#737 new
Brian May

OpenGPG Signing doesn't work.

Reported by Brian May | April 29th, 2014 @ 05:45 PM

I created a signing identity with OpenPGP and can sign messages with other email clients, but with MailMate, when I try to send the email I get the following error:

USERID_HINT <neutered>  
NEED_PASSPHRASE 0<neutered>A 0<neutered>A 17 0  

Doesn't this mean that it should be OK to sign?

Running gpg (GnuPG/MacGPG2) 2.0.22
and the latest beta for MailMate 4199

Comments and changes to this ticket

  • benny

    benny April 29th, 2014 @ 10:04 PM

    Based on the output, it seems like it's hanging. You can try enabling debug output like this (in the Terminal):

    defaults write com.freron.MailMate MmDebugSecurity -bool YES

    And then launch MailMate like this:


    Part of the output is the gpg2 command used and its arguments. You can try that manually and see if that works.

    Thanks in advance.

  • Brian May

    Brian May April 29th, 2014 @ 10:37 PM

    input: 'Content-Type: text/plain

    gpg2 --no-verbose --batch --no-tty --openpgp --status-fd 2 --digest-algo SHA1 --textmode --armor --detach-sign --local-user "[neutered]" Input string (45): "Content-Type: text/plain\r\n\r\ntestsetsetset" Result: Failure Output string (0): "" Detail: [GNUPG:] USERID_HINT [neutered] Detail: [GNUPG:] NEED_PASSPHRASE [neutered] [neutered] 17 0 Detail: [GNUPG:] GOOD_PASSPHRASE Detail: [GNUPG:] BEGIN_SIGNING H2 Detail: gpg: DSA key [neutered] requires a 256 bit or larger hash Detail: gpg: signing failed: General error 2014-04-29 15:11:32.953 MailMate[57649:507] Warning: Unknown security problem (OpenPGP): unknown
    2014-04-29 15:11:32.954 MailMate[57649:507] Warning: Unknown security problem (OpenPGP): unknown
    2014-04-29 15:11:32.981 MailMate[57649:507] Warning: Unknown security problem (OpenPGP): unknown

    Apparently, it's the strength of my key that doesn't work with the command line option of "--digest-algo SHA1" Changing it from "--digest-algo SHA1" to "--digest-algo SHA256" works.

  • benny

    benny May 1st, 2014 @ 07:21 AM

    • State changed from “new” to “accepted”

    Ah, I think this is actually a known issue which I haven't fixed yet. A workaround is available with the following setting:

    defaults write com.freron.MailMate MmOpenPGPHashFunction -string sha256

    This is not a permanent solution, but it might work for you for now. (Restart MailMate.)

  • John Goodleaf

    John Goodleaf January 20th, 2015 @ 07:04 PM

    I am encountering the same error and have taken the steps suggested above.

    MM's signing dialog looks like:


    The console lists this:

    2015-01-20 10:54:49.591 MailMate[63122:10568022] Warning: Unknown security problem (OpenPGP): unknown

    Not particularly detailed.

    I am using MM build 5035 and the newest GPG Suite (Beta 4 for Yosemite).

  • Bill Cole

    Bill Cole May 3rd, 2015 @ 07:30 PM

    I was having this problem as well and it SEEMED like the preference change didn't take, because even after the change when I tried again to re-send the failed test message from the Drafts folder, the debug output showed:

    gpg2 --no-verbose --batch --no-tty --openpgp --status-fd 2 --digest-algo SHA1 --textmode --armor --detach-sign --local-user "bill@scconsult.com"

    This appears to be because MM is saving drafts which were set to be signed when they were saved with this header:

    Content-Type: multipart/signed;
    boundary="=_MailMate_432EC9DA-1963-489E-BD0A-1D3F06BFD353_="; micalg=pgp-sha1; protocol="application/pgp-signature"

    The workaround for this is to open the draft that couldn't be signed before the setting change, unset the signature toggle, save it, then re-open it and turn signing back on.

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