Blank e-mails from Outlook 2016

Gpg4win help-en
1

I’m using GPG4win 3.0. For some reason, my PGP encrypted e-mails are received as empty mail by the recipient. I can see the e-mail is encrypted in the sent mail folder. Anyone have any idea how I can troubleshoot this?

This is Outlook 2016 with Exchange online as the back end.

Thanks,

Francois

2

Hi Francois,

Any chance that the recipient is not using the latest GpgOL Plugin and you send HTML Mails by default?

The newest GpgOL Plugin supports proper OpenPGP/MIME Encryption, older Version of the Plugin work only well with the NO-MIME (Somethimes called PGP/INLINE) Encryption method. So it could be, that you have to convince your recipient to upgrade their version or you have to change your encryption standard (in the Addin-Options) to NO-MIME encrpytion.

Best wishes,
Jochen

3

Jochen,

Thank you very much for clarifying how GpgOL works. My understanding is that the recipient is not using GpgOL - they are using Symantec Desktop Email Encryption. I will try out the NO-MIME option.

As to that change to the encryption standard in the addin-options to NO-MIME encryption - are you referencing to the one checkbox option titled “Send OpenPG mails without attachments as PGP/Inline”?

Thanks!

4

Exactly. Though I think PGP/Inline is a bad word, as the text of the mail is just taken and replaced inline with the encrpyted version. And PGP/Inline follows no standards, other then OpenPGP/MIME[1]. Since PGP/Inline is no standard we used to call it NO-MIME since these difficulties, but it mostly works with non-standard or non-open software.

Best Wishes,
jochen

[1] - https://tools.ietf.org/html/rfc3156

5

Unfortunately, I had that option already checked. I’ll try without it and see if it makes a difference.

The other thing that I could try I guess is to see what the server is actually sending. I’ll check with out Exchange administrators to see if that’s possible.

Thanks,

Francois

6

Another problem may be, that Symantec Desktop Email Encryption recognizes the encrypted data but is unable to decrypt it. Thats why there is no block with “BEGIN PGP DATA” displayed, or any text at all. But I can’t tell for sure, I don’t know what encryptions Symantec Desktop Email Encryption supports and if the newer curves and encryptions are support by that. So it could be an compatibility issue, since Symantec Desktop Email Encryption is not Open Source and maybe doesn’t follow all standards that could be an issue.

Best Wishes,
Jochen