Migrate Exchange 2010 to Office 365 Using Cutover, IMAP & Automated Migration Approach

Summary: This writeup describes the multiple ways, using which you can easily migrate Exchange 2010 to Office 365. The motive behind this was to create a comprehensive guide that could assist in the technical migration process. Go through the step-by-step guide to learn the different approaches mentioned below.

Microsoft ended support for Exchange Server 2010 in October 2020. Since Microsoft will no longer offer regular updates and technical assistance for any intended or unintended issues that may occur, this means that your organization will be severely vulnerable to cyber-attacks and other security threats. Hence, it’s high time that you plan to migrate Exchange 2010 to Office 365 if you are still in the same on-premise environment. 

Talking about different methods to perform the migration, then there are numerous ways available. Some of them are provided by Microsoft (manual approaches) that use PowerShell commands and require other technical know-how. 

Anyway, the question might have come to your mind: when it comes to migrating from an Exchange On-Premise environment, why does Office 365 come into the picture? Let’s find out!

Why Choose Office 365 When Migrating from Exchange 2010 Environment?

Technically speaking, Office 365 has proved to be a better option than the Exchange server in many aspects. It has several benefits both technical and financial.

• Office 365 is a cloud-based interface, so, you don’t have to worry about maintenance costs.
• Unlike an on-premise Exchange server, Microsoft ensures 99.99% uptime for the Office 365 suite. That signifies that your data is available to you almost always.
• In addition to that, Office 365 automatically takes care of the security updates whereas for Exchange servers the admins have the responsibility to look for the updates and all. So, when you use Office 365, the IT admins of your organization can focus on other important tasks.
• Besides, Microsoft 365 comes with a flexible subscription plan for its users, so you have the freedom to choose a plan that suits your organization.

Above all, Office 365 plays an important role and helps in increasing the productivity of an organization to an extent.

However, you can experience all these perks if you successfully execute the migration process. And, to do so, you need to choose an appropriate method!

Now, let’s talk about various methods to migrate Exchange 2010 to Office 365.

What Options Do You Have to Perform Exchange 2010 to Microsoft Office 365 Migration?

For Microsoft-offered methods, you can take the help of the Exchange Admin Center (EAC) in Microsoft 365 to migrate Migrate Exchange 2010 to Office 365.

The options for migration vary depending on the source environment and the result that the user wants. The options (supported by Microsoft) for transferring data in Office 365 are;

Method 1: Staged Migration

Staged migration supports migration from on-premises Exchange 2003 or Exchange 2007 only. This kind of migration is targeted at users who are willing to establish a permanent mail coexistence with Exchange Online and their on-premises environments. It demands that users implement directory synchronization when they deploy Exchange Online. This option is applicable for users who have Enterprise Exchange licenses only. For the migration, IT admins have to provide a list of users to migrate in each batch by using a comma-separated values (CSV) file. 

Migration Tasks That Need to be Performed

Here is a list of tasks that you need to perform when you’re ready to get started with your staged migration.

1. Confirm domain ownership.
2. Utilize directory synchronization for user creation.
3. Compile a roster of mailboxes for migration.
4. Establish a connection between Microsoft 365 or Office 365 and your email system.
5. Initiate the mailbox migration process.
6. Launch the staged migration batch.
7. Transform on-premises mailboxes into mail-enabled users for seamless email access by migrated users.
8. Direct your email traffic straight to Microsoft 365 or Office 365.
9. Remove the staged migration batch.
10. Conclude post-migration tasks.

Method 2: Cutover Migration

The cutover migration option is for users who want to migrate their whole environment in one go. However, it can migrate less than 2,000 mailboxes and is aimed at business users who are running Exchange 2003 or later versions. This option is available to Office 365 Enterprise users and Microsoft 365 Apps users. Though Cutover migration supports the migration of 2000 mailboxes, Microsoft recommends migrating 150 users or fewer at once.

Detailed Cutover Migration to Migrate Exchange 2010 to Office 365 using PowerShell

In this section, we’ll walk through the step-by-step procedure to carry out a cutover migration using PowerShell.

1. Start Preparing for Cutover Migration :

• Add on-premises Exchange organization as an accepted domain
• Configure Outlook Anywhere on the on-premise Exchange server
• Verify whether you can connect with Outlook Anywhere or not
• Assign necessary permissions to access mailboxes in the Exchange 
• Deactivate Unified Messaging (UM)

2. Create Migration EndPoint:

Office 365 uses a migration endpoint for connecting and communicating with the source email system. To create a migration endpoint, first, you need to connect to Exchange Online.

Then, try executing the following commands in Exchange Online PowerShell;

$Credentials = Get-Credential

New-MigrationEndpoint -ExchangeOutlookAnywhere -Name CutoverEndpoint -ConnectionSettings $TSMA.ConnectionSettings

3. Create a Cutover migration batch:

• Specify the admin user account credentials for the Exchange server.

•  If the connection settings are not detected by the Autodiscover service, then try entering the following information.

The fully qualified domain name (FQDN) of the Exchange server that hosts the mailboxes that you’re migrating and the FQDN of the proxy server for the Exchange server.

• Give a name for the migration batch and hit Next.

• List the admins who should receive the report and select whether you want to manually or automatically start the migration.

4. Start the cutover migration batch:

Run the following command to start the migration batch named ExampleCutoverMigration to migrate Exchange 2010 to Office 365.

Start-MigrationBatch -Identity ExampleCutoverMigration

5. Route your mail to Office 365:

Once the migration process is complete, you need to make sure that the MX record is pointing to Office 365 which previously was pointing to the source email system.

By confirming this, you will be sure that your emails are successfully delivered to the destination. 

6. Remove the Cutover Migration Batch

Once everything is in its place, notify the users that their emails are now in Office 365. After that, you can delete the cutover migration batch by running the following PowerShell command.

Remove-MigrationBatch -Identity ExampleCutoverMigration

7. Start assigning users licenses before they expire.

Method 3: IMAP Migration

IMAP migration is for users who want to migrate only emails from their current environment. It allows the migration of a maximum of 500,000 items from a user’s mailbox. Further, the maximum size that can be migrated is 35 MB. IT admins need to provide a list of users to migrate in each batch by using a CSV file to carry out the migration.

Since Staged migration doesn’t support the migration of Exchange 2010, we’ll not elaborate on the process. On the other hand, will discuss the other two procedures in detail. 

Complete IMAP Migration Process to Migrate Exchange 2010 to Office 365 Including PowerShell

As you already know IMAP migration is applicable to migrate emails only. However, there are certain tasks you need to consider before the migration.

1. Prepare for IMAP Migration

• Add on-premises Exchange organization as an accepted domain
• Add each user to Office 365 so that they will have a mailbox
• Obtain the fully qualified domain name (FQDN) 
• Set up firewall requirements
• Assign administrator permissions 
• Sign in and import the cmdlets to use Exchange Online PowerShell

2. Create Comma Separated Value (CSV) file for IMAP migration

• Determine the users whose mailboxes you want to migrate 
• Each row contains certain attributes such as Email Address, User Name, and Password which are necessary for the migration

3. Create IMAP migration endpoint 

Office 365 uses a migration endpoint for connecting and communicating with the source email system. The migration endpoint also defines the number of mailboxes to migrate concurrently and the number of mailboxes to synchronize simultaneously.

Run the below command to create a migration endpoint to migrate Exchange 2010 to Office 365;

New-MigrationEndpoint -IMAP -Name IMAPEndpoint -RemoteServer imap.contoso.com -Port 993 -Security SSL

To verify whether it worked or not, run the below command;

Get-MigrationEndpoint IMAPEndpoint | Format-List EndpointType,RemoteServer,Port,Security,Max*

4. Create an IMAP migration batch

• Prepare a CSV file: In the CSV file that you will use to migrate, make sure that the content of users’ mailboxes contains a row for each user. 
• On the “Select the mailboxes” screen, locate the CSV file that you prepared in the previous step, and then click Next. Refer to the following screenshot:

• Next, on the IMAP Configuration screen, specify the connection settings for the server from which you want to migrate mailbox data for a smooth migration. Have a look at the screenshot below:

• Provide a name for the migration batch, and click Next.
• Choose an option whether you want to manually or automatically start the migration.

5. Route your mail to Office 365:

Previously MX record was pointing to the source email system, so once the migration process is complete, you need to make sure that the MX record is pointing to Office 365.

By confirming this, you will ascertain that your emails are successfully delivered to the destination. 

6. Remove IMAP Migration Batch

Once you are sure that everything is in its place, notify the users that their emails are now in Office 365. After doing that, you can delete the cutover migration batch by running the following PowerShell command.

Remove-MigrationBatch -Identity IMAPBatch1

[Note: Usually, a large-sized migration process is accomplished in batches. You have to create multiple batches. So, how would you manage migration batches in Exchange Online?

Well, it’s simple. Admins can use the E-mail migration wizard in the Exchange Admin Center by using Exchange Online PowerShell. Admins can also control when a migration batch is started.]

As you can see whether it’s a Cutover migration or an IMAP migration, the execution process is very lengthy and time-consuming.

Hence, it’s suggested to opt for the next method which is a comparatively easy and quick approach when migrating Exchange 2010 to Office 365 migration.

Let’s have a look at the approach.

Method 4: Minimal Hybrid to Quickly Migrate Exchange 2010 Mailboxes to Microsoft 365

Pre-requisites

• Must Use Exchange 2010, Exchange 2013, and/or Exchange 2016 server on-premises.
• Must be planning to migrate to Office 365 in a few weeks or less.
• Must not intend to continue to run directory synchronization to manage users

Steps of Minimal Hybrid Migration to Perform Exchange 2010 to Office 365

• Step 1. Verify You Own the Domain.
• Step 2. Start Express Migration with Minimal Hybrid
• Step 3. Create Users in Office 365 by Running Directory Synchronization
• Step 4. Assign Microsoft 365 Licenses to Your Users
• Step 5. Start User Mailbox Data Migration.
• Step 6. Update DNS Records to Mail Flow.

Let’s dive in.

Also Read: How to Perform Office 365 Tenant to Tenant Migration Step By Step?

Method 5: The Best Way to Migrate Exchange 2010 to Office 365 Using the Below Tool

If we talk about migrating Exchange 2010 mailboxes to Office 365, then choosing a tried and tested solution is a must. Any unfortunate incident during the process can cause serious harm to an organization.

Migrate Exchange 2010 to Office 365 Using the Professional Tool

However, if you are feeling overwhelmed with the above process then you can always opt for professional software i.e. SysTools Exchange to Office 365 Migration Tool. It can help you execute the Exchange 2010 to Office 365 migration without worrying about data loss or using any complicated commands.

Just a few clicks and the rest is left to the software.

Additional Benefits of Using The Above Software:

• The tool allows you to easily transfer emails, contacts, and calendars without a single loss of data.
• It preserves the folder hierarchy of the source account even after the migration. 
• Additionally, it maintains data integrity throughout the process.
• In addition to that, you can migrate the ‘n’ number of Exchange mailboxes to Office 365. And, the tool does not put any limitations on account size or number of mailboxes.
• It provides you with various smart features such as Workload Selection and Date Filter.
• This software also facilitates ‘Re-run Exchange Migration’ so that you can retry the migration of failed items.
• Also, with the ‘Stop & Start Migration’ function, you can easily pause and resume the process any time you want.

Let’s go through the working steps of the tool.

Step By Step Detailed Working to Perform Exchange 2010 to Office 365 Migration

Step 1. Download from the given link. Follow the guidelines and run it on your computer.

Download Tool Purchase

Step 2. Select the Source and Destination as Exchange & Office 365 respectively. Further, click on the workloads (such as Emails, Contacts, and Calendars) that you want to migrate.

Step 3. Go to the Source tab, and select the Exchange server version as required. Then, fill out the necessary fields.

Step 4. Next, navigate to the Destination tab, and enter the Office 365 Admin Email and Application ID. After that, validate the permission.

Step 5. Go to the Users tab, Fetch source users through various options, and map them with the destination.

Step 6. At last, click on Start Migration to migrate Exchange Server 2010 to Microsoft Office 365.

If you have hosted Exchange, and you want to migrate from hosted Exchange to Office 365, then follow this guide.

Note: If you looking to migrate from offline EDB files to Office 365, then, we recommend users go with SysTools Exchange Recovery Tool which permits users to migrate Exchange 2010 mailboxes into Microsoft 365. The users just need to load the EDB file containing Exchange mailboxes into the software and choose Office 365 as the export option. This utility offers numerous advanced sets of features that ensure that the migration process is completed without any hassle. You can download a free trial version of the software on Windows OS to get an overview of the working features of the software.

Download Tool Purchase

Decommission Exchange 2010 After Office 365 Migration

Decommissioning Exchange Server 2010 after migrating to Office 365, requires various steps to ensure a seamless data transition and safe removal of legacy Exchange version. 

Check out some of the most critical ones discussed below: 

1. Mailbox Verification – This is one of the most important steps that admins should check right after the migration, whether all mailboxes are successfully migrated to Office 365 or not. You need to make sure no mailboxes remain on Exchange Server 2010. 
2. Public Folder – The second important factor that you need to check is a public folder, if your organization is using a public folder then make sure to migrate them to Office 365, if required, or decommission them with the Exchange server 2010.
3. Mail Services – Once you have ensured proper migration of the mailbox data and public folders, then the next important factor is to update the DNS records and firewall rules to ensure uninterrupted email communication to the new mail service i.e. Office 365. Ensure Autodiscover is pointing to Office 365.
4. Certificate Management – If Exchange 2010 uses SSL certificates, then you can remove or replace them as required.
5. Uninstall Exchange 2010 – Once you followed all the steps discussed above and are confident that Exchange 2010 is no longer required, then follow these steps to uninstall it:

• Migrate arbitration mailboxes (e.g., discovery search mailbox) to another Exchange server or you can remove them respectively.
• Then using the Exchange Management Console (EMC) or Exchange Management Shell (EMS) you can uninstall Exchange Server 2010 from each server in the organization.

6. Verify and Track – Post uninstallation, you need to monitor email flow and client connectivity to ensure everything is functioning correctly without Exchange Server 2010.
7. Backup and Documentation – Before uninstalling, ensure you have backups of Exchange configuration and mailboxes. Document the decommissioning process for future reference.

By following these steps, you can decommission Exchange Server 2010 after migrating to Office 365, efficiently. Moreover, you can also ensure smooth business communication without hampering the productivity.

Final Words

On-premise Exchange servers have a major limitation that can’t be denied. And, that is Exchange servers work on a fixed life cycle. After that, Microsoft stops at the end of support. This means you will be able to continue running the Exchange version (in this case Exchange 2010) but after it reaches the end of support it will no longer fix bugs or update security features. Hence, to keep your crucial on-premise data protected it’s advisable to migrate Exchange 2010 to Office 365 using an appropriate method.

Frequently Asked Queries

Q1. Why is Office 365 better than Exchange?

Microsoft Office 365 offers a cloud storage facility, which is fairly beneficial for users, in terms of collaboration, accessibility, and productivity. With Office 365, you get professional business communication software like Microsoft Teams, Skype for Business, etc along with email solutions like Exchange Online. Being a subscription-based model, users find it more appealing than the Exchnage server. These are only a few factors that set Office 365 above the Exchange server.

Q2. How long does it take to migrate Exchange 2010 mailboxes to Office 365?

It depends upon various factors such as the total size of data to migrate, the approach to perform this migration, system configuration, network bandwidth, etc. For instance, if you have to migrate 1TB of data to Office 365, and you choose a manual method, then it can take days to complete. Whereas, if you choose the above-mentioned software then you can migrate the data to the destination within the same day following these steps. 

5 Quick Steps to Migrate Exchange 2010 to Office 365

• Step 1. Download, & Run Tool on PC.
• Step 2. Select Workload & Apply Date Filter.
• Step 3. Use Exchange Server Details to Login.
• Step 4. Login with Office 365 Admin Credentials.
• Step 5. Validate Permissions & Click on Start.

Q3. How to decommission Exchange 2010 after migration to Office 365?

Before decommissioning Exchange 2010, you should not use the Exchange Server 2010 for at least 2 days (1 week or 2 is suggested).

Follow the below-listed steps accordingly:

Step 1. In the very first step, you have to remove Public Folders.

• Go to Toolbox >> Public Folder Management Console >> Remove Public Folders.

Step 2. Now, you have to remove Exchange Mailboxes. 

• Navigate to Exchange Management Console >> Remove User Mailboxes

Step 3. Then use below PowerShell cmdlets to Remove Arbitration Mailboxes in the Exchange Management Shell 

• Get-Mailbox -Database -Arbitration | Remove-Mailbox – Arbitration –RemoveLastArbitrationMailboxAllowed

Step 4. Now you have to delete the Public Folder database and Mailbox Database.

• Go to Server Configuration >> Mailbox location in the Exchange Management Console >> Remove Public Folder database and Mailbox Database.

Step 5. Then you have to delete or remove Offline Address Book details from the Organization 

• Navigate to Configuration >> Mailbox >> Offline Address Book tab located in the Exchange Management Console.

Step 6. Now you can uninstall the setup of Exchange Server 2010 from the Control Panel of your system.

Step 7. If you want to remove Exchange Server roles, then use the below listed PowerShell commands and administrator.

• setup.com /mode:Uninstall /roles:HT