Hi,
for context, I run a small mailserver, used by mainly me and a couple of
friends and famely. I also run a few webservices which sometimes send
transactional emails to people who sign up there. (Mainly a weblate
instance with around 150 or so users).
The total volume of sent emails is likely below 10 mails per day and I
reckon I only sent 1-3/month to google and far less to MS.
I spent the whole weekend (again) trying to get mails from my server not
to be marked as spam by Google and Microsoft.
After trying about everything under the sun I ended up switching the
sending IP from the one I have had sole control over in the last 5 or so
years to a newly rented VPS. This seemed to dramatically improve google
opinion of me. (The old IP never sent spam in the last 5 years, it is
not and never was (in that timeframe) listed on any blocklist).
While I can't fathom the reasoning behind this, I'm happy that I finally
have a chance of my emails being actually read by gmail users.
Now Hotmail and Outlook.com seem to be a whole different beast. Both the
old IP and the new one go into spam, in 100% of my tests. (I have a
friend with a hotmail account and used https://glockapps.com for testing
this a bit more systematically.)
Which leads me to the question: What on earth would I need to do to be
able to send emails to MS controlled mailservers which people will
actually read?
When I originally set this up, I also jumped through all the available
hoops at MS for weeks, being redirected to the same webform with every
2nd automated reply. They also were only ever talking about outright
mail rejections, which I never experienced. I think at one point I got a
reply that they don't know or have any influence of what their spam
filter does :shrug:.
Google has only been marginally better, of course with that whole IP
switching thing being required.
Original sending IP: 176.9.145.28
New sender: 5.45.96.14
Best,
Marcus
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