gpg4win with outlook 2003 problem

I have just installed gpg4win and have two problems with it.

Firstly it seems to stop outlook 2003 from sending e-mails.

When I try to send an e-mail I get the message “Microsoft Office Wordmail could not be started. Close any open dialogue boxes in Word and try again”. There are no open dialogue boxes visible.

I think this is caused by GPG4Win because I then went to `Tools/Options/Other/Advanced Options/Add-In Manager and unchecked the GpgOL box in Outlook 2003.

E-mails could then be sent OK.

Secondly, when GpgOL is selected in the Add-In manager a button appears on the toolbar to start the Certificate Manager, but here is none to encrypt a is suggested in the manual. Maybe this is related to the problem with not being able to send e-mails with GpgOL selected.

So my second question is, how do you encrypt e-mails in Outlook 2003 ?

I don’t know if I have set the program up correctly.

Does anyone use this program with Outlook 2003 successfully ?

If so, can you please give me some advice on how to set it up.

I have tried it on two computers with the same results - one with Windows 7 Home and the other with Windows 7 Pro.


I have the same issue and I believe it is related to 64Bit Windows. I am not sure why they haven’t updated the product to work with Outlook 2010, 2013 and 64Bit as they are much more common in today’s tech.

Hi Carol, Hi Bruce,

thanks for trying Gpg4win, we are sorry to hear that you are having problems with it.
Please consider that we are operating this with very low funding (some donations)
and volunteer work in the last year, so we make available what we have,
because it works for many people. For some it does not and we try to improve the
situation, which can be difficult for technical or funding reasons.

The Outlook 2003 and Outlook 2010 plugins are two different products, they interface
differently with Outlook so their problems are generally unrelated. Outlook 2003 has some technical limitations that our software cannot easily overcome. When in doubt fall back to use attachments
and use file encryption, decryption, verification for secure communication with Outlook 2003.

Outlook 2010 does not do MIME handling yet, so it is only basic support. We have not done 64bit yet, it was too much work so far. We probably will at some time.

Best Regards,
ps.: Flattr Gpg4win at,
if you appreciate this answer and my work within the Gpg4win Initiative.

Dear Carol, and Bruce,

You can’t reasonably expect Gpg4win and GpgOL to continue to support, free, a Microsoft product that is now a whole 12 years old and obsolete - Outlook 2003, for heaven’s sake! As Bernhard Reiter says, with great restraint, the work on it is being done on a shoestring, much of it by volunteers for the love of it, and I for one am extremely grateful. Werner Koch, the progenitor of GnuPG, is only now getting a living wage out of it (see ).

That said, there is a commercial variant of GpgOL called gpg4o which may solve your problems, at least for Outlook 2010 and up, produced by Giegerich and Partner (see It’s not cheap, starting at €47 for the Home and Student version, but it’s very good; I got it some time back on special offer, and it’s been very reliable.

Alternatively you could move to Thunderbird and the Lightning calendar extension as a replacement for Outlook, and use the (free) Enigmail encryption add-on, which is also excellent.

If you must stick with Outlook 2003, I suggest using the form of encryption that Outlook was designed to work with, namely S/MIME, for which you will need a personal email encryption certificate. You can get one free from, or from Comodo I think. I wrote an article describing how to use Outlook or Windows Live Mail with S/MIME, which you can find here: .

The 32-bit/64-bit issue is not particularly relevant. Not that many programs actually need to be compiled as 64-bit to work efficiently, as opposed to operating systems; 32-bit application code will be around for a long time yet.


Martin Ward

Actually I am looking for a version that supports Office 2010 64Bit so if will work for that I am willing to pay for it. I have a Win 7 Machine (office 2003) with gpg4win software working perfectly however the second system doesn’t work. I did see some discussion about running it in a specific mode so I can try that. Your suggestion has a free demo so that is perfect. The issue I can across was the connection with our Mac systems. The Mac version is very easy to setup and run (donation coming). Do you know if the Giepa version is fully compatible with LIVE decryption within Outlook 2010?

(Sorry if I sounded ungrateful, it was not my intention)

Hi Bruce - I’m not sure what you mean by “live decryption within Outlook 2010”, but basically if you click on an encrypted message in the list pane, the ciphertext is displayed in the reading pane and a dialog box immediately comes up to ask you for the passphrase. Give it, and the message is immediately decrypted in the reading pane. Cleverly, for an HTML message, there is an encrypted attachment containing the HTML layout which is automatically applied on decryption to show the message in its full glory. The passphrase is remembered for a few minutes, so if you move to another message and then back, the message is automatically decrypted again.

When you send a message, a copy is automatically encrypted with your public key as well, and placed in the Sent folder, so you can decrypt it when you go back to look at it.

I suggest that you try out gpg4o; you get 45 days of the trial version, which should be long enough to discover most of the kinks.

You didn’t sound too ungrateful, I was just being a bit sensitive on the Gpg4win team’s behalf, I suppose, because I think many of us don’t really appreciate the degree of subtle thought and careful software engineering that goes into building tools on which, at the extreme, someone’s life or freedom might depend. And all we have to do is download and double-click, to get them for free. I’m also feeling a bit grouchy because I’m trying to run a server hosting a Tor exit node, which appears to be an invitation to be blamed for everything from comment and email spam to DMCA content and beyond. People who try to torrent over Tor should be shot. But I digress. Good luck with your quest.


Hi there,
we hope to provide a 64bit Free Software (free as in liberty) of GpgOl in the future,
which will be inspectable.

Best Regards,

Actually I am trying to use gpg4win with Win 7 64bit and Outlook 2010. I moved backwards to 2003 as I had success with it on a different system. Is the current 2.2.x gpg4win plugin compatible with Win 7 64bit and Outlook 2010? I have the Mac version setup and running great however I have a user that works in Windows and want the communication as seamless for her as it is on the Mac side.