Top 3 Office 365 Transition Pains

June 23rd, 2015 by Rocket IT

We get a lot of questions about Office 365. Clients ask us about it. Friends, families and neighbors ask us about it. Sometimes our doctors ask us about it. If someone who knows us hasn’t asked yet, we know it’s only a matter of time… Or that they live under a rock. And we’re happy to talk about it!

We know making a cutover can be daunting, and knowledge is the best way to prepare.

If you’re considering the move to Office 365, be sure to read this first.

Office 365 migrations have become a regular part of our routine, so we’ve become pretty familiar with the transition pains. We want you to be able to avoid these common speed bumps, so I asked our engineers to put together the top 3 issues they see during these projects, and then I asked them how to solve them.

    1. Often there is confusion about distribution groups, email forwarding rules, and public calendars/meeting rooms. To clear up the confusion (or avoid it altogether), make sure you’re using a process that accounts for these items, and that you (or whoever is leading your Office 365 migration) have the expertise to understand the best tools within Office 365 to manage these abstract items.
    2. Not all of a user’s email made it to Office 365. It’s important to leave your old service on and accessible for a bare minimum of 2 weeks. This acts as a backup for you. We actually recommend leaving it on for a month to be safe.
    3. There are configuration issues with the old email service and/or the DNS (domain name service). Often, the day of a cutover is stressful because there are issues where it takes time for the domain changes to migrate across the internet. Sometimes the old mail service is the one causing trouble. To solve this, make sure the person handling the Office 365 project has a strong understanding of how DNS and the old mail server works long before it’s time to cutover.

As you can see, doing your research and making sure you’re thoroughly prepared with a backup can save you from a lot of unnecessary speed bumps. Taking some of these precautions (like keeping your old service on for a little longer) can help with bigger and less common issues you may experience as well. It’s always best to be prepared. If you’re reading this article, you’ve already taken the first step on the right path towards a smooth transistion. For more information about moving to Office 365, contact us at


EHAbout the Author-

 Eric Henderson is Rocket IT’s Service Manager. He is also the tallest person at Rocket IT (by a fraction of an inch) and has the best beard at Rocket IT (when Matt Hyatt is clean shaven).