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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 service technicians

Goal is to build up a valid understanding of the problem, how it came to be and possible solutions.

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. (http://gpg4win.de/doc/en/gpg4win-compendium_29.html, 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.