Hi,

Comcast/Charter (found out about that one Saturday night when trying to reply to a legit individual message) both reject the message as soon as a blocked server connects, you don't even get to say HELO. Microsoft, when they decide you're evil and put you on their internal blacklist, reject after Mail from:. I find these rejections quite annoying, because clearly this means their spam analytics software is missing out on a lot of details that could help them make a more informed decision about whether to accept the message. Are my SPF and DKIM in order? (Yes I know spammers can and probably often do also have good SPF and DKIM but it's just one factor.) Is the message to a valid recipient? Does the content look spammy, as whatever their AI systems are would define spammy? Does my sending domain have a good reputation with this provider? Am I sending to someone I've sent messages deemed non-spammy to in the past? Am I perhaps replying to a message from this person which their software can, if they choose to, objectively prove was sent to me through their servers by that person?

But oh no, if your IP is on one of the blacklists we check, we won't just consider that a factor in delivery decisions, this means you must be totally evil and we're not even going to let you talk to us at all, even if it was your evil neighbors that got your entire IP range on that list. Go away and don't come back until you've solved your spam problem that probably isn't even your problem. Goodbye!

Jayson

On 3/18/2024 8:54 AM, Stephen J. Turnbull wrote:
Jayson Smith writes:

  > What I mean is that I'd love to find a good, reliable smarthost I
  > can direct my SMTP server on my VPS to use.

You could try some of the services listed here:
Hosting: https://wiki.list.org/COM/Mailman%20hosting%20services
Consulting: https://wiki.list.org/COM/Mailman%20consulting%20services
They might have a better idea or offer exactly the service you want.

Otherwise, I think you kinda have to move your VPS to the service you
want to use, and on top of the monthlies for running a server they'll
charge you for email volume.  AWS SES for example is 10,000 emails for
$1 billed monthly, and there's a throughput charge as well but that
too is probably negligible unless you're mailing videos.  They do
promise an IP with a clean reputation and they bonk your neighbors
(and you) automatically for sending more than a tiny amount of spam,
so I'd expect it to stay that way.  FWIW ....

  > The real problem I'm seeing is that seemingly within the last few
  > years, at least some VPS providers (Linode and Digital Ocean for
  > sure) have started getting entire IP ranges put on blocklists.

This is nothing new.  Effort-minimizing admins have been blocking
whole netblocks for well over a decade.  I think one new aspect is
that non-admins have borrowed the technique of mass-reporting to try
to shut down all aspects of an individual's or organization's Internet
presence.  I wouldn't block at the SMTP CONNECT level based on IP or
domain alone for the reasons you give for running your own smtpd, and
I doubt Google or Microsoft do.  But I know a lot of admins who do.

I don't know what to do about it.  I think my own server at my
university got on Microsoft's bad side once, but it got better fairly
quickly.  I did contact Microsoft but I don't know if it had anything
to do with getting off their blocklist, the only reply I got was a
'bot saying thank you for contacting Microsoft, check this link.  I
don't think they have their best minds working on the problem.
Instead they get customers by being too big to block, is my guess.


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