Ventura + GPGMail 7.0 (2152) Cannot send encrypted mails

Matthias's Avatar


06 Nov, 2022 08:27 AM

Am I the only one with problems on sending (GPG) encrypted mails? Either I get "cannot save draft due to attachments" or "select SMTP server to send mail". Sending unencrypted and S/MIME mails works fine. I vaguely remember having this problem before (saving drafts), after another macOS update, one or more years ago.

  1. 1 Posted by Nico on 08 Nov, 2022 10:34 AM

    Nico's Avatar

    Thats the reason why I did not upgrade to Ventura and I am still waiting for psotive feedback :-D

  2. Support Staff 2 Posted by Luke Le on 08 Nov, 2022 08:46 PM

    Luke Le's Avatar

    Hi Matthias,

    we are hearing from a couple of people who are running into this problem, but where not able to reproduce it ourselves. Does this happen every time or can you somehow trigger it reliably? That would be very helpful.



  3. 3 Posted by Matthias on 09 Nov, 2022 07:36 AM

    Matthias's Avatar

    Hi Lukas,

    It is 100% not working for me. (No problems with macOS 12.) Some details: I have 4 IMAP accounts configured in (and 4 SMTP servers accordingly). My main account has 2 e-mail addresses; for both addresses I have S/MIME certificates as well as my PGP key. This IMAP server is Cyrus, the SMTP server is Exim.

    I tried saving drafts on IMAP server and locally; I tried saving drafts encrypted and not encrypted (GPGMail setting). No difference, all combinations not working.

    I tried to get some debug output by setting
    (sudo) defaults write org.gpgtools.common DebugLog 1 and looking /var/log/system.log … but nothing PGP related in there.

    Anything else I can provide to help reproduce this?


  4. Support Staff 4 Posted by Luke Le on 16 Nov, 2022 03:06 PM

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    Hi Matthias,

    thank you for your patience.
    It's good (bad of course for you) that this is reproducible. Do you have a screenshot of the error message by any chance? Is their any additional detail to only not being able to send the message?

    Would you consider having a remote debug session with us where one of our developers (in this case I) would log onto your computer and debug the problem directly on your machine?
    Requirement would be to disable SIP temporarily (only during the debugging session) and install Xcode.



  5. 5 Posted by Matthias Zepf on 17 Nov, 2022 10:38 AM

    Matthias Zepf's Avatar

    Hallo Lukas,

    ja, das können wir gerne machen. Wir müssen nur einen geeigneten Zeitpunkt finden (bin wie viele im Jahresendstress); am besten mal abends oder am Wochenende. Wie stellst Du Dir den Remote-Zugriff vor, Apples VNC?


  6. Support Staff 6 Posted by Luke Le on 24 Nov, 2022 08:52 AM

    Luke Le's Avatar

    Ah super. Wie würde es morgen gegen 20.00 bei dir aussehen (UTC+1, CET)?

    Liebe Grüße


  7. 7 Posted by Matthias Zepf on 24 Nov, 2022 11:48 AM

    Matthias Zepf's Avatar

    Also, Freitag, 25.11., ja, machen wir.

  8. Support Staff 8 Posted by Luke Le on 25 Nov, 2022 06:16 PM

    Luke Le's Avatar

    Hi Matthias,

    ich habe mittlerweile die Ursache und Lösung für dieses Problem gefunden und bin aktuell dabei ein hotfix GPG Suite vorzubereiten die diesen Fix inkludiert. Sobald diese bereit steht geb ich dir Bescheid. Die Remote debug session ist so also nicht mehr notwendig.

  9. 9 Posted by Matthias Zepf on 25 Nov, 2022 06:22 PM

    Matthias Zepf's Avatar

    Danke, auch recht! :)

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