Cutover Migration from Exchange 2016 to Office 365 (Part 2)

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There are different migration methods for moving your on-premise mailboxes to Office 365. Cutover migration is one of the easiest method available. Other migration methods are, Staged, Hybrid and IMAP. In the previous article, I talked about pre-requisites of Cutover migration. Here I will show steps to perform cutover migration from Exchange 2016 to Office 365 (Part 2).

Cutover Migration from Exchange 2016 to Office 365 (Part 2)

The diagram below shows on-premise Exchange organization scenario. The Exchange organization contains single Exchange 2016 server. Outlook Anywhere is working properly as shown in previous post. There are 9 user mailboxes in on-premise Exchange server. All 9 mailboxes will be migrated to Office 365. Similarly, there is one mail-enabled security group and a room mailbox. There is also one shared mailbox called Since the organization is small and there are few mailboxes, Cutover migration option is best for the scenario.

Cutover Migration from Exchange 2016 to Office 365 (Part 2)

Migration Steps

Step 1: Create Security Group

The on-premise Exchange server consists of one mail-enabled security group. So the group needs to be created in Office 365 Exchange Admin Center (EAC) before moving mailboxes to cloud. Log on to Office 365 portal. Go to Admin > Exchange. Exchange Admin Center (EAC) will open.

new security group

Click recipients in the features pane. Select groups tab. Click + Add and click security group.

marketing security group

Type same name and alias of group as on-premise security group name. In the email address field, select * domain name and click save.

Step 2: Create Cutover Migration Batch

Log on to Office 365 portal. Go to Admin > Exchange. Exchange Admin Center (EAC) will open.

Cutover Migration from Exchange 2016 to Office 365 (Part 2)

Click recipients in the features pane. Select migration tab. Click + ‘Add” and click Migrate to Exchange Online option as shown above.


In the migration type page, choose Cutover migration as shown above and click Next.

migration credential

Enter any on-premise email address that is going to be migrated. Similarly, enter the migration account credential that we created before on step 3. Click Next.

confirm migration endpoint

Verify the permission as shown above and click Next.

migration batch name

Type migration batch name. Here, I typed Exchange-to-Office-365. Click Next.

start migration batch

Click Browse and select the user that will get migration report. Choose the option, automatically start the batch to start the migration batch automatically. Click new to start the migration. The time taken to complete the migration process depends upon number of mailboxes and their size and speed of Internet connection. Go to migration tab.

migration status

Here, you can view the migration status. To view more detail of the migration click View Details as shown above.

migration detail more

As you can see above all mailboxes have synchronized and migrated. There are no items skipped. If there are any failures then you can review the errors and preparation steps. You can always re-start migration batch. You can now go to recipients and view new migrated recipients on Office 365 portal as shown below.


As you can see above all user mailboxes are created in Office 365. You can now point MX record to Office 365. Similarly, security group members are also replicated. Room mailbox is also replicated.

Step 3: Assign Office 365 License

Assign Office 365 license to new Office 365 users. After Cutover migration, user accounts are automatically created in Office 365. To use Office 365 services, you need to assign Office 365 licenses to the users. By default, Office 365 users can use Office 365 services for 30 days without license.

Step 4: Point MX and Autodiscover Record to Office 365

After the migration is complete, you can point the MX record to Office 365. Emails will continue to go to on-premise Exchange server until you point the MX record to Office 365. MX records are changed after the migration is successful. The process of changing MX records from on-premise Exchange to Office 365 is the actual Cutover. Similarly, point autodiscover record to Office 365 so that Outlook application can be automatically configured with new Office 365 mailbox. Remember, you need to re-create Outlook profile after migrating on-premise mailboxes to Office 365 using this Cutover migration method. Log on to your domain hosting provider’s portal like GoDaddy and change public DNS records.

  • Point Autodiscover CNAME record to
  • Point MX record to

You also need to update Autodiscover Service Connection Point (SCP) on on-premise Active Directory so that internal users can setup Outlook application with new mailbox residing on Office 365. To update SCP, type following cmdlet in EMS in on-premise Exchange Server.

[PS] C:\Windows\system32>Set-ClientAccessService -Identity MBG-EX01 -AutoDiscoverServiceInternalUri

If you have split DNS server configuration and have domain as internal Active Directory domain or have zone in the DNS server then you need to add Autodiscover CNAME record and point to domain.

Step 5: Stop and Delete Migration Batch

At final stage, stop and delete the migration batch from Office 365.

In this way you can migrate Exchange 2016 mailboxes to Office 365. After migration, you can also setup single sign-on so that users can login to Office 365 mailbox using on-premise Active Directory credential. After migration is successful and DNS records are pointed to Office 365, you can decommission on-premise Exchange 2016.

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Bipin is a freelance Network and System Engineer with expertise on Cisco, Juniper, Microsoft, VMware, and other technologies. You can hire him on UpWork. Bipin enjoys writing articles and tutorials related to Network technologies. Some of his certifications are, MCSE:Messaging, JNCIP-SEC, JNCIS-ENT, and others.

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