5 Biggest Office 365 Migration Challenges and How to Overcome Them

Migrating from an on-premises environment to one hosted in Microsoft’s public cloud offers compelling benefits for organizations. Moving to Office 365 lets you to continue enjoying popular programs such as Word, Outlook, OneNote, Excel, Publisher and PowerPoint, but it also gives you document synchronization on different platforms, easy collaboration within your organization and the ability to access the service anytime, anywhere. As with any transition of this magnitude, an Office 365 migration can present several roadblocks that hinder an otherwise smooth transition process. Here are five of the biggest Office 365 migration challenges and how to overcome them:

How to Overcome 5 Major Office 365 Migration Challenges

Building hybrid solutions

The migration process is usually straightforward for organizations that want to move all employees from on-premises applications to Office 365. The process is more challenging for organizations that want to retain some aspects of their on-premises environments while moving the rest to Office 365. This second method is commonly the case for organizations that need Office 365 for their mobile workforce but also want to keep on-premises solutions for employees working behind a desk. A hybrid solution makes sense for a large organization that needs to maintain data stores for thousands of users.


Implement a single sign-on with Active Directory Federation Services to get the best of both Office 365 and the familiar on-premises solutions.

Difficulty transitioning some areas

Some company aspects are easy to migrate while others are more complex. Exchange data, when migrated correctly, leads to an almost unnoticeable change for the end-user. For more complex systems such as SharePoint Online, migrating to Office 365 might introduce changes that prove quite challenging to users. A key example is a linked Excel spreadsheet, which can pose some issues when migrated to Office 365. Links directed to legacy environments that are not SharePoint will not be updated automatically. Another example is that permission models on SharePoint Online differ from legacy ECM systems, since the latter do not use concepts such as inheritance.


Set realistic expectations, and keep in mind that like-for-like migrations for legacy ECM systems, previous versions of SharePoint and file shares do not exist. Providing reports with details such as file source location, file name or SharePoint Online location can help minimize user confusion.

Overcoming low bandwidth

Smaller organizations with limited bandwidth and lots of data to migrate can sometimes become frustrated by the lengthy migration time from on-premises to Office 365.


Use the migration tools to help overcome this problem; the tools will bypass mailbox data multiple times before making the actual cut-over. This way your data is imported to Office 365 multiple times before finally moving mail. Once the final switch is made, your mail will be waiting for you in Office 365.

Unifying email

Transitioning to Office 365 requires all users to give up their previous email platforms and adopt the Exchange platform. Additionally, Office 365 limits email attachments to 25MB. Users of rival platforms such as Gmail or Lotus Notes can reset these changes.


Manage user expectations and the cultural shift to avoid resistance and employee backlash. Introduce file-sharing programs to replace large file attachments.

Calming security fears

Some employees might harbor fears about moving their on-premises data to the cloud. However, these fears are mostly unfounded because Microsoft has plenty of safeguards in place to ensure your data is safe during the migration process and after the transition.


Assure your employees that Microsoft takes security seriously. Office 365 Trust Center can answer all security questions that your employees might have regarding the safety of their data. Moving to Office 365 is a multi-phased project that often requires technical consulting and support. At Agile IT, our Office 365 migration services have helped hundreds of companies seamlessly migrate millions of mailboxes to Office 365 with minimal business disruption. We’ve encountered nearly every issue imaginable and troubleshooted to find the most cost-effective long-term solution. If your organization is interested in migrating to Office 365 but wary about the challenges that lay ahead, please contact us today, and we’d be happy to answer your questions.

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