Move all users with the same manager to the cloud at the same time.However, it could be the Team Calendar that is now auto-populated by Outlook that is causing your pain. You may think it’s AutoDiscover, or some setting on the Hybrid server. When that mailbox is moved, users on-prem suddenly get prompted for credentials. The issue arises when a mailbox is moved to the cloud, has a manager and there are other users with the same manager. Basically what’s happening is Outlook is checking with AD to see you your manager is, finding all users accounts with that manager and creating a group of calendars in Outlook’s calendar view.
However, there is a ‘little known’ feature that Outlook 2010 has called Team or Group Calendar. You’ve also identified all Shared Mailboxes that will be moved with the groups of users that access them.
Planning this now will save a lot of help desk calls and hours of troubleshooting issues. If you are in need of a Hybrid server, you also know that AutoDiscover will go through that server. Depending on which Exchange version you have now, your client access might be 2007, 2010 or 2013. So you’re moving to the Cloud? Your Outlook client is 2010 or 2013? Want to make sure that users do not experience pop-ups in their client? Assuming you’ve done a bit of homework, you have your Client Access Strategy all line up.
