GPGMail no longer working after macOS update

We do our best to ensure that macOS updates won't disable GPGMail. For that to work, please ensure you have our auto check for updates enabled:

Go to Mail.app > Preferences > GPGMail
In the updates section you find the relevant checkboxes.

GPGMail_pref.jpeg

macOS minor updates are mostly unproblematic. This statement does not apply to major updates for macOS. When Apple releases such a new version of macOS they change a lot of things in Mail.app. The fact that GPGMail no longer works is related to the circumstance, that Apple does not provide any APIs for Mail.app. If you think they should, please let them know via their feedback form.

Important: We highly recommend a conservative approach regarding major macOS updates. In case GPGMail is an essential part of your workflow do not update to the latest macOS release without checking our website for announcements regarding the OS update. Nobody will get hurt, if you are not on the new release on day one, but your known workflows may break.

Damn, too late - now what?

1. Get rid of the message about the incompatible GPGMail on every start of Mail.app

To temporarily disable GPGMail

  1. shut down mail.app
  2. open finder
  3. navigate to /Library/Mail/Bundles or ~/Library/Mail/Bundles and copy GPGMail.mailbundle to your desktop
  4. now delete GPGMail.mailbundle from the original folder

Restart mail. GPGmail should be gone from Mail.app > Preferences. To re-enable mail, close Mail.app and move the bundle file back to the Bundles folder.

2. Decrypt incoming mails

With GPGMail disabled encrypted mails will show with two attachments: Mail Attachment and encrypted.asc.

To decrypt such a message

  1. drag encrypted.asc to your desktop
  2. open TextEdit and drag the encrypted.asc on the TextEdit icon in the dock
  3. that will show the encrypted message in text form
  4. press ⌘A, right click and select Services > OpenPGP: Decrypt Selection
  5. that will result in the decrypted message (and signature)

decrypt.jpg

To view the garbled output in human readable form

  1. save the decrypted text as .txt file
  2. rename the .txt to .eml
  3. double click the .eml file

Mail will open and display an email with the decrypted content.

3. Use GPGServices to encrypt and sign messages

Creating an encrpyted (and signed) mail using GPGServices is not that hard.

  1. write your draft
  2. press ⌘A to select all text then
  3. right click and select Services > OpenPGP: Encrypt Selection
  4. add recipients to your liking in GPGServices and optionally sign the message
  5. this will created an encrypted (and signed) text message which you then can send to your friends

draft_macOS_workaround.jpg

A working GPGMail on the receiving machine will automatically decrypt the incoming mail (depending on the password settings).

Should you be missing the "Encrypt Selection" option please open System Preferences > Keyboard > Shortcuts > Services and ensure this option is enabled.