sky desktop with no progress bar, and then after about 3 minutes it goes back to the login window (without ever installing or restarting).

If I then select check for updates the same updates will all be presented and I can repeat the process. Manually downloading and installing an update such as 10.6.8 combo updater works as it should, and then check for updates no longer presents that particular update as an option.

This seems to be the result of some setting or 3rd party application as I've got 3 out 7 computers experiencing this exact same problem. What could cause this and how can I fix it?

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Try doing a Repair Disk and Repair Permissions in Disk Utility, just to be sure.

Also, look in the All Messages log stream in the Console utility and then run Software Updates, and see if any of the log messages give you a clue what's going on.

Also look at the Installer log.

Try running sudo softwareupdate -ia from Terminal and see what the output says.

If these things provide clues but you still can't solve it, update your Question with the relevant logs/output.

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In March 2012, one of the certificates that Apple signed their updates with expired. Any update downloaded before then will not run without errors. I don't remember what was written to the system log.

The solution is to re-download the updates, or, temporarily set your system clock to (before March, 2012). If the updates have already been downloaded, you don't need a network connection while they are installed. And, after the installation completes, you can reset your system clock back to the proper date.

Note that this also affected some DVD installers for iWork and other applications.

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This question was asked 60 days after the certificates expired. – Ramhound May 27 '13 at 23:32
Yes, and any updates which were on the OP's macs which had been downloaded already to the disk at that point would have had that exact same problem. Your point? – Kent May 28 '13 at 0:06

I had the same issue, a 10.6.8 combo update I had downloaded a couple of years ago now refuses to install, with no valid reason. Software update appears not to see the need of a 10.6.8 update even though the OSX is still on 10.6. I also note that I can no longer find the full 10.6.8 combo updater on Apple Downloads website.

In the end my solution revolved around

  1. using disk utility to repair permissions.
  2. then downloading the 10.6.7 combo update from the apple downloads site manually, then installing that and attempting to update from there.
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