Hi folks,

I’m having a strange situation on one of my macOS X Servers (10.13.6) running 
postfix 3.1.1.

The server is configured to only use virtual_domains and virtual. When an email 
is received externally on port 25 for one of those domains, it’s accepted and 
handed off to Dovecot happily. All such received mail works perfectly. Here is 
a log excerpt of a successful receipt:

2020-03-10 11:53:47.417928+1000 0x3afa0e   Info        0x0                  
96460  smtpd: connect from office.externaldomain.com.au[203.1.1.1]
2020-03-10 11:53:47.985328+1000 0x3afa0e   Info        0x0                  
96460  smtpd: F075E1803D04: client=office.externaldomain.com.au[203.1.1.1]
2020-03-10 11:53:48.001337+1000 0x3afdd7   Info        0x0                  
96498  cleanup: F075E1803D04: 
message-id=<968781c4-1a74-42be-b4ce-141ea65e9...@externaldomain.com.au>
2020-03-10 11:53:48.005938+1000 0x35759a   Info        0x0                  
74101  qmgr: F075E1803D04: from=<j...@externaldomain.com.au>, size=859, nrcpt=1 
(queue active)
2020-03-10 11:53:48.032335+1000 0x3afa0e   Info        0x0                  
96460  smtpd: disconnect from office.externaldomain.com.au[203.1.1.1] ehlo=2 
starttls=1 mail=1 rcpt=1 data=1 quit=1 commands=7
2020-03-10 11:53:49.699136+1000 0x3b00c5   Info        0x0                  
96565  smtpd: connect from localhost[127.0.0.1]
2020-03-10 11:53:49.702840+1000 0x3b00c5   Info        0x0                  
96565  smtpd: AB8771803D0F: client=localhost[127.0.0.1]
2020-03-10 11:53:49.705075+1000 0x3afdd7   Info        0x0                  
96498  cleanup: AB8771803D0F: 
message-id=<968781c4-1a74-42be-b4ce-141ea65e9...@externaldomain.com.au>
2020-03-10 11:53:49.705801+1000 0x3b00c5   Info        0x0                  
96565  smtpd: disconnect from localhost[127.0.0.1] ehlo=1 mail=1 rcpt=1 data=1 
quit=1 commands=5
2020-03-10 11:53:49.706072+1000 0x35759a   Info        0x0                  
74101  qmgr: AB8771803D0F: from=<j...@externaldomain.com.au>, size=1555, 
nrcpt=1 (queue active)
2020-03-10 11:53:49.719987+1000 0x3b006e   Info        0x0                  
96562  smtp: F075E1803D04: to=<j...@home.myvirtualdomain.com>, 
orig_to=<j...@myvirtualdomain.com>, relay=127.0.0.1[127.0.0.1]:10024, 
delay=2.1, delays=0.36/0/0/1.7, dsn=2.0.0, status=sent (250 2.0.0 from 
MTA(smtp:[127.0.0.1]:10025): 250 2.0.0 Ok: queued as AB8771803D0F)
2020-03-10 11:53:49.720777+1000 0x35759a   Info        0x0                  
74101  qmgr: F075E1803D04: removed
2020-03-10 11:53:49.825969+1000 0x35759a   Info        0x0                  
74101  qmgr: AB8771803D0F: removed

However, when I use the `mail` command on the server, specifically `mail 
j...@myvirtualdomain.com <mailto:j...@myvirtualdomain.com>`, I get a mail loops 
back to itself error:

2020-03-10 11:55:43.060996+1000 0x3b04ce   Info        0x0                  
96627  cleanup: 061A21803DE0: 
message-id=<20200310015543.061a21803...@home.myvirtualdomain.com>
2020-03-10 11:55:43.062048+1000 0x3b04cb   Info        0x0                  
96626  qmgr: 061A21803DE0: from=<r...@home.myvirtualdomain.com>, size=338, 
nrcpt=1 (queue active)
2020-03-10 11:55:43.972784+1000 0x3afa0e   Info        0x0                  
96460  smtpd: connect from home.myvirtualdomain.com[10.0.5.201]
2020-03-10 11:55:43.973557+1000 0x3b04d3   Default     0x0                  
96629  smtp: warning: host home.myvirtualdomain.com[10.0.5.201]:25 greeted me 
with my own hostname home.myvirtualdomain.com
2020-03-10 11:55:43.974021+1000 0x3b04d3   Default     0x0                  
96629  smtp: warning: host home.myvirtualdomain.com[10.0.5.201]:25 replied to 
HELO/EHLO with my own hostname home.myvirtualdomain.com
2020-03-10 11:55:44.013568+1000 0x3b04d3   Info        0x0                  
96629  smtp: 061A21803DE0: to=<j...@myvirtualdomain.com>, 
relay=home.myvirtualdomain.com[10.0.5.201]:25, delay=1.5, 
delays=0.59/0.04/0.87/0, dsn=5.4.6, status=bounced (mail for 
myvirtualdomain.com loops back to myself)
2020-03-10 11:55:44.013989+1000 0x3afa0e   Info        0x0                  
96460  smtpd: disconnect from home.myvirtualdomain.com[10.0.5.201] ehlo=1 
quit=1 commands=2
2020-03-10 11:55:44.015809+1000 0x3b04ce   Info        0x0                  
96627  cleanup: 039A91803DE7: 
message-id=<20200310015544.039a91803...@home.myvirtualdomain.com>
2020-03-10 11:55:44.016665+1000 0x3b04cb   Info        0x0                  
96626  qmgr: 039A91803DE7: from=<>, size=2383, nrcpt=1 (queue active)
2020-03-10 11:55:44.017420+1000 0x3b04cb   Info        0x0                  
96626  qmgr: 061A21803DE0: removed

This is preventing all automated system emails from being delivered.

The DNS is seemingly correct. The relevant myvirtualdomain.com 
<http://myvirtualdomain.com/> is defined in virtual_domains. I’m assuming that 
the fact that everything works via smtp indicates that the configuration is 
correct?

Is this even a postfix config issue? Or is it possibly a problem somewhere 
else, i.e. with the `mail` command? Where can I begin to look to troubleshoot 
this further? What configuration info can I provide that might help? A full 
dump of `postconf -n`? All of master.cf?

Thank you,

Jay

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