The eMail in the Sent Items appears empty (everything is white, but in the eMail's source code there is some little markup). There is NO attachment and S/MIME is NOT enabled. Remote Server returned '550 5.6.0 : ConversionFailedException, Content conversion: Invalid S/MIME encrypted message.
I'm using Outlook 2016 with GpgOL 2.4.2 (Gpg4win 3.1.10) on Windows Server 2016 Standard (Terminal Server) and with Exchange 2013 on Windows Server 2012 Standard.