Using Exchange Deployment Assistant to Help Plan a Migration to Office 365

I am a planner, I really don’t like to walk into situations not prepared.

When I am doing an assessment for a company, I will always get the client to set goals; Current State and Future State. When you have clear goals from the client, there is less likely to be a surprise along the way. Take your time and plan the migration well. You and your client cannot afford downtime during the migration

Let’s walk through a typical migration to Office 365.

Current State:

  • 1500 Users Accounts that are mail enabled
  • 15 – Windows Server 2003 SP2 Servers (2 DCs, 3 File/Print Cluster, 3 Exchange Cluster, 1 FW, 1 SharePoint, etc…)
  • 4 – Exchange Server 2003 SP2 (2 WFE and 2 BE Clustered)
  • Windows XP SP3 w/ Office 2000
  • 15 Physical Servers

Future State:

  • 1500 User Accounts in Office 365 on Enterprise Plan E3
  • SharePoint Online
  • Lync Online
  • Exchange Online
  • File and Print to remain on premise
  • Replace 15 physical servers with 3 new physical servers
  • 3 new physical servers running Windows Server 2008 R2 Enterprise (Enterprise is key, because it gives you the licenses to run 4 virtual servers)
  • 10 new virtual servers
  • I will then Visio the solution. (Note: this one only shows the ADFS and DirSync setup)

One of the tools in my belt is the Exchange Server Deployment Assistant. This is an online tool from Microsoft that allows you to enter information about your current Exchange environment, your future Exchange environment and then it will spit out a beautiful plan for you to follow.

Exchange Server Deployment Assistant

Select the End Goal for Exchange, for us this is Hybrid. The reason that we choose this and not Cloud only is because we want that Hybrid server for Migration purposes. We are not going to move 1500 accounts over night. When the migration is complete, the Exchange 2010 Hybrid server will be removed.

What is your current on-premises mail system? Exchange Server 2003

The next four questions are customizable depending on your goals

Do you want all users to use their on-premises credentials when they log on to their Exchange Online mailbox?

Do you want to route inbound mail for both your on-premises and Exchange Online mailboxes through your on-premises organization?

Do you want mail sent between Exchange Online and your on-premises organizations to go through an Edge Transport server in your perimeter network?

Do you already use Forefront Online Protection for Exchange to protect your on-premises mailboxes?

Once you click next it will compile a custom plan for you, to move to Office 365. This online checklist will remember your choices as you check them off. You can also download a PDF of the plan.




What I love about this is that includes detailed actions that you can share with the client and some nice pics that can be used to show the client the setup and mail flow during the migration.

Happy Migrating… :)


Thanks for visiting and reading my posts. I am always looking for more ideas. Please comment or email me with what you would like to see.

Kelsey Epps

Office 365 MVP

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