Make your Office 365 migration as seamless as possible

Theresa Miller covers the benefits of hybrid Exchange, group considerations, communications, and other advice for a smooth transition.

A seamless migration is critical to the success of your Office 365 deployment. Clearly, moving to the cloud shouldn’t interrupt day-to-day business services, and your technical choices should proactively support this goal.

Communicating the business experience and value

Communication is the crux of many deployments. No, I’m not talking about email messages (yet)—unfortunately, it is not unusual for there to be a disconnect between the IT department and what the business needs. Even great products cannot provide a good user experience without your team taking the time to understand what the business expectations are. The IT department can design the best and most impressive solution in the world, but if it doesn’t work smoothly for the user’s workflow, then they will pave their own path. I have witnessed this time and time again—the user always finds a way around the system if they weren’t part of the decision making.

Leadership integration with the business will bring the most success for your Office 365 deployment. Of course, we have all found that doing this is sometimes easier said than done. Good luck!

Technical implications and benefits of hybrid deployments

There are many technical considerations for a seamless Office 365 deployment, and most importantly, they all start with a hybrid deployment. Why would you deploy hybrid? Primarily for your Exchange migration, as it allows for the easy movement of mailboxes back and forth between your existing datacenter and the cloud. Crucially, hybrid also provides a failback option should some unforeseen need send you back on-premises—having a back out is priceless.

The seamlessness of a hybrid Exchange environment is enhanced by some other technical benefits. Let’s run through some that are noteworthy:

  • Mail routing between sites is seamless, regardless of where the mailbox is located.
  • Shared Free/Busy calendar availability will function regardless of the location of the mailbox.
  • One Global Address List for all users, again, whether they are in the cloud or on-premises.
  • Single Outlook Web App URL. If your enterprise uses OWA, it is less confusing to the user if the same URL can be used no matter the mailbox location.
  • You can move mailboxes between on-premises and the cloud as needed, which is beneficial for providing failover, failback, and troubleshooting potential issues.

In my opinion, hybrid really is the best option for migration from on-premises Exchange to Office 365, since it offers your organization the most versatility.

More technical considerations

There are a few other technical considerations to keep in mind regarding public folders and groups:

Be aware that if your organization currently has Exchange public folders, they can only reside in one place. You must decide if they will be in Exchange Online or remain on-premises. They are also challenging to move, so for the most seamless approach, most organizations look at third-party options.

There are many different group types available to ensure that your organizational permissions and email lists are in check, but note that not all groups will move easily to Office 365. You may need to do some work either before they are migrated or after to make sure things are working seamlessly. Let’s take a look at the different types of groups:

  • Security/Email Distribution Groups: These group types are sets of users with similar needs. The great news is that they will migrate to Office 365.
  • Mail-enabled Security Groups: These can be migrated to Office 365 in hybrid scenarios. New groups will not be mail-enabled, so you will need to do this manually after migrationtake some time to identify them and for their move.
  • Dynamic Distribution Groups: These groups are built from a query on a common field in Active Directory (for example: location). These cannot be migrated, and must manually be recreated in Office 365. Do some research to handle these groups.
  • Office 365 Groups: These groups provide functionality to the entire suite, including Outlook, OneDrive, SharePoint, OneNote, Skype, Yammer, Dynamics, Delve, calendaring groups, and more.

With the proper of Office 365 group migrations, they too can be done in a way that is seamless to the organizational user.

Protecting your data for any situation

Be sure to plan for a data backup strategy. I recently covered this topic here at, so be sure to check out that post for more detail. Also, be sure to use retention hold to guarantee that you are keeping data for any potential litigations—that’s another topic I covered recently.

By planning your strategy in advance of your migration, you will ensure a seamless approach and the best user experience possible.

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