Exchange 2013 Office 365 Hybrid Cloud On-Premise Outlook Connection Problem

Question

Hi Everyone,
   We are required to migrate FROM the cloud TO an on-premise Exchange 2013 server.  We set up a trial of Office365 and linked our test domain to that account.  The test domain mimics our current domain, but ends in .net instead of .org.
 We set up a test Exchange 2013 server with a few database servers.  Internally, we can connect without issue (Outlook).  We mapped our test CAS to face the Internet, and can access what we need without issue.  We also set up the Hybrid
configuration on both the Exchange 2013 and Office365 servers.  We have validated that DirSync works, and migration can occur up to the cloud and back down to the on-premise server.
Now, here is the issue:
We have our DNS records still pointing to Office365, so when we add an Office365 mailbox to Outlook (internal to the network or outside the network) we see absolutely no issues.  We migrated a mailbox today to our on-premise server, but upon doing so,
can no longer connect to, or add, that mailbox to Outlook.  When we put this integration in to effect for production, we want to be able to migrate mailboxes on-premise from the cloud, and we want to make sure users can still access their mailboxes.  This
also goes for distribution groups, conference rooms, etc.
I see that most suggestions say to change your DNS record to point to the on-premise Exchange server, which is great, but after doing so Office365 accounts experience the same issue as above.  We NEED to make sure that when we batch migrate, the users
DO NOT lose connectivity to their accounts.  We need both Office365 accounts and Exchange on-premise accounts are accessible internally and externally.  As an extra tid-bit, we HAVE configured Outlook Anywhere on Exchange 2013, but see no difference.
Any thoughts on this?  Office365 and Exchange 2013 see eachother and recognize that the hybrid environment is set up good, but it appears we are missing some configurations.  Currently, we have a CNAME record points our autodiscover to autodiscover.outlook.com.
Any help would be MUCH appreciated.  Thanks!
Dan

Answer 1

Hi,
Here is an article on Move mailboxes between on-premises and Exchange Online organizations in 2013 hybrid deployments, for your reference:
http://technet.microsoft.com/en-us/library/jj906432(v=exchg.150).aspx
I want to make sure OWA works well with the moved mailbox.
To use CNAME based autodiscover method, we need to have all domain names present in a SAN certificate.
With Exchange 2013 CU1, we now have the option of adding multiple SMTP domains to Exchange Federation/Hybrid configuration and we can specify which of these domains should act the "autodiscover" domain.
To configure an SMTP domain as the autodiscover domain, you can run following command:
Set-HybridConfiguration -Domains "domain1.com, domain2.com, domain3.com", "autod:domain.com"
More details, please refer following blogs:
http://www.msexchange.org/articles-tutorials/office-365/exchange-online/configuring-exchange-2013-hybrid-deployment-and-migrating-office-365-exchange-online-part11.html
http://www.msexchange.org/articles-tutorials/office-365/exchange-online/configuring-exchange-2013-hybrid-deployment-and-migrating-office-365-exchange-online-part12.html
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Thanks
Mavis Huang
TechNet Community Support