SSL/TLS connections not coming through from PHP?

Question

PHP

Server - VDS (Debian 6.0)
PHP version 5.3.16-1~dotdeb.0

Problem:
All attempts to send mail from PHP scripts via smtp.gmail.com over SSL/TLS connection fail.

Ports are not closed because i can connect and send mail via openssl

PHP works with openssl module

enabled From phpinfo:
SSL Version OpenSSL/0.9.8o
and
OpenSSL support enabled
OpenSSL Library Version OpenSSL 0.9.8o 01 Jun 2010

Here is what phpmailer says when trying to connect using TLS

…
SMTP <- FROM SERVER:220 mx.google.com ESMTP hj19sm16658219lab.13
SMTP -> TO SERVER: EHLO mydomain.com
SMTP <- FROM SERVER: 250-mx.google.com at your service, [my IP] 250-SIZE 35882577 250-8BITMIME 250-STARTTLS 250 ENHANCEDSTATUSCODES
SMTP -> TO SERVER: STARTTLS
SMTP <- FROM SERVER:220 2.0.0 Ready to start TLS
SMTP -> TO SERVER: RSET
SMTP <- FROM SERVER:
SMTP -> ERROR: RSET failed:
SMTP -> NOTICE: EOF caught while checking if connected The following From address failed: [email protected] Mailer Error: The following From address failed :

[email protected] Mailer Error: The following From address failed: [email protected] How to overcome?

Answer 1

Obviously Google doesn't like the return address in the From field.