Have you try to change the incoming server pop3 to port 110 and the outgoing to port 25 in the tools menu>account settings>highlight your e-mail>click change>click more setting>click advanced tab, if enabled remove the checkmarks next to this server requires an authentification connection (ssl), ans select outgoing tab and place a check next to my outgoing server (smtp) requires authentification, click ok and next then finish. windsman.
Thanks for everyone's replies. I found out the culprit! It was my work account that was causing all the issues. I know for a fact that when I tried to add my work email, it said after a while of searching for the settings that the connection is unencrypted so I chose to continue and that's how it has always been but randomly my work account would fail to synchronize which somehow was affecting my Hotmail/Outlook accounts as well! Now I got rid of my work account email which I don't really need at home since I can access the emails from the webmail link and the problem with the Outlook Connector is gone
Maybe it wouldn't be an bad idea to check deeply first the own installation/setup/ config before point the finger to someone else, even if that someone is Microsoft!