What happened is that Rogers bought Shaw and ever since a lot of things have "changed", in our opinion for the worse, which has nothing to do with Microsoft or Outlook. We've seen these complaints from other users too.
Shaw WebMail works fine but Rogers/Shaw servers reject IMAP and POP3 connections with exact same credentials; with SSL or without - all the same.
When clients call Shaw/Rogers, the offshore tech support often has no clue and just waste time by saying the same as posted on Shaw/Rogers support page giving you their standard (OLD) IMAP and POP settings. Then when it does not work, they just say that Shaw/Rogers do not support any web clients and if WebMail works, that is the only thing that they support.
PATHETIC and terrible service IMHO. We've been switching clients away from Rogers/Shaw who in our and their opinion became much worse, including support.
P.S. In our experience changing from "classic" to "modern" setting in Shaw WebMail Preferences hasn't helped those with whom we tried.