Trying on port 25 Trying myserver... <-- 220 myserver ESMTP Sendmail 8.14.1/8.14.1; Mon, 10 Dec 2007 04:26:33 +0100 (CET) --> EHLO localhost (wait upto 300 seconds) <-- 250-myserver Hello localhost [127.0.0.1], pleased to meet you <-- 250-ENHANCEDSTATUSCODES <-- 250-PIPELINING <-- 250-8BITMIME <-- 250-SIZE <-- 250-DSN <-- 250-ETRN <-- 250-DELIVERBY <-- 250 HELP --> MAIL FROM: SIZE=278 (wait upto 600 seconds) <-- 250 2.1.0 ... Sender ok --> RCPT TO: (wait upto 3600 seconds) <-- 250 2.1.5 ... Recipient ok --> DATA (wait upto 300 seconds) <-- 354 Enter mail, end with "." on a line by itself --> . (wait upto 120 seconds) <-- 250 2.0.0 lBA3QXVc007077 Message accepted for delivery --> QUIT (wait upto 120 seconds) <-- 221 2.0.0 myserver closing connection When I try port 465 (SMTP + SSL) Trying myserver... (and after around 60 seconds) ... premature end-of-file from server ... ... premature end-of-file from server ... premature end-of-file from server premature end-of-file from server