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Transfer Or Migrate Mailbox from Exchange 2019 to Office 365

Published By Nilesh Kumar
Debasish Pramanik
Approved By Debasish Pramanik
Published On March 6th, 2024
Reading Time 12 Minutes Reading

Even though it has been only a few years since the launch of the latest on-premise Exchange 2019, organizations have already started to look for alternatives. Since waiting for the inevitable is of no use. Hence, we have prepared this guide to migrate mailbox from Exchange 2019 to Office 365.

Here you are going to find the complete knowledge required to complete a successful data transfer. This move towards a cloud-based communication manager is bound to bring a multitude of advantages.

5 Quick Steps to Migrate Mailbox from Exchange 2019 to Office 365

  • Step 1. Install and run the software on your computer.
  • Step 2. Choose Exchange and Office 365 as platforms.
  • Step 3. Enable mailbox categories and apply date filter.
  • Step 4. Login with Exchange and Office 365 credentials.
  • Step 5. Create mapping, select users, and start migration.

Before we begin it is important to put an end to all doubts in the minds of organizations that are still hesitant to perform a transfer. 

Importance of Migration From Exchange 2019 to Office 365 and Its Benefits

Businesses worldwide are rushing to adopt the cloud within their workflow. Moreover, emails continue to be the cornerstone in both inter and intra-business communication. Therefore, Exchange 2019 to Office 365 migration ensures that you won’t get left behind in productivity, security, or collaboration.

The best way to accept a better platform is to go through the advantages it provides and compare it with the limitations of the current system. This is more than true when we wish to build a case to migrate mailbox from Exchange 2019 to Office 365.

All offline Microsoft products follow a fixed lifecycle model and Exchange 2019 is no different. Although it is still going to get official support till Jan 9, 2024, and Microsoft plans to provide extended support till October 14, 2025. The existence of specific expiry dates in itself is a cause for concern. Not to mention all hardware-related issues still fall under the clients themselves irrespective of the support end date.

On the other hand Office 365 users get to enjoy a maintenance-free service that automatically expands to keep up with all demands. Apart from this Office 365 comes with a multitude of other features including the legacy office suite (Powerpoint, Excel, Word), and collaboration tools (Sharepoint, Teams, OneDrive).

Some key areas where Office 365 outperforms the On-Premise server are

  • Scalability: Adding or removing users and licenses can be done in just a few clicks.
  • Anytime, Anywhere Access: Use the net to access all your data from any device.
  • Enhanced Security: Threat detection, encryption, and compliance features.

Read Also: Advantages and Disadvantages of Moving Exchange to the Cloud

transfer Exchange mailbox 2019 to Microsoft 365

Preparation for Exchange 2019 to Office 365 Migration

These steps are required regardless of the migration method.

Start with an Outlook Anywhere Setup: The steps slightly differ depending on the Outlook version; here we give the steps for Outlook version 2010

  • In the console tree, go to Server Configuration > Client Access.
  • Click Enable Outlook Anywhere in the action pane.
  • In the wizard, enter your organization’s external hostname for Outlook Anywhere access.
  • Choose an external authentication method: Basic or NTLM. Basic sends credentials in clear text, while NTLM offers enhanced security.

Caution: Avoid using Negotiate Ex authentication as it can lead to authentication issues; it’s only there for testing purposes and is reserved for future Microsoft use.

  • If you plan to use SSL offloading with an SSL accelerator, check the box for “Allow secure channel (SSL) offloading.” Ensure your SSL accelerator supports this feature.

Warning: Only select SSL offloading if you’re certain it’s supported by your accelerator; otherwise, don’t, as it may cause Outlook Anywhere to fail entirely.

  • Click “Enable” to apply these settings and activate Outlook Anywhere.
  • Finally, click “Finish” to close the wizard.

Ensure Required Permissions: Any one of the following permissions must be with the individual migrated mailbox from Exchange 2019 to Office 365

  • Domain Admins group membership in AD DS of the on-premises organization.
  • FullAccess permission for each mailbox with WriteProperty permission to change the TargetAddress.
  • Receive As permission for the mailbox database that holds the user data with the WriteProperty permission to change the TargetAddress

Pause Unified Messaging Temporarily:

  • Within the Exchange Management Console’s console root, navigate to the Recipient Configuration node.
  • In the result pane, choose the user whose mailbox you wish to deactivate for Unified Messaging.
  • Click “Disable Unified Messaging” in the action pane.
  • Confirm your decision to disable Unified Messaging for the user by clicking “Yes” in the confirmation dialog box.

What are the Different Ways for Exchange 2019 to Office 365 Migration?

There are various techniques that you can use to proceed with the transition. Some of them are from Microsoft and there are some automated solutions as well. Let’s get started!

#Technique 1. Automated Solution to Migrate Exchange 2019 to Office 365

The only solution any organization requires is none other than a tried and tested Exchange to Office 365 migration tool. It comes with a user-friendly interface to make the migration process as simple as possible. Combine the ease of use with the state-of-the-art algorithms, and you have the complete solution to deal with all migration scenarios.

Download Now Purchase Now

Moreover, the features speak for themselves:

    • Transfer all emails, contacts, and calendars at the same time
    • Ready to move data from multiple user mailboxes simultaneously
    • Ability to shift and Migrate Exchange 2013 to Office 365 as well
    • Newly arrived data can be moved via the Delta migration feature
    • Navigate to specific periods and move data accordingly using the Date filter
    • Yielding multiple mapping options for linking Exchange users to Office 365.
    • Note and transfer scheduled events in calendars without any changes.
    • Includes a retry option to redo migrations again.
    • Give specific priority to critical mailboxes before migration.
    • Get both subdomain and organizational-level support for user mailbox migration.
    • Enjoy a high-quality dashboard to get real-time updates on migrations.
    • Retains compatibility with both Windows (10, 11) and Windows Server (2012, 2016).

Steps to Migrate Mailbox from Exchange 2019 to Office 365 via the Utility

Step 1. Download the software on your system, Open it, and select Exchange and Office 365 as the source and destination, respectively.

Select Exchange as Source and Office 365 as Destination

Step 2. Scroll down, where you will find the option to select the Workloads that need to be transferred. Also, apply the Date Filter for more precise data transfer.

In Workload Section, make the task selection, and apply Date Filter

Step 3. Then, navigate to the Source section Pick Exchange Server 2019 as the version from the drop-down menu, and fill in other details as prompted. Then Validate and hit Next.

Type in Exchange Server details

Step 4. In the Destination Section, add the Admin Email and user-generated Application ID, after which you can validate and move forward by pressing Next.

Enter Office 365 Details

Step 5. Then, on the next screen, you can choose the method by which User Mapping will take place.

Map Users Via Fetch, Import, Download

Step 6. Once the user preview is visible, set a priority to the most critical ones, validate, and press Start Migration.

Hit the Start Migration Button

Also Read: Steps toMigrate Exchange 2010 to Office 365Easily

#Technique 2. Cutover Method to Migrate Mailbox from Exchange 2019 to Office 365 Manually

Microsoft itself only recommends it for no more than 150 mailboxes.

Step 1. Domain Verification To verify your domain for Office 365

  • Log in to Microsoft 365.
  • Navigate to Setup > Domains.
  • Click “Add domain” on the Domains page.
  • Choose “Add domain” and enter your on-premises Exchange domain, then click “Next.”
  • On the Verify Domain page, select your DNS provider and follow their instructions.
  • After 15 minutes, click “Done,” then “Verify now,” and finally, “Finish.”

Step 2. Connect Office 365 to Email System To establish the connection

  • Access the Exchange Admin Center (EAC).
  • Go to Migration in the Recipients section.
  • Click “More,” then select “Migration endpoints.”
  • On the Migration Endpoints page, click “New.”
  • Choose “Outlook Anywhere” and click “Next.”
  • Enter the necessary information on the “Enter on-premises account credentials” page.
  • On a successful connection, settings are displayed. Click “Next.”
  • For failed tests, provide the Exchange server (FQDN) and RPC proxy server (FQDN).
  • Specify the endpoint name and click “New” to create the migration endpoint.

Step 3. Create Migration Batch To initiate the migration batch

  • In EAC, visit Recipients > Migration.
  • Click “New” > “Migrate to Exchange Online.”
  • Select “Cutover migration” and click “Next.”
  • Confirm migration endpoint info and click “Next.”
  • Create a batch with a name (no spaces) and click “Next.”
  • Choose to start the batch immediately or later and press “New” to build the batch.

Step 4. Start the Migration Start the migration

  • In EAC, go to Recipients > Migration.
  • Select the batch on the dashboard and click “Start.”
  • A “Syncing” status indicates a successful start.

Step 5. Reroute Emails to Office 365 Update MX records

  • Log in to your domain provider’s control panel.
  • Access DNS or MX record settings.
  • Identify existing MX records.
  • Add Office 365 MX records with lower priorities.
  • Optionally, delete or modify existing MX records.
  • Wait for DNS propagation (up to 48 hours).
  • Test email delivery to Office 365.
  • Monitor email traffic for any issues.
  • Update email clients if necessary.
  • Verify email routing (optional).

Step 6. Delete Batch To remove the migration batch

  • In EAC, visit Recipients > Migration.
  • Select the batch and click “Delete.”
  • Confirm the batch removal in the Migration section.

migrate Exchange mailbox 2019 to Microsoft 365

# Technique 3. Minimal Hybrid Data Transfer Technique

If complete data transfer is out of the question, then you can set up a mixed system via a hybrid approach.

Step 1. Domain Verification 

  • Repeat the verification process from the Cutover Migration section.

Step 2. Initiating a process to migrate mailbox from Exchange 2019 to Office 365

  • Go to the Microsoft 365 Admin Center.
  • Then, navigate to Setup > Migrations.
  • Select “Email” within the Migrations page.
  • Then, visit the “Migrate your email” page and click “Get started.”
  • Download the Hybrid Configuration Wizard.
  • Run the downloaded application.
  • Accept the default values for the On-premises Exchange Server Organization.
  • Use current Windows credentials for both Exchange and Microsoft 365.
  • Choose “Minimal Hybrid Configuration” on the Hybrid Features page.
  • Finally, select “Update” to prepare on-premises mailboxes for migration.

Step 3. Provision users through Directory Synchronization:

  • On the “User Provisioning” page, opt for “Synchronize my users and passwords one time.”
  • Download the Azure AD Connect wizard and run it with the default settings.
  • View the synchronized users on the Data Migration page, which will automatically close afterward.

Step 4. Licensing for Microsoft 365 

  • Provide Microsoft 365 licenses to users which enables the migration of Exchange 2019 to Office 365.

Step 5. Initiating Mailbox Migration

  • Navigate to Setup > Data migration.
  • Then, choose “Exchange” as your data service.
  • Finally, select the users you want to migrate and click “Start migration.”

Step 6. DNS Records Update 

  • A Record: Update to point to the IPv4 address of your choice.
  • CNAME Record: Modify to create an alias for a specific domain or subdomain.
  • MX Record: Change to specify the mail server for receiving email.
  • TXT Record: Adjust for domain verification or SPF/DKIM settings for email authentication.

# Technique 4. Migrate Mailbox from Exchange 2019 to Office 365 in Staged Manner

It should be employed when the number of mailboxes is more than 2,000 

Step 1. Domain Verification

  • Perform domain verification as you would in a cutover migration.

Step 2. User Creation

  • Use directory synchronization to create users.
  • Ensure licenses are assigned within 30 days.
  • Employ Microsoft Azure Active Directory Synchronization Tool (AAD Sync) for user creation.

Step 3. Create Mailbox List

  • Generate a mailbox list in CSV format.
  • Remember that EmailAddress is mandatory, while other fields are optional.

Step 4. Connect to Office 365

  • Follow the same steps as in a cutover migration to establish a connection between Office 365 and your email system.

Step 5. Batch Creation for Staged Migration

  • Sign in to the Exchange Admin Center (EAC).
  • Navigate to Migration > Batch.
  • Create a new migration batch and follow the provided instructions.
  • In the Migration Onboarding section, specify the batch name and migration path.
  • Select “Staged migration” as the migration type.
  • Review prerequisites and configure migration endpoints.
  • Upload the user CSV file.
  • Set up migration settings.
  • Schedule the batch migration.
  • Monitor the batch status, which should transition to “Synced.”
  • Finalize the batch by choosing your migration group and preferred option in the details pane.
  • Batch status should now show as “Completed.”

Step 6. Initiate Staged Migration

  • Access EAC, and navigate to Recipients > Migration.
  • On the dashboard, choose the batch and click Start.
  • A migration status of “Syncing” indicates a successful start.

Step 7. Mailbox Conversion

  • Convert on-premises mailboxes to mail-enabled users to ensure uninterrupted mail flow and retain proxy addresses.

Step 8. Email Routing to Office 365

  • Make the necessary DNS record adjustments to redirect emails to Office 365.
  • Follow the instructions provided by your domain registrar.

Step 9. Remove Staged Migration Batch

  • Log in to EAC and find Migration > Batch.
  • In the migration dashboard, select the batch and opt for deletion.

Post Migration Duties to Take Care of

  • Assign licenses and activate accounts
  • Build new Autodiscover DNS records
  • Retire On-Premise Servers

Following the tips outlined in this discussion, anyone can migrate mailbox from Exchange 2019 to Office 365. Here we covered the benefits of going with the shift and also provided a variety of approaches for the same. Out of the many different methods, the automated tool is the easiest and least likely to encounter issues. Therefore, users are recommended to follow the advice of industry experts and try out the automated utility themselves.

Frequently Asked Questions

Q 1. What Migration Methods are Available for Migrating Mailboxes to Office 365 from Exchange 2019?

Ans.  At present, the four best solutions help to execute the transition hassle-free, and they are as follows:

Q 2. Can I Perform a Cutover Migration from Exchange 2019 to Office 365?

Ans. Yes, small organizations that want to move fewer than 2000 mailboxes can opt for the Cutover migration method.

Q 3. What are the Key Steps Involved in Migrating Mailboxes from Exchange 2019 to Office 365?

Ans. Prepare Exchange, verify domain, create migration endpoint, batch migration, verify migration, update DNS, decommission Exchange.

Q 4. What Considerations Should I Keep in Mind for Mailbox Data during the Migration Process?

Ans. Consider data integrity, migration speed, user communication, mailbox size, and potential downtime.

Q 5. How Does the Migration Process Impact End-Users?

Ans. End-users may experience temporary disruptions in email access & need to update settings and adapt to new features in Office 365.

Q 6. Can I Migrate Other Data besides Mailboxes, such as Public Folders or Archives?

Ans. Yes, you can migrate public folders, archives, and other data using specified migration tools or manual methods, which allows you to do the same.

Q 7. What are the Licensing Requirements for Office 365 Users Post-Migration?

Ans. After the migration, users need licenses to access Office 365 services, like Exchange Online, depending on their required features.


By Nilesh Kumar

As a Chief Technical Writer, I know the technical issues faced by home and professional users. So, I decided to share all my knowledge via this blog. I love to help you with challenges while dealing with technical jargon.