gpg4win with gpgol and MS-Office worked well for quite some time.
I can't say, what happened, but since a few weeks I am no longer able to sign/encrypt email messages with outlook:
I always get the following (German) message: "An empty email can't be signed or encrypted"
I can decrypt received emails without any problem.
Notes:
- gdpol is reported to be responsible for a "slow start" of outlook (0.02 sec.)
- I've already deactivated and re-activated the GPGOL add-in in Outlook
- I've already re-stalled the most recent gpg4win