They can’t even do HTTPS correctly. Domains like this won’t even work https://www.hotmail.co.uk/ as the certificate is only valid for the following names:
*.mail.live.com , *.hotmail.com , hotmail.com , hotmail.msn.com , hotmail.co.jp , hotmail.co.uk , hotmail.live.com , www.hotmail.msn.com , mail.live.com , people.live.com
And then if you do eventually get through to a domain which doesn’t give you an SSL error you will be greeted with the following message
Why Hotmail Fails - HTTPS
Those choices ultimately seem futile as I’m sure you will end up breaking access somewhere down the road. This is a lot more fuss than say, Google’s implementation?