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How to Migrate Exchange 2019 to Office 365 Using 5 Different Techniques 

Published By Deepa Pandey
Anuraag Singh
Approved By Anuraag Singh
Published On February 20th, 2024
Reading Time 8 Minutes Reading
Category Exchange Server

Summary: In this detailed article, we are going to cover the most asked query, i.e., how to migrate Exchange 2019 to Office 365 without any data loss. We are going to talk about the 5 different ways, that can be used to carry out this entire process. Some have a few shortcomings and some have their advantages. Let’s get into it!

Undoubtedly, the launch of Exchange 2019 has brought a new set of technology, features, and services. But, still, it works on a fixed life cycle policy. Microsoft will end mainstream support for Exchange 2019 by the year 2024.

Organizations are now realizing the practicality of hosted Exchange servers and deciding to switch partially or fully to a reliable platform like Office 365. The adoption rate of Office 365 users has only increased with time. If you go by the numbers, then, according to Microsoft’s annual report for 2021, Microsoft 365 or Office 365 consumer subscribers increased to 51.9 million.

Let’s discuss why users prefer Office 365 over the On-premise Exchange server & This how-to guide explains various ways to migrate Exchange 2019 to Office 365. 

Service Benefits of Microsoft 365 That Entice Users to Migrate Exchange 2019 to Office 365

Several service benefits of Microsoft 365 can entice users to migrate from Exchange 2019 to Office 365, some of them are as follows:

  • Microsoft 365 is a cloud-based business productivity suite, which means that all of your emails and other data are stored in the cloud, instead of your local servers. Which eventually delivers several benefits, including reduced costs for hardware and maintenance, as well as increased scalability and flexibility.
  • As it is a cloud-based suite, you can access your email, contacts, calendar, and other data from anywhere with an internet connection. This means that you can work from home, on the road, or anywhere else, and still have access to your important data.
  • Microsoft 365 includes a variety of collaboration tools, including Teams, SharePoint, and OneDrive for Business, that allow you to work with others on documents, projects, and other tasks which increases collaboration. This eventually helps you to increase productivity and efficiency, especially for remote or distributed teams.
  • It includes advanced security features, such as multi-factor authentication, data encryption, and advanced threat protection. Furthermore, it helps to keep your data safe and secure.
  • Microsoft 365 is constantly updated with new features and capabilities, ensuring that you always have access to the latest technology and functionality.
  • Moving to Microsoft 365 can save you money on hardware, maintenance, and IT staff costs, as well as provide a predictable subscription-based pricing model.  Microsoft 365 comes with a flexible subscription plan for its users, so you can choose a plan as per your requirements.
  • Microsoft 365 provides a comprehensive set of tools and services that help to streamline business operations, increase productivity, and reduce costs. These benefits are attractive to many users and can make the migration from Exchange 2019 to Office 365 a smart choice for businesses of all sizes.

Now, to execute a successful migration from Exchange 2019 On-Premise to Office 365, you have to choose a convenient method.

How to Decide Which Method to Migrate Exchange 2019 to Office 365?

Before starting the migration process, it’s advised to review the various methods, benefits, & limitations, and ensure whether it fulfills your expectation or not.

As an administrator, you can migrate mailbox items such as emails, contacts, calendars, etc, from the Exchange server. So, walk through the following Sections and see which method meets all your needs and select according to that.

Method 1. Migrate On-premise Mailbox Data to Office 365 Using Cutover Migration

Cutover migration;

  • If your current On-Premise Exchange organization is Microsoft Exchange Server 2013 or later.
  • If your On-Premise Exchange organization has less than 2000 mailboxes.

[Note: Though Cutover migration supports migration of 2000 mailboxes, it’s recommended to migrate 150 users or less.]

Migration Steps:

  1. Prepare for a Cutover Migration – Before starting the process, you need to make a few changes to your Exchange Server environment.
  • Configure Outlook Anywhere on your On-premise Exchange server.
  • Must use a certificate issued by a trusted certification authority (CA) with your Outlook Anywhere configuration.
  • The migration administrator must have the necessary permissions to access the On-premise mailboxes for the migration. (Migration administrators must be assigned the FullAccess permission for each on-premises mailbox or Receive As permission on the mailbox database)
  • Ensure that the mailboxes that you want to migrate are not hidden from the address lists.
  • Disable Unified Messaging(UM).
  • Create security groups and remove delegates.
  1. Ensure You Own the Domain – To create an email address for a new Office 365 mailbox, the SMTP address of each on-premises mailbox is used during the migration. So, the on-premises domain must be a verified domain to carry out Cutover migration.
  2. Connect Office 365 to Your Email Systems – Create an Outlook Anywhere migration endpoint. It contains the settings and credentials required to connect the on-premise server with Microsoft 365.
  3. Create the Cutover Migration Batch – When on-premises mailboxes are migrated to Office 365 using Cutover migration, it’s done in a single batch. So, you need to create the batch.
  4. Begin Cutover Migration Batch – Using EAC start the migration manually to migrate Exchange 2019 to Office 365.

Must Read: Microsoft Office 365 eDiscovery Export Tool – Know How it Works

Method 2. Migrate Exchange 2019 to Office 365 Using Staged Migration

If you have more than 2000 mailboxes and want to plan your migration in small batches, then you can use Staged migration. To talk about the pre-requires, your source email system must be a Microsoft Exchange Server 2003 or 2007.

Since this how-to guide is dedicated to migrating Exchange 2019 to Office 365, we’ll not elaborate on these migration steps.

Method 3. Migrate Exchange 2019 Emails to Office 365 Through IMAP Migration

Before attempting this method, you must ensure that the source email system supports IMAP. Also, disable all MRM and archival policies.

Know More About IMAP Migration

  1. This migration method is limited to moving only the user’s mailbox or other mail folders. That means it’s incapable of migrating contacts, calendars, or tasks.
  2. It allows you to migrate a maximum of 500,000 items from a user’s mailbox.
  3. The biggest email you can migrate using IMAP migration is 35 MB.
  4. You need access to the user mailbox in your source email system to migrate emails.

After considering the facts about IMAP migration, you can tell that this manual approach is unfit for migrating entire mailbox items to Office 365.

Also Read: Save Emails from Outlook 365 to Hard Drive Using Multiple Methods

Method 4. Use Hybrid Migration to Migrate Exchange 2019 Mailboxes to Office 365

You can use the Hybrid Configuration Wizard to set up a hybrid migration. But, before configuring a hybrid deployment, you should know that it does not support all the Microsoft 365 plans that support Azure Active Directory synchronization.

Method 5. Utilize a Professional Tool to Migrate Exchange 2019 to Office 365

Another preferred method to move Exchange 2019 data to Office 365 is using tried and tested software like SysTools Exchange to Office 365 Migration Tool. It will automate the migration process entirely and even a naïve user can work with the tool easily. 

Software Working Steps for Exchange Server 2019 to Office 365 Migration:

Step 1. Download the software from the below URL. Follow the instructions and launch it on your computer.

Download Now Purchase Now

Step 2.  Choose the Source as Exchange and Destination as Office 365. Also, enable workload by clicking on the categories (such as Emails, Contacts, and Calendars) checkbox.

Step 3.  On the Source tab, choose the Exchange server version as Exchange 2019 and fill in other necessary fields. Validate required permissions and click on Next.

Step 4. On the Destination tab, provide the Office 365 admin email and application ID and validate the permission. Click on the Next button.

Step 5. Create a mapping between the source and destination user accounts. Click on the Fetch users option to fetch source users, and map them to the destination. Validate required permissions and finally, click on the Start Migration button to migrate Exchange 2019 to Office 365 step by step.

To Conclude

Microsoft On-Premise Exchange servers have a fixed lifecycle policy and no one can ignore this fact. Hence, the wise choice would be to migrate Exchange server data to a well-known cloud platform Office 365. And, if you are currently using Exchange 2019 server then refer to this how-to guide and carry out the migration using a convenient method.

Hence, in this complete guide, our sole motive is to provide you with the most trusted, and secure way to migrate mailboxes from Exchange 2019 to Office 365. Moreover, it is always a great idea to use a professional solution to carry out the crucial data migration as discussed above.


Q1. How to perform Exchange 2019 to Office 365 migration in 5 steps?

As it is evident from the above blog the migration process requires pre-planning and a streamlined execution. Moreover, if you are approaching with a manual method then it is not possible to complete the migration in just 5 steps. However, if you switch to the automated tool described above then you can execute the process in just 5 steps as mentioned below.

  • Step 1.  Download and install the software on your PC.
  • Step 2. Choose Exchange and Office 365 as platforms.
  • Step 3. Enable desired workload and set date filter.
  • Step 4. Login with Exchange and Office 365 details.
  • Step 5. Set user accounts and click on the start button.

Q2. Can I migrate public folder data using this software?

No, using the above tool you can not migrate public folders, but SysTools offers dedicated Public Folder Migration Software that can perform this task without any hassle.

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