Migration from Exchange 2010 to Office 365 step by step | Wintellisys® (2023)

It's tempting for many organizations to migrate from Exchange 2010 to Office 365. The former is getting old. With Exchange, the infrastructure is on-premises, which means you have to invest in maintenance. Your data is not that secure. Perhaps worst of all, in the event of a disaster, your data can be more difficult to recover.

Office 365 is easier to manage and saves costs in the long run. The program offers more features and is much more secure. The software is up to date and keeps your data much safer.

Here, atWintellisys, we understand how difficult the migration process can be. It's complex, time-consuming, and requires extensive planning. Also, many things can go wrong during a migration.

In this guide, we will discuss different migration methods. We'll help you determine the best course of action for your business. After reading this, you will have a better understanding of how to perform a successful Exchange 2010 to Office 365 migration.

Microsoft Exchange Server Deployment Wizard

Before you start, you should be familiar with itMicrosoft Exchange Server Deployment Wizard.It's a free tool from Microsoft. You can use it to develop the appropriate migration plan.

When you start it, you'll need to answer a few questions about your current environment. The tool then creates a step-by-step checklist. It contains solutions for the most common migration scenarios.

The Microsoft Exchange Server Deployment Wizard is intended for single domain, single forest environments. A more complex deployment may require some guesswork.

Native Migrationspfade

You may be familiar with IMAP migrations. This method can be used as a shortcut to transfer mailboxes from pre-2000 versions of Exchange. However, IMAPs do not transfer tasks, contacts or calendars. IMAP is mainly used for migrating non-Exchange email systems to Office 365.

For a migration from Exchange 2010 to Office 365, Microsoft supports three native paths. They are:

  • Cutover-Migration.This is usually the easiest option. Essentially, it involves cutting mailboxes from the source server and pasting them into the new environment.
  • Hybride Migration.This approach enables Office 365 and Exchange 2010 to coexist. It is considered the most complicated of the three native paths.
  • PST import (also known as manual approach).This method is relatively archaic. It should only be used if you don't have a lot of data to move around.

Read on to see each method in more detail.


In theory, the cutover method sounds simple. You need to get all users from the source server. Then paste them into Office 365.

In practice, however, it is much more complicated. You should have a good understanding of the process before you begin.

The migration itself requires attention, but it can actually take more time to plan and prepare. Some things to include in your to-do list are:

  • Upgrade your Exchange 2010 server to SP3.While this task is not mandatory, it is highly recommended. It can save you a lot of trouble down the road.
  • Configure and enable Outlook Anywhere.For Exchange 2010, this is not the default. To do this manually, install the RPC over HTTP component and a trusted SSL certificate on your server. Test the configuration manually before proceeding to save yourself trouble later.
  • Disable Unified Messaging and directory synchronization.
  • In Office 365, verify your domain and create a mail-enabled security group.
  • Assign Permissions. A dedicated user account should have the following minimum permissions:
  1. application impersonation
  2. View only configuration
  3. Recipients with read access
  4. User Management Administrator
  • Create a migration endpoint using the Exchange admin center.
  • Build the cutover migration batch.
  • Check if the data transfer was completed successfully.
  • Assign licenses to users.
  • Implement post-migration cleanup procedures.

Note that this is not an exhaustive list. As you go through the process, you'll likely have other steps to complete.

Hybride Migration

Stage migration is also available for older versions of Exchange. Then there is hybrid deployment. This is considered the more modern approach.

With hybrid migration, local and online exchanges can coexist. This method is perfect when you need to move a lot of data. It's the only native method available for 2,000+ boxes. In fact, hybrid deployment is recommended if you have over 150 mailboxes.

This method can be used as an intermediate step. Some companies only use it for the final environment. Users are distributed across both on-premises and online environments. This depends on what each user needs.

Deploying a hybrid environment can take weeks of planning. You need to collect data about the infrastructure and current configurations. This information is used to plan migration stages. The data will also help you implement appropriate tests.

For this operation you need to use theHybrid configuration wizard(HCW). As soon as you start the program, it will search for the correct Exchange server. It verifies the user credentials to continue the deployment.

Then you need to enable Federation Trust. This allows users to freely share information such as calendar tasks.

In the next step, the connection between online and on-premises Exchange servers is established. A window will open asking you to select the server that will receive Office 365 emails. The server should have the appropriate SMTP certificate on port 25. In addition, the port cannot be blocked by the router or firewall software.

Next, set up the server for the Send connector. You must also identify the transport certificate. This enables secure communication between Exchange 2010 and Office 365.

Finally, enter the fully qualified domain name. This completes the transfer.

But you're not done yet. You should analyze the wizard logs. The txt files will show you each task that the wizard has performed. This allows you to pinpoint exactly where problems are occurring. Understanding the txt files will help you locate and solve any problems.

In short, the wizard is easy to run, but the tasks it performs are complex. You should analyze the tasks it performs before creating a hybrid environment. That way, you can avoid problems where possible and adjust your plan if needed.


PST import, also known as the manual approach, is your third native option. You must use the Office 365 PST import service.

The general idea: Start by exporting mailboxes to PST files. Then upload them to the Office 365 organization. To achieve this, an administrator has to do manual work. You need to create an Office 365 environment from scratch.

You should use PowerShell and New-MailboxExportRequest. These tools allow you to perform bulk exports.

PST import: Migrate from Exchange 2010 to Office 365 step by step

  1. Place PST files on a shared file server or mailbox.
  2. Upload them to the Azure location.
  3. Create a CSV mapping file.
  4. Import PST files into respective user mailboxes. Use the PST import service for this step.

Microsoft also accepts physical drives. To do this, you need to place PST files on physical drives and send them via email. The service costs $2 per GB of data.

Limitations of Native Approaches

Any native approach has its limitations.

Cutover Migration Restrictions

  • This is an all or nothing approach. You cannot select certain items to import.
  • It should not be used on servers with more than 150 mailboxes.
  • It does not allow coexistence of Exchange 2010 and Office 365.

Hybrid migration limitations

  • You will likely encounter obstacles.
  • The process takes a lot of time.

PST import restrictions

  • Physical disk service costs can add up.
  • It's not fast, automatic, or reliable. It should only be used if you don't have a lot of data to move around.
  • You must create your Exchange 2010 environment from scratch.

In general, all native methods can have these limitations:

  • You must use PowerShell.This scripting language is powerful and good to know. However, mastery may take a while. If you're not already fluent, you need to learn it along the way. This can cause unnecessary stress and lead to poor results.
  • You need to update your servers.This results in the best possible migration experience. If your servers aren't updating, be prepared to do some maintenance.
  • There are no filter options.You can't choose which specific items you want to move to Office 365.
  • Your business will experience downtime.During migration, your servers are not always available. You need to schedule work hours around the time the transfer occurs. Especially when you want to migrate public folders, downtime occurs.

The easiest method

The limitations of native approaches are causing many organizations to look for alternatives.

A migration tool might be the way to go. This method provides an easier experience for the admin. The process is automatic and implements convenient features. Some of the most popular migration tools feature:

  • No upgrades required.You don't need to update your servers to the latest versions.
  • No downtime.Migration tools can run in the background. This allows users to continue operating as usual.
  • Automatic configuration.The software does most of the administrator's work. It includes a checklist of requirements and configuration tasks. For example, tools can automatically create users in Office 365. They then assign the required management roles.
  • Advanced filter options.Use this feature to migrate specific user groups. You can even choose to migrate just some of your items. This is done via folder and time filters. For example, you can choose to import only the most recent calendars and emails.
  • Planning.This feature allows you to easily configure migration jobs. Schedule them to run during selected timeframes. Once that's done, you can forget about them.
  • migration reports.You will receive regular reports. They will describe in detail how the transition works. They will also inform you when everything is completed.

The final result

The benefits of migrating from Exchange 2010 to Office 365 are worth the effort. Your office will have an interface that is much easier to navigate and manage.

Remember that you have several options. Native paths can serve as convenient methods. That's when you're familiar with the processes.

If you don't want to do it yourself, third-party migration tools are the way to go. They ensure that the transfer runs as smoothly as possible. This allows you to focus on other aspects of your business.

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We hope this article has helped you and that you have successfully migrated from Exchange 2010 to Office 365. We also create a guide forSwitching from Exchange 2007 to Office 365for those who have an older version.

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