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Enigmail users see only attached gpgolXXX.dat file when signed or encrypted by GpgOL
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Description

When I send an e-mail to recipients who use a Thunderbird/Enigmail combination, the only thing they see is an empty body in the mail and an attachment which is called gpgolXXX.dat. This happens in case the e-mail is encrypted, but also when it's just signed.

Kind Regards

Details

Version
2.0.1

Event Timeline

You could try to use NO-MIME (or PGP/INLINE) instead of the OpenPGP/MIME standard. You can change the way of packaging your encrypted content in the GpgOL Addin Options.

aheinecke added a subscriber: aheinecke.

This means that the MAPI to MIME conversion did not happen.

How are you sending the mail. Is it through an Exchange server and if so which version is the Exchange server running?

For a previous version we had a vague verbal report that there was maybe a problem with Exchange 2007. We only tested with exchange >= 2010 and Office 365 and Outlook.com with all these it worked.

Also, can you please send such a signed mail to aheinecke@intevation.de maybe there is some other problem in there.

Dear Andre

I just sent two mails with the information. The first one is only signed, the second (actually third) is also encrypted.

Answers to your questions:

  • We use Exchange server 2013
  • I use Outlook version 1705 (Build 8201.2200 Click-to-Run) which is part of our Microsoft Office 365 ProPlus.

I sent the mails with my work mail which is kevin.holvoet@cert.be

Thank you very much. Both the signed only and the encrypted mail are fully valid for me (checked on the IMAP server and with kmail) and don't contain any references to gpgolXXX.dat. This means they were correctly converted to valid PGP/MIME Mails.

I see a potential problem though: Is the Enigmail / Thunderbird user also on your Exchange server? (maybe a collegue?)
There might also be a problem with Exchange <> Exchange.

My next TODO here would be to connect an Enigmail / Thunderbird to an Exchange and then test if it somehow receives mails that were not properly converted.

aheinecke claimed this task.
aheinecke added a project: Info Needed.

I tried to reproduce this with current GpgOL and it just worked. Even if I connected Enigmail to Exchange (Outlook.com).

If this still happens with the upcoming Gpg4Win-3.0.2 please comment and reopen.

Hi Andre

I don't know if you've had the time yet to test a Exchange <-> Exchange
setup? I have send multiple mails to colleagues who are connected to the
same Exchange server and they used both Enigmail/Thunderbird and GpgOL/Outlook
2016 to receive a mail I've send with GpgOL/Outlook 2016. The result seems
to be the same again, with an unreadable mail with a strange .dat file.
I've seen that mid-January an update was released with multiple fixes to GpgOL,
so I'll make sure my colleague and myself install the last version on our
Outlook installation and we'll test it again. I'll let you know then what
the outcome is.

Kind Regards
Digihash

I already created a new issue for this in the new version of gpg4win (v3.1.0) with GpgOL v2.1.0. This is the issue: T3917.

I couldn't find this issue back immediately, but now I did. Sorry for that.

Which issue do you want to keep or can you link them one way or another? Maybe I can send some tests again to see try to reproduce the problem on your side like we did with this issue.

Kind Regards
Digihash

Let's use the new issue as the problem is described completely there and it makes it more clear.