Thus said [email protected] on Mon, 23 Feb 2026 12:25:22 -0500:

> A more  accurate description of the  issue is that google  and verizon
> bounce mail  back when there are  multiple "CC" or "To"  _headers_ (as
> per RFC 5322), not just multiple recipients.

Yes, I've  seen this (not  in practice)  mentioned on Google's  RFC 5322
restrictions pages. They  seem to be selective in which  features of RFC
5322 they enforce. For example, they don't enforce the line length limit
at all  and gladly  allow the  receiving of  lines that  violate Section
2.1.1 Line Length Limits.

In all my years  of handling email I cannot recall a  single time that I
saw spam  that included multiple  To or Cc  headers, so I'm  curious how
effective it is as an indicator and cause for rejection. The restriction
apparently comes from  an interpretation of RFC 5322  Section 3.6. Field
Definitions which includes a table of the number of times a given header
is permitted in a message.

> I dunno  if postfix can  condense headers this  way, or perhaps  I can
> wrap localhost:SMTP  in a script (using  scan & anno?!) and  then send
> the altered message to postfix for outbound delivery

Now,  for Mark's  problem, I'm  surprised  his local  postfix MSA  (mail
submission  agent)  doesn't  clean  up  the  message  already.  I  tried
sending some messages  that included multiple To  headers and new-inject
condensed them into  one To header, however, I notice  that the original
qmail-inject does not. Postfix should be able to handle this but I don't
use postfix so someone else will  have to comment---it might be possible
to use a postfix "milter" to handle this.

Good luck.

Andy

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