How to migrate Exchange 2016 to Exchange 2019?

What you need to know about Exchange 2016 and 2019?

If you're considering using Exchange 2016 or 2019, there are a few key things you must know. Microsoft ended mainstream support for Exchange 2016 on October 13, 2020, and will end extended support on October 14, 2025. After the extended support date, there will be no further updates or security patches released for Exchange 2016, so migrating to a newer version is advisable for organizations who want to continue receiving support and updates from Microsoft. The following points are some of the enhancements in Exchange 2019 over 2016.

Exchange 2016 to 2019 migration

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Improved security: Exchange 2019 includes enhanced security features such as Windows Server Core support, improved encryption and data loss prevention.
Enhanced performance: Exchange 2019 offers improved performance, meta cache database, search infrastructure and scalability over Exchange 2016, making it better suited for large organizations with heavy email usage.
Improved mailbox experience: Exchange 2019 includes new features such as modern attachments, which enables you to share a link to the file in OneDrive instead of sending a copy. This feature saves space in users' mailboxes and improves collaboration.
Modern public folder support: Exchange 2019 provides support for modern public folders and integrates them with the In-Place eDiscovery and Hold workflow, which offer improved search performance and scalability over the traditional public folders.
Improved support for hybrid deployments: Exchange 2019 includes improved support for hybrid deployments such as a cloud based Hybrid Configuration Wizard (HCW), making it easier for organizations to migrate to Office 365.
In addition to the new features that are introduced in Exchange 2019, it is important to consider and know what has been discontinued in 2019.

Exchange 2016 to Exchange 2019 coexistence

Exchange 2016 and Exchange 2019 can coexist in the same Active Directory configuration. However, you must consider the following factors to ensure that they can coexist together.

Compatibility with other applications: Ensure that any other applications that are used in your organization are compatible with Exchange 2019. These include email clients, antivirus software, backup software, and monitoring tools.
Cumulative Updates: You must have the CU11 or later installed on your Exchange 2016 servers including the Edge Transport servers.
Hardware and software requirements: Exchange 2019 has specific hardware and software requirements that must be met in order to be installed and run correctly such as operating system, processor type and speed, and memory. Ensure that you take care of these requirements before the migration.
Exchange licensing: If you are upgrading from Exchange 2016, ensure that you have the necessary licenses for Exchange 2019.

What is the best way to migrate from Exchange 2016 to 2019?

EdbMails Exchange email migration tool is an ideal solution to migrate your mailboxes and upgrade Exchange 2016 to 2019. It enables you to migrate all of your mail data, user folders, public folders, contacts, calendars, permissions, mail header data, tasks, journals, notes, and more from your source Exchange server to the target server while maintaining complete data consistency. Additionally, EdbMails supports migrating to Office 365, Live Exchange, and Hosted Exchange migration. In this Exchange 2016 to 2019 migration guide, we describe the prerequisites, system requirements, migration with EdbMails and post migration activities.

Exchange 2016 to 2019 migration checklist

Here is a checklist of points when migrating from Exchange Server 2016 to 2019

Backup Exchange server mailboxes, public folders, and store the copy in a secure location.
Verify that your current Exchange Server environment meets the prerequisites for installing Exchange Server 2019. Check the version and edition of the Exchange server and Windows server operating system you have.
Inform the possible changes to your end users and stakeholders.
Estimate the migration cost, network requirements and bandwidth required.
Install Exchange Server 2019 on the server including additional roles and permissions.
Configure the new Exchange Server 2019 environment, by creating mailboxes, public folders, and client access rules.
Test the new Exchange Server 2019 environment thoroughly to ensure that it is functioning correctly.
Migrate mailbox and public folder data from the old Exchange Server 2016 environment to the Exchange 2019 environment, using EdbMails.
Decommission the old Exchange Server 2016 after migrating to and testing the Exchange Server 2019 environment.

I. Exchange 2016 to 2019 migration prerequisites

Step 1: Check that your system meets the Exchange 2019 setup requirements

Before you migrate your mailbox data to Exchange 2019, ensure that your current environment and hardware is compatible for the transfer. The following links will help you to know about the hardware, network, .NET framework and operating system requirements for installing Exchange server 2019.

Exchange server version	Coexistence scenario	Requirement	Migration
Exchange 2019	Possible. Can coexist with Exchange 2016	Install Cumulative Update 11 (CU11) or later on Exchange 2016	EdbMails can help you migrate Exchange 2016 to Exchange 2019 directly

Additional Notes:

Exchange 2019 requires Active Directory forest functional level of Windows Server 2012 R2 or higher.
The Domain Controllers need to be running on Windows Server 2012 R2 Standard or Datacenter and higher.
You must install .NET Framework 4.8 on a Cumulative Update (CU) of 4 to 12.
The Mailbox and Edge Transport servers require Windows Server 2019 Standard or Datacenter and higher. See the Exchange server 2019 supportability matrix for more information.

Step 2: Prepare your system with the following prerequisites for Exchange 2019
Complete the following prerequisites for Active Directory, Windows 2019 Mailbox server, and Windows 2019 Edge Transport servers before installing Exchange server 2019.
1. Windows Server prerequisites for Exchange 2019
2. Prerequisites for preparing Active Directory (AD)

Step 3: Decide on the migration path from Exchange 2013 to 2019

Consider if you want to perform a staged, cutover or a hybrid Exchange migration. EdbMails can help you with the following migrations without downtime or data loss. The advantage with it is that you can keep using your mailboxes during the migration without disconnecting your Exchange server.

Current environment and requirement	Ideal migration approach	Migration flow
You want to perform a full migration to Exchange 2019 in a single event and in a limited time frame.	Exchange 2016 to 2019 cutover migration	In this approach, you set up your target Exchange server and migrate everything in a single sitting. Suitable for large mailbox migration
You have little time and want to migrate mailboxes in phases or over the weekends	Exchange staged migration	In this approach, you migrate your mailboxes and mail data in stages and transfer the most recent data first followed by the others.
You want to migrate Exchange 2016 mailboxes to a Hybrid 2019 and Office 365 environment	Migrate Exchange 2016 to 2019 Hybrid	In this approach, you migrate from the source server to a Hybrid Exchange and Office 365 environment.

Note: The migration path depends on the number of mailboxes you want to migrate, size of the data and your organizational requirements. Use the Exchange deployment assistant to help you decide on the path.

Step 4: Set up the target Exchange Server 2019 for migration
Given below is a list of key points for installing and preparing the Exchange 2019 server for migration.
Note: If you have already installed and configured Exchange 2019 in the target environment, skip to point 4 in this step.
1. Prepare the AD and domains
  1. Before installing Exchange Server 2019, prepare your Active Directory forest and its domains for the new version of Exchange.
  2. If you have a separate team to manage the Active Directory schema, you must extend the active directory schema, else proceed to the next step to prepare the Active Directory.
  3. If you have multiple domains you need to additionally prepare the Active Directory domains.
2. Install Exchange server 2019
  Ensure that you meet the server system requirements and prerequisites as outlined previously. Next, install Exchange 2019 mailbox server and edge transport server using the setup wizard. Microsoft recommends installing Exchange 2019 on Windows Server core for best experience.
3. Prepare a clean Exchange 2019 target environment
  1. Install and upgrade Exchange 2019 to the latest cumulative update to keep your server up to date.
  2. Create and configure a Send connector to send mail outside the Exchange organization.
  3. By default, Exchange automatically creates receive connectors for inbound mail flow when the mailbox server is installed. However, if you want to configure custom receive connectors for certain mail flow scenarios, follow the steps in the link.
  4. Add accepted domains to allow recipients to send and receive email from another domain.
  5. Configure the default email address policy to add the accepted domain to every recipient in the organization.
  6. Configure external URLs (domains) on the virtual directories in the Client Access (frontend) services on the Mailbox server to allow clients to connect to your server from the internet (outside the organization’s network).
  7. Configure internal URLs on the virtual directories in the Client Access (frontend) services on the Mailbox server to allow clients to connect to your server from the internal network.
  8. Configure SSL certificates from a third-party certificate authority for services such as Outlook Anywhere and Exchange ActiveSync.
  9. Verify the Exchange server installation by running the command Get-ExchangeServer on the Exchange Management Shell (EMS)
4. Create mailboxes and Public folder on the target Exchange
  You must create mailboxes and mail enabled Public folders on the target for the migration. Also, assign suitable licenses to them.
  1. Steps to create mailboxes in Exchange server
  2. Steps to create Public folder in Exchange server
5. Install cumulative updates (CU) on Exchange server 2016
  For migrating Exchange server 2016 to Exchange 2019, it is required that you have installed the latest cumulative updates (CU) on the source 2016 server.
6. Create trust relationship between forests (Optional)
  A forest trust is an authentication between two domains within the same Active Directory forest which creates a trust between two root domains for exchanging information. By creating a trust in advance, it is possible to address the trust issues during or after the migration.
  Note: This step applies to Windows Server 2008, Windows Server 2008 R2 and Windows Server 2012. Creating a trust relationship is not required for SBS based environments.
7. Assign management roles to the admin account
  Ensure that you have set the following permissions to the admin account on the source (2016) and target server (2019)
  1. On the source
    1. ApplicationImpersonation
    2. View-Only Configuration - Run the cmdlet New-ManagementRoleAssignment using the Exchange Management Shell to assign the View-Only Configuration role to the admin.
    3. Organization Management role group. It is an elevated permission that is required to migrate Public folders.
  2. On the target
    1. ApplicationImpersonation
    2. View-Only Recipients
    3. View-Only Configuration
8. Verify the mailbox of the admin account
  Check to see if the admin account that has been assigned management roles has a valid and non-hidden mailbox on the Exchange 2016 server.
9. Configure the throttling and message-size limits
  Change the EWS throttling and message size limits on the target Exchange 2019 server by following the steps outlined in the links.
  1. Change the EWS throttling settings on Exchange server
  2. Change message size limits on target Exchange 2019

II. Migrate from Exchange 2016 to 2019

After you complete the prerequisites and are ready for the migration, use EdbMails to migrate to Exchange 2019 from 2016. It can save you time and effort, and enables you to perform the migration without the need for technical knowledge or PowerShell scripts.

Method 1: Full Exchange 2016 to Exchange 2019 migration
- Step 1: Download and install EdbMails Exchange migration tool
  - Download EdbMails and install the application on the source Exchange 2016 server or any other computer. You can also perform the migration by installing EdbMails on Windows 7, 8, 10 or 11 computers.
  - Launch the application and click 'Login' or 'Start Your Free Trial'.
  See a detailed list of EdbMails system requirements for Exchange migration.
  
  Note: If the Standard folders (such as Inbox, Calendar, Contacts) on your source Exchange server mailboxes are initialized with a different language, follow the details to migrate these folders to the respective system folders on the target (destination) server.
  For Instance: If your source Inbox folder is named 'Boîte de réception', which is in French language and you migrate this folder directly to the destination server, then by default it will not be mapped to the 'Inbox' folder on the target server. In order to map the folder with the french name to the respective folder, change the regional settings on the target server to match that of your source mailbox folder language (in this case, it is French).
- Step 2: Select the Exchange to Exchange migration method
  Select the option 'Live Exchange migration' in EdbMails to migrate Exchange 2016 to the new server.
- Step 3: Connect to the source Exchange 2016 server
  In the Exchange server connection window, select 'Connect using Global Admin User'. To migrate multiple user mailboxes, you can also load the mailboxes using a CSV file. See the different Exchange server connection methods supported by EdbMails.
  Tip: With EdbMails, you can migrate mailboxes, archive mailboxes and Public folders from the source Exchange to the target server. It is a secure application and does not store your credentials anywhere.
- Step 4: Select the mailboxes from Exchange 2016 for migration
  Select the mailboxes and folders that you want to migrate to Exchange server 2019
  Tip: If this is the first time you’re migrating with EdbMails, the migration is a full migration. On subsequent migrations from the same source to the target, the migration is incremental. You can also make use of the other mailbox migration options in the application such as removing deleted source items from the target and forcefully updating the items.
  Click 'Migrate to Live Exchange' to set up the connection with the target server.
  Tip: EdbMails provides the following additional settings to help you fine-tune the migration and meet your specific needs and requirements.
  1. Additional Include and Exclude Filter Options
  2. Filter emails by Date: This option enables you to specify and migrate emails to Exchange 2019 within a specific date range.
  3. Filter emails by Size: This option is useful if you want to exclude large attachments or emails from the migration.
  4. Filter emails by domain: You can also filter emails by the sender address or the email domain.
- Step 5: Log in to Exchange Server 2019 as Global Administrator
  You can connect to the mailboxes as a global admin user or load multiple mailboxes with a CSV file. Select the migration scenario as Mailboxes, Public folder or Archive mailbox depending on your requirements.
  Tip:After you connect to the target server, select the mapping method. EdbMails can automatically match and map the mailboxes and folders between the two Exchange servers and saves time when you’re migrating a large number of mailboxes.
- Step 6: Start the Exchange migration 2016 to 2019
  After the mailbox mapping activity, set the ‘Action’ to ‘Migrate’ and start the migration. You can monitor the progress of the operation and verify the number of emails, folders, and mailbox items that have been successfully migrated with the text-based log report. EdbMails also enables you to pause and resume the migration anytime.
Method 2: Exchange 2016 to 2019 migration hybrid
The Hybrid migration involves migrating your mailboxes from Exchange 2016 to a Hybrid 2019 and Office 365 environment. See the prerequisites for a Hybrid deployment and ensure that you meet the following requirements.
1. Verify the prerequisites for a hybrid deployment.
  - These include having a valid SSL certificate, a supported version of Exchange and Active Directory, meeting the networking and firewall requirements and installing the latest cumulative updates (CU) on the source Exchange
2. Configure Exchange 2019 with a hybrid configuration.
  - Set up a trust relationship between the on-premises Exchange organization and Office 365, as well as configuring the required connectors and other settings.
3. Register any custom domains you want to use in Hybrid with Office 365
4. Install at least one instance of Mailbox server for Exchange 2016
5. Update any Edge Transport servers to the latest CU.
6. Deploy the Azure Active Directory Connect to enable Azure AD synchronization.
After you have completed the necessary prerequisites, use the Hybrid Configuration Wizard (HCW) to configure the hybrid deployment. Next, use EdbMails to migrate mailboxes to Exchange hybrid. If your Exchange 2016 is in a Hybrid environment, you can simply perform Exchange to Office 365 hybrid migration by setting up the respective target server.
Note: If you want to migrate Public folders within the Hybrid environment, it is not possible to migrate the Public folders directly to Office 365. See this workaround solution for migrating Exchange hybrid public folders on premises
Method 3: Migrate to Exchange 2019 from 2016 with EDB file
If you have a database EDB file from Exchange 2016, you can also use EdbMails to migrate the EDB to Exchange 2019. This is the best method to migrate mailboxes to the target if your source Exchange server is down, or if you do not have access to it. For instance, the application can repair corrupted EDB files in Exchange 2016 and restore your mailboxes for migration. The following steps describe the procedure to import mailboxes from the EDB file to Exchange.
- Step 1: Install EdbMails and select EDB to Exchange migration
  Take a copy of the EDB file. Download and install the application and select the EDB migration option.
- Step 2: Select the Exchange 2016 EDB file which contains the mailboxes
  Select the offline EDB file from your computer that you want to migrate to Exchange. If your EDB file is in the Dirty Shutdown state, EdbMails can resolve Exchange 2016 dirty shutdown errors without data loss.
- Step 3: Preview the mail data and select mailboxes to migrate to 2019
  After the recovery operation, EdbMails displays all your mailboxes, mail items where you can preview them. Select the required ones and click 'Migrate to Live Exchange' as shown.
- Step 4: Map and import mailboxes from EDB file to Exchange 2019
  Perform the mailbox and folder mapping and start importing your mailboxes to the target Exchange. EdbMails can also migrate the mailbox to another database in Exchange 2016. Verify the folders, emails and other mailbox items after the migration is complete.
Method 4: Exchange 2016 to 2019 upgrade with PST files
You can use the PST migration method, if you are looking to upgrade Exchange 2016 to 2019. This approach is helpful if you have exported the user mailboxes as PST files or want to move arbitration and system mailboxes to the target Exchange server.
- Step 1: Set up EdbMails Exchange migration software
  Take a complete backup of all your PST files before the migration. Install the application on your computer and select the Exchange migration option in the selection page.
- Step 2: Select the option 'Migrate PST to Exchange'
  To migrate multiple PST files, close the Connect to Exchange (Source) connection window and select the PST to Live Exchange option as shown.
- Step 3: Add the PST files in bulk to migrate to Exchange
  Select and add multiple PST files that contain the user mailboxes. Verify the added files and continue to the next step.
- Step 4: Start the mailbox migration from PST to Exchange 2019
  Connect to the Exchange server from the connection window and select the required mailbox connection option. Finally, match and move mailboxes from Exchange 2016 to 2019. Verify the emails, folders, calendars and other mailbox items that have been migrated with the log report.

III. Post-migration tasks

Step 1: Update the MX records to point to Exchange 2019 server
To receive messages on the Exchange server 2019, change the DNS records known as MX records to enable email to work with the new server you have migrated to. In addition, configure the Autodiscover record to allow Outlook to connect to the migrated mailboxes.
Step 2: Create a new Outlook profile for users in the new domain
Ensure that you have the latest version of Outlook that is supported with Exchange 2019. configure the Outlook profile for each user in your domain if Outlook has problems connecting to the new Exchange server.
Step 3: Decommission and uninstall Exchange server 2016
Wait for a few days to check that you’re receiving emails correctly and that everything is working as expected and finally decommission the source server.
Here are the steps to decommission Exchange 2016 server:
1. Remove all connectors that were configured on the Exchange 2016 server.
2. Remove the Exchange 2016 server from the list of accepted domains on Exchange 2019.
3. Remove the Exchange 2016 servers from the network and uninstall any Exchange-related components.
4. Remove the Exchange 2016 server from the Exchange organization.
5. Uninstall the Exchange 2016 software from the Control Panel.
6. Remove the server from the Active Directory domain.
7. Reclaim the server's license.

Note: Test the migration thoroughly and ensure that all data and configurations have been successfully transferred to the new server. It is recommended that you contact Microsoft Support before decommissioning Exchange 2016 for your organization.

Exchange migration troubleshooting

See Exchange migration troubleshooting guide for possible solutions related to migration errors.

Advantages of EdbMails for Exchange migration

EdbMails provides compelling benefits if you are planning to migrate from Exchange 2016 to 2019.

Provision for granular brick level migration of specific items.
EdbMails maintains complete data consistency
Facility to migrate Public folder to Shared mailbox
Direct mapping of mailboxes between the source and the target
Delete duplicate emails in Exchange and Office 365
Expert and free 24x7 support assistance for the migration.

Frequently Asked Questions (FAQ)

What are the main steps to migrate Exchange 2016 to 2019?
Here are the main steps to migrate and upgrade from Exchange 2016 to 2019
1. Configure the prerequisites for Exchange 2019
2. Upgrade Exchange Server 2016 to the latest Cumulative Update
3. Install Exchange Server 2019 on a new server or virtual machine
4. Migrate your mailboxes from 2016 to 2019 with EdbMails
5. Test the migration and configure MX records
6. Finally, decommission Exchange Server 2016
What are the requirements for migrating from Exchange 2016 to 2019?
- Your current Exchange Server 2016 deployment must be at least at Service Pack 1 (SP1) level.
- You must have a 64-bit version of Windows Server operating system installed on the server where you want to install Exchange Server 2019.
- Your current Active Directory (AD) forest and domain functional levels should be at least Windows Server 2008 R2.
- You should have sufficient disk space to install Exchange Server 2019.
What are the changes in Exchange 2019 compared to Exchange 2016?
The following are some of the changes in Exchange 2019 compared to Exchange 2016
1. Exchange 2019 no longer supports Outlook 2003 or older versions.
2. Exchange 2019 supports only the latest version of Outlook on the web (formerly known as Outlook Web App).
3. Exchange 2019 supports only the latest version of the Exchange Management Shell.
4. Exchange 2019 introduces new features, such as support for modern authentication and support for Edge Transport servers on Windows Server 2019.
How to migrate Exchange 2016 Public folders to 2019?
EdbMails supports Exchange 2016 to 2019 Public folder migration. Here are the steps for the approach.
1. Ensure that both Exchange 2016 and Exchange 2019 are fully patched and up to date.
2. Create a new public folder mailbox on the Exchange 2019 server.
3. Launch EdbMails and select the Exchange migration
4. Select the source and destination servers, as well as the specific public folders you want to migrate.
5. Select if you want to include subfolders and items.
6. Migrate the source Exchange Public folders to the target Exchange.
What are the methods to migrate Exchange 2016 to Exchange 2019?
There are several methods you can use to migrate from Exchange 2016 to Exchange 2019.
1. In-place upgrade: This method involves upgrading the existing Exchange 2016 servers to Exchange 2019 servers.
2. Side-by-side migration: This method involves installing Exchange 2019 on a new server and then moving mailboxes and other data from the Exchange 2016 servers to the new Exchange 2019 servers.
3. Hybrid deployment: This method involves integrating Exchange 2016 and Exchange 2019 in a hybrid configuration, allowing you to move mailboxes between on-premises Exchange servers and Exchange Online in Office 365.
Exchange 2016 cross forest migration: In this method, you create a trust relationship and migrate your 2016 mailboxes to 2019 across AD forests.

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Exchange 2016 to Exchange 2019 migration

Steps to migrate Exchange 2016 to 2019

What you need to know about Exchange 2016 and 2019?

Exchange 2016 to Exchange 2019 coexistence

What is the best way to migrate from Exchange 2016 to 2019?

Exchange 2016 to 2019 migration checklist

I. Exchange 2016 to 2019 migration prerequisites

II. Migrate from Exchange 2016 to 2019

Method 1: Full Exchange 2016 to Exchange 2019 migration

Method 2: Exchange 2016 to 2019 migration hybrid

Method 3: Migrate to Exchange 2019 from 2016 with EDB file

Method 4: Exchange 2016 to 2019 upgrade with PST files

III. Post-migration tasks

Exchange migration troubleshooting

Advantages of EdbMails for Exchange migration

Here are the main steps to migrate and upgrade from Exchange 2016 to 2019