Same thing here! I thought I had gone crazy until I started interacting with more more people online that had the same exact problem. Honestly, it became an obsession to figure out for me because I started feeling stupid not being able to figure it out...turns out there was no way out of this corner case!

Microsoft bought Skype in May 2011 for $8.5 billion. Think about the magnitude of dysfunction for a post-merger integration to only partially succeed despite this price tag!

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.