I am getting this message every time I start mail.app.

I've read this tech note, but neither checkbox is selected.

I've run Keychain First Aid, and no problems were found.

How do I fix Mail.app in Lion that keeps asking for keychain password?

UPDATE: Thanks everyone for the help.. I finally deleted the Keychain prefs. Re-entered passwords as required, and that worked.

  • I've experienced the same with Teamviewer. No solution still.
    – Hoshts
    Aug 17, 2012 at 8:29
  • 1
    What does codesign -vv /Applications/Mail.app/ return?
    – Lri
    Aug 17, 2012 at 13:32
  • Thanks Lri, I will try this on Sunday, when I visit this client again.
    – ICL1901
    Aug 17, 2012 at 15:48
  • responds: valid on disk, satisfies its Designated Requirement
    – ICL1901
    Aug 19, 2012 at 15:11

3 Answers 3


Quit Mail. Open Keychain Access (Applications > Utilities). Select your Login keychain. Run Keychain First Aid (Keychain Access menu > Keychain First Aid).

Put in your password and run a verify. If there's any red, select repair and run it. Run another verify to make sure the errors are fixed.

Delete all of your mail entries. In the search bar, try putting in things like "pop," "imap", "gmail", even your email address. Quit Keychain Access.

Launch Mail. Get into the preferences (Mail menu > Preferences > Accounts). Fill in the passwords for each of your accounts. Also, go to the SMTP/Outgoing server menu, and edit. Fill in the passwords there as well. Close and save. Exit mail.

Launch mail. Make sure it retrieves mail properly. Send test emails to make sure it sends properly.


  • in the question, I wrote that I have tested Keychain. No issues. The computer uses iCloud so no POP/IMAP. It does receive mail ok. Other ideas are welcome. I'm not sure why you got upvoted though..
    – ICL1901
    Aug 17, 2012 at 15:47
  • 2
    Why the hostility? I may have been upvoted because this is a good start to repairing password remembering problems. That aside: OK, instead of searching for those strings, search for iCloud, or "@me", or "@mac". Am I dumbing this down too much for you? Basically, get rid of any keychain entries that are related to the email address you're having problems with. Does any other application have password issues? If not, the next logical step would be to blow away mail prefs.
    – Harv
    Aug 17, 2012 at 16:14
  • Apologies Harv. Long Day. Thanks for the follow up. I'll look at it on Sunday.
    – ICL1901
    Aug 18, 2012 at 4:02
  • We've all had that, it's not a problem. Let's get your issue dealt with!
    – Harv
    Aug 18, 2012 at 20:34
  • 1
    @GeneJ I wouldn't write it off so easily. You're right: in my experience the Office suite tends to act a bit funny in general, but I have seen Outlook remember passwords properly. Keep digging.
    – Harv
    Nov 27, 2012 at 18:55

What worked for me was deleting the Keychain prefs. Re-entered passwords as required, and that worked. phew!


@Hoshts I have just experienced the same problem with TeamViewer. In my case, it was a problem with the proxy. In the Preferences, I had to manually set the proxy settings (instead of Use webbrowser proxy) and it worked fine.

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