Sure enough, the next morning, Outlook was immediately able to connect to the mailbox at the new tenant.
Support says that propagation may take up to one day. I tried adding the mailbox to my own Outlook, to test it on another machine, but that didn’t work either. REG ADD HKCU\Software\Microsoft\Office\16.0\Outlook\AutoDiscover /v ExcludeSrvRecord /t REG_DWORD /d 00000001īut that made no difference, even after a reboot. REG ADD HKCU\Software\Microsoft\Office\16.0\Outlook\AutoDiscover /v ExcludeHttpsRootDomain /t REG_DWORD /d 00000001 There is no question in my mind that there are some weak links in the sync process for Outlook for Mac 2011 and Office 365, which is especially sensitive during the migration process. I am now on the phone with a MS engineer who seems to be more informed. REG ADD HKCU\Software\Microsoft\Office\16.0\Outlook\AutoDiscover /v ExcludeScpLookup /t REG_DWORD /d 00000001 It has stumped the first and second tier technical support people. Microsoft Support suggested running some commands to reconfigure Autodiscovery on the machine: Oddly, after running that tool, one user was suddenly able to connect, but the other two were not. Running that tool confirms what I suspected, that there is an Autodiscover issue:
Apparently that tool no longer exists (not found error), but the helpful Microsoft Support and Recovery Assistant for Office 365 tool can be downloaded here. The message “An encrypted connection to your mail services is not available” takes you to MS KB2989972, which suggests running the Outlook Connectivity Guided Walkthrough. If you try directly from Outlook, this happens: If you try to add the Office 365 account to a new profile from the Mail applet the Control Panel, you may see this:
After setting up the domain in the new Office 365 account, we got email flowing immediately (verified by logging in with OWA), but we were unable to set up Outlook pointing to the new tenant. I’m helping a customer move a domain with a few mailboxes from one Office 365 tenant to another.
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