[tsukikage]

IP reputation is a gamble, and there is no recourse. If you're lucky, awesome. But if you're unlucky and switching host isn't an option, you pretty much have to involve a large third party to act your behalf - there is zero appetite in the industry for interacting with individuals.

The best solution I've been able to find is to self-host /almost/ everything, but route outgoing mail through Amazon SES.

The pricing for vanity email volumes is negligible (a few cents a year), and they have people whose full time job is wrangling IP reputation / Office 365 / etc.

This setup has survived several ISP/hosting switches; at times when I am lucky with IP reputation I route only mail going to Office 365 recipients via SES and deliver the rest directly; at times when I am less lucky, everything goes via SES.

[jeroenhd]

The whole IP reputation problem seems to mostly be a Google/Microsoft problem.

Unfortunately, most of the world seems to use one of those two platforms.

Routing mail to those two services via a third party seems like the wisest choice. May I ask how you implemented that?

[tsukikage]

I use exim4. So after doing the usual SES setup, I can change the smarthost router to look like this:

  SMARTHOST_FOR_MS = email-smtp.us-east-2.amazonaws.com::587
  smarthost:
    debug_print = "R: smarthost for $local_part@$domain"
    driver = manualroute
    domains = ! +local_domains
    transport = remote_smtp_smarthost
    route_list = hotmail.com SMARTHOST_FOR_MS byname ; \
                 live.com SMARTHOST_FOR_MS byname ; \
                 outlook.com SMARTHOST_FOR_MS byname ; \
                 msn.com SMARTHOST_FOR_MS byname ; \
                 live.co.uk SMARTHOST_FOR_MS byname ; \
                 hotmail.co.uk SMARTHOST_FOR_MS byname ; \
                 * DCsmarthost byname
    host_find_failed = defer
    same_domain_copy_routing = yes
    no_more

If there was a much larger list of problem destinations I'd maybe do something nicer involving separate routers and a domainlist, but those cover all the cases that are broken right now.

[graemep]

You can usually switch host. Some have better IP reputations than others.

There are quite a few other providers of email forwarding services, although I might look at SES myself if its that cheap as I have issues with hotmail (I seem to be OK with most mail to email on MS hosted email on other domains, oddly enough).

[tsukikage]

> You can usually switch host

...it took OP 8 months of "rolling the gacha" and waiting to get a clean IP; no mention of costs. Not really a solution in my book. If you're willing to wait 8 months for working email, I put it to you you're actually using some other provider for your life and the thing you are playing with is a toy.

I've been self-hosting my email for a pretty long time. I first started down the reputation rabbit hole when a provider decided to shut up shop after a decade of operation, causing me to lose my lovely fixed IP block with its decade-old clean rep. Waiting/playing around isn't really an option when your email is broken and you need it working /today/ because it's not a throwaway toy - your digital life is tied to it.

Still, as I said at the start, if you get lucky, awesome for you.

[xrisk]

Did switching your deliverer to SES have any effect on how clients like Gmail “tagged” your email? (Promotional category or something IIRC)

[tsukikage]

Nope. The biggest impact on gmail was making sure I had DMARC, DKIM and SPF all set up correctly.

(I tried several other relay services like mailgun and those /did/ have noticeable impact - SES was the first one I tried that didn't, so I stuck with it).