There are several places where someone finds information about how to trouble shoot a crypto application problem.

TODO: link to the sections in the gpg4win compendium and other documentation.

For problems with adele see EmailExercisesRobot.


  1. If the problem is with GpgOL, try the operation with GpgEX or Kleopatra, to exclude Outlook's influence. Note that if GpgEX/Kleopatra works, you have a fallback solution to just work via files and send them by attachment, so can can still use crypto, but with less comfort.
  2. If GUI frontend applications fail, try to do the operations on the command line. This way you can often exclude that the problem is within the frontend. And you sometimes get additional helpful messages.
  3. Look at or activate and look at additional diagnostic output. (, TODO link or refer to specific section in the official docs.) There are many ways where additional output can be found or enabled.
  4. Try to reproduce, sometimes a different installation or a different computer gives you an idea about the difference between a running and a problem case.
  5. Precisely check the version numbers of components.
  6. Check general operating or usage issues. Things like a full harddrive or wrong filesystem permissions.

Hints / Tips

Checking the package integrity

If the downloaded package seems to be broken, please check the integrity of the downloaded package, by validating the checksum. You find a List of the checksums and a guide for *Nix systems here. If you have a Windows System, open the terminal and compare the output of

"certutil -hashfile FileToHash.exe sha1"

to the ones on the site. Older Windows systems have to download a Windows Patch which provides this functionality.

Command line operations

The manual of the GnuPG (crypto engine) will describe the command line usage in detail, but for testing we give some simple commands here.

First you need to open the "cmd.exe" command line application in windows. Then you can type commands at the prompt. For good results, create a new directory and change into it with cd and create or copy a testfile you can operate on for, example hello.txt.

An example to use your own key to sign something with CMS with double verbose output:

gpgsm.exe -vv --sign hello.txt >hello.p7s

An example to decrypt something with OpenPGP, no extra output

gpg --decrypt hello.gpg

and now with full diagnostic output (be careful when sharing with others, this may contain sensitive information), usually you start with no diagnostic output, then add "-v"s and additional "--debug" options.

gpg --debug-all -vvv hello.gpg

Passphrase on the command line

The private key, which is protected by a passphrase, is handled by gpg-agent. This means that with GnuPG 2.1 adding --passphrase on the command line will no longer work out of the box. If you really don't want a passphrase (you have it in a script or the command line history anyway) It is suggested to remove the passphrase from that key. Other options are:


  gpg --pinentry-mode loopback --passphrase <yourpassphrase> -d <somefile>

Windows > 8 and Server 2012 Task Scheduler Problems

GnuPG uses (as suggested by Microsoft and usual) %APPDATA%\gnupg to store data on Windows. When launched from the Task Scheduler %APPDATA% is not always set to the correct users directory. (If you launch it with system privileges it is another place altogether). GnuPG as a result is unable to find the Keys or configuration in the directory Windows provides.

This is a known Windows bug. See the Knowledge Base article Or This technet discussion

Instead of the Workaround mentioned in the knowledge base article GnuPG provides you with the option to set the Home directory as part of the command. (--homedir) Which makes it easy to workaround that bug.

For example:

  gpg --homedir c:\Users\aheinecke\AppData\Roaming\gnupg --encrypt -r <recipient> <file>

Would ignore the broken value of %APPDATA% and use the keys stored in c:\Users\aheinecke\AppData\Roaming\gnupg instead. Make sure access rights are set accordingly of course so that this works with the user the Scheduled task runs under.

GpgOL won't load in Outlook

First check that it is enabled under File->Options->Add-Ins Com-Add-Ins. If that does not work or it can't be enabled there:

Check in the Windows Registry that

HKEY_CURRENT_USER\Software\Microsoft\Office\Outlook\Addins\GNU.GpgOL LoadBehavior

is set to 3.

In the following Registry Keys replace <VERSION> with your Outlook Version. The <VERSION> values are:

Additionally, if they exist, delete all "REG_BINARY" Entries under:




Finally create the Registry Key:


And add a REG_DWORD entry with name "GNU.GpgOL" and value "1".

GpgOL does not work

Check if you have one of the known incompatible Addons.

Enable GpgOL debugging

GpgOL can log what it does internally. You might be asked for such a debug log to analyze a problem.

To enable it:

The value of enableDebug -> If set to 1 it logs less and should not leak any private data except Mail Addresses. If set to 1922 the log will contain the plaintext of decrypted messages, so only use that if you have a test mail or some unconfidential mail.

TroubleShooting (last edited 2018-05-14 06:59:16 by AndreHeinecke)