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I have a lot of experience managing O365/Azure, and these issues all come down to the config of MFA in the O365/Azure tenant. They may even be intentional for "security" purposes.

To be fair, O365 and Azure change all the time. I've seen these issues on neglected O365 tenants, usually MFA was setup years ago and never touched again.

Do we work at the same company or is O365 that bad? We just had a big discussion on Slack as to what that checkbox actually does, because it's apparently nothing...

This seems to be super path dependent.

I've seen google devices nag daily, and O365 stay logged in for weeks/months.

Too few measurements to have a strong opinion on which scenario is more likely, but it does seem interesting that a number of configuration or other issues seem to be solved by : just aske for auth again.

> Ticking the 'dont ask again' option has no effect.

There is an option that can be set that has the effect. It is a horrible that the check box is still there after the option is set.