How to Plan a Successful Microsoft 365 Deployment?

Microsoft 365

Migration to Microsoft 365 can be smooth only when it’s planned accordingly. With proper planning, you can prevent a lot of issues and mishaps. In this article, we will be going through the process of migration from on-premises Exchange Server to Office 365 (Microsoft 365). We will be discussing the planning work, the deployment preparation, and the actual migration process.

Planning Stage

Before diving into setting up the Microsoft 365 tenant and all the mailboxes, you must ensure that the decision to move to Microsoft 365 is good for the company. There are no limitations that might affect the business. Although Microsoft 365 has a lot of features, it has some limitations when it comes to mailbox size and archive size.

You should plan the subscriptions that will be assigned to the users, depending on their needs. With Microsoft 365, you can have a mix and match of subscriptions. However, they have their features and limitations. Once the list of assignments is complete, you can assigned the budget needed for this project and have an approval by the stakeholders. Then, prepare the roadmap of the setup.


Licensing is an important part of the migration. You need to have the right licenses assigned for the right job. Here are the normal licenses which companies tend to go for:
  • Office 365 Business Basic
  • Office 365 Business Standard
  • Office 365 Enterprise E3
The Basic license gives you a mailbox and 1 TB OneDrive. If you need the Microsoft Office package with software assurance, you would go for the Standard license. If you want unlimited archive mailbox and the users want to use their Microsoft Office package on a Remote Desktop Server (RDS), then you need to go for the E3 license. So, you must plan well and choose the right license for the right purpose.


You need to get the list of exported mailboxes in your Exchange Server, along with the size of the mailboxes and their priority. The list needs to be spring cleaned to see which mailboxes are needed and which are not. Remember that on Microsoft 365, user mailboxes need a paid subscription. So, allocating the right budget is essential.

You would also need to consider the authentication. Since it’s a cloud offering, you need to enable the multi-factor authentication and may also consider setting up of Azure Active Directory Sync so that the users will only have one username and password for local service and cloud.

Deployment Preparations

Now, you need to ensure that all the client devices are compliant with both the operating system and Microsoft Office installation. Having a streamlined setup will help with the inventory, support, and company software audit.

The users must be informed on what’s going to happen and how they will be benefitted from this change. The users must be trained on how this new system will allow them to increase their productivity and collaboration, while having full mobility and security on their accounts. This is very important as the users should be confident to use Outlook, OneDrive, SharePoint, Teams, and other tools. You must also ensure that the users’ devices and data policies are updated accordingly and that the users are aware of this.

Data Migration

Migration of data can be an issue, especially if you have limited resources and the setup is not ready to have this kind of process. So, it’s suggested to rely on an application for smooth and quick data migration. Stellar Converter for EDB is one such application that can help in the migration of data from on-premises Exchange Server to Office 365.

With Stellar Converter for EDB, you can open offline or live database and see the entire structure of the database. You can selectively move the mailboxes from multiple databases directly to Office 365. You can export user mailboxes, shared mailboxes, disabled mailboxes, user archives, and public folders. It automatically matches the mailboxes from source to destination and allows to export priority mailboxes first.

Post Migration

Post migration, you need to perform a clean-up process to remove Exchange Server from the Active Directory Schema. There is a whole process to smoothly uninstall the Exchange Server, along with any DNS entries. The firewalls need to be cleaned up as well when it comes to rules and access list which were related to the server, along with any subnets which were specific to the Exchange Server. Otherwise, this may cause security issues with open ports and configuration issues on the user computers.


When deciding migration path for Office 365 migration you need right planning and coordination, you can successfully perform the migration from on-premises Exchange Server to Microsoft 365. Planning and preparation must be done beforehand as there are a lot of things that can go wrong during and after the migration. Always consult the Exchange Administrators and the business stakeholders during the planning stage for their inputs.

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