I have been using hotmail for years and have relied on the convenience of Messenger bringing up a popup alerting me to new mail out of my icon tray.
Well I have tried some third party stuff and have found only one to work with hotmail. poppeeper go to poppeeper.com it seems to install pretty much automatically without having to mess with POP settings. This program will do what messenger did as far as notifiying you of email.
Optional: If you want poppeeper to redirect you to you hotmail (now outlook) use the URL function and enter www.hotmail.com
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