The initial debug advice I got was helpful, so I thought I'd take the next step and add relaying to gmail (back to that in a minute), but apparently I just don't get it still. Rolling back to my previously working setup failed also, this time with a new error: 421. I don't get much help looking for explanations of 421 on the web.
# cat /etc/mail/smtpd.conf listen on lo0 table aliases db:/etc/mail/aliases.db accept for local alias <aliases> deliver to mbox accept for any relay # echo 'test' | mail -s TEST scott send-mail: command failed: 421 Temporary failure smtpd -d -T smtp output: info: OpenSMTPD 5.3 starting debug: bounce warning after 4h debug: using "fs" queue backend debug: using "ramqueue" scheduler backend debug: using "ram" stat backend info: startup [debug mode] debug: init server-ssl tree debug: init client-ssl tree debug: enabling parent -> control debug: enabling control -> scheduler debug: enabling lka -> parent debug: enabling mda -> parent debug: enabling mfa -> parent debug: enabling mta -> parent debug: enabling queue -> parent debug: enabling scheduler -> control debug: enabling smtp -> control debug: enabling parent -> lka debug: enabling control -> queue debug: enabling lka -> queue debug: enabling mda -> queue debug: enabling mfa -> smtp debug: enabling mta -> queue debug: enabling queue -> control debug: enabling scheduler -> queue debug: enabling smtp -> parent debug: enabling parent -> mda debug: enabling control -> smtp debug: enabling lka -> smtp debug: enabling mda -> lka debug: enabling mfa -> control debug: enabling mta -> lka debug: enabling queue -> smtp debug: enabling smtp -> lka debug: enabling parent -> mfa debug: enabling control -> mfa debug: enabling lka -> mda debug: enabling mda -> control debug: disabling mfa -> smtp debug: enabling mta -> control debug: enabling queue -> mda debug: enabling smtp -> mfa debug: enabling parent -> mta debug: enabling control -> parent debug: enabling lka -> mta debug: enabling queue -> mta debug: enabling smtp -> queue debug: enabling parent -> smtp debug: enabling control -> lka debug: enabling lka -> control debug: enabling queue -> lka debug: enabling parent -> queue debug: enabling control -> mda debug: disabling lka -> mda debug: enabling queue -> scheduler debug: parent_send_config_ruleset: reloading debug: enabling control -> mta debug: disabling lka -> mta debug: parent_send_config_mfa: reloading debug: disabling lka -> smtp debug: queue: done loading queue into scheduler debug: parent_send_config: configuring smtp debug: mfa ready debug: enabling mfa -> smtp debug: smtp: listen on 127.0.0.1 port 25 flags 0x0 cert "" debug: smtp: listen on IPv6:fe80::1%lo0 port 25 flags 0x0 cert "" debug: smtp: listen on IPv6:::1 port 25 flags 0x0 cert "" debug: smtp: will accept at most 501 clients debug: enabling lka -> mda debug: enabling lka -> mta debug: enabling lka -> smtp debug: smtpd: scanning offline queue... debug: smtpd: offline scanning done debug: enabling control -> parent debug: enabling control -> parent debug: smtp: new client on listener: 0x104603b5f980 smtp: 0x104813690000: STATE_NEW -> STATE_CONNECTED smtp-in: New session 000000005744eced from host 1000@localhost [local] smtp: 0x104813690000: >>> 220 foo.bar.org ESMTP OpenSMTPD smtp: 0x104813690000: <<< EHLO localhost smtp: 0x104813690000: STATE_CONNECTED -> STATE_HELO smtp: 0x104813690000: >>> 250-foo.bar.org Hello localhost [local], pleased to meet you smtp: 0x104813690000: >>> 250-8BITMIME smtp: 0x104813690000: >>> 250-ENHANCEDSTATUSCODES smtp: 0x104813690000: >>> 250-SIZE 36700160 smtp: 0x104813690000: >>> 250 HELP smtp: 0x104813690000: <<< MAIL FROM: <sc...@foo.bar.org> smtp: 0x104813690000: >>> 250 Ok smtp: 0x104813690000: <<< RCPT TO: <sc...@foo.bar.org> info: forward file is empty smtp: 0x104813690000: >>> 421 Temporary failure smtp-in: Failed command on session 000000005744eced: "RCPT TO: < sc...@foo.bar.org>" => 421 Temporary failure smtp: 0x104813690000: STATE_HELO -> STATE_QUIT smtp-in: Closing session 000000005744eced debug: smtp: 0x104813690000: deleting session: done I wondered if somehow I gummed up my queue when I was diddling around with the relay settings. # ls /var/spool/smtpd/ a0 Ok, so that's my just-failed message, so I flush it, just to be sanitary: # smtpctl remove a0b31f71a4e509ff (BTW, is there a way to flush ALL queued messages? smtpctl(8) doesn't allude to it. If there isn't, what's the proper way to do so?) -Scott