Why is the FSF's GnuPG bot "Edward" unable to decrypt my encrypted emails?

1

I am facing a problem when attempting to send an encrypted email via Enigmail (Thunderbird) in Ubuntu 14.04. I was following the Email Self-Defense guide https://emailselfdefense.fsf.org/en/ everything going smoothly up to the Step 3.B.

I sent this message to the GPG Bot (see the screenshot):

enter image description here

Despite trying to deliver my encrypted email to Edward, the GPG bot over 10 times, using different settings, the he wasn't able to successfully decrypt the message. His reply being "I'm sorry, I was not able to decrypt your message. Are you sure you encrypted it with my public key?".

enter image description here

Please notice that I followed the instructions to the best of my knowledge, and apparently the last digits C09A61E8 belong to edward-en@fsf.org, implying it really is his public key.

Could you please advise, what am I doing wrong? Thanks a lot!

peter b

Posted 2014-08-21T08:08:37.933

Reputation: 13

Did you use HTML email? If so can you try with a text only email (i.e., without HTML part) – martijnbrinkers – 2014-08-21T08:38:28.027

check also if your mail client reformat the message after the encryption. (there are few option in the Enigmail Menu to avoid this and set it up in the best way to work with gpg) – None – 2014-08-21T08:45:47.317

@martijnbrinkers OK, so after 10 more attempts, the problem seemed to be in html as you were saying. The thing is that I tried to format it as "Plain Text" several times before when writing the message, including pressing Shift while clicking on "Write". – None – 2014-08-21T11:22:01.823

@ddddavidee you're right, there are several settings in Thunderbird and Enigmail itself that point to send as "html" (e.g. the signature text) or "plain" text, so I was confused... and still am, since I believe that I just might have been lucky to send it that the other side was able to decrypt it. I think I need to practice more :-) – None – 2014-08-21T11:23:18.110

Answers

0

As was found out in the comments to the question, it turns out that this problem was because the message is being sent as HTML, albeit possibly without any explicit formatting.

Sending as plain text should allow everything to work properly, and should not have any negative side effects on what you really want sent.

It's possible that Edward simply doesn't understand HTML mails, and that a regular mail client wouldn't have the same issues. However, sending OpenPGP encrypted, ASCII armored data as HTML adds nothing but unnecessary size.

a CVn

Posted 2014-08-21T08:08:37.933

Reputation: 26 553

And don't use inline PGP. – frlan – 2014-08-21T19:48:17.210

Asked: 2014-08-21T08:08:37.933

Viewed: 660 times

Active: 2014-08-21T14:32:09.993