GPGMail: Passphrase

Andreas's Avatar


11 Dec, 2017 11:41 AM

As of late when I have Apple Mail open. It keeps asking me for the PGP password/passphrase.
I keep having to type it in, sometimes multiple times in a row for no apparent reason. The remember option is not available only show option.

That it stops asking me for my passphrase and use what it has been told to.

macOS                   10.12.6     16G1114
GPG Suite               2017.2      2063    (e459897)
GPGMail                 2.7.1       1254    (7d871d1)
GPG Keychain            1.4.1       1391    (b5c89a4)
GPGServices             1.11.2      969     (e5438f7)
MacGPG                  2.2.3       895     (17e3e67)
GPG Suite Preferences   2.1.1       993     (05eb1a6)
Libmacgpg               0.8.1       826     (9410d73)
pinentry                0.9.7       6       (6aeb033)
  1. 1 Posted by Andreas on 11 Dec, 2017 07:21 PM

    Andreas's Avatar

    It got worse and I ended up getting the following error msg.

    Search keys failed!
    Code = 0
    Error text:
    gpg: suche nach "andi@******" auf hkps-Server
    gpg: Keine Handhabungsroutine f"ur Schl"usselserverschema `hkps'
    gpg: Suche auf dem Schl"usselserver fehlgeschlagen: Schl"usselserverfehler

    It seems to be a common occurance on OS X (or whatever rebranded name the fruit tree uses now) that the GPG stops working without reason.
    If you open Terminal and /usr/local/MacGPG2/bin/gpg2 --verbose --search-keys 0x00000000
    You will probably end up with
    gpg: no running Dirmngr - starting '/usr/local/MacGPG2/bin/dirmngr'
    gpg: waiting for the dirmngr to come up ... (5s)
    gpg: connection to the dirmngr established
    gpg: error searching keyserver: End of file
    gpg: keyserver search failed: End of file

    Or something along those lines. I did the following and it resolved the problem.

    1. Download the latest copy or nightly if you like ( but it should also work with the standard stable version.
    2. Close system preferences, and also Mail (or what ever you are using, Thunderbird, Outhouse, etc.)
    3. Open .dmg, double click Uninstall.
    4. Follow onscreen instructions.
    5. Check in System preferences that GPG Suite is gone.
    6. Double click Install.
    7. Follow onscreen instructions.
    8. Check in System preferences the GPG Suite settings are correct, and correspond to what you used to have.
    9. Open terminal and /usr/local/MacGPG2/bin/gpg2 --verbose --search-keys 0x00000000
    10. You should have a very verbose response, from your chatty mac, with loads of RSA keys. Q to quite it.
    11. Open up mail. All should now work, although it will probably ask for you GPG password or passphrase.

    I'm assuming with the new OS X etc security patches things get borked, and there are no options to do a repair prefs. This is the alternative.

    Have phun :)

  2. 2 Posted by Andreas on 13 Dec, 2017 11:31 AM

    Andreas's Avatar

    Correction it does not work with the standard, but does for 2017-12-09 GPG Suite 2017.2 (2068n).

    So don't accept the updates later or it will bork again. There is clearly something buggy in the standard version.

  3. Support Staff 3 Posted by Luke Le on 13 Dec, 2017 02:35 PM

    Luke Le's Avatar

    Hi Andreas,

    we are very sorry you are experiencing issues with the latest version of GPG Suite.
    It is unfortunately true that there are two bugs which are affecting a very small set of our users in the latest stable, which we only found out about after releasing it.
    Both bugs are fixed in the current nightly version.

    The passphrase bug you were seeing is related to GPG Suite picking a custom GnuPG installation (which you probably have installed a very long time ago) instead of our own.
    The keyserver bug is triggered by a crash in gnutls in case no dirmngr is running and a keyserver other than the popular key server. It is related to a use of macOS API in a child process which is not allowed according to Apple.

  4. Support Staff 4 Posted by Steve on 22 Dec, 2017 09:32 PM

    Steve's Avatar

    A fix for both problems you were seeing is included in the latest GPG Suite 2017.3 release.

    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.


  5. Steve closed this discussion on 22 Dec, 2017 09:32 PM.

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