GPGMail: Apple Mail "An error occurred while trying to sign this message"

Nico's Avatar


14 Mar, 2018 09:56 AM


Been using GPG Suite for a long time. This morning, I can't send SMIME signed message, I get the following :

"An error occurred while trying to sign this message with a certificate from “[email blocked]”. Verify that your certificate for this address is correct, and that its private key is in your keychain."

I have several email accounts with SMIME certs and the behaviour is the same for all. Certs are in Keychain, with PK, and valid.

Uninstalled PGP Suite, reinstalled, same thing.

All I could google are old threads from years ago with nothing interesting.

Any clue ?



  1. Support Staff 1 Posted by Steve on 16 Mar, 2018 07:23 PM

    Steve's Avatar

    Hi Nico,

    welcome to the GPGTools support platform. Sorry you are having problems using GPG Suite.

    Could you see what happens if you remove and re-import your S/MIME certs to macOS keychain.

    Does that change anything?


  2. 2 Posted by Nico on 18 Mar, 2018 09:10 AM

    Nico's Avatar

    Hi Steve,

    Thanks for the answer. Removing and re-adding one of the cert did not change anything.

    Unfortunately, I will not be able to give more info on the matter, as I thought my Mac was starting to under perform and has not been reinstalled in a while (yeah, Mac OS is not what it used to be anymore ...) I decided to do a clean install over the weekend, not especially for my GPG Suite issue, but it just needed it I think.

    That being said, of course it did solve my issue, but unfortunatly it will not help much people who might have the same issue I had in the future.

    For me it was probably an Apple Mail related issue. If I had gone further in my troubleshooting, I might have started by forcing the install of a combo update, but I felt it was not a nice thing to do to that machine that was already performing "not as good"

    Thanks anyway,


  3. Support Staff 3 Posted by Steve on 19 Mar, 2018 09:44 AM

    Steve's Avatar

    Thanks for the update. Sorry you had to go through a clean install. But glad to hear, this issue is no longer happening for you. I'm closing this discussion. Should you need further assistance or have questions you can re-open this discussion here or open a new one any time.


  4. Steve closed this discussion on 19 Mar, 2018 09:44 AM.

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