The way Microsoft accounts work is almost completely opaque to users. I’ve been in similar scenarios — the switch directory or switch organisation technique usually worked for me - but wasn’t enough for this person. They never really give you enough information to tell what’s going on… maybe it’s a security risk to have consumers who are anything other than bewildered Kafkerian characters struggling against a faceles…
Now, if Microsoft bought Atlassian — that would be absolute theoretical maximum limit of peak confusion when logging into an app. “Warning: You are about to login to Microsoft Atlassian Fogbugz Trello. Have you cleared sufficient space in your calendar, notified your next of kin, put your affairs in order, and taken your sedatives?”
It's once your sessions start expiring or you're trying to use the other services in meaningful ways that the journey begins.