Latest (monthly) Outlook doesn't load GpgOL add-in


Seems there’s a compatibility problem with the last couple of versions of Outlook from the faster channel. As of now, it says,

Location: C:\Program Files (x86)\Gpg4win\bin\gpgol.dll
Load Behavior: Not loaded. A runtime error occurred during the loading of the COM Add-in

Since this worked after installing Gpg4win 3.1.3, I’d expect it’s probably because of the Outlook changes. Outlook is “Version 1809 (Build 10827.20138 Click-to-Run)” this week but this was already a problem last week.

Is this likely to be fixable in 3.1.3 or does this require a new version?

(I’m on the faster channel just to catch these and other… surprises… before they hit the general population, so not unexpected that this might happen occasionally.)

I do not think the update is the problem. I just forced an update on my machine and it still works with 3.1.3:

That error is pretty general. It can mean that the file does not exist in that location or that there was an error during startup.

We have an issue that if Gpg4win is installed / updated multiple times while Outlook is running, then the gpgol.dll might be removed on reboot.

My first step in analyzing this would be to check that the dll exists in that place and / or reinstall Gpg4win.

The next step would be to turn on debugging as described under:

And see if a log is created. More steps would be to profile the load with dependency walker etc. but before we go into that please check above.


Are you using Office 2019 or have early access to it? I would be interested to see if GpgOL works with that out of the box as it should according to documentation.

Oh yes, sorry, only had the 64-bit DLL and 32-bit Outlook. That’d have been it then.

If I’ve had Outlook running while updating, that’d have to have been one of the “ghost” processes that Outlook leaves sometimes… well, all too often…

Like just now, reinstalling Gpg4win failed even when I’d killed all of Outlook beforehand. Some of the other things I use might have kept something open. (Possibly Thunderbird/Enigmail, LibreOffice document signing, Kleopatra in the background…)
Retried the installation successfully and rebooted. Had to manually enable the Outlook add-in too, but it seems to work now.

As to Outlook 2019 - well, I’m on ProPlus and the new-style interface, so what I’m using is the “full” version that 2019 is a (fairly recent) limited-functionality snapshot of.