Hi @JohnTheRipper,
see GpgOL not decrypting sent emails - #6 by dadaok, too. I don’t comment here on the log settings again.
Uncheck the draft encryption if you have no secret key available on the system, otherwise you risk loosing the contents of draft mails.
You could check with “always show security approval dialog” if the right certificate is selected for yourself.
Regarding
it is not possible to see encryption attachment files in Outlook.
Do you mean that there is no hint at all that there is an attachment to the mail? Is this true for all kinds of attachments? Or only pdf?
And please check yourself again if you have any known incompatible AddOns: https://wiki.gnupg.org/GpgOL/IncompatibleAddons
Maybe try to deactivate most of your ones for testing, as one of the ones listed as incompatible is a pdf converter AddIn, I’d deactivate the Acrobat and Adobe ones for starters.