I have a hotmail throwaway account (it has since been migrated to outlook with the microsoft buyout) and its spam filter is completely backward. There is currently 373 e-mails in my inbox (100% spam, expected since it is a throwaway...) and 4 e-mails in my spam folder--100% of them the account registration/confirmation e-mails that I was wanted.
I have migrated to fastmail for all of my personal e-mail, which I have been pretty happy with. So far I haven't caught any legit email which has been categorized as spam and negligible spam that has made it through into my inbox (mailing lists notwithstanding--I sort them using automation rules). My one complaint is that there is no way to turn off their "thou shall not receive executable attachments" filter so I still need people to play the "set windows to show the file extension, change it to .txt, and then attach it" game when people want to send compiled code via e-mail.
In any case, it is certainly a much better situation than the gmail spam filter I used while in school, which had about a 10% chance of marking outside messages as spam--in fact it even started marking e-mails sent by my professor (via the university gmail) as spam...
Honestly not sure, but certainly sometime in the 20th century. It was my main e-mail back then, I migrated to Yahoo! shortly after the Microsoft buyout and kept the HoTMaiL as a throwaway. When Google announced Gmail and the 1GB (with projection to infinite) storage I switched to them as soon as I got an invite, but when they changed their slogan from "Don't be evil" to "Do the right thing" with the Alphabet restructure I ditched it and moved to my own domain with Fastmail. If Fastmail starts to show signs of evil it will be as easy as updating my domain records to point toward OurMailIsActuallyGoodIPromiseThisTime.com and click through the certificate warnings on my mail clients.
That Hotmail branding survived long after the purchase; in the last few years it's the same interface as their 365 business offering now, and under outlook.com branding.
When I last had to wrangle with MS (c.5 years ago, who were dropping all our email _replies_ to customers, they had a third party that you could pay to ensure your emails got through ... apparently the problem was our domain was on an IP hosted by a company who'd previously hosted (but didn't now) a company on a different IP and that other company has sent some spam.
I have migrated to fastmail for all of my personal e-mail, which I have been pretty happy with. So far I haven't caught any legit email which has been categorized as spam and negligible spam that has made it through into my inbox (mailing lists notwithstanding--I sort them using automation rules). My one complaint is that there is no way to turn off their "thou shall not receive executable attachments" filter so I still need people to play the "set windows to show the file extension, change it to .txt, and then attach it" game when people want to send compiled code via e-mail.
In any case, it is certainly a much better situation than the gmail spam filter I used while in school, which had about a 10% chance of marking outside messages as spam--in fact it even started marking e-mails sent by my professor (via the university gmail) as spam...