You want your move to Microsoft 365 to be as flawless as possible. Any downtime or lost data could result in some seriously negative ramifications. You need to know your options, the benefits of those options, and then make a decision based on what will work best for your organization.

Cutover migration
One of the fastest ways to get your organization into Microsoft 365 is a cutover migration. This consists of migrating from your current email platform into Microsoft 365 with the “transaction” occurring at a single point in time, which is why it’s called a cutover. With a Cutover Migration there would be a definitive point when your entire organization moves from their current email platform into the Microsoft 365 platform.

The proverbial “flipping of the switch”, the cutover task itself can take under an hour to perform if a fair amount of staging and prep work happens on the front end. By staging and prepping, I’m referring to tasks such as moving your data into Microsoft 365 (email, calendars, contacts, etc.) or setting up other components as needed, such as AAD Connect and an Encrypted SMTP Relay. The overall process could take anywhere from 4-8 weeks to complete depending on the size of your organization, but in the end, everyone would move over together.

Hybrid migration
If you are not a fan of making the switch for the entire organization all at once, then a Microsoft 365 hybrid migration might be a better fit. In a hybrid migration, you can move a chosen number of users or departments at a time into Microsoft 365, allowing your company to move over at a gradual pace. There are additional requirements though that need to be considered when choosing this option.

To begin with, you will need to set up a server that will function as the Hybrid Server to host the connection between your on-premise Exchange Server and Microsoft 365. You’ll also need to utilize directory synchronization (such as AAD Connect) since hybrid configurations rely on them.

How to choose between a hybrid vs cutover Microsoft 365 migration
Here are some questions to help guide you on your way to making an informed decision:

How many mailboxes, distribution groups, public folders, etc. will you be moving into Microsoft 365?
We normally see larger organizations (250 users and above) more prone to choosing the hybrid migration path to better support their user base during the migration to Microsoft 365, especially if they have multiple locations. Smaller organizations can be more agile in their preparation for the move and an Microsoft 365 cutover migration is often a simpler approach, although mailbox size could be a consideration for them as well.

What is your current email platform?
We see clients moving from all types of email platforms into Microsoft 365. In a hybrid migration, an Exchange platform is required, so if you are running anything other than Exchange or anything older than Exchange 2010, hybrid is not an option.

Are you currently utilizing Microsoft Teams, Skype for Business or SharePoint On-Premise?
If the answer is yes, either a cutover or hybrid Microsoft 365 migration would work, however, there are a fair number of caveats – or “gotchas” as we like to call them – that need to be addressed. Such as whether you are currently utilizing the full functionality of Skype for Business with features like PSTN. That would be a deeper discussion than we are able to address here.

Do you have additional complexity with your environment?
This could include things like multiple Active Directory environments from past mergers/acquisitions or the need to move to a new domain and having that occur simultaneously. In cases like these, we see most clients choose the hybrid option to allow for additional testing and a slower phased approach for deployment.


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