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Windows Server 2003 Migration Plan

windows server 2003 migration

As you probably already know, support for Windows Server 2003 is ending. Many businesses are already up-to-date, but if you're still on Windows Server 2003 or Small Business Server 2003, you're going to want to start looking into options to make this transition as seamless as possible. 

Discover what you're currently using

You need to figure out and catalog all the software and workloads running on Windows Server 2003. The Microsoft Assessment and Planning (MAP) Toolkit

Assess your inventory

Once you have a catalog, you need to assess what's in it. Catagorize according to type, criticality, complexity, and risk, and start prioritizing to help identify possible issues. This should help you determine an optimal order of how migration should occur.

Determine what you want to migrate to

Figure out what option is best for your business. Most businesses decide that Windows Server 2012 R2 is the best route for them, however, Windows Azure could also be a great option for some businesses. Our Microsoft Licensing Certified Professionals can help you figure out which is the best route for your business based on factors like speed, ease of migration, cost, and desired functionality. Here's a breakdown of your options:

  • Windows Server 2012 R2 with on-premises hardware and hypervisor

  • Windows Server 2012 R2 with Microsoft Azure infrastructure as a service (IaaS)

  • Windows Server 2012 R2 with Cloud OS Network IaaS

  • Microsoft Azure platform as a service (PaaS)

  • Software as a Service (SaaS) and Office 365

  • Windows Server 2008 (32-bit)

Need to migrate your business to a new server? Give our Microsoft Certified Licensing Experts a call today!

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Migrate from Windows Server 2003

At this step, you should now know exactly how many licenses you need and what type. Now you need to purchase these and start migrating. If you don't have an IT department, you may want to look into having a system integrator help you out (Wazitech is one we recommend).


Make sure to clearly identify the applications and workloads that are relevant to Windows Server 2003/R2.

There are five key server roles to consider for migration from Windows Server 2003/R2:

  • File Server
  • Web Server
  • Active Directory
  • Domain Controller
  • Terminal Services

Server roles are the some of the easiest (File Server) and potentially some of the hardest (Active Directory) migration scenarios. Only a thorough analysis of what exists today and what the desired end state is will show exactly what effort is needed to migrate these roles from Windows Server 2003/R2.

Don't forget about Microsoft Applications (SQL Server, Exchange Server, SharePoint, SharePoint Services) as well as third-party applications and other services.

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