On 2021/04/21 10:23, Neil Youngman via mailop wrote:
> On 21/04/2021 11:00, Chris wrote:
> > Aside from the possibility that the message is simply wrong, or the
> > implementation broken, is your mail server acting like most other
> > servers when presented with a failure (soft or hard)?
> > 
> > Your posting seems to be that you give up after the second try.
> >
> > Most servers will try at least 5 times for such, only giving up after
> > hours (sendmail defaults at 4 days).
> 
> It doesn't behave exactly like a normal mail server, but it does retry
> more than five times. Not all retries are from the same IP, but I have 
> observed that retries from the same IP don't get delivered.
> 
> Neil Youngman

Retries from different IPs (even within the same /24 or so) will
certainly cause problems for some greylisting software.

Also make sure the addresses used in SMTP are identical for each try
(say, not changing the sender address etc.)

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