On Mon, Sep 20, 2021 at 7:26 AM Jaroslaw Rafa via mailop
<mailop@mailop.org> wrote:
>
> I want to return to an old issue, which repeatedly happens again and again,
> that is, Google putting emails from me to recipient's spam folder. What's
> absurd, this happens not only to Gmail addresses to which I am writing for
> the first time, but also to recipients with whom I have previously
> corresponded and who marked my messages as non-spam. It even happens when
> I'm replying to a message I got from a Gmail user, which is totally absurd!
> It can even happen in a middle of an email exchange - ie. I have once
> exchanged a few messages with a Gmail user without problems, then suddenly
> one of my subsequent messages in the conversation went to Spam.

I send only a small volume of emaail from my Linux box to Gmail -- a
couple of personal newsletters and alerts and stuff. I don't have much
trouble with it, and I attribute that to using IPv4 (not IPv6), using
DKIM, and using SPF with -all.

I've also experimented with sending OUT via Gmail from Linux - using
my personal Gmail account as the actual sender for emails from shell
scripts and etc. It's not really a scalable solution, but it works
fine for my spamtrap monitoring alerts. Depending on what you're
doing, maybe that's something worth looking at. More info:
https://www.spamresource.com/2020/09/lets-send-mailthrough-gmail.html

The question of whether or not Google cares about the pseudo-TLD is a
tough one. On one hand, my employer has thousands of clients sending
mail successfully from subdomains -- we position it as a best
practice, and I don't see evidence of "trickle down" domain reputation
impact. On the other hand, it could be more of a filtering signal at
very low volumes, or it could be that other eu.org users are causing
enough reputation issues to make that bleed through over to your
subdomain. You'd think I'd be seeing evidence of that with ESP
clients, though, if that were the case.

In your shoes, I might try doing a bit of deliverability testing --
set up a periodic send of a boilerplate email to a personal Gmail
account and report that to Gmail as a false positive whenever you see
it getting filtered, using
https://support.google.com/mail/contact/bulk_send_new

I know you're referring to 1:1 email here, not bulk, but I do think
this would likely apply.

Cheers,
Al Iverson


-- 
Al Iverson // Wombatmail // Chicago
Deliverability: https://spamresource.com
DNS Tools: https://xnnd.com
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