#2092 new
Laurent Michel

GPG broken with latest update?

Reported by Laurent Michel | September 10th, 2018 @ 10:42 PM

I used to have GPG email signing working flawlessly. This morning I updated to the latest and greatest of MailMate.... And found that every email signing request fails :-(

Nothing else has changed on my Mac. Any ideas?


Comments and changes to this ticket

  • benny

    benny September 11th, 2018 @ 06:56 AM

    I don't (yet) have reports about a general issue. In what way does it fail? Do you get any error messages? Do you have a “Show Details” button which might tell us more about how it fails?

  • Jeroen Leenarts

    Jeroen Leenarts September 11th, 2018 @ 08:28 AM

    I did a clean install this weekend on a new Macbook. After installing GPGTools everything was working.

    You mention latest and greatest. Is that the release version r5523?

    I know having the gpg2 command line tool available is required. Maybe something changed in your paths inadvertently. I'd check that. maybe even try reinstall GPGTools. Or check your home-brew install.

  • benny

    benny September 11th, 2018 @ 08:31 AM

    Yes, r5523 is the latest release.

    Note that you can enable a debug variable in a Terminal window to see how MailMate calls gpg2:

    defaults write com.freron.MailMate MmDebugSecurity -bool YES

    Then launch MailMate like this:


    That might also help.

  • Ulrike

    Ulrike September 11th, 2018 @ 09:50 AM

    I have the same problem that Laurent reports: After upgrading to r5523, signing (haven't tried encrypting) has ceased to work, with no other changes to the machine (still running Sierra).

    There is in fact a detailed error message, it reads "Signing or encryption failed for unknown reasons."

    I set the debug variable as recommended and get "Warning: Refused to send email with unresolved security warnings. Please report this issue." in the terminal. The email is in fact not sent with no other feedback in the GUI (hm...).

    I don't see the actual call to gpg2 in the terminal, am I looking in the wrong place?

  • Mathias Woringer

    Mathias Woringer September 11th, 2018 @ 12:04 PM

    I haven't changed anything on my El Capitan Mac (I'm also using an older version of GPG from last year).

    I can't decrypt encrypted mails from my colleagues, although I have their public key. I'm also using OSX mail as well and the decryption works flawlessly.

    Here is the error message:

    Result: Failure
    Output string (0): "" Detail: gpg: invalid option "--compliance"

    So this update definitely broke the old GPG. I'm not sure I want to install the latest GPG version though.

  • Lars

    Lars September 11th, 2018 @ 12:12 PM

    That option was introduced with GnuPG 2.1.16 released November 18th, 2016. Which version are you using exactly?

  • Mathias Woringer

    Mathias Woringer September 11th, 2018 @ 12:33 PM

    I have the GPG Suite 2016.10 21 version.

  • Mathias Woringer

    Mathias Woringer September 11th, 2018 @ 12:39 PM

    Installing GPG update now.

    And that fixes the problem for me.

  • Lars

    Lars September 11th, 2018 @ 12:42 PM

    That is still running on GnuPG 2.0.30 which is why that option is not recognised; the next update after that, which is GPG Suite 2017.1, made the jump to GnuPG 2.2.

    Most recent would be GPG Suite 2018.3 from earlier this year, which fixes important security issues.

    Even if benny solves this compatibility issue, it is most likely an excellent idea to update that outdated software.

  • benny

    benny September 11th, 2018 @ 12:48 PM

    I think it's fine if MailMate requires a more recent (and safer) version of gpg2. As long as it is available via GPGTools (and maybe homebrew).

    @Ulrike: You also have to launch MailMate from the Terminal window to get the error messages in the same window:

  • Laurent Michel

    Laurent Michel September 11th, 2018 @ 01:04 PM

    Ok, I enabled debugging and here ios what I captured. First, see the screenshot for what appears in the UI of MailMate. Second, here is what shows up in the terminal window:

    ldm at abraracourcix in ~
    $ /Applications/MailMate.app/Contents/MacOS/MailMate
    2018-09-11 09:00:23.495 MailMate[92756:4395904] altered replacementRange: {0, 16}
    2018-09-11 09:00:23.495 MailMate[92756:4395904] replaceString:
     gpg2 --no-verbose --batch --no-tty --compliance "openpgp" --status-fd 2 --textmode --armor --local-user "<ldm@redacted.org>" --detach-sign
     Input string (53): "Content-Type: text/plain; markup=markdown\r\n\r\n\r\n"
     Result: Failure
     Output string (0): ""
     Detail: gpg: invalid option "--compliance"
     gpg2 --no-verbose --batch --no-tty --compliance "openpgp" --status-fd 2 --textmode --armor --local-user "<ldm@redacted.com>" --detach-sign
     Input string (243): "Content-Type: text/plain; charset=utf-8; markup=markdown\r\nContent-Transfer-Encoding: quoted-printable\r\n\r\n\r\nThis is a test attempt at sending from one address of mine to another a s=\r\nigned e..."
     Result: Failure
     Output string (0): ""
     Detail: gpg: invalid option "--compliance"

    So there is a --compliance option that gpg2 does not like.

    I checked my gpg version:

    $ which gpg2
    ldm at abraracourcix in ~
    $ gpg2 --version
    gpg (GnuPG/MacGPG2) 2.0.30
    libgcrypt 1.7.0
    Copyright (C) 2015 Free Software Foundation, Inc.
    License GPLv3+: GNU GPL version 3 or later <http://gnu.org/licenses/gpl.html>
    This is free software: you are free to change and redistribute it.
    There is NO WARRANTY, to the extent permitted by law.
    Home: ~/.gnupg
    Supported algorithms:
    Pubkey: RSA, RSA, RSA, ELG, DSA
            CAMELLIA128, CAMELLIA192, CAMELLIA256
    Hash: MD5, SHA1, RIPEMD160, SHA256, SHA384, SHA512, SHA224
    Compression: Uncompressed, ZIP, ZLIB, BZIP2

    Maybe I need to upgrade this? If that's the issue, maybe the UI should simply tell me. Let me know.



  • Laurent Michel

    Laurent Michel September 11th, 2018 @ 01:10 PM

    And upgrading gpg2 solved the issue!

    Perfectly happy to upgrade. It would be nice if the UI had told me that this was a required upgrade.



  • benny

    benny September 11th, 2018 @ 01:56 PM

    @Laurent: Yes, it wasn't on purpose. I didn't actually know --compliance was a new gpg2 setting.

  • Laurent Michel

    Laurent Michel September 11th, 2018 @ 02:04 PM

    @benny: Not a problem! I should have thought about updating GPG. Loves MailMate to death ;-)

  • Ulrike

    Ulrike September 12th, 2018 @ 06:26 AM

    Upgrading gpg2 solved the issue for me, as well.

    Thanks for talking us through this, benny! (Btw, I did start MailMate from the terminal - but it's all good now, so never mind.)

  • benny

    benny September 12th, 2018 @ 07:19 AM

    • State changed from “new” to “resolved”

    I'm glad it works for everyone. I'll look into improving some of the error output which wasn't as helpful as it should have been.

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