On Fri, Nov 04, 2022 at 08:45:15AM +0000, Gino Ferguson wrote:

> Thanks for the replies. 
> 
> Before I wrote my question I have tried this ('canonical_classes' was the 
> default):
> sender_canonical_maps = regexp:/etc/postfix/custom_rewrite_sender

- Firstly, DO NOT use sender_canonical_maps, it fails to rewrite "Cc:".
  Use "canonical_maps".
- Secondly, strongly consider processing incoming mail (where you
  perform DKIM verification) on a separate machine, or in a separate
  Postfix instance from outgoing mail (where you perform DKIM signing).
- Sign outgoing DKIM mail in exactly one stage of your outgoing mail
  processing, as late as possible in the pipeline.


> Today morning we did test it again but added 
> header_checks = regexp:/etc/postfix/custom_rewrite

NO.  Header checks *cannot* parse email addresses in headers.
If you think this works, you're mistaken.

> /etc/postfix/custom_rewrite:
> /^(.*)@originalsender.fqdn$/ REPLACE ${1}@masqueraded.fqdn

NO.

> And the masquerading worked and the DKIM is good.
> 
> Now I'm confused.

Use "canonical_maps" with envelope_recipient excluded from
canonical_classes, or perform rewriting only on the outbound MTA, where
it is OK to not do recipient validation (I prefer and recommend divide
and conquer).

-- 
    Viktor.

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