I got the chance to work on what you recommended. Thank you Wietse. main.cf: # transactional email for the ministry sender_dependent_relayhost_maps = regexp:/etc/postfix/sender_relay.regexp
sender_relay.regexp: # email sent from the ministry domain will use the raystedman: smtp transport and relay to smtp-relay.gmail.com /@raystedman\.org$/ raystedman:[smtp-relay.gmail.com] master.cf: # ministry transactional email will use this transport and ip address raystedman unix - - n - - smtp -o smtp_bind_address=xxx.xxx.xxx.234 [rsm@mail0 mail0]$ sudo systemctl restart postfix [rsm@mail0 mail0]$ journalctl -u postfix -f Aug 28 22:08:13 mail0.raystedman.org postfix/smtpd[49119]: connect from mail0-p.raystedman.org[xxx.xxx.xxx.174] Aug 28 22:08:13 mail0.raystedman.org postfix/smtpd[49119]: 0B5D085D65D: client=mail0-p.raystedman.org[xxx.xxx.xxx.174] Aug 28 22:08:13 mail0.raystedman.org postfix/cleanup[49123]: 0B5D085D65D: message-id=<cdbed6cbe27b92e1b49745731a388a01@swift.generated> Aug 28 22:08:13 mail0.raystedman.org postfix/qmgr[49108]: 0B5D085D65D: from=<webmas...@raystedman.org>, size=606, nrcpt=1 (queue active) Aug 28 22:08:13 mail0.raystedman.org postfix/smtpd[49119]: disconnect from mail0-p.raystedman.org[xxx.xxx.xxx.174] ehlo=1 mail=1 rcpt=1 data=1 quit=1 commands=5 Aug 28 22:08:13 mail0.raystedman.org r238/smtp[49124]: fatal: unknown service: [smtp-relay.gmail.com]/tcp Aug 28 22:08:14 mail0.raystedman.org postfix/qmgr[49108]: warning: private/r238 socket: malformed response Aug 28 22:08:14 mail0.raystedman.org postfix/qmgr[49108]: warning: transport r238 failure -- see a previous warning/fatal/panic logfile record for the problem description Aug 28 22:08:14 mail0.raystedman.org postfix/master[49106]: warning: process /usr/libexec/postfix/smtp pid 49124 exit status 1 Aug 28 22:08:14 mail0.raystedman.org postfix/master[49106]: warning: /usr/libexec/postfix/smtp: bad command startup -- throttling Aug 28 22:08:14 mail0.raystedman.org postfix/error[49125]: 0B5D085D65D: to=<g...@headingup.net>, relay=none, delay=1.1, delays=0.1/1/0/0.01, dsn=4.3.0, status=deferred (unknown mail transport error) It looks like we tried to use one of the randmap transports (r238) instead of raystedman: and we are seeing a fatal error. I can get this to work if I remove the "raystedman:" in sender_relay.regexp. Aug 28 22:20:04 mail0.raystedman.org postfix/smtpd[49287]: connect from mail0-p.raystedman.org[xxx.xxx.xxx.174] Aug 28 22:20:04 mail0.raystedman.org postfix/smtpd[49287]: AE32785D663: client=mail0-p.raystedman.org[xxx.xxx.xxx.174] Aug 28 22:20:04 mail0.raystedman.org postfix/cleanup[49291]: AE32785D663: message-id=<fceb9d1a72d5285837cff4128b663302@swift.generated> Aug 28 22:20:04 mail0.raystedman.org postfix/qmgr[49282]: AE32785D663: from=<webmas...@raystedman.org>, size=606, nrcpt=1 (queue active) Aug 28 22:20:04 mail0.raystedman.org postfix/smtpd[49287]: disconnect from mail0-p.raystedman.org[10.81.198.174] ehlo=1 mail=1 rcpt=1 data=1 quit=1 commands=5 Aug 28 22:20:05 mail0.raystedman.org r238/smtp[49292]: AE32785D663: to=<g...@headingup.net>, relay=smtp-relay.gmail.com[142.250.30.28]:25, delay=0.61, delays=0.1/0.01/0.27/0.23, dsn=2.0.0, status=sent (250 2.0.0 OK 1598671205 w64sm252467qkb.5 - gsmtp) Aug 28 22:20:05 mail0.raystedman.org postfix/qmgr[49282]: AE32785D663: removed Here we selected one of the randmap transports (r238) and relayed to smtp-relay.gmail.com as expected. So we are still left with binding this sender_relay to a specific ip address. Thanks, Greg www.RayStedman.org