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I just noticed that a folder containing personal documents was still on my main disk. I copied to my personal disk (password protected), but I want to also delete the copies which are stored in the multiple backups that Time Machine has made over the years.

Is this possible?

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This, of course, breaks the very idea of backup -- but sometimes that's precisely what one wants. I would hope this is possible, but not easy to do -- too easy, and it defeats the purpose of backing up a file; impossible and it defeats another sort of data security. – Daniel Apr 16 '12 at 14:21
up vote 9 down vote accepted

This functionality is built into Time Machine.

Launch Time Machine. Right click on the folder of choice, and select "Delete All Backups..." from the menu. This will comb through all your backups and delete all traces of that folder and its contents.

enter image description here

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I just approved an edit to your answer; is it correct? It seems reasonable and likely, but I'm not entirely certain. – CajunLuke Sep 28 '12 at 2:15

There's this pretty good comercial tool called Back-In-Time ($30; but I purchased it as part of a MacUpdate Promo pack). It will let you delete a single item from the TimeMachine backup, or even ALL backups of some item (though it doesn't seem to work reliably if the item has been renamed and thus backed up under different names).

Of course, there are cheaper options, too. See this question, and this video tutorial.

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