GPGMail: Issues with decrypting mail sent with GPG4O

Alex Abdo's Avatar

Alex Abdo

25 Jan, 2017 05:56 PM


When I receive mail that is encrypted using GPG4O and that is composed in HTML, GPGTools does not decrypt the message. Instead, it is shown as a totally blank email. When I view the raw source, I can see the base-64 encoded source, decode it, and then decrypt it just fine. But GPGTools doesn’t seem to be doing that for some reason.

Any thoughts?


That GPG Tools would present the decrypted version of either the HTML or of the plain text version of it.

macOS           10.12.1     16B2657
GPG Suite       2017.1b2    31b 
GPGMail         2.7b2       1192b
GPG Keychain    1.3.3b1     1249b
GPGServices     1.11        916 
MacGPG2         2.0.30-1b2  887-
GPGPreferences  2.0.2b2     912b
Libmacgpg       0.7         775 
pinentry        0.9.7       4
  1. Support Staff 1 Posted by Luke Le on 25 Jan, 2017 06:54 PM

    Luke Le's Avatar

    Hi Alex,

    Could you please forward such a message so we can have a look at the structure?
    Since it's not encrypted to our key we won't be able to read the contents.


  2. 2 Posted by Tobias on 29 Jan, 2017 02:45 PM

    Tobias's Avatar

    my name is Tobias and I am part of the gpg4o team.
    We would gladly help GPG Tools resolving this issue.

    To test compatibilty between OpenPGP impelmentation we provide the mail address
    [email blocked] where you can send us signed and encrypted mails.
    The public key can found on SKS - keyid 9B058941 74DEBFA4

    You can get into contact with us so we can provide you with testmails and/or information.

    Best regards

  3. Support Staff 3 Posted by Steve on 30 Jan, 2017 07:24 PM

    Steve's Avatar

    Done. Let's wait for the test reply so we can try and reproduce the problem.

  4. Support Staff 4 Posted by Steve on 15 Mar, 2017 10:51 PM

    Steve's Avatar

    Hi Alex,

    we are now in touch with Tobias from GPG4O who sent us various text mails. All test mails which we received where successfully decrypted and none showed as a blank email.

    Have you updated to macOS 10.12.3 by now? And could you please download and install our latest GPG Suite nightly build and see if the problem persists. That page also has sig and SHA256 to verify the download.

    All the best,

    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.

  5. 5 Posted by Alex Abdo on 24 Mar, 2017 04:55 PM

    Alex Abdo's Avatar


    Thanks so much for following up. I updated to 10.12.3 and installed the
    latest nightly build (from 3/22). I just solicited a few test emails
    from someone running GPG4O, and they decrypted just fine. I'm not sure
    if it's because of the update or because of something else, but I will
    definitely keep monitoring.

    I did notice in several of the emails sent to me that Apple Mail
    duplicated the decrypted text. An example is attached. Not sure what's
    going on, although it doesn't appear to be affecting my ability to see
    what the sender wrote. Also, it doesn't happen for subsequent emails in
    the thread—just the original one.

    Thanks again!


  6. Support Staff 6 Posted by Steve on 27 Mar, 2017 02:22 PM

    Steve's Avatar

    Alex, thanks for the feedback. Good to hear mails are now decrypting as expected.

    We have a ticket for the remaining problem. I connected this discussion with the existing ticket. That means, should this discussion get closed, it will be re-opened as soon as the ticket is closed. That way you'll stay in the loop and get notified as soon as we have news. Feel free to open a new discussions should you run into further problems or need assistance.

    All the best,

  7. Support Staff 7 Posted by Luke Le on 27 Mar, 2017 02:42 PM

    Luke Le's Avatar

    @Tobias: Could you tell us how to properly display these kind of messages? What we're currently doing is display the content of the PGPexch.htm file as part of the "normal" message content. That's also I believe why it's displayed twice. Once the text/plain part and the PGPexch.htm. How do you display these kind of messages?

  8. 8 Posted by Alex Strobel on 28 Mar, 2017 07:15 AM

    Alex Strobel's Avatar

    Hi Luke Le,

    my name is Alex Strobel and I am part of the gpg4o team too. Tobias asked me to answer your question regarding the email format. A few days ago I have had some discussion regarding how to display images within the HTML attachment wih Steve. Is this the same support case here?

    What gpg4o does is called PGP/Partitioned (a format that Symantec PGP Desktop Encryption uses too) and basically it is sending a plain text email with the original HTML body the user typed in outsourced to an attachment.
    gpg4o does this conversion to plain text to be "backward compatible" with mail clients that don't understand the PGP/Partitioned format. In gpg4o we prefer to show the HTML attachment before (instead) the plain text.

    Best regards
    Alex Strobel (call me AlexS to differ between us two Alex :)

  9. Support Staff 9 Posted by Luke Le on 28 Mar, 2017 09:48 AM

    Luke Le's Avatar

    Hi Alex,

    thank you for this explanation (we've been having the discussion on inline images :))
    So basically email clients that support PGP/Partitioned can simply ignore the text/plain part and show the contents of PGPexch.htm instead?
    If I understood that correctly, we'll make the necessary changes to GPGMail.

  10. 10 Posted by Alex Strobel on 28 Mar, 2017 03:29 PM

    Alex Strobel's Avatar

    Ah, ok. Sorry :)
    Yes, this is exactly the way gpg4o display such emails. If there is a PgpExch.htm it is displayed prior to any other text in this email.

  11. Steve closed this discussion on 07 Aug, 2017 04:47 PM.

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