On Mon, Jul 06, 2020 at 07:40:27PM +0000, Drew Tomlinson wrote:

> I use postfix for my own domain and have been forwarding my email to
> outlook.com for years.  Recently, email has just been disappearing
> between my server and my inbox so I set it to forward my email to
> gmail.com.  Shortly after, I saw some messages like these in the logs:

You're running into intentional breakage caused by SPF and DMARC.
Sadly, this means that (simple) mail forwarding no longer works
reliably.

> In reading Google documentation, I learned SPF is failing.  Further
> reading revealed this is a common problem with forwarded email since
> it is not being sent by an authorized IP address.  Other articles
> suggested the workaround for this is to change the "Mail From:" to
> reflect my domain since I have SPF configured for it.  And maybe this
> is what is meant by SRS (Sender Rewriting Scheme)?

Even changing the envelope sender is not enough.  With DMARC you
need to also change the "From:" header in the message.

The simplest thing to do is to encapsulate the original message
as attachment to a new message.

    From: <your.address@your.domain.example>
    To: <y...@gmail.com>
    Subject: forwarded message from: <envelope-sender>
    MIME-Version: 1.0
    Content-Type: message/rfc822

    Return-Path: <envelope-sender>
    Received: ...
    ... original message header ...

    ... original message body

You'd need to forward your mail to a script that performs the
requisite encapsulation.  There are multiple ways to do that.
Nothing directly built-in.

-- 
    Viktor.

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