Outlook hanging when requesting passphrase for signing key

I have installed Gpg4win 3.0.0 working with Outlook 2016 64 bit. I have multiple private keys in my Kleopatra keyring. When I hit send, I am prompted to select the proper key from my key ring, but after selecting the key, Outlook hangs. After a long wait, if I kill the Outlook process, I am then prompted for the key passphrase. It seems that there is an issue with requesting the passphrase after selecting a private key for signing.

Any thoughts on how to reslove this?



Hi Paul,

are those two private keys OpenPGP keys?

(CMS keys may trigger downloading of revocation information.)

Best Regards,

I have three OpenPGP keys - I can select anyone of them from a dialog window that pops up after hitting send in Outlook. After selecting the key is when Outlook hangs. I have tried to sign an file from within Kleopatra, and all works well - select file, select key, provide passcode for the key.

I should also mention that I am on Win10.

Thanks for the help


One other point - I noticed in the GnuPG tracker there is an issue logged - T3460 - password display box remains hidden, that sounds very familiar. I looked everywhere for a passcode box or a window that was hidden on the desktop, but could not find anything.



An update on this

Using GPA as my keyring Gpg4win is fully functional in Outlook. It looks like the problem lies Kleopatra.


thanks for the details in the report.
I’ve seen several seckeys with Kleopatra that could be selected fine,
so we have to find out how to reproduce the problem you have been seeing.