GPGol - Problem encrypting email

I am using outlook 2003/sp2 and gpg4win 1.0.0. Decryption works fine, however if I encrypt or sign a message, the program asks for my pass phrase but always sends the email in plain (unencrypted) text.

Any help would be appreciated.


It turns out that things do work if I use html format to compose the messages.


This would be indeed a serious problem.

I can’t repduce the problem.
Can we first concentrate on the encryption:
Can you send me an encrypted testmail
to - you should find my
key via the keyservers.

Yes, this is strange. I installed gpgol on a second computer running Outlook 2003/sp1 and it works fine when composing with plain text.

Can you send me a text encrypted and a html encrypted email also with the Outlook 2003 SP1?

I’ve got a similar problem.

If Outlook is set to send plain-text emails, encryption and signing do nothing. It appears to work correctly as it asks which key to sign the message with, but nothing happens to the email.

If Outlook is set to send HTML emails (which I despise intensely) then I can sign messages correctly. However if I try to encrypt a message, as soon as you click on send it pops up a dialog box entitled “Encryption Failure” with the message “Invalid Value” and then sends the email unencrypted.

Decrypting messages works correctly though.

This is using WinGPG 1.0.0 and Outlook 2003 SP2 with all patches that were available as of yesterday.

I now created a bug entry for GPGol:;pr=643

I propose to discuss this serious
problem there instead of in this forum.
Otherwise the developers don’t get

I just learned that the GPGol Bug tracker
has a serious disadvantage: it is not
possible to add a comment to an existing
bug as guest. But it is also not possible
to get a real account.

Therefore lets keep discussion here.

I was able to reproduce the problem (details below):

gpg4win 1.0.1, WinXP SP2, MSO Outlook 2003 SP1

  • I only tried for plain text since I made it default and I never compose HTML emails.
  • Encrypt alone works.
  • Sign fails.
  • Encrypt and Sign also fail.
  • Decrypt works.

I applied the MSO 2003 SP2 patch and the outcome is still the same.

I can confirm this. At home, everything works fine, but at work encrypting and signing does nothing. The major difference is that Outlook at work is connected to an Exchange server (using IMAP), while at home I am using standard SMTP. Perhaps this is (part of) the problem?

I was having similar problems using GPGOL with our office Exchange server. I think I’ve identified the issue. I went into the Mail Format tab under options and Outlook and turned off using Word 2K3 as the editor. I am able to send and receive encrypted and signed emails without any difficulties.
I will continue using it and will report back
Thanks for this product… I killed my machine twice with PGP Desktop 9 and it was nice to find something that would work.
Bob D

Outlook 2003 SP2> Menu > Tools> Options> Mail Format.
I have both options to edit and to read rich format text already disabled. I still cannot use the sign option.

I had this setting already in the beginning. I find html/rich text emails and abomination to email; people who want to send decorated stuff should send them as attachments. The signing does not work; it actually ruins the encrypt option.

I can confirm the problem. I suffer from the same problem.
If I am writing a plain text mail, it is neither encrypted, nor signed although key and passphrase were requested.
When switching to html it works fine. No probs.
I do not use word as editor. I ONLY use plain text.
Pls check, since it is a crucial bug. Investigation is definitely necessary.

Thanks in advance!


Please try GPG Tools from I think if you have upgraded to MS Outlook 2003 this problem is caused and its there in GPGol.


I did not upgrade. I have made a clean office install, but rstored office settings via the wizard.
Some more questions:

  1. Do I have to deinstall gpg4win?
  2. Do I install it in the same directory?
  3. What happens to my configuration?
  4. If I have to install an other “product”, in order to fix a problem, then there is defenitely a bug in gpg4win. Preferingly it should be fixed there.