The 4 biggest Office 365 migration challenges and how to overcome them

 In Cloud, Office 365

Office 365 (O365) makes it easier for small, medium, and large organizations to create, communicate, and share in the cloud. Leveraging the Microsoft cloud can greatly reduce corporate expenditures on infrastructure and upkeep, and save money on hiring costly data managers to maintain systems.

While some companies have already made the switch to O365, many remain uncertain about the transition, with most fearing the migration process itself. As with any major transition, an O365 migration can present some roadblocks, but many are easily addressed for a smooth transition to the cloud.

Here are four of the biggest challenges SHI sees companies face when migrating to O365 and how to solve them.


  1. Building hybrid solutions. The migration process is relatively simple for organizations seeking to move all of their users from an on-premises environment to O365. The challenge is when companies want to retain key pieces of their on-premises environments while moving specific users to O365. This scenario is most common for companies that want to empower their mobile workforce while keeping on-premises solutions in place for those behind a desk. A hybrid solution makes sense especially for large organizations that need to maintain large public data stores for their several thousand users. Implementing single sign-on with Active Directory Federation Services can help maintain the coexistence between cloud and on-premises for the best of both worlds and a familiar experience.
  2. Overcoming low bandwidth. One of the greatest threats to user experience and quick O365 migration is a slow Internet connection. Small organizations with lower bandwidth and a lot of data to move take longer to migrate from Exchange on-premises to O365. Without a high-speed connection, migration tools can help overcome this barrier by taking multiple passes over mailbox data before completing the actual cutover. The data is imported to O365 multiple times before moving mail to O365. This process is seamless for end users – once the switch is made, their mail is ready and waiting in O365.
  3. Unifying email. To transition to O365, all users must shed their previous email platforms and adopt the Exchange look and feel. Users of other platforms, like Gmail and Lotus Notes, might resist the migration for this reason. In some cases, it might be difficult to transfer all the users’ notes and contacts with their email. In addition, O365 restricts sending attachments greater than 25 megabytes, which can throw liberal email sharers for a loop. The key is to manage user expectations through the transition to avoid backlash and resistance from users familiar with an old way of thinking. By managing this culture shift and introducing new ways of achieving the same result that users expected of the old system — for example, introducing file sharing programs to replace oversized email attachments — organizations can successfully make the transition.
  4. Calming security fears. Many organizations fear transitioning to O365 for security reasons. Although the migration forces users to move data from corporate-owned mail stores to Microsoft servers, migration to O365 is a controlled process with safeguards in place to ensure data is secure both during and after the transition. Microsoft takes security seriously and the O365 Trust Center answers all security questions an organization might have about the transition.

While companies can migrate to O365 on their own, the most effective way to transition their environments, and to address these roadblocks, is by relying on a Microsoft partner. SHI can anticipate and limit the disruption of hybrid deployments, low bandwidth, email conversions, and security concerns by meeting with customers, learning their environments, understanding their needs, and crafting a migration plan to ensure a smooth transition from on-premises to O365. If your company is interested in moving to O365, but are still wary about the migration process, please contact our Professional Services Organization at

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