GPGMail: Suddenly asking for passphrase for every email

Jon Farhat's Avatar

Jon Farhat

09 May, 2018 01:17 AM

My save to keychain is checked and this has been working fine for some time. I usually sign all my emails, and encrypt only a few. I expect to add passphrase for encryption, but for some reason it's now asking me to for a passphrase for just a signed one... which it never did before.

And, I can't turn it off, because it always defaults for at least signing, thus blue icon check, even if lock is not activated.

How it worked for months... now changed for no reason.

macOS                   10.13.3     17D47
GPG Suite               2018.1      2083    (9658b70)
GPGMail                 3.0b4       1272    (461cda15)
GPG Keychain            1.4.2       1403    (128637e)
GPGServices             1.11.2      969     (e5438f7)
MacGPG                  2.2.3       900     (cead4f9)
GPG Suite Preferences   2.1.1       993     (05eb1a6)
Libmacgpg               0.8.2       829     (943132e)
pinentry           9       (db18340)
  1. Support Staff 1 Posted by Steve on 09 May, 2018 07:41 AM

    Steve's Avatar

    Hey Jon,

    the pinentry requests you are seeing could be happening due to the migration from MacGPG 2.0 to 2.2.

    Please visit the following KB-article and let me know if that brings you back to the expected state.


    PS: PS: To benefit from the latest security fixes from apple, you may want to check for pending macOS updates in the MacAppStore. General info about Apple security releases including the latest macOS release.

  2. 2 Posted by Jon Farhat on 09 May, 2018 12:58 PM

    Jon Farhat's Avatar

    Since this update everything has gone pear-shaped. The program is unusable and your suggested fixes are not working. WHY did you guys screw this up?

    Keychain access no longer has gnupg.

    gpg --import < ~/.gnupg/secring.gpg
    MacBook-Pro:~ jon$ gpg --import < ~/.gnupg/secring.gpg
    -bash: /Users/jon/.gnupg/secring.gpg: No such file or directory
    MacBook-Pro:~ jon$

  3. Support Staff 3 Posted by Steve on 09 May, 2018 01:54 PM

    Steve's Avatar

    Should you be available, could you hop on our live chat here:

    We can't promise a solution, but we'd like to inspect this problem in more detail. When joining the live chat, please post the URL of this discussion so we know which case you are contacting us about.

    All the best

  4. Support Staff 4 Posted by Steve on 09 May, 2018 04:31 PM

    Steve's Avatar

    Resolved by updating macOS to 10.13.4. After the update the password for Jon's OpenPGP key was again stored in macOS keychain as expected.

    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 09 May, 2018 04:31 PM.

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