Attaching smtp trace. Note:Emacs is built without starttls support on this machine -- perhaps that matters. 220 mx.google.com ESMTP b4sm4419441pba.75 250-mx.google.com at your service, [71.202.188.217] 250-SIZE 35882577 250-8BITMIME 250-STARTTLS 250 ENHANCEDSTATUSCODES Process smtpmail deleted MAIL FROM: SIZE=523 530 5.7.0 Must issue a STARTTLS command first. b4sm4419441pba.75 QUIT 221 2.0.0 closing connection b4sm4419441pba.75 ë-Eè­Û+jf§