Ten major Office 365 migration gotchas to avoid

Migrating to Office 365 is becoming increasingly popular among businesses both large and small. The upside of moving from an on-premises environment to one hosted online by Microsoft offers compelling benefits. But switcher beware: Early Office 365 adopters have come back from their migration path battle-worn by a slew of unexpected perils they encountered along the way.

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Migrating to Office 365 is becoming increasingly popular among businesses both large and small. The upside of moving from an on-premises environment to one hosted online by Microsoft offers compelling benefits. But switcher beware: Early Office 365 adopters have come back from their migration path battle-worn by a slew of unexpected perils they encountered along the way.

Whether you are thinking of going hybrid or are pushing all in on Office 365, you will undoubtedly run into wrinkles. Often in the process of determining how you will migrate to your new environment, you miss out on a few key gotchas. We've searched high and low for the real-world obstacles IT pros have encountered in making the move to Office 365. As you might imagine, the universal dependence on email means most gotchas fall into the Exchange component of Office 365, but we uncovered significant migration issues with other facets of Office 365 as well.

Following are our top 10 hidden snags, and how to avoid them.

Office 365 gotcha No. 1: Allowing migration chatter to become migration confusion

You don't have to look far for advice when it comes to migrating to Office 365. Everybody and their sister is offering tidbits of deployment and migration assistance -- or looking for them. Opinions are great, and simple commiseration with admins having similar migration pains is sometimes even better. But all the talk and advice can get bewildering, especially when it comes to the details of deployment and migration.

If you're looking for solid, step-by-step help in deploying Office 365, check out Exchange Server Deployment Assistant. This free tool from Microsoft will allow you to choose a scenario that makes sense for your organisation's needs. Answer a few simple questions, and Exchange Server Deployment Assistant gives you all the steps necessary to make your migration work, including how to set up single sign-on, AD synchronisation, certificate configuration, and more.

Office 365 gotcha No. 2: Making unrealistic design decisions regarding on-premises vs. cloud

Unless it's a greenfield deployment of Exchange Online through Office 365, you're looking at a migration. In that case, with an existing Exchange environment, you're typically taking a hybrid approach, mixing on-premises Exchange mail use with Office 365 use.

How long to remain in hybrid mode depends on your organisational goals. You may maintain a hybrid environment for an extended (or even indefinite) period because you don't wish to move all mailboxes to the cloud, allowing greater on-premises control for certain mailboxes. Or you may have sites that experience latency issues connecting to cloud-based mailboxes, in which case you should consider maintaining on-premises Exchange servers for those locations.

Unfortunately, some decisions will not be cut-and-dry. Whatever you do, don't fall into the one-solution-fits-all trap. To hybrid or not to hybrid, and for how long, is a dilemma worth deliberating.

Office 365 gotcha No. 3: Failing to ensure prerequisites are met for hybrid deployments

You've done your due diligence on your design decision and have decided the hybrid approach is best. You're going to blend some of your existing on-premises Exchange instances with Office 365 accounts. But there's a catch. You may not be able to connect to Office 365 from your on-premises environment if you don't have the prerequisites in place.

Hybrid deployments can be configured with Exchange 2007 through 2013 environments. However, with Exchange 2007/2010 environments there must be at least one Exchange 2013 Client Access and Mailbox server in place to run the Hybrid Configuration wizard. It's recommended you run the two roles on the same server. If your organisation doesn't have Exchange 2013 (CU1 or higher) in place, you'll have to update your environment before going hybrid.

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