My OS is Windows 8.1 Update 1 x64. I have Outlook 2013 and just installed GPG4Win (latest, 2.2.2, full version).
When I now launch Outlook 2013, I still don't see any UI/options to setup certificates and send encrypt an encrypted email (perhaps to myself as a test message). How do I get started?
I must use Outlook, so suggesting another mail client is a non-starter.
My company, Encryptomatic.com, has released a new open pgp encryption addon for MS Outlook 2016 thru 2007. It supports both 64 and 32 bit versions of Outlook. Installer is signed. Supports key servers, signing, etc. We think its important that email encryption is accessible and easy, so we made it completely free for personal use. Can't post the link here but you can get it on our website.
Sorry for the plug, but it seemed quite relevant to the subject.
Take a look at gpg4o (enter link description here). It is not free but it just does the job. IMHO the best PGP solution for Outlook.
They also offer a trial which persuaded us to 100%.
For Outlook 2010 and 2013 you need to install Outlook Privacy Plugin with Gpg4win (OpenPGP encryption plugin). I believe that above will fix your issue
