Can't send iCloud mail in Mac OS 10.15.2 with GPG signature enabled

emshusterman's Avatar


10 Jan, 2020 03:42 AM

Which of our tools is giving you problems?

GPG Mail v4.0 build 1515

Attach a screenshot of the version info for all installed components (how to:

Describe your problem. Add as much detail as possible.

Mail suddenly stopped sending GPG signed messages on the iCloud account yesterday. Worked fine until then. Error logging shows server authentication error. No issue with GPG signature turned off.

What did you expect instead

To be able to continue to send signed mail...

Describe steps leading to the problem.

Nothing. Suddenly started happening yesterday.

Are you using any other plugins?


  1. 1 Posted by dib on 10 Jan, 2020 10:02 PM

    dib's Avatar

    Just confirming your issue. I spent a good amount of time with Apple Support today documenting this issue. I believe it is an apple problem. When you have a signature section, you get a 550 5.7.1 Command rejected after sending the message. It also affects mail relayed to apple mail servers via SMTP.

  2. Support Staff 2 Posted by Luke Le on 10 Jan, 2020 10:45 PM

    Luke Le's Avatar


    Thank you for bringing this issue to our attention. We are trying to get in touch with someone at Apple to figure out what is going on. Unfortunately in this case we can't do anything on our side.

  3. 3 Posted by emshusterman on 10 Jan, 2020 11:07 PM

    emshusterman's Avatar

    OK thanks. I also spent a lot of time with Apple yesterday and sent extensive logs.

    So no fix yet?

    Sent from my iPhone

  4. 4 Posted by dib on 11 Jan, 2020 02:04 PM

    dib's Avatar

    It appears that Apple have fixed their servers. I just sent an email with a signature.

  5. Support Staff 5 Posted by Luke Le on 11 Jan, 2020 02:05 PM

    Luke Le's Avatar

    Can confirm. we are seeing the same.

    That was a quick turnaround for once.

  6. 6 Posted by emshusterman on 11 Jan, 2020 10:39 PM

    emshusterman's Avatar

    Yes, seems to work now. Thanks.

  7. emshusterman closed this discussion on 11 Jan, 2020 10:39 PM.

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