Change SMTP mail flow in hybrid scenario

After building a hybrid Exchange environment as outlined in a couple of previous blog posts we have an Exchange 2013/2016 environment where some Mailboxes exist on-premises and some Mailboxes exist in Exchange Online. Autodiscover is still pointing to the on-premises environment, and so are the MX records. Inbound SMTP mail flow from the Internet is still accessing the on-premises Exchange 2016 Edge Transport servers before being delivered to the intended recipients.


Figure 1. The Exchange hybrid environment with Mailboxes on-premises and in Exchange online.

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Upgrade Hybrid Server to Exchange 2016

I’m running a coexistence scenario with Exchange 2013 and Exchange 2016 without too many issues. My hybrid server is running on Exchange 2013 from the beginning, and it is time to upgrade this server to Exchange 2016.

If you have configured your Exchange environment correctly the hybrid server is nothing special. In my environment the hybrid server is just used for sending SMTP messages between Exchange Online and Exchange on-premises, and it is used for migrating Mailboxes back and forth.

Upgrading the existing Exchange 2013 hybrid server to Exchange 2016 is actually just a matter of installing a new Exchange 2016 Mailbox server, configure it correctly like the old Exchange 2013 hybrid server and rerun the Hybrid Configuration Wizard application.


Figure 1. The new hybrid server (hybrid02) will be installed next to the old hybrid server (hybrid01)

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New Hybrid Configuration Wizard

With Exchange Server 2013 CU9 and Exchange Server 2016 Microsoft has released a new version of the Hybrid Configuration Wizard (HCW). Instead of running the HCW online, it is now a small stand-alone application which is installed on the hybrid server.

Installing and running the Hybrid Configuration Wizard is so easy, initially I didn’t want to write a blog post about it at all. But writing one doesn’t harm, so here we go…

The HCW is only a configuration tool, it configures both Exchange 2013/2016 on-premises as well as Exchange Online. It gathers information regarding the hybrid servers, where to deliver and receive SMTP messages and what certificates are used.

To install the new HCW and reconfigure the hybrid configuration, logon to the Exchange Control Panel and click Hybrid:


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User cannot logon to Office 365 after moving user account in Active Directory

When you have implemented Directory Synchronization between your on-premises Active Directory and Office 365, and you move a user in Active Directory out of the DirSync scope (for example to an Organizational Unit that’s not synchronized) the user is removed from Office 365.

However, when you move the user back to an Organizational Unit that’s synchronized (i.e. in-scope) the password is no longer synchronized. So, when this user tries to logon to Office 365 services, the logon attempt fails. Only when you change the password in Active Directory, the new password is synchronized to Office 365, and the user is able to logon again to the service.

Very similar to this, when a disabled user in the on-premises Active Directory is enabled, the password is not synchronized to Office 365.

This is a known issue with DirSync or Azure AD Connect (up to November 2015). On November 4, 2015 Microsoft released a new version of Azure AD Connect that fixes this particular issue (together with a number of other fixes of course).

You can find more information regarding the updated version of Azure AD Connect on Sander Berkouwer’s blog A new version of Azure AD Connect was released today. You can download the new version of Azure AD Connect on the Microsoft Download Site.

Autodiscover in a hybrid scenario

In the previous articles I showed you how to implement DirSync, create an Exchange hybrid environment with a migration endpoint and how to migrate Mailboxes from Exchange on-premises to Exchange Online. Not a single word on autodiscover though, and even when autodiscover is pointing to your on-premises Exchange environment, it continues to work for Mailboxes that have been migrated to Exchange Online. This is one of the advantages of an Exchange hybrid scenario.

This is what happens: when you move a Mailbox from Exchange on-premises to Exchange Online, the Mailbox on-premises is converted to a Mail-Enabled User (Remote Mailbox) and a target address is set to Exchange Online (i.e.

When an Outlook client does an Autodiscover request to the Exchange environment it detects the user is a Mail-Enabled User, and that a target address is set. Based on this target address a new Autodiscover request is initiated. So, Outlook does a request for a user called, Autodiscover returns a Mail-Enabled User with target address Next, Outlook wil try an Autodiscover request for this SMTP address.

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