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GPGMail: Problem decrypting on OSX Sierra

• Edit

Mark El-Khoury

23 Mar, 2017 05:33 PM

Hi :)
I’ve had troubles automatically decrypting email on GPGTools for OS X Sierra. After some testing this is what I noticed:
- If an email is encrypted AND signed, i can decrypt it normally. - If an email is encrypted only and NOT signed, it does not get decrypted by GPGTools on Mail.app. I would have to download the encrypted email to my file system and decrypt it using the command line.

Expected
If an email is encrypted but not signed, it should still be decrypted with the same key

Additional info
Feel free to reach out to me directly if you need more info. Thanks :)

Mac OS X        10.10.5             (14F1713)
Libmacgpg       0.7         769 
GPGMail         2.6.1       1151
GPG Keychain    1.3.1       1223
GPGServices     1.11        907 
MacGPG2         2.0.30      875 
GPGPreferences  2.0         887 
Pinentry        0.9.7       2

1. Support Staff 1 Posted by Luke Le on 23 Mar, 2017 05:37 PM

   

   Hi Mark,

   we're very sorry you're seeing this issue.

   the version info you've posted are showing a Yosemite installation. Are you testing on two different computers?
   Is there any chance that the message goes through an MS Exchange server?
   Would you mind posting a screenshot of your message that can't be decrypted?

   Thanks!

   • Edit

2. 2 Posted by Mark El-Khoury on 23 Mar, 2017 05:45 PM

   

   Hi Luke, you are correct the issue was on a different machine (Sierra VM) so i did not include debug information. I believe the message was not going through an MS Exchange server, I will confirm and get back to you if it is actually going through MSExchange.

   I just retested the issue, and noticed that it now properly decrypts as I saved my PGP key in the keychain on the Sierra machine. I believe the issue was that if it is encrypted but not signed, I was not getting prompted to enter my PGP passphrase at all, so the message would stay in encrypted form, as if I hit ‘cancel’ on the prompt to enter my passphrase.

   • Edit

3. Support Staff 3 Posted by Luke Le on 23 Mar, 2017 05:47 PM

   

   Hi Mark,

   hmm... this sounds strange, since even if you didn't have your private key pair on your Sierra machine, GPGMail should have shown an error banner above the message, telling you, that the message couldn't be decrypted due to a missing private key.

   Please keep us updated on this issue.

   • Edit

4. 4 Posted by Mark El-Khoury on 23 Mar, 2017 05:47 PM

   

   Hey Luke,

   I just verified, and the outbound email does go through an MS Exchange server.

   > On Mar 23, 2017, at 1:45 PM, Mark El-Khoury <[email blocked]> wrote:
   >
   > Hi Luke, you are correct the issue was on a different machine (Sierra VM) so i did not include debug information. I believe the message was not going through an MS Exchange server, I will confirm and get back to you if it is actually going through MSExchange.
   >
   > I just retested the issue, and noticed that it now properly decrypts as I saved my PGP key in the keychain on the Sierra machine. I believe the issue was that if it is encrypted but not signed, I was not getting prompted to enter my PGP passphrase at all, so the message would stay in encrypted form, as if I hit ‘cancel’ on the prompt to enter my passphrase.
   >
   >> On Mar 23, 2017, at 1:37 PM, Luke Le <[email blocked]> wrote:
   >>

   • Edit

5. Support Staff 5 Posted by Luke Le on 23 Mar, 2017 05:50 PM

   

   Aaah ok, that might be related as well.
   After releasing the Beta 3, we have found a few issues with encrypted messages going through MS Exchange. Unfortunately MS Exchange really likes to alter the structure of PGP/MIME message, which lead to the problem, that they were no longer properly recognized as encrypted messages in some cases.

   We have since fixed this issue in the nightly of GPG Suite.
   It would be great if you could test it and report back if it helps.

   https://releases.gpgtools.org/nightlies/

   Disclaimer: This is a development version which has not been thoroughly tested yet - bugs or crashes are to be expected. Thanks for helping us test.

   • Edit

6. 6 Posted by Mark El-Khoury on 23 Mar, 2017 05:56 PM

   

   Looks like the latest release has successfully resolved this issue! This was consistently reproducible a few days ago but I can’t reproduce this anymore.

   Thank you so much for your quick responses :)

   • Edit

7. Support Staff 7 Posted by Luke Le on 23 Mar, 2017 05:57 PM

   

   Oh that is very great to hear!
   You're very welcome :)

   Have a nice day!

   Closing this discussion. Feel free to open a new one anytime should you have questions or run into problems.

   • Edit

8. Luke Le closed this discussion on 23 Mar, 2017 05:57 PM.

9. Luke Le re-opened this discussion on 23 Mar, 2017 05:57 PM

10. Luke Le closed this discussion on 23 Mar, 2017 05:58 PM.

11. Steve closed this discussion on 23 Mar, 2017 09:15 PM.