I can hardly imagine what level of dysfunction is possible in an organisation as large as Microsoft. I have only worked in small companies, less than 30 employees, and my mind has already been blown.
Fair enough w/r/t the company size...but...how is it I dont have these types of authentication issues in the Google universe, or Facebook Universe? It isn't like I need a separate login for Youtube vs Google Sheets vs Google Drive vs Duo vs GChat. It suggests that it can work if the organization tries to do it correctly.