I have a personal Office 365 subscription and use it for my email amongst other things. I use the OWA client on a couple of different computers and find its behavior vexing. If I leave the computer on and the OWA window open I get automatically logged out after a period of inactivity. This is annoying because I lock the computer so I know I am safe. What makes it even more annoying is the fact that there is a check box that says “Keep me signed in.”


It doesn’t matter if the check box is checked. I get logged out anyway. Then I usually get a timeout message to add insult to injury:


Yeah, I am sure the Office 365 team is sorry. Except that I know a dirty little secret about Office 365. It is not just one team at Microsoft. Office 365 is bolted together using components from many teams and even different divisions. That is presumably why OWA ignores the “Keep me signed in” check box. It probably doesn’t even know that setting exists. The back end email service, Exchange Online, uses its own copy of the MSODS (now known as the Windows Azure Active Directory or WAAD) user database. In fact, there are probably a half dozen copies of a tenant’s user datastores with background processes to synchronize information between them. This user preference to remain logged in is either not synchronized from the main tenant WAAD database to the Exchange Online copy,  the OWA team decided to ignore the setting, or it could be that the preference is not stored in WAAD at all but instead is part of the main login cookie in the browser and OWA isn’t reading this part of that cookie. I wouldn’t be surprised if it is way more complex behind the scenes. This isn’t to say that there aren’t a lot of conscientious people at Microsoft working to improve Office 365. Rather, it is just an  enormously complex system and it is really hard to get everything right in a complex system. Add to that the preference of management to add new features rather than refine existing features and I am left with little hope that this will be fixed any time soon.