On Thu, 2026-02-26 at 11:03 -0600, Roger Heflin wrote:
> >     3. Outright Rejection (SMTP Level)
> >     In 2024 and 2025, Google implemented stricter requirements for
> > bulk
> >     senders (like SPF, DKIM, and DMARC authentication). If an email
> > is
> >     so poorly authenticated that Gmail considers it a "hard fail"
> > or a
> >     malicious spoof, it might be rejected entirely before it even
> >     reaches your account. In this case, the email doesn't go to
> > Spam or
> >     the Inbox—it simply never arrives.
> > 
> >     4. Filter Specificity Issues
> >     Sometimes a filter fails because it’s looking for the wrong
> > thing.
> >      * The "From" name vs. Email address: If you filtered the name
> > "John
> >     Doe" but he sends from a different email address than the one
> > you
> >     saved, the filter won't trigger.
> >      * Hidden "via" addresses: Many newsletters use third-party
> > senders
> >     (like Mailchimp). If the "Reply-to" address doesn't match the
> >     "Sender" address, a simple filter might miss it.
> >     Pro Tip: To make your filter "bulletproof," instead of just
> >     filtering by email address, try filtering by the domain (e.g.,
> >     from:*@company.com) or a unique word that always appears in
> > those
> >     emails.
> > 
> > I wouldn't expect any of those things to apply in this case.
> > 
> I don't know why you think none of those apply.
> 
> This is a #3 rejection.  SMTP decided something was wrong with the
> message and outright rejected--that is exactly what this rejection
> message is.  So clearly gmail has a few more (half-assed) rules of
> some sort than Gemini knows about, which is not a shock since no AI
> will know about what Gmail is doing since Gmail almost certainly does
> not document it any place public that Gemini(or any other public AI)
> would have been able to scrape.

If it's #3 then a SPF, DKIM, DMARC etc. problem would be caused by the
list server, i.e. not Stephen nor me. If it's not that, then who knows.

The reason I asked Gemini and not (say) ChatGPT is that it's run by
Google, so is presumably more likely to have correct answers to this
question.

poc
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