Freron MailMate

Comments and changes to this ticket

• 

  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?

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  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.

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  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:

  /Applications/MailMate.app/Contents/MacOS/MailMate
  

  That might also help.

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  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?

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  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.

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  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?

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

  I have the GPG Suite 2016.10 21 version.

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

  Installing GPG update now.

  And that fixes the problem for me.

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  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.

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  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:

  /Applications/MailMate.app/Contents/MacOS/MailMate
  

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  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:
  OpenPGP
   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"
  OpenPGP
   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
  /usr/local/bin/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
  Cipher: IDEA, 3DES, CAST5, BLOWFISH, AES, AES192, AES256, TWOFISH,
          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.

  Best,

  ---

  Laurent

  • Screen_Shot_2018-09-11_at_9.02.08_AM.png 142.5 KB

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  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.

  Thanks!

  ---

  Laurent

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  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.

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

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

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  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.)

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  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.