Apple Mail (web)

hal's Avatar


05 Apr, 2012 08:20 PM


Your program looks and works great. So thank you!

But everytime I launch Apple Mail, it always nags me for the passphrase which gets alittle annoying. Even when I select, the "Save in Keychain" checkbox on the passphrase prompt box, or actually even when I select "Download updates automatically" in the Pref pane, and then I quit and relaunch Mail, it does NOT retain these settings, and then I get the Passphrase prompt again! It's annoying. Am I doing something wrong? Anyway this can be fixed?

I'm using the latest versions of everything:

Mac OS X Lion 10.7.3 (11D50d)
Apple Mail Version 5.2 (1257) with GPGMail 2.0a30
on a MacBook Air 13-inch, Mid 2011



  1. 1 Posted by Hal Wong on 05 Apr, 2012 09:08 PM

    Hal Wong's Avatar

    Hey, it looks like I fixed it! I'm not sure exactly what I did but I'll explain step by step. So using Spotlight, I pulled up the Keychain Access tool that is bundled with OSX. Next I selected "Keychain Chain" in the main menu, then "Keychain First Aid". Then I authenticated myself, selected "Repair" and let it run. Afterwards, I got "No problems found. Repair Complete" while I noticed a strange looking empty keychain called PrivateEncryptedDatak which is this upon further investigation.

    ~/Library/Application Support/Adobe/AIR/ELS/com.adobe.amp.4875E02D9FB21EE389F73B8D1702B320485DF8CE.1/PrivateEncryptedDatak

    So, I selected that weird Keychain in the left sidewindow, did an option click, and selected "Unlock Keychain". Next, I was prompted for a password, which I tried all my system passwords to no avail. Finally, I tried an empty password and it worked. Then I option clicked again and selected "Delete Keychain" and clicked "Delete References and Files". Then I relaunched Apple Mail, and no more nagging Passphrase message! I'm not sure if it was a result of the Repair or the cleanup of this weird empty Keychain but everything works as expected now. Thought I would share this info because I see a few people complaining about the same thing.



  2. Support Staff 2 Posted by Luke Le on 06 Apr, 2012 10:50 AM

    Luke Le's Avatar

    Hi Hal,

    what you're describing are known issues which will be fixed in the GPGMail 2.0 stable version which is to be released soon.

  3. 3 Posted by Hal on 06 Apr, 2012 11:28 PM

    Hal's Avatar

    As I mentioned in my reply, I seemed to have fixed this issue. I do agree that the whole process is very flakey. I had to also go into the System Preferences and enable "Use Keychain to store passphrases". It required many relaunching of Apple Mail and reboots for it to stick, but eventually, I got it working. I'm no longer prompted for the passphrase when opening up Apple Mail, and it appears it work properly now.

  4. Support Staff 4 Posted by Steve on 07 Apr, 2012 08:05 AM

    Steve's Avatar

    Great to hear you are now setup. The current process might be confusing and we are thinking about how to better deal with this, but changes like integrating the whole GPGPreferences into GPGMail aren't easily done. Also not all settings that can be made in the GPGPreferences might be GPGMail related etc.

    So, yes this will most likely be tweaked on the long run, but don't ask us what our solution will look like (yet). :)


  5. Steve closed this discussion on 15 Apr, 2012 12:25 PM.

Comments are currently closed for this discussion. You can start a new one.

Keyboard shortcuts


? Show this help
ESC Blurs the current field

Comment Form

r Focus the comment reply box
^ + ↩ Submit the comment

You can use Command ⌘ instead of Control ^ on Mac