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After getting a regular gmail TLS SMTP session to work, I am trying to implement PIPELINING.

According to the spec:

http://tools.ietf.org/html/rfc2920

(which doesn't mention if username/password can be pipelined with AUTH LOGIN, but this seems to be working)

It does say I can group:

   C: MAIL FROM:<[email protected]>
   C: RCPT TO:<[email protected]>
   C: DATA

Which I do, and gmail server responds with two code 250s as expected (but no prompt to send the mail)

Then I send my body:

"Date: "    + sMailDate  + CRLF                                 
"From: "    + sMailFrom  + CRLF                                 
"To: "      + sMailTo    + CRLF                                 
"Subject: " + "Gmail Test"  + CRLF + CRLF 
"Dear User, SMTP can be a very time consuming"

and the gmail server just closes the connection.

ADDED

After a good deal of work the solution is here: http://www.coastrd.com/smtps