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I was setting up Postfix on (Ubuntu 12.10). This is my main.cf file content :

    smtpd_banner = $myhostname ESMTP $mail_name (Ubuntu)
    biff = no
    append_dot_mydomain = no
    readme_directory = no
    # TLS parameters
    smtpd_tls_cert_file=/etc/ssl/certs/ssl-cert-snakeoil.pem
    smtpd_tls_key_file=/etc/ssl/private/ssl-cert-snakeoil.key
    smtpd_use_tls=yes
    smtpd_tls_session_cache_database = btree:${data_directory}/smtpd_scache
    smtp_tls_session_cache_database = btree:${data_directory}/smtp_scache  
    myhostname = osamaHP
    alias_maps = hash:/etc/aliases
    alias_database = hash:/etc/aliases
    myorigin = /etc/mailname
    mydestination = ubuntu.localhost, localhost.localdomain
    relayhost = [smtp.gmail.com]:587
    mailbox_size_limit = 0
    recipient_delimiter = +
    inet_interfaces = all
    inet_protocols = all
    mynetworks = 127.0.0.0/8 xxx.16.0.0/24 [::1]/128 xxx.16.0.101
    proxy_interfaces = xxx.16.0.1
    smtp_sasl_auth_enable = yes
    smtp_sasl_password_maps = hash:/etc/postfix/sasl_passwd
    smtp_sasl_security_options = noanonymous
    smtp_tls_CAdile = /etc/ssl/certs/Equifax_Secure_CA.pem

When I tried to send an email

mail from:-------@gmail.com
250 2.1.0 Ok
rcpt to:------@gmail.com
250 2.1.5 Ok
data
354 End data with <CR><LF>.<CR><LF>
TestTestTest
.
250 2.0.0 Ok: queued as 320DB223C63

this is my mail.log file

Jun 23 14:39:30 osamaHP postfix/smtp[11766]: 320DB223C63: to=<-------@gmail.com>, relay=none, delay=91, delays=31/0.01/60/0, dsn=4.4.1, status=deferred (connect to smtp.gmail.com[173.194.70.109]:587: Connection timed out)
Jun 23 14:39:45 osamaHP postfix/smtp[11791]: connect to smtp.gmail.com[173.194.70.108]:587: Connection timed out
Jun 23 14:39:45 osamaHP postfix/smtp[11791]: 7F6F6223AA2: to=<--------@gmail.com>, relay=none, delay=4610, delays=4549/0.01/60/0, dsn=4.4.1, status=deferred (connect to smtp.gmail.com[173.194.70.108]:587: Connection timed out)

Notes: - Port 25 is not blocked by ISP - When I used port 465 , I got this log

Jun 23 20:09:16 osamaHP postfix/smtpd[4881]: E7A3622385D: client=unknown[192.168.1.13]
Jun 23 20:09:23 osamaHP postfix/cleanup[4885]: E7A3622385D: message-id=<20130623170916.E7A3622385D@osamaHP>
Jun 23 20:09:23 osamaHP postfix/qmgr[4878]: E7A3622385D: from=<jbr.osama@gmail.com>, size=296, nrcpt=1 (queue active)
Jun 23 20:09:23 osamaHP postfix/smtp[4886]: CLIENT wrappermode (port smtps/465) is unimplemented
Jun 23 20:09:23 osamaHP postfix/smtp[4886]: instead, send to (port submission/587) with STARTTLS

then I changed it to port 587 and I used STARTTLS, then I got

Jun 23 20:25:23 osamaHP postfix/smtpd[5311]: connect from unknown[192.168.1.13]
Jun 23 20:25:49 osamaHP postfix/smtpd[5311]: SSL_accept error from unknown[192.168.1.13]: -1
Jun 23 20:25:49 osamaHP postfix/smtpd[5311]: warning: TLS library problem: 5311:error:140760FC:SSL routines:SSL23_GET_CLIENT_HELLO:unknown protocol:s23_srvr.c:628:
Jun 23 20:25:49 osamaHP postfix/smtpd[5311]: lost connection after STARTTLS from unknown[192.168.1.13]
Jun 23 20:25:49 osamaHP postfix/smtpd[5311]: disconnect from unknown[192.168.1.13]

Does anybody have an idea about what happens here ?

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