When I compose an email in Outlook and set it on the ribbon to be either encrypted, signed, or both, then click to send it, nothing happens. When I click send again, sometimes (usually) the pop-up for selecting keys come up. If it does, I choose the keys (all mine, GPG-type keys, for test emails, as appropriate for either encrypting to myself or signing or both). On completing that, nothing happens, i.e., the email is never sent. This is a dead-end, as far as I can tell.
I used the tried-and-true clipboard method to create an encrypted email, pasting the ciphertext into the email manually, and this decrypted automatically when received. I can also create a signature this way, and the signature is verified automatically on receipt. I can create an encrypted-then-signed email in two steps using the clipboard, but when received it only verifies the signature automatically without decrypting the email automatically, too. (Email is now "SHA-256" followed by "-----BEGIN PGP MESSAGE----- " and the rest of the ASCII ciphertext. I can use the clipboard to decrypt it manually, though.
When I look at emails I received in the past, they often come to me as an email attachment, the attached email itself containing a .asc attachment. When I open that email, and then decrypt the (second, i.e., .asc) attachment using the GPA file assistant that pops up, the signature is automatically verified. The file is also decrypted, but the file manager does not allow me to copy the path or open the file, as I can see in the file assistant, even if it has a valid file extension. (Many are just the filename "encrypted" at this point.) When I manually enter the path (cumbersome!) the decrypted email file "encrypted" is indeed there deep in a Windows directory. When I open it with a text editor I see it is S/MIME content, so I add the extension .eml, and then, finally, I can see the contents in readable form. Surely, this doesn't seem very automated.
I am running Outlook 2016 over Windows 10 Enterprise.
I had just downloaded and installed the latest version of GPG4WIN 3.03, with correct signatures.
I am excited to see the new Outlook automation features, and am looking forward to when they are working for me. If I can send you some logs or such, please let me know exactly what to do.