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After upgrading to Yosemite, Apple Mail no longer recognizes my S/MIME certificate. This was working in Mavericks. I've checked Keychain and the certificate is valid, even evaluated it as S/MIME for my email address and it passed. However, emails I send do not contain the certificate and I cannot figure out any way in Apple Mail to sign them.

Certificate evaluates successfully

I've read Apple's help article and it says an icon should display next to the From: field on new emails. However, I only use a single account with Apple Mail, so the From: field doesn't display. If I do add another account, just so that field displays, no signing icon is shown when I create a new email.

Any help would be greatly appreciated.

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  • I had this issue last week, fixed it for a day (by resetting mail), but now two days later it won't recognize my cert again. I'm having the same issue with a valid comodo certificate. Oct 20, 2014 at 14:33
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    I was successfully able to send signed emails as a reply to a signed email assuming I hadn't tried to send a new signed email in the open session of mail: 1. Start Mail 2. Try to send new signed email 2-results: fail 3. Try to reply to a signed mail with a signed mail 3-results: fail 4. Restart mail 5. Try to reply to a signed mail with a signed mail 5-results: successful 6. Try to send a new signed email 6-results: failed 7. Try to reply to signed mail from step 5 with a signed mail 7-results: fail Oct 20, 2014 at 16:14
  • @Dez When you say "resetting mail", what do you mean? I'll give that shot. Ironically, the upgrade worked fine on my Hackintosh, but not my MacBook.
    – Jon
    Oct 20, 2014 at 20:58
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    Sorry... I meant to quit and reopen mail. I'll update my comment... and I can't update it... nevermind. That's what I meant. Oct 20, 2014 at 20:58
  • Also found that I can't read email encrypted with my certificate unless I exit/open the mail app Oct 21, 2014 at 6:19

1 Answer 1

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I solved this problem by selecting my private key under my certificate (issued by Comodo) and in the get info window:access control tab deleting Mail.app from the "Always allow access..." list and adding it back immediately. When I saved the changes (to the keychain) and opened Mail, I was able to sign my messages again.

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