On 2023-01-10 at 13:59 -0800, Dan Mahoney wrote:
> The way postfix handles these aliases, is that it preserves the
> original envelope sender and recipient (which we don’t want anyway),
> and o365 is rejecting on that envelope sender/recipient (that it’s
> not allowed to deliver to our internal envelope recipient, which is
> not unreasonable, but still surprising we haven’t hit it before.

Postfix is keeping the alias as envelope recipient?? Or just in the To:
header?

I think O365 is simply seeing that the sender is a mail it should be
handling itself but the mail comes from outside and rejects it.

I'm sure it's possible to configure it to allow that. I don't know how
to do that, though. Marking the sender and external and the postfix IP
as trusted, probably.

Regards




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