On Sat, Feb 18, 2017 at 05:43:03PM +0000, Chris Green wrote:
> I am trying to diagnose why messages from on system fail to arrive
> whereas identical messages from another similar system arrive
> successfully.
> 
> Both systems are single board computers running postfix 2.9.6 under
> Debian.  The main.cf on both systems is identical.  Both systems are
> connecting to the same SMTP server for relaying.
> 
> On the system where the message is sent and received successfully I
> see (in /var/log/mail.log):-
>     Feb 18 17:32:51 pi postfix/pickup[25898]: 2009B22C52: uid=1000 
> from=<chris>
>     Feb 18 17:32:51 pi postfix/cleanup[25978]: 2009B22C52: 
> message-id=<20170218173251.2009b22...@pi.zbmc.eu>
>     Feb 18 17:32:51 pi postfix/qmgr[21159]: 2009B22C52: from=<ch...@zbmc.eu>, 
> size=294, nrcpt=1 (queue active)
>     Feb 18 17:32:52 pi postfix/smtp[25980]: 2009B22C52: to=<ch...@zbmc.eu>, 
> relay=mail3.gridhost.co.uk[95.142.156.18]:587, delay=0.97, 
> delays=0.15/0.11/0.36/0.35, 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 08DEC26AEC71)

Here the relayhost seems to be using a content filter, and on the 
line above is reporting what it has heard through the filter.  It 
also reports the queue ID on the other side of the filter, to wit:
"08DEC26AEC71".

>     Feb 18 17:32:52 pi postfix/qmgr[21159]: 2009B22C52: removed
> 
> 
> 
> On the system that appears to send OK but the message never
> reaches its destination I see:-
> 
>     Feb 18 18:32:18 odin postfix/pickup[15648]: 05E963BC3: uid=1001 
> from=<chris>
>     Feb 18 18:32:18 odin postfix/cleanup[15989]: 05E963BC3: 
> message-id=<20170218173218.05e963...@odin.zbmc.eu>
>     Feb 18 18:32:18 odin postfix/qmgr[14084]: 05E963BC3: 
> from=<ch...@zbmc.eu>, size=296, nrcpt=1 (queue active)
>     Feb 18 18:32:19 odin postfix/smtp[15991]: 05E963BC3: to=<ch...@zbmc.eu>, 
> relay=mail3.gridhost.co.uk[95.142.156.18]:587, delay=1.2, 
> delays=0.22/0.11/0.65/0.19, dsn=2.0.0,
>     status=sent (250 2.0.0 Ok: queued as EDA7EE0C39)

Here we didn't get anything from the content filter.  The answer of 
the question, "Why not?" is probably in the logs on the relayhost.

>     Feb 18 18:32:19 odin postfix/qmgr[14084]: 05E963BC3: removed
> 
> 
> Does that 'queued as EDA7EE0C39' in the second case mean that the 
> message has been put on a queue rather than being sent?  But why?  
> The messages are virtually identical, the destination address is 
> the same, etc.

If you don't control the relayhost, talk to the admin there.
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