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?
Best Answer
If Outlook was configured using autodiscover it should handle the redirect with mailbox moves. There are three things I've encountered that require the profile rebuild with 2013/20116 clients.
Behind the scenes, the reason you don't have to recreate the profiles in a Hybrid migration is because the mailbox ID"s are the same when you move them to Exchange Online. In Staged/Cutover migrations you are creating new mailboxes wiht new ID"s. It's much like just moving it to a new Database in a local Exchange deployment. Autodiscover will update it's location and when Outlook performs the autodiscover request it should update the path to the mailbox and then request the connection.