O365 Global Admin permissions issue

So my boss is an office 365 Global Admin same as myself. But he’s having to enter his creds on every Office 365 web page or subsite and now he can’t see thumbnails of videos i posted on Stream. my Videos have Org-wide read perms. so obviously there is a general permission problem with his account. I have no idea where to look.

Does this happen in a browser in privacy mode or from other computers? I’ve run into a similar problem when administrators have multiple O365/Microsoft workplace accounts trying to SSO. It was a real pain to sort that one. The other possibility is a conditional access policy that is forcing him to re-login so you will want to take a look at the conditional access logs (you might, just during troubleshooting logging in, throw him into the conditional access exclusion group where you should have the break glass account… but absolutely don’t leave him there when you aren’t trouble shooting).

Thank you Isaac. It turns out to be a Safari issue. He used Chrome and could repro the issue.