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Messages no longer decrypting, pinentry-mac crashing

• Edit

michael.myers

19 Mar, 2012 05:38 PM

I've been using GPGMail version 2.0a30 for a while now without an issue. I have OS X 10.7.3. Today I logged into OS X and opened Mail, and none of my encrypted emails could be read. The PGP ciphertext is displayed in the message window, and the area above the message header displays the error "MESSAGE_BANNER_PGP_DECRYPT_GENERAL_ERROR_TITLE". When I click "Show Details" I get the message "MESSAGE_BANNER_PGP_DECRYPT_GENERAL_ERROR_MESSAGE" ... I wish that was more helpful.

I tried clicking "Fix" under "GPGMail" under "GPGTools" in System Preferences, but it didn't fix my situation. For the record, GPG continues to work fine in Thunderbird.

The contents of Console:
3/19/12 1:31:30.521 PM Mail: Using V2 Layout
3/19/12 1:31:30.590 PM [0x0-0xd58d58].com.apple.mail: objc[89711]: Class FlippedView is implemented in both /Applications/Mail.app/Contents/MacOS/Mail and /Users/mmyers/Library/Mail/Bundles/GPGMail.mailbundle/Contents/MacOS/GPGMail. One of the two will be used. Which one is undefined.
3/19/12 1:31:30.591 PM Mail: Logging Level: 1
3/19/12 1:31:30.594 PM Mail: GPG_PATH: /usr/local/MacGPG2/bin/gpg2
3/19/12 1:31:30.596 PM Mail: Can't load config (/Users/mmyers/.gnupg/gpg-agent.conf): Error Domain=NSCocoaErrorDomain Code=260 "The file “gpg-agent.conf” couldn’t be opened because there is no such file." UserInfo=0x7ffd1b546ac0 {NSFilePath=/Users/mmyers/.gnupg/gpg-agent.conf, NSUnderlyingError=0x7ffd1b5469d0 "The operation couldn’t be completed. No such file or directory"}
3/19/12 1:31:30.596 PM Mail: Can't load config (/Users/mmyers/.gnupg/gpg-agent.conf): Error Domain=NSCocoaErrorDomain Code=260 "The file “gpg-agent.conf” couldn’t be opened because there is no such file." UserInfo=0x7ffd1b549b30 {NSFilePath=/Users/mmyers/.gnupg/gpg-agent.conf, NSUnderlyingError=0x7ffd1b549740 "The operation couldn’t be completed. No such file or directory"}
3/19/12 1:31:30.597 PM Mail: Can't load config (/Users/mmyers/.gnupg/gpg-agent.conf): Error Domain=NSCocoaErrorDomain Code=260 "The file “gpg-agent.conf” couldn’t be opened because there is no such file." UserInfo=0x7ffd1d93ce80 {NSFilePath=/Users/mmyers/.gnupg/gpg-agent.conf, NSUnderlyingError=0x7ffd1d93caa0 "The operation couldn’t be completed. No such file or directory"}
3/19/12 1:31:30.601 PM Mail: GPG_PATH: /usr/local/MacGPG2/libexec/pinentry-mac.app/Contents/MacOS/pinentry-mac
3/19/12 1:31:30.601 PM Mail: sizeof(partCountForStatusCode) 84
3/19/12 1:31:30.648 PM Mail: * GPGMail: Enabled - Account for signing found.
3/19/12 1:31:30.654 PM Mail: Loaded GPGMail 2.0a30
3/19/12 1:31:31.285 PM Mail: CFPropertyListCreateFromXMLData(): Old-style plist parser: missing semicolon in dictionary.
3/19/12 1:31:32.123 PM Mail: NSExceptionHandler has recorded the following exception:
GPGException -- Decrypt failed!
Stack trace: 0x10fa67c69 0x7fff8b806d5e 0x111507cee 0x1114bac48 0x1114bbba2 0x1114b9b60 0x7fff8d5bd640 0x1114b96ff 0x7fff8d5bd1c2 0x7fff8d5bcff7 0x7fff8d5bcf35 0x7fff8d5bca0a 0x10d47384a 0x10d473732 0x10d4732c8 0x7fff8f9ccb05 0x7fff8d5b514a 0x7fff8f9936d8 0x7fff8f9a6936 0x7fff920a58ba 0x7fff920a6799 0x7fff912e63da 0x7fff912e7b85
3/19/12 1:31:32.200 PM ReportCrash: Saved crash report for pinentry-mac[89718] version ??? (???) to /Library/Logs/DiagnosticReports/pinentry-mac_2012-03-19-133132_localhost.crash

I'm attaching the crash report to this message.

Is this problem related to GPG-Agent?

• pinentry-mac_2012-03-19-133132_localhost.crash 30.6 KB

1. Support Staff 1 Posted by Luke Le on 19 Mar, 2012 05:51 PM

   

   It is in fact related to pinentry crashing. I've seen this problem before on my own mac but couldn't reproduce it after a while.
   Could you please try to install GPGMail or GPGTools Installer from http://nightly.gpgtools.org?

   That should most definitely fix the problem.

   • Edit

2. 2 Posted by michael.myers on 19 Mar, 2012 05:55 PM

   

   Thanks for your suggestion Luke.

   I reinstalled GPGTools, and afterward I checked my ~/.gnupg directory and saw a 0 byte file was present named gpg-agent.conf. Now when I open Mail.app, I am prompted to allow pinentry-mac the access to my Keychain, and if I do, then decryption works just fine. No more crashing.

   Why am I prompted to allow pinentry-mac to have access to my Keychain? I could be wrong, but I don't recall doing this before. Also, the prompt message says that "authenticity cannot be verified" (I guess this has something to do with OS X doing a code signature check?). I'm always paranoid about these sorts of prompts. ;-)

   • Edit

3. Support Staff 3 Posted by Luke Le on 19 Mar, 2012 06:02 PM

   

   Ah good, so at least a little progress.

   Try to write this information in your .gnupg/gpg-agent.conf:

   default-cache-ttl 1800
   pinentry-program /Users/mmyers/Library/Mail/Bundles/GPGMail.mailbundle/Contents/Frameworks/Libmacgpg.framework/Resources/pinentry-mac.app/Contents/MacOS/pinentry-mac
   max-cache-ttl 21600

   That might make things go back to normal.

   As for the keychain and verification problem, could you please post some screenshots?

   • Edit

4. 4 Posted by michael.myers on 19 Mar, 2012 07:07 PM

   

   Ok, the gpg-agent.conf file had since been filled in with the pinentry-program path in GPGTools:

   pinentry-program /usr/local/MacGPG2/libexec/pinentry-mac.app/Contents/MacOS/pinentry-mac

   I replaced that with the lines you suggested. It still works.

   As for the keychain approval prompt, I received it only once (even though I answered "Allow", not "Always Allow"). Once I switched to the other copy of the pinentry-mac executable as you suggested, I received the prompt again, and was able to take a screenshot (attached).

   • Screen_Shot_2012-03-19_at_3.03.26_PM.png 30.9 KB
   • Edit

5. Support Staff 5 Posted by Luke Le on 19 Mar, 2012 08:22 PM

   

   The one time question is only coming up, because this is a new version of pinentry-mac app. It's shown once for every new version, that's OS X's rule for apps accessing the keychain.

   • Edit

6. Support Staff 6 Posted by Steve on 20 Mar, 2012 12:36 PM

   

   We've created two tickets for this problem. If you want to receive notifications when anything is done related to this problem feel free to subscribe to:

   • http://gpgtools.lighthouseapp.com/projects/65162/tickets/137
   • http://gpgtools.lighthouseapp.com/projects/66001/tickets/86
   • Edit

7. Support Staff 7 Posted by Steve on 27 Mar, 2012 11:59 AM

   

   Again: please subscribe to the lighthouse tickets for updates. Closing this discussion for now. Should you have more problems or need help with anything please open a new discussion any time and we'd be glad to help you out.

   All the best, steve

   • Edit

8. Steve closed this discussion on 27 Mar, 2012 11:59 AM.

9. Steve closed this discussion on 02 Sep, 2012 10:05 PM.

10. Steve closed this discussion on 14 Aug, 2013 10:48 AM.