Thanks for the reply Victor. Logs below as requested. Not sure why you would think I have port 587 inbound opened. Like I said I have done a lot of reading. and I am aware that port 587 is recommended for smtp. I have enabled it in postfix master.cf with saslauth. I have port 587 outbound open in my firewall.
I have checked with netcat and connection is timing out to gmail-smtp-in.l.google.com (173.194.78.26). > postconf -n alias_database = hash:/etc/aliases alias_maps = hash:/etc/aliases allow_percent_hack = no broken_sasl_auth_clients = yes command_directory = /usr/sbin config_directory = /etc/postfix daemon_directory = /usr/libexec/postfix data_directory = /var/lib/postfix debug_peer_level = 2 debugger_command = PATH=/bin:/usr/bin:/usr/local/bin:/usr/X11R6/bin ddd $daemon_directory/$process_name $process_id & sleep 5 home_mailbox = Maildir/ html_directory = no inet_interfaces = all inet_protocols = ipv4 mail_owner = postfix mailbox_command = /usr/bin/procmail-wrapper -o -a $DOMAIN -d $LOGNAME mailbox_size_limit = 0 mailq_path = /usr/bin/mailq.postfix manpage_directory = /usr/share/man mydestination = $myhostname, localhost.$mydomain, localhost, AAA.uk mynetworks = 127.0.0.0/8 newaliases_path = /usr/bin/newaliases.postfix queue_directory = /var/spool/postfix readme_directory = /usr/share/doc/postfix-2.10.1/README_FILES sample_directory = /usr/share/doc/postfix-2.10.1/samples sender_bcc_maps = hash:/etc/postfix/bcc sendmail_path = /usr/sbin/sendmail.postfix setgid_group = postdrop smtpd_banner = $myhostname smtpd_recipient_restrictions = permit_mynetworks permit_sasl_authenticated reject_unauth_destination smtpd_sasl_auth_enable = yes smtpd_tls_CAfile = /AAA/AAA/ssl.ca smtpd_tls_auth_only = yes smtpd_tls_cert_file = /AAA/AAA/ssl.cert smtpd_tls_key_file = /AAA/AAA/ssl.key smtpd_use_tls = yes unknown_local_recipient_reject_code = 550 virtual_alias_maps = hash:/etc/postfix/virtual mail log Mar 14 19:01:26 server postfix/postfix-script[9127]: starting the Postfix mail system Mar 14 19:01:26 server postfix/master[9129]: daemon started -- version 2.10.1, configuration /etc/postfix Mar 14 19:10:53 server postfix/pickup[9130]: E9A2640D325E: uid=0 from=<a...@aaa.uk> Mar 14 19:10:53 server postfix/cleanup[9732]: E9A2640D325E: message-id=<1426360253.9...@aaa.uk> Mar 14 19:10:53 server postfix/qmgr[9131]: E9A2640D325E: from=<a...@aaa.uk>, size=655, nrcpt=1 (queue active) Mar 14 19:11:24 server postfix/smtp[9734]: connect to mx2.hotmail.com[65.55.33.135]:25: Connection timed out Mar 14 19:11:54 server postfix/smtp[9734]: connect to mx4.hotmail.com[65.55.37.120]:25: Connection timed out Mar 14 19:12:24 server postfix/smtp[9734]: connect to mx3.hotmail.com[65.55.37.72]:25: Connection timed out Mar 14 19:12:54 server postfix/smtp[9734]: connect to mx2.hotmail.com[65.55.92.152]:25: Connection timed out Mar 14 19:13:24 server postfix/smtp[9734]: connect to mx3.hotmail.com[65.55.92.152]:25: Connection timed out Mar 14 19:13:24 server postfix/smtp[9734]: E9A2640D325E: to=<a...@hotmail.com>, relay=none, delay=150, delays=0.02/0.01/150/0, dsn=4.4.1, status=deferred (connect to mx3.hotmail.com[65.55.92.152]:25: Connection timed out) Mar 14 19:21:26 server postfix/qmgr[9131]: E9A2640D325E: from=<a...@aaa.uk>, size=655, nrcpt=1 (queue active) Mar 14 19:21:56 server postfix/smtp[10329]: connect to mx3.hotmail.com[65.55.37.72]:25: Connection timed out Mar 14 19:22:26 server postfix/smtp[10329]: connect to mx3.hotmail.com[65.55.37.104]:25: Connection timed out Mar 14 19:22:56 server postfix/smtp[10329]: connect to mx1.hotmail.com[65.55.92.184]:25: Connection timed out Mar 14 19:23:26 server postfix/smtp[10329]: connect to mx2.hotmail.com[65.54.188.72]:25: Connection timed out Mar 14 19:23:56 server postfix/smtp[10329]: connect to mx4.hotmail.com[65.55.37.72]:25: Connection timed out Mar 14 19:23:56 server postfix/smtp[10329]: E9A2640D325E: to=<a...@hotmail.com>, relay=none, delay=783, delays=633/0.01/150/0, dsn=4.4.1, status=deferred (connect to mx4.hotmail.com[65.55.37.72]:25: Connection timed out) Mar 14 19:41:26 server postfix/qmgr[9131]: E9A2640D325E: from=<a...@aaa.uk>, size=655, nrcpt=1 (queue active) Mar 14 19:41:56 server postfix/smtp[11249]: connect to mx4.hotmail.com[65.55.33.135]:25: Connection timed out Mar 14 19:42:26 server postfix/smtp[11249]: connect to mx4.hotmail.com[207.46.8.167]:25: Connection timed out Mar 14 19:42:56 server postfix/smtp[11249]: connect to mx4.hotmail.com[65.54.188.126]:25: Connection timed out Mar 14 19:43:26 server postfix/smtp[11249]: connect to mx1.hotmail.com[65.55.92.136]:25: Connection timed out Mar 14 19:43:56 server postfix/smtp[11249]: connect to mx4.hotmail.com[65.55.92.136]:25: Connection timed out Mar 14 19:43:56 server postfix/smtp[11249]: E9A2640D325E: to=<a...@hotmail.com>, relay=none, delay=1983, delays=1832/0.01/150/0, dsn=4.4.1, status=deferred (connect to mx4.hotmail.com[65.55.92.136]:25: Connection timed out) Mar 14 19:47:22 server postfix/pickup[9130]: 9CA5D41C3D71: uid=0 from=<root> Mar 14 19:47:22 server postfix/cleanup[11488]: 9CA5D41C3D71: message-id=<20150314194722.9ca5d41c3...@aaa.aaa.uk> Mar 14 19:47:22 server postfix/qmgr[9131]: 9CA5D41C3D71: from=<r...@aaa.aaa.uk>, size=938, nrcpt=1 (queue active) Mar 14 19:47:23 server postfix/local[11490]: 9CA5D41C3D71: to=<r...@aaa.aaa.uk>, orig_to=<root>, relay=local, delay=61, delays=60/0.01/0/0.6, dsn=2.0.0, status=sent (delivered to command: /usr/bin/procmail-wrapper -o -a $DOMAIN -d $LOGNAME) Mar 14 19:47:23 server postfix/qmgr[9131]: 9CA5D41C3D71: removed Mar 14 19:47:47 server postfix/qmgr[9131]: E9A2640D325E: from=<a...@aaa.uk>, size=655, nrcpt=1 (queue active) Mar 14 19:48:01 server postfix/postsuper[11631]: E9A2640D325E: removed Mar 14 19:48:01 server postfix/postsuper[11631]: Deleted: 1 message Mar 14 19:48:17 server postfix/smtp[11621]: connect to mx1.hotmail.com[65.54.188.94]:25: Connection timed out Mar 14 19:48:47 server postfix/smtp[11621]: connect to mx4.hotmail.com[65.55.33.119]:25: Connection timed out Mar 14 19:49:17 server postfix/smtp[11621]: connect to mx3.hotmail.com[65.55.37.104]:25: Connection timed out Mar 14 19:49:47 server postfix/smtp[11621]: connect to mx3.hotmail.com[65.54.188.110]:25: Connection timed out Mar 14 19:50:17 server postfix/smtp[11621]: connect to mx2.hotmail.com[65.55.92.184]:25: Connection timed out Mar 14 19:50:17 server postfix/smtp[11621]: E9A2640D325E: to=<a...@hotmail.com>, relay=none, delay=2364, delays=2213/0.01/150/0, dsn=4.4.1, status=deferred (connect to mx2.hotmail.com[65.55.92.184]:25: Connection timed out) Mar 14 20:19:59 server postfix/pickup[9130]: 290714155B8E: uid=0 from=<root> Mar 14 20:19:59 server postfix/cleanup[13198]: 290714155B8E: message-id=<20150314201959.290714155...@aaa.aaa.uk> Mar 14 20:19:59 server postfix/qmgr[9131]: 290714155B8E: from=<r...@aaa.aaa.uk>, size=539, nrcpt=1 (queue active) Mar 14 20:19:59 server postfix/local[13200]: 290714155B8E: to=<r...@aaa.aaa.uk>, orig_to=<root>, relay=local, delay=0.05, delays=0.02/0.01/0/0.02, dsn=2.0.0, status=sent (delivered to command: /usr/bin/procmail-wrapper -o -a $DOMAIN -d $LOGNAME) Mar 14 20:19:59 server postfix/qmgr[9131]: 290714155B8E: removed Mar 14 20:24:59 server postfix/pickup[9130]: CC49240D325E: uid=0 from=<root> Mar 14 20:24:59 server postfix/cleanup[13592]: CC49240D325E: message-id=<20150314202459.cc49240d3...@aaa.aaa.uk> Mar 14 20:24:59 server postfix/qmgr[9131]: CC49240D325E: from=<r...@aaa.aaa.uk>, size=2107, nrcpt=1 (queue active) Mar 14 20:24:59 server postfix/local[13594]: CC49240D325E: to=<r...@aaa.aaa.uk>, orig_to=<root>, relay=local, delay=0.04, delays=0.02/0.01/0/0.02, dsn=2.0.0, status=sent (delivered to command: /usr/bin/procmail-wrapper -o -a $DOMAIN -d $LOGNAME) Mar 14 20:24:59 server postfix/qmgr[9131]: CC49240D325E: removed -- View this message in context: http://postfix.1071664.n5.nabble.com/Postfix-Outward-Connections-Time-out-What-I-have-learned-so-far-tp75691p75694.html Sent from the Postfix Users mailing list archive at Nabble.com.