GPG Mail: macOS 13.2 Mail app: can no longer send email or save drafts

Matt Ruffalo's Avatar

Matt Ruffalo

25 Jan, 2023 07:07 PM


I'm no longer able to send email or save drafts through the builtin Mail app, after updating to macOS 13.2. When attempting to send a signed email, I see "Cannot send message", offering to let me choose a new mail server, with Connection Doctor as one option in this window (the Connection Doctor shows everything is okay with my SMTP server).

Additionally, if I leave a message open for a while, during which would save it as a draft, I see

""" This message can't be saved to the Drafts mailbox.

The message contains one or more attachments that are too large to be saved in the Drafts mailbox. Try deleting some attachments.

... but there are no message attachments. This behavior started with updating my computer to macOS 13.2 on Monday.

I'm able to send email and save messages as drafts after disabling GPG Tools, but I'd rather continue to send digitally-signed messages. For now I'm back to using Thunderbird -- I look forward to being able to use the macOS Mail app again.

Thank you!

  1. Support Staff 1 Posted by Steve on 25 Jan, 2023 07:10 PM

    Steve's Avatar

    Hi Matt,

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

    What you are reporting sadly is a known issue in GPG Suite 2022.2 which can appear in cases where a S/MIME certificate is available for the sender account.

    Our latest hotfix GPG Suite inlcudes a fix for this problem, which will be part of the next GPG Suite release.

    Can you please install that and report back if it resolves the issue for you.

    All the best,

    Disclaimer: Hotfixes are GPG Suite builds containing our latest source code, so bugs and crashes may occur.

  2. 2 Posted by Matt Ruffalo on 25 Jan, 2023 07:21 PM

    Matt Ruffalo's Avatar

    Thank you, Steve -- I installed the hotfix and can send mail and save drafts again :thumbsup:

    Much appreciated!

  3. Support Staff 3 Posted by Steve on 25 Jan, 2023 07:40 PM

    Steve's Avatar

    Glad this is solved for you. The patch will be part of the next GPG Suite. You can stay on the nightly build until then and will receive an update notification once the stable release is out and you have automatic update checks enabled.

    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 25 Jan, 2023 07:40 PM.

  5. Steve re-opened this discussion on 30 Jan, 2023 08:02 PM

  6. Support Staff 4 Posted by Steve on 30 Jan, 2023 08:02 PM

    Steve's Avatar

    We are still investigating this problem. We want to make sure what the cause is and that the fix which is already included in the nightly build applies in all scenarios our users may be using.

    It would be helpful, if you could send us the output of the following terminal command (easy to find via Spotlight):

    defaults read org.gpgtools.gpgmail DefaultSecurityMethod

    The output will either be 0 or 1 - sending that via a reply to this email wuold be great.

    Thank you & best regards,

  7. Steve closed this discussion on 30 Jan, 2023 08:02 PM.

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