never used GPG4Win before
installed today following step by step instructions in compendium. i am failing at the testing stage (page 69) - no popups or feedback of any kind from Kleopatra - i am not asked for my public key - there are no buttons or interface for gpg4win anywhere in Outlook that i can see
GPG4Win v2.2.0, Outlook 2010, Windows 7 x64
I suggest that you remove GPGOL and use the Outlook Privacy Plugin instead.
I have a system similar to yours, and when I installed GPG4Win/GPGOL, I had all sorts of errors referring to missing files when I started Outlook 2010. I could not use encryption, and when I tried to turn the add-on off or remove it, it crashed Outlook. The only way I could get rid of it was to uninstall GPG4Win (very thoroughly, using Revo Uninstaller), and fortunately GPGOL went with it. Then I reinstalled GPG4Win, carefully deselecting the GPGOL option.
You can find the Outlook Privacy Plugin here:
and some useful comments (including one from me!) on the wiki at:
There is also a commercial solution at http://gpg4o.de, but it is quite expensive.