How to Upgrade from Exchange Server 2010 to Exchange Server 2016 or 2019: A Complete Guide!

Upgrading from Exchange Server 2010 to Exchange Server 2016 or Exchange Server 2019 is a critical step for organizations seeking to enhance their email infrastructure and security. Microsoft Exchange Server is a robust platform that manages emails, calendars, contacts, and tasks. However, with the evolution of features and security standards, upgrading to a newer version of Exchange is essential for performance, scalability, and support.

In this comprehensive guide, we will walk you through the process of upgrading from Exchange 2010 to Exchange 2016 or 2019, covering all technical aspects, best practices, and essential tips.

Why Upgrade from Exchange Server 2010 to a Newer Version?

Before diving into the upgrade process, it’s important to understand why upgrading your Exchange server is necessary. Microsoft Exchange 2010 reached its end of support on October 13, 2020. This means it no longer receives critical security updates, patches, or bug fixes, which can leave your organization vulnerable to security risks.

Moreover, newer versions of Exchange (2016 and 2019) offer several benefits over Exchange 2010, including:

• Improved Performance: Both Exchange Server 2016 and 2019 have optimized performance, including faster mailbox database performance and better search functionality.
• Enhanced Security: Exchange 2016 and 2019 have improved security features like better threat protection, improved data loss prevention (DLP), and enhanced compliance tools.
• Modern Features: With new capabilities like cloud integration, hybrid configurations, and easier administrative management, the newer versions help organizations stay aligned with the latest technology trends.
• Support for Newer Operating Systems: Exchange 2010 runs on outdated operating systems, which are no longer supported by Microsoft. Exchange 2016 and 2019 run on modern Windows Server versions.

Upgrading ensures that your organization benefits from the latest features, security improvements, and support from Microsoft.

Pre-Upgrade Considerations

Upgrading the Exchange Server is a complex process that requires careful planning and attention to detail. Here are some key considerations before you begin the upgrade:

1. Review System Requirements

Both Exchange 2016 and 2019 have specific hardware and software requirements. Before starting the upgrade, ensure that your environment meets these requirements:

• Exchange 2016: Requires Windows Server 2012 or later.
• Exchange 2019: Requires Windows Server 2019 or 2022.
• Both versions need 64-bit processors, at least 8GB of RAM (preferably more for larger installations), and adequate disk space for the mailbox databases and transaction logs.

Ensure your server infrastructure is updated and capable of supporting the newer version of Exchange.

2. Backup Your Environment

Before proceeding with any upgrade, always back up your Exchange environment, including:

• Mailbox databases
• Active Directory
• Exchange configurations and settings

Having a solid backup ensures you can recover data in case of any issues during the upgrade process.

3. Evaluate the Current Exchange 2010 Environment

Assess your current Exchange 2010 environment to identify any potential issues that may arise during the upgrade. This includes:

• Ensuring your Exchange 2010 is running on the latest service pack and cumulative update.
• Checking for any third-party applications or custom configurations that may conflict with the new Exchange version.
• Identifying any Exchange 2010 features or functionalities that are deprecated in Exchange 2016 or 2019.

Step-by-Step Guide to Upgrading from Exchange 2010 to Exchange 2016 or 2019

Step 1: Prepare Your Active Directory (AD)

Before upgrading Exchange, ensure that your Active Directory (AD) is ready to support the new version of Exchange. Here’s how:

• Prepare Active Directory Schema: The first step in the upgrade process is to extend the Active Directory schema to accommodate Exchange 2016 or 2019. This is done using the Exchange setup /PrepareAD command.
• Run this command on a server that has the AD schema update tools installed:

Setup.exe /PrepareAD        

• Prepare AD Domains and Organizational Units: This step prepares your AD domains and organizational units to support Exchange 2016 or 2019. It can be done by running:

Setup.exe /PrepareDomain        

Step 2: Install Exchange Server 2016 or 2019 Coexistence

Exchange 2010 cannot be directly upgraded to Exchange 2016 or 2019. You need to install the newer version in coexistence with Exchange 2010.

• Install the New Exchange Server: Install Exchange 2016 or 2019 on a new server. This will allow the two versions to run in parallel, providing a smooth transition.
• Configure Coexistence: Set up coexistence between Exchange 2010 and the new version. This will ensure that the email flow works properly between both versions. You will need to configure the send connectors, receive connectors, and mail routing to enable seamless communication between the servers.

Step 3: Migrate Mailboxes from Exchange 2010 to Exchange 2016/2019

The next step is to migrate the mailboxes from the old server (Exchange 2010) to the new one (Exchange 2016 or 2019).

• Prepare Mailboxes for Migration: In Exchange 2010, you need to move mailboxes to the new Exchange environment. This can be done using New-MoveRequest in PowerShell.

New-MoveRequest -Identity "MailboxUser" -TargetDatabase "NewDB"        

• Batch Migration: If you have many mailboxes, you can use batch migration to migrate multiple mailboxes at once. Use the Exchange Admin Center (EAC) or PowerShell commands for batch migration.
• Example:

Get-Mailbox -Database "MailboxDatabase2010" | New-MoveRequest -TargetDatabase "MailboxDatabase2016"        

• Verify Mailbox Migration: Ensure that mailboxes have been successfully migrated by running the Get-MoveRequest command to verify progress.

Step 4: Update DNS Records and Mail Routing

Once the mailboxes are successfully moved, it’s time to update the DNS records:

• Update MX Records: Ensure that your MX records point to the new Exchange 2016 or 2019 server to handle all incoming mail traffic.
• Update Autodiscover: The Autodiscover service should be updated to reflect the new Exchange version. This ensures that users can connect seamlessly to their mailboxes from Outlook and mobile devices.

Step 5: Decommission Exchange 2010

After migrating all mailboxes and ensuring that mail flow is functioning properly, you can begin decommissioning Exchange 2010:

• Remove Mailbox Databases: Delete the Exchange 2010 mailbox databases once they’re no longer needed.
• Uninstall Exchange 2010: Use the Exchange setup wizard to remove Exchange 2010 from the server.
• Run the following command to uninstall:

Setup.exe /mode:uninstall        

• Clean Up AD: Once Exchange 2010 has been uninstalled, remove any remaining Exchange 2010 objects from the Active Directory.

Step 6: Post-Upgrade Tasks

After completing the upgrade process, there are a few tasks to ensure everything is running smoothly:

• Update Mail Flow Rules: Review and configure any mail flow rules in the new version of Exchange.
• Test Mail Functionality: Verify that all mail features, such as calendar sharing, meeting scheduling, and email routing, are functioning as expected.
• Check Hybrid Configuration: If you are running a hybrid Exchange environment with Office 365, ensure that the hybrid configuration is working properly.

How Automated Solution Can Simplify the Process?

While the steps outlined above are essential for a successful upgrade, the manual migration process can be slow and complex, especially if you are managing a large Exchange environment. This is where Exchange Migrator significantly speeds up the upgrade and migration process, making it more efficient and less error-prone.

Benefits of Using this Smart Solution!

1. Faster and Smoother Data Migration

Migrating from Exchange 2010 to Exchange 2016 or 2019 typically involves moving data from one server to another, which can be time-consuming and prone to issues if done manually. It allows for bulk migration, enabling you to move multiple mailboxes and their associated data at once, significantly reducing migration time. The tool handles the migration process in the background, so users won’t experience major disruptions.

2. Simplified Migration Process Without Coexistence Setup

One of the most challenging tasks during an upgrade is setting up coexistence between the old and new Exchange environments. This involves configuring mail routing, user access, and security settings, which can lead to complications. This eliminates the need for a complex coexistence setup. With the tool, you can directly migrate mailboxes from Exchange 2010 to Exchange 2016/2019 without needing to set up a coexistence infrastructure.

The migration happens seamlessly, without any manual configuration of send/receive connectors and server interconnections, thus making the process much simpler and more efficient.

3. Complete Data Integrity and No Data Loss

One of the biggest concerns during any email migration is ensuring that no data is lost. It ensures 100% data integrity, migrating all mailbox data including emails, attachments, calendars, contacts, tasks, public folders, and more, without any data loss. The tool also offers an option to perform incremental migrations, ensuring that no emails are missed during the process.

4. Built-in Error Handling and Reporting

During manual migrations, errors are common — whether due to connectivity issues, server misconfigurations, or permission problems. It offers robust error handling and logs every step of the migration. This allows administrators to identify issues early and resolve them before they affect the entire migration. Detailed reporting ensures that you are fully aware of the migration progress at every stage.

5. Reduced Downtime and Improved Efficiency

The specified solution ensures that your Exchange upgrade happens quickly, allowing your organization to experience minimal downtime. Because the tool handles migration efficiently, users will have access to their mailboxes with little to no interruptions. This is particularly beneficial for organizations where email access is critical for daily operations.

6. Automated Post-Migration Cleanup

Once the migration is complete, the tool can also assist in cleaning up the old Exchange 2010 environment, ensuring that all data and configurations are properly removed. This automated post-migration cleanup saves you time and effort, allowing for a smooth transition to Exchange 2016 or 2019.

Common Issues During Upgrade and How to Address Them

1. Compatibility Issues: Third-party applications or custom scripts may not work as expected in the new Exchange version. Ensure that all dependencies are updated for compatibility with Exchange 2016 or 2019.
2. Mailbox Migration Failures: Sometimes, mailbox migrations can fail due to database corruption, connectivity issues, or permissions. Use the Get-MoveRequestStatistics cmdlet to troubleshoot migration problems.
3. Coexistence Problems: Issues can arise during coexistence if there is incorrect mail routing or configuration between the old and new versions. Ensure that connectors are correctly configured and that both versions are fully patched.

Conclusion

Upgrading from Exchange Server 2010 to Exchange 2016 or Exchange 2019 is a crucial process that ensures your organization stays up-to-date with the latest features, security patches, and performance improvements. By following the outlined steps—preparing Active Directory, installing the new Exchange version, migrating mailboxes, and decommissioning the old server—you can achieve a smooth and efficient upgrade.

Take time to thoroughly plan and test the migration process to minimize disruptions. Remember, the key to a successful upgrade lies in proper planning, communication, and execution.

For more information on Exchange Server upgrades, best practices, and troubleshooting tips, feel free to check out Microsoft Exchange documentation.

People Also Ask!

1. Can I upgrade directly from Exchange Server 2010 to Exchange 2016 or 2019?

No, you cannot directly upgrade from Exchange Server 2010 to Exchange 2016 or 2019. The upgrade process involves installing Exchange 2016 or 2019 alongside Exchange 2010 in a coexistence environment, and then migrating mailboxes and services to the new version. After the migration is complete, Exchange 2010 can be decommissioned.

2. What are the system requirements for Exchange Server 2016 or 2019?

• Processor: 64-bit processor (x64 architecture) with a minimum of 8 cores for optimal performance.
• RAM: At least 8 GB of RAM (16 GB or more is recommended for larger environments).
• Disk Space: A minimum of 30 GB of free disk space for the installation, with additional space for mailbox databases and transaction logs.
• Operating System: Windows Server 2012 or later for Exchange 2016, and Windows Server 2019 or 2022 for Exchange 2019.
• Active Directory: Exchange 2016/2019 requires an Active Directory schema update.

3. What versions of Exchange Server can coexist with Exchange 2010 during the upgrade process?

During the upgrade process, you can coexist with the following versions of Exchange Server:

• Exchange 2013 (for a transitional period before migrating to 2016/2019)
• Exchange 2016 or Exchange 2019 (which is the ultimate goal after the migration)

Exchange 2010 cannot coexist directly with versions later than Exchange 2019.

4. How do I prepare Active Directory for Exchange Server 2016 or 2019?

Before installing Exchange 2016 or 2019, you need to extend the Active Directory schema. This can be done using the following commands:

• Extend Active Directory Schema: On the Exchange 2016/2019 server, run:
• On the Exchange 2016/2019 server, run:

Setup.exe /PrepareAD        

• Prepare Domains and Organizational Units: Then, prepare the domains and organizational units by running:

Setup.exe /PrepareDomain        

This ensures that Active Directory is ready for the new version of Exchange.

5. How do I migrate mailboxes from Exchange 2010 to Exchange 2016/2019?

To migrate mailboxes from Exchange 2010 to 2016/2019:

• Install Exchange 2016 or 2019: Set up the new Exchange server in coexistence with Exchange 2010.
• Move Mailboxes: Use PowerShell cmdlets or the Exchange Admin Center (EAC) to move mailboxes from the old Exchange server to the new one. The basic command is:

New-MoveRequest -Identity "UserMailbox" -TargetDatabase "NewDatabase"        

You can migrate mailboxes in batches for larger environments by using the Get-Mailbox cmdlet to select groups of mailboxes.

6. How do I configure mail flow between Exchange 2010 and Exchange 2016/2019?

To ensure smooth mail flow between Exchange 2010 and 2016/2019, you need to configure send connectors, receive connectors and mail routing. Here are the basic steps:

1. Create Send and Receive Connectors: In Exchange 2016/2019, configure a Send Connector to route outgoing mail to Exchange 2010 and vice versa for receiving mail.
2. Mail Routing: Ensure that internal mail routing works between the two versions, typically using the SMTP protocol.
3. DNS and Autodiscover Configuration: Ensure that MX records and Autodiscover are updated to reflect the new Exchange server.

7. What happens to public folders during the migration?

Public folders require special consideration during the migration process. Exchange 2010 public folders cannot be directly migrated to Exchange 2016/2019. Follow these steps:

1. Create a New Public Folder Database: In Exchange 2016 or 2019, create a new public folder database.
2. Migrate Public Folders: Use the New-PublicFolderMigrationRequest cmdlet to migrate public folders from Exchange 2010 to Exchange 2016/2019.

This process requires careful planning and testing to ensure that public folder migration happens without disruption.

8. How do I handle client access and Outlook connectivity during the upgrade?

During the coexistence phase, Exchange 2010 and Exchange 2016/2019 must both handle Outlook client connections. The key steps are:

1. Autodiscover Configuration: Ensure that Autodiscover records are pointing to the new Exchange 2016/2019 server.
2. Outlook Profile Redirection: Users with Outlook profiles configured for Exchange 2010 will need to be updated to connect to Exchange 2016 or 2019. This typically happens automatically once the mailbox is migrated.
3. Exchange Web Services (EWS): Ensure that both versions of Exchange have EWS configured to allow for seamless client access.

9. How do I update DNS records during the upgrade process?

Once the migration is complete and mailboxes are moved to Exchange 2016/2019, update the following DNS records:

1. MX Records: Point your organization's MX records to the new Exchange server to route incoming email.
2. Autodiscover Records: Update the Autodiscover DNS records to ensure that Outlook clients connect to the new Exchange version.
3. Service Location Records (SRV): Make sure the appropriate SRV records are pointing to the correct Exchange server.

These DNS updates will ensure proper mail routing and client connections post-migration.

10. How do I decommission Exchange 2010 after the upgrade?

Once all mailboxes and services are fully migrated to Exchange 2016/2019, you can begin decommissioning Exchange 2010:

• Remove Mailbox Databases: Delete any remaining mailbox databases on Exchange 2010.
• Uninstall Exchange 2010: Use the following PowerShell command to uninstall Exchange 2010:

Setup.exe /mode:uninstall        

• Clean Active Directory: Use Active Directory Sites and Services to remove Exchange 2010 server entries. Also, run the Remove-ExchangeServer cmdlet to clean up AD.

Once Exchange 2010 is removed from both your servers and Active Directory, your migration to Exchange 2016 or 2019 is complete.

11. What should I do if mailbox migrations fail?

Mailbox migration failures can occur due to various reasons, such as corrupted mailboxes, insufficient permissions, or connectivity issues. Here’s how to troubleshoot:

• Check Event Logs: Review the Event Viewer logs on both Exchange 2010 and Exchange 2016/2019 servers for errors or warnings.
• Use the Get-MoveRequest Cmdlet: This PowerShell cmdlet can provide detailed information on failed migrations:

Get-MoveRequest | Get-MoveRequestStatistics        

• Permissions: Ensure that the migration account has appropriate permissions to perform mailbox moves.
• Run Mailbox Repair: If a mailbox is corrupted, you may need to run a Mailbox Repair Request.

12. What is the best approach for managing hybrid configurations?

If you're integrating Exchange 2016 or 2019 with Office 365 in a hybrid configuration, follow these best practices:

1. Hybrid Configuration Wizard (HCW): Use the Hybrid Configuration Wizard in Exchange 2016/2019 to configure hybrid mail flow and coexistence with Office 365.
2. Mail Routing: Set up mail flow connectors to route messages between on-premises Exchange and Office 365.
3. Directory Synchronization: Ensure Azure AD Connect is set up to synchronize on-premises AD with Azure AD for a unified directory experience.

13. How do I test the upgrade process?

Testing is a crucial step before and after the upgrade:

1. Verify Mail Flow: Test both internal and external mail flow to ensure emails are correctly routed between Exchange 2010 and 2016/2019.
2. Test Client Access: Test Outlook connectivity for users whose mailboxes have been migrated to ensure proper functionality.
3. Test Public Folders: If using public folders, ensure that users can access them after migration.