Time Machine not deleting old back ups?

I keep getting the error
"This backup is too large for the backup volume. The backup requires...."
I use the same 500GB volume for backups all day, every day. I thought the program was supposed to automatically delete old back ups to make room? I do not see any additional settings to confirm this but if you manually delete back up files, it really kind of screws things up. I see back ups that are 4-6 weeks old on the back up volume so there are plenty it could delete. Has anyone else seen this and how do you resolve this problem?
TIA

mqcarpenter wrote:
I keep getting the error
"This backup is too large for the backup volume. The backup requires...."
I use the same 500GB volume for backups all day, every day. I thought the program was supposed to automatically delete old back ups to make room? I do not see any additional settings to confirm this but if you manually delete back up files, it really kind of screws things up.
Do you mean via the Finder? If so, yes, it does.
If you have deleted any this way, do the following:
1. Turn TM Off.
2. Use Disk Utility (in your Applications/Utilities folder) to do a +Repair Disk+ (not permissions) on your TM drive. If it finds errors that it can't fix, try again until it does or you get the exact same results. If they can't be fixed, stop here and post back with the results.
Download the +Time Machine Buddy+ widget from: http://www.apple.com/downloads/dashboard/status/timemachinebuddy.html. It shows the messages from your logs for one TM backup run at a time, in a small window. Copy and post the messages here (be sure to get them all, as sometimes they overflow the small window).
Also, is there other data on your TM drive? If so, is it in the same partition as TM's backups?

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