Neither TLS or SSL support in M1 seems to work with M$ Entourage. I tested it with Thunderbird and it worked okay. Not sure why. I'll test it with outlook soon, but most problems with Entourage are also problems with Outlook/Win32 and oddly the Mac mail client as well. (I'd suspect 1 and 3 but not 1,2,3 or 2,3)