Decriptyon Failed: Decryption Failed

I got this strange problem.
One of my users just changed his laptop. He brought over both the public keys he had and his private key. But after the installation he is unable to decrypt anything. The only thing we see is a box with the error Decryption Failed: Decryption failed and the list of the recipients as in the attached file.

-On the new laptop he is using GPG4Win 2.3.3, while on the old one he was using 2.3.0. He uses GPGoL on Outlook 2013.
-We tried to load a separate backup of both private and public keys, with no changes
-We tried to export again the public key and test it, with no change, with both backups.
-We tried to certify every public key he had, one by one, with no changes. Same with changing the Trust status.
-We tried uninstalling and reinstalling with no changes

I have no more ideas. Someone can help?
PS: We still have to try creating a new secret key and test it, but it is a last resort because it would force the user to recreate his list of contacts AND lose all previous still encrypted mails.

Thx to anyone who will try to help.


Hi Matteo, may have things to try.

E.g on the command line, some diagnostic message may give you an idea
what is wrong. (You are trying OpenPGP, yes?)


Thx for the help, but the link provided is of almost no use for me, since:
-We are working in a Windows 7 environment, meaning the %APPDATA% bug is not at fault
-I can try to encrypt and decrypt files using command line, but the only things i am interested in are emails from the Outlook client, with no attachments.
-I can try to use GPGEX or Kleopatra directly, but the user will never accept a loss in functionality like the one proposed, and i agree with him. The only advantage of this solution is to exclude Outlook as the culprit.

Is there a location where Kleopatra/GPGoL plugin for Outlook 2013 stores error logs?

Hi Matteo,

if everything works on the command line, with Gpgex and Kleopatra,
this is an important step in diagnosing the problem. So it is a problem
with GpgOL and on Windows 7.

In order to rule out external factors, I suggest trying to installl 2.3.0 on the new machine.
If it works then, there is a difference between Gpg4win releases. If it does not work,
there is something else that is different between the setup of both machines.

If you follow the links on there is a section
in the Gpg4win compendium to switch on further diagnostic messaging for GpgOL.

Best Regards,

I will try using both the command line and using the 2.3.0.
When the user is ready to give me the pc for some time, I’ll do my tests and report the results.