On Mon, Mar 09, 2020 at 11:02:37PM -0500, Noel Jones wrote:

> Turn off debug logging and start here:
> http://www.postfix.org/DEBUG_README.html#mail

That was not debug logging. :-(  That's just what "normal"
logging looks like with MacOS...

On Tue, Mar 10, 2020 at 12:09:42PM +1000, Jay wrote:

> All such received mail works perfectly. Here is a log excerpt of a
> successful receipt:
> 
> 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 11:53:49.702840+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 11:53:49.706072+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)

The message with queue-id F075E1803D04 got processed via a
content_filter at [127.0.0.1]:10024 as AB8771803D0F, with no apparent
issues.

> 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 11:55:43.062048+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)

Here a message with queue-id 061A21803DE0 was instead handed off for
delivery via [10.0.5.201] (on port 25!), and loop detection kicked in. 
You'll have to provide more configuration details, or figure out on your
own why local mail submission is redirected that way.

Noel's referral to:

> http://www.postfix.org/DEBUG_README.html#mail

is appropriate here, you should post the requisite "postconf -nf" and
"postconf -Mf" output, without rewrapping the text.

-- 
    Viktor.

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