![]() Therefore do yourself a favor and recycle the app pool when the moves are complete. Recycling the application pool will refresh the cache and Outlook will connect successfully. The workaround is documented at and it seems to suggest that the timeout can be up to 12 hours. They will be ping-ponging Outlook profile reconfiguration autodiscover requests until the Autodiscover application cache expires and the information is refreshed. Therefore it will proxy the connection to the old Exchange 2010 server, which then bounces it back to Exchange 2016. After a mailbox is moved, the application still thinks that the mailbox is on the old server. ![]() ![]() Instead, the issue lies in the fact that the Autodiscover application on the Exchange 2013/2016 server caches configuration information. It even crossed my mind that there may be a dodgy HOSTS file entry that overrides DNS settings. My initial thoughts were that Outlook is not up to date and it fails to connect via MAPI-HTTP (enabled by default in Exchange 2016), or there may be a proxy (mis)configuration. I just finished moving some mailboxes from Exchange 2010 to Exchange 2016, only to be called because users' Outlook failed to connect to their mailbox. It doesn't happen too often, but when it does then it can be inconvenient.
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