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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?

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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.

  1. The Client was manually configured to point to Exchange. In this case, it's not using autodiscover so it's not picking up the changes after the mailbox move.
  2. The Client profile has issues. I'm not sure what causes it, but in some cases, the profiles will just not update with the new location. You can watch and see autodiscovery steps happening, but the local profile seems to ignore them. This was more frequent a year or so ago, I have not seen this in a while (so I assume an update has fixed some of these issues along the way)
  3. Not having the required updates. Office clients should be fully patches.

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.

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