Tips for Office 365 Cutover Migration?

Office 365 integration and Office 365 migration are distinct processes. A cutover migration in Office 365 deployment is the migration of all user mailbox contents from the source mail system to Office 365 – all at once. Using this method, you can move mailboxes, mail contacts, mail users, and mail-enabled groups. 

On the other hand, integration happens with the user’s existing directory services and with the on-premises installation of SharePoint Server, Skype for Business Server 2015, or Exchange Server. The integration process allows you to manage and synchronize user accounts for both the environments. 

Before starting integration with the on-premises environment, you must acquaint yourself with network planning and performance tuning. When Office 365 integration happens with on-premises server products, a hybrid environment is created which is supported by Microsoft Azure as well.

You are now at the point where you have information about your messaging system, you have a detailed report on your current Microsoft licenses, and you know how much data you need to migrate. Congratulations – you are now at the point where you can see the different Office 365 business and business plans and decide which is best for your organization. Note that Microsoft now allows mixing and matching Office 365 subscriptions, which is good news for all small and large businesses. This means you can maximize your existing investment in recent versions of Microsoft Office and meet the different demands of your staff depending on their roles.

A cutover office 365 migration is a complex process involving in several factors and must be carried out after careful planning. Here are a few handy tips to practice cutover migration for the migration of mailboxes.

Know the Possibilities and Limits

While cutover migration supports the transfer of up to 2000 mailboxes, it takes a few days to transfer all the mailboxes. Each user having an on-premises Exchange mailbox will be a new user in Office 365 once the migration is completed.

Configure Outlook Anywhere 

Before you begin the migration process, you must configure Outlook Anywhere on the on-premises Exchange Server. It should be noted that for Exchange 2013, Outlook Anywhere is automatically configured.


For a cutover migration, you have to use a reputed certification authority (CA)-issued certificate with the Outlook Anywhere configuration. The Outlook Anywhere and Autodiscover services have to be added to the certificate.

Optional Verification

To verify that using Outlook Anywhere, you can connect to your Exchange organization, connect Outlook to your on-premises Exchange mailbox from outside the corporate network. It can also be done using the Exchange Remote Connectivity Analyzer Tool of Microsoft. Another way is to let the connection get tested automatically when Office 365 is connected to the email system at a later stage in the cutover migration procedure.


The on-premises mailboxes you are trying to migrate must be accessible by your on-premises user account that’s used to connect to the on-premises Exchange organization. Hence, the on-premises user account should have the necessary permissions.

The admin must have ‘Full Access’ permission for all on-premises mailbox or the ‘Receive As’ permission on the mailbox database storing user mailboxes.

Turn Off Unified Messaging (UM)

In case the UM is on for the mailboxes that are being migrated, it must be disabled. After the migration is complete, turn on the Cloud Voicemail.

Security Groups

For having security groups in Office 365, before the commencement of the cutover migration, an empty mail-enabled security group must be provisioned in Office 365.

There are several advantages of Office 365 migration such as the simplicity and speed of the process, migration of all old emails at once, etc. Remembering the above-listed tips would be helpful while carrying out a cutover migration as well as Office 365 integration.

If you are like most people, the main reason for migrating to Office 365 is that you want to move your email to the cloud. Therefore, it is important to start gathering the technical details of your current mail server and conducting an audit report identifying all active users and groups and the size of their mailboxes.

Office 365 has a number of technical requirements that you must consider before migrating. The main thing that surprises people is that Windows XP and Office 2003 are not supported. In addition to ensuring that your operating system and browser work with Office 365, it is also important to specify the versions and licenses of Microsoft Office software that you already have. Like most organizations, you probably use a combination of versions of Microsoft Office, which is great – but it’s important to understand what you currently have so that you can make the right decision about the right combination of Office 365 plans. the best for your organization.

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