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While trying to search in Mail.app, I somehow seem to have selected all Mail in one inbox and flagged them all (as important). Somehow a matter of two keystrokes.

How can I undo that? I want to remove the flags from all the Mail that didn't have flags 1 minute ago, without removing flags from the Mail that was actually flagged previously.

Clicking "Edit" in the menu bar shows that the Undo action is greyed out. I tried cmd-z anyway but it didn't do anything.

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There is initially an undo until you change mailbox. Once it's gone, it's gone. Even if you go back to the correct folder & reselect all the mails in the original selection, undo has 'expired'.

This leaves you with only the option to re-make the same selection & remove the flag. You can no longer get back to the original flagging.

I just tested this quite extensively on some junk I could afford to lose flags on.

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  • I did not change my mailbox
    – user150109
    Commented Jan 17, 2023 at 15:49
  • I could re-word it to 'until you perform some action that removes the undo'… that still leaves the same answer, once it's gone it's gone. There's an outside chance you could use Time Machine to recover the folder, but I don't think that works any more on newer macOS & even when it did, it was unreliable [not something I'm going to test just for 'fun']
    – Tetsujin
    Commented Jan 17, 2023 at 15:52
  • btw, by change mailbox, I just mean 'click any other folder'.
    – Tetsujin
    Commented Jan 17, 2023 at 15:52
  • I clicked search, then started typing, then while the list of mail items were filtered by search they flashed blue for a split-second (in my memory), when the search results displayed (no longer selected) they were all flagged, and at this moment I froze, and immediately looked for undo
    – user150109
    Commented Jan 17, 2023 at 15:58
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    just tested search. Whilst still in search, flag then undo is possible, even if the selection choice in there is changed. It disappears as soon as any other folder is selected, or search is exited. If I return later [without having done any other undo-able action] to the same search term, I get the undo back… but it's a false hope, because it doesn't actually work.
    – Tetsujin
    Commented Jan 17, 2023 at 16:05

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