Tag Archives: hybrid

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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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. user@tenantname.mail.onmicrosoft.com).

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 kim@exchangelabs.nl, Autodiscover returns a Mail-Enabled User with target address kima@exchangelabsnl.mail.onmicrosoft.com. Next, Outlook wil try an Autodiscover request for this SMTP address.

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Moving Mailboxes in a Hybrid Configuration – Part II

Before you start moving mailboxes you have to make sure that all accepted domains used by mailboxes on-premises are configured in Office 365. This can be tricky, you wouldn’t be the first admin that experience failed migration because of a domain.local email address on an on-premises Mailbox J

Now, when you want to move a mailbox from Exchange on-premises to Exchange Online, navigate again to the Exchange Admin Center, and under recipients select migration. Click the + icon and select migrate to Exchange Online to start the new migration batch wizard.

For the migration type, select Remote move migration which is supported by Exchange 2010 or later.


Click Next to continue. Select the mailboxes you want to migrate to Exchange Online, you can use the people picker feature (click the + icon under Select the users that you want to move) for this, or you can use a CSV file to select the mailboxes you want to move.


Continue reading Moving Mailboxes in a Hybrid Configuration – Part II

Moving Mailboxes in a Hybrid Configuration – Part I

In three earlier blog posts I explained how to implement directory synchronization and how to create an Exchange hybrid configuration:

These steps will create a hybrid configuration between your on-premises Exchange 2013 environment an Exchange Online, but to move mailboxes from Exchange on-premises to Exchange online (or vice versa) you need to create an endpoint. This an on-premises Exchange 2013 server (but it can be more) where the Mailbox Replication Service (MRS) is running, used to move mailbox data from one server to another. The process is similar to an on-premises mailbox move where the MRS is responsible.

Create a migration endpoint

To create an endpoint you have to go to the Exchange Admin Center in Office 365 and login as an Office 365 tenant administrator. You can get there via the Microsoft Online Portal, select Admin | Exchange, or navigate directory to the Exchange Admin Center, and login as an Office 365 tenant administrator.

In the Exchange Admin Center dashboard, under Recipients select migration. At this point an empty screen will be shown:


Continue reading Moving Mailboxes in a Hybrid Configuration – Part I

Exchange 2016 – What’s new?

Now that Microsoft has Exchange Server 2016 it’s time to have a closer look at what’s new in the product. It might not be a surprise that it looks a lot like Exchange Online. Not surprisingly since Microsoft is developing Exchange for the cloud, and Exchange on-premises is just a spin-off of Exchange Online, released on a quarterly basis.

It might be blunt to say, but Exchange 2016 is nothing more than Exchange 2013 Service Pack 2, if you look at the version numbering with PowerShell (Get-ExchangeServer | Select Name,AdminDisplayVersion) you’ll see that it’s actually a minor upgrade from 15.0 (Exchange 2013) to 15.1 (Exchange 2016).

The question can be raised why a new version? It’s all about the support lifecycle, and get rid of support for Exchange Server 2007. Customers need a new version, from a support point of view or from a license point of view (software assurance).

But, back to Exchange 2016… it is a new version, and with a new version also new features are introduced and other features are deprecated or removed.
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