7 Microsoft 365 Migration Challenges and Ways to Address Them

Ready to migrate your organization from an on-premise environment to Microsoft 365? Prepare to face some challenges—especially if you’re new to the cloud migration game.

While some discovery tools are available for Microsoft 365 beginners, they aren’t always easy to learn and use. And even if you find them simple, operating them requires significant effort – effort which you can direct elsewhere.

The good news is certain steps can help you overcome the hurdles associated with the transition so you can start reaping benefits like seamless coordination and enhanced productivity.

Here’s a look at some of the biggest Microsoft 365 migration challenges and how to overcome them:

1. Structuring Hybrid Solutions

Hybrid setups are crucial for organizations with large databases or the need to coexist with on-premise applications and previous functionalities. Unfortunately, Microsoft 365 basic and enterprise plans do not facilitate such hybrid deployments.

The solution is to use the Active Directory Federation Service with single sign-on, which enables full access to the on-premise and Microsoft 365 features while eradicating complexities during the migration.

2. Throttling Issues

While migrating from on-premise servers to Microsoft 365, inefficiencies and throttling issues of tools can hamper the quality of data transferred. The outcome of this is poor performance management for the users.

To resolve the issue, enterprises should tap into 365’s turbo mode features that support high-speed migration. This requires an Azure account, but that’s about it. Once you’ve set one up, you can sit back, relax, and enjoy hassle-free turbo migration.

3. Inadequate Bandwidth

Small businesses with limited bandwidth and tons of data to migrate can become frustrated with the lengthy migration time from on-premises to Microsoft.

You might experience downtime while your systems are being moved or upgraded, preventing you from functioning properly during the transition.

Plus, if you need to transfer many terabytes of data, you must ensure you have sufficient bandwidth available to finish the migration of current and historical data.

To overcome the challenge, use migration tools that bypass mailbox data multiple times before switching. This means your data is transferred to Microsoft 365 various times before finally importing mail. In other words, your mail will be waiting for you in Microsoft’s cloud once the final switch is made.

4. Legacy Archive Export

Exporting legacy archives can pose a challenge while performing Microsoft 365 migration. Archiving a message means the file will be removed from your mailbox, reduced in size, and replaced with a shortcut pointing to it. Journal reports—the legally-defensible copies of the message—are also a part of the archive.

While you can use third-party solutions to migrate the files to the cloud, there might still be some issues. For example, stubs might break as you export the archives to the cloud, which makes data accessible for users.

To ensure you meet compliance requirements, consult with your legal team before exporting any of the archives.

5. DNS Misconfiguration

Although DNS problems won’t prevent organizations from completing a migration, they can stop Microsoft 365 features from working. Leaving crucial details unchecked, such as whether the DNS provider supports SRV records, could result in users being unable to send instant messages, emails, and more.

Make sure to verify that your preferred DNS provider is compatible with Microsoft 365 before switching. Otherwise, your employees might lose their ability to email, costing you response time and potentially customers.

6. Problems in Transitioning

Some system aspects are simple to migrate, while others are more complicated. For instance, linked Excel spreadsheets in SharePoint can create issues when migrated to Microsoft 365. Essentially, links directed to non-SharePoint legacy environments will not be updated automatically. Adapting to such changes can prove quite challenging for users.

The solution to this is to set realistic expectations upfront. Offering reports with details such as SharePoint Online location or file name and source location can help reduce user confusion.

7. Security Fears

Transferring data from an on-premise server or database to Microsoft 365 is usually the riskiest part of the entire migration. Although Microsoft has plenty of safeguards in place to protect your data, there’s still a risk of hackers infiltrating your networks, stealing user information, and selling that information on the web. You need to be proactive about security if you want to avoid data breaches during the migration process.

As a premier Gold Microsoft 365 Partner, Great Service can help you address security challenges. Through multiple partners, we proactively monitor the dark web and will notify you if any of your employee credentials are for sale. We offer this service at no additional charge to every company that buys their Microsoft 365 licensing (comes with no minimum term commitment) from us.


Planning, user adoption, and training are key to successful Microsoft 365 migrations. It is important to ensure that users understand how to maximize the benefit of the new features and how to use them effectively. The transition must be smooth and effective by addressing the challenges so that users are comfortable with the new system, making them more likely to stick with it.

7 Tips to Migrate to Microsoft 365 Infographic


7 Microsoft 365 Migration Challenges and Ways to Address Them

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