1. Check whether you are using the newest version of Gpg4win
The download button ontop of the Gpg4win homepage shows the current version of Gpg4win.
You can find your installed Gpg4win version number in the README file (via start menu folder of Gpg4win) or open start->Settings->Control Panel->Programs.
2. Check whether it is really a Gpg4win bug
Gpg4win integrates a number of tools that are actually maintained by other development teams.
Therefore problems and bugs of general nature, i.e. not related to the cross-compilation and/or packaging by the Gpg4win team, should be reported to the respective project teams (usually you need to register before submitting or commenting a bug):
Of course, it is not always easy to decide whether it is a bug of Gpg4win or a module. In these cases and depending on the type of the problem, either ask on one of the Gpg4win mailing lists or forums for advice or create a bug report in the Gpg4win bug tracker.
3. Check whether the problem is already reported
Search through the list of open bugs and try to identify whether one of the entries already describes your problem. Add your additional comments there.
4. Provide version number
If you report a new bug or add comments to a existing bug report, describe the exact version of the Windows System, Gpg4win, and if appropriate of MS Office and Outlook.
5. Notes how to reproduce the bug
If possible provide a step by step method how you reproduce the bug.
6. Add debug information
If appropriate, attach a debug log of the procedure where you produced the bug. Look at the instructions for the several Gpg4win components in the Gpg4win Compendium.
If you feel able to, just send a excerpt with the relevant information.