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If you start a new mail server in 2022 (or migrate from a previous address), you have to apply to be whitelisted by outlook.com and the many domains owned by Mi

If you start a new mail server in 2022 (or migrate from a previous address), you have to apply to be whitelisted by outlook.com and the many domains owned by Microsoft. They no longer accept mail from servers they haven't seen before. Companies such as google, microsoft, and facebook would rather that email died, and are actively working to destroy it through neglect, so that people will shift their messaging to proprietary networks they happen to own. Email has problems - spam being one of them, but it's as potentially important as IP routing itself, and we should work to preserve it.

thaumaturgy 5y ago
> They no longer accept mail from servers they haven't seen before. Interesting. This tracks with my experiences too, but is there a good source for this that I can reference in the future? I got out of hosting email last year entirely because of intractable deliverability problems with the big three: Google, Microsoft, and Comcast. Comcast's issues mostly appeared intermittent and the result of incompetence. Google and Microsoft have clearly been competing to see who can kill small email service providers the fastest.
- lytefm 5y ago
  I contacted Microsoft, actually received an answer from them and got an IP unblocked. Google can be tough though. If their Algorithms don't like you, good look. I was responsible for a new IP/Email setup and while all other relevant providers liked our mail and Google Postmaster tools didn't show anything bad, all our mail went to Spam in GMail. I found out why when even mails from completely different senders would usually go to Inbox but hit Spam once our Website or email was included: Despite showing it as "high reputation", GMail must have considered it as utter trash. Changed to a different, older domain and all has been fine since.
  - jbotz 5y ago
    How did you contact them? I had problems getting mail to MS years ago and at the time wasn't able to get anyone to do anything or even respond. At some point later the problem went away, though.
    - lytefm 5y ago
      I contacted them via https://support.microsoft.com/en-US/supportrequestform/8ad563e3-288e-2a61-8122-3ba03d6b8d75 https://support.microsoft.com/en-US/supportrequestform/8ad56...
eps 5y ago
Another fascinating fact is that forwarding Outlook spam to abuse@outlook.com will get you shitcanned ... as a spammer! You can't make this up. They pass all abuse reports throuh their spam filter and this affects your server's reputation. Then at some point they start rejecting emails from you with a 5xx code that stands for "your IP is on our blacklist". Contacting "Hotmail sender support" will yield "We see no problems on our end, kindly fuck off". You have to then go through a ritual of summoning a manager, taking anywhere from 2 to 5 days, at which point they will say "we put a mitigation in place, will take up to 48 hours to propagate", but it works right away. If it doesn't, it means that they mistyped your server address and the next chance to ask them to fix this will be, you guessed it, in 48 hours. So a week of bounces in total. Ran into this 3 times in a course of a year, then took a closer look at the logs and - yep - in all three cases it was triggered by sending a report to abuse@outlook.com. It's just such a magnifecent clusterfuck it's jaw-dropping.
cpncrunch 5y ago
It's actually not that big of a problem. I moved to a new server with a different IP last year, and also the year before, and as long as you have SPF, DMARC, DKIM and reverse DNS set up, generally everything works. I think I just had to got whitelisted from one or two. A few years ago I did have major problems with hotmail and icloud, but recently it doesn't seem to be an issue. I think I didn't have DKIM set up when I was having problems. I have noticed that google will auto-junk your email if you don't have SPF, DMARC and DKIM set up, and you must set DMARC to "reject".

thaumaturgy 5y ago

> They no longer accept mail from servers they haven't seen before. Interesting. This tracks with my experiences too, but is there a good source for this that I can reference in the future? I got out of hosting email last year entirely because of intractable deliverability problems with the big three: Google, Microsoft, and Comcast. Comcast's issues mostly appeared intermittent and the result of incompetence. Google and Microsoft have clearly been competing to see who can kill small email service providers the fastest.

lytefm 5y ago
I contacted Microsoft, actually received an answer from them and got an IP unblocked. Google can be tough though. If their Algorithms don't like you, good look. I was responsible for a new IP/Email setup and while all other relevant providers liked our mail and Google Postmaster tools didn't show anything bad, all our mail went to Spam in GMail. I found out why when even mails from completely different senders would usually go to Inbox but hit Spam once our Website or email was included: Despite showing it as "high reputation", GMail must have considered it as utter trash. Changed to a different, older domain and all has been fine since.
- jbotz 5y ago
  How did you contact them? I had problems getting mail to MS years ago and at the time wasn't able to get anyone to do anything or even respond. At some point later the problem went away, though.
  - lytefm 5y ago
    I contacted them via https://support.microsoft.com/en-US/supportrequestform/8ad563e3-288e-2a61-8122-3ba03d6b8d75 https://support.microsoft.com/en-US/supportrequestform/8ad56...

eps 5y ago

Another fascinating fact is that forwarding Outlook spam to abuse@outlook.com will get you shitcanned ... as a spammer! You can't make this up. They pass all abuse reports throuh their spam filter and this affects your server's reputation. Then at some point they start rejecting emails from you with a 5xx code that stands for "your IP is on our blacklist". Contacting "Hotmail sender support" will yield "We see no problems on our end, kindly fuck off". You have to then go through a ritual of summoning a manager, taking anywhere from 2 to 5 days, at which point they will say "we put a mitigation in place, will take up to 48 hours to propagate", but it works right away. If it doesn't, it means that they mistyped your server address and the next chance to ask them to fix this will be, you guessed it, in 48 hours. So a week of bounces in total. Ran into this 3 times in a course of a year, then took a closer look at the logs and - yep - in all three cases it was triggered by sending a report to abuse@outlook.com. It's just such a magnifecent clusterfuck it's jaw-dropping.

cpncrunch 5y ago

It's actually not that big of a problem. I moved to a new server with a different IP last year, and also the year before, and as long as you have SPF, DMARC, DKIM and reverse DNS set up, generally everything works. I think I just had to got whitelisted from one or two. A few years ago I did have major problems with hotmail and icloud, but recently it doesn't seem to be an issue. I think I didn't have DKIM set up when I was having problems. I have noticed that google will auto-junk your email if you don't have SPF, DMARC and DKIM set up, and you must set DMARC to "reject".