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"I’ve had exactly one problem with deliverabilty during that time, where someone with a Hotmail account complained to never have received my mail - even though

"I’ve had exactly one problem with deliverabilty during that time, where someone with a Hotmail account complained to never have received my mail - even though the Microsoft server claimed to have accepted it according to my logs. While Microsoft can be notoriously intransparent and unforgiving with (not) accepting mail, in this case it turned out to be a blacklisting issue. I had just moved servers and IP addresses shortly before, with the new IP having been on an internal MS blacklist. I raised a ticket with their mail infrastructure department, and to my surprise, the IP was cleared soon after." Unfortunately, MS and others have now adopted an "opt-out" blacklisting policy. Even with a clean IP, you'll have these problems if you set up your own server. (I've been running my own mail servers for 30 years.)

Melatonic 5y ago
Dont you only usually get blacklisted though if you are sending mass amounts of emails? They mostly blacklist spammers or people suspected of spamming.
- StayTrue 5y ago
  In the past this was true. Now some providers look for a minimum volume of emails to establish a reputation. It's diabolical.
terlisimo 5y ago
This is how I learned what DMARC is. A friend with email @live.com said he never received any of my emails. No spam, no bounce, just silent drop. I went through MS knowledge base which thankfully said that DMARC/DKIM are pretty much required. After setting up opendmarc, everything was fine.
- cpncrunch 5y ago
  Also required for gmail these days. But once you've set up SPF/DMARC/DKIM everything tends to work smoothly without too many deliverability problems. There might be a few blacklists to negotiate when moving to a new ip, but it's generally pretty straightforward these days. I remember a few years ago bashing my head against a brick wall trying to solve problems delivering to hotmail and icloud, but that was before I set up DKIM and DMARC which I think might have been the issue.

Melatonic 5y ago

Dont you only usually get blacklisted though if you are sending mass amounts of emails? They mostly blacklist spammers or people suspected of spamming.

StayTrue 5y ago
In the past this was true. Now some providers look for a minimum volume of emails to establish a reputation. It's diabolical.

terlisimo 5y ago

This is how I learned what DMARC is. A friend with email @live.com said he never received any of my emails. No spam, no bounce, just silent drop. I went through MS knowledge base which thankfully said that DMARC/DKIM are pretty much required. After setting up opendmarc, everything was fine.

cpncrunch 5y ago
Also required for gmail these days. But once you've set up SPF/DMARC/DKIM everything tends to work smoothly without too many deliverability problems. There might be a few blacklists to negotiate when moving to a new ip, but it's generally pretty straightforward these days. I remember a few years ago bashing my head against a brick wall trying to solve problems delivering to hotmail and icloud, but that was before I set up DKIM and DMARC which I think might have been the issue.