We're doing a hybrid migration from on-premise Exchange 2013 servers to cloud hosting with Office 365. We're moving mailboxes in batches, starting with internal IT staff, and so far a bunch of us have had problems connecting until we deleted and re-created our Outlook profiles. (This is on several clients, but for argument's sake let's stick with the most important: Outlook 2016 for Mac and Windows.)
It seems this is expected if you're doing a "staged migration", but we're doing a hybrid migration, and I haven't seen anything to suggest it should be required.
Really not looking forward to trying to get all our users to re-create their profiles. We could force it through Group Policy, but that would be a bit complicated since we're moving people in batches.
Is there something I'm missing here? Some autodiscover setting that may not be configured correctly? Or is this expected and necessary?