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Sometimes I can't, and sometimes I can. I want to be able to ⌘-Z after I accidentially delete a message. Or multiple messages. I want the Undo feature!

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Not an answer to your question at all, but just because some don't know: the integration of Mail in Time Machine is excellent. Just first activate Mail and then open Time Machine, and you'll see the starfield for Mail rather than for Finder. (Likewise: other time-machine-aware applications at en.wikipedia.org/wiki/…) –  Arjan Mar 10 '10 at 20:53

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For what it's worth Mail.app can undo deletions but it's limited. It can only do one undo and doesn't work on some accounts depending on the server's IMAP implementation (for example GMail accounts tend not to work). It depends if the server allows Mail.app to undo the IMAP action and whether or not the action has occurred on the server.

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It does appear to be a GMail thing. –  Josh K Mar 14 '10 at 23:05
    
See this thread: discussions.apple.com/thread/5527652?tstart=0 –  Mike Marcacci Aug 3 at 3:22

If you use IMAP with gmail...

Go to settings and then to the IMAP portion of the settings (it is currently called "Forwarding and POP/IMAP").

  • Change to Auto-Expunge off.

This will keep Mail and Gmail from immediately deleting (forever) any mail you delete. Then choose either archive the message of move the message to trash.

  • Moving to trash means that it will be deleted (again...forever) in 30 days.
  • Archiving it is similar in that it won't show up in your inbox, but it will stick around and will also be searchable in gmail.
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