I see on Bing that I keep showing up as logged in under my employers account -...
I see on Bing that I keep showing up as logged in under my employers #office365 account - does that mean all my bing searches are the property of my employer, same as my Office 365 Word, or SharePoint stuff?
(yes, just using work VPN means there is probably a MITM attack going on against my traffic)
Self-replies
and by mitm attacks from your employer I mean ssl intercept products like this one, that on the face of it appear to allow an employer to read traffic.
And down the rabbit hole... look at this, why bother hacking password stores directly when you can instead hack a MITM server - target those things to harvest passwords.
https://security.stackexchange.com/questions/2914/can-my-company-see-what-https-sites-i-went-to