Many companies not making the migration off of Windows Server 2003 before support ends in July cite cost as the reason; either they can't afford it or they haven't got the budget this year but will later in the year or next year. If you are in such a scenario, you should still begin preparing for the eventual move and not wait until you have the money to begin planning. That way you can hit the ground running when the funds are there. Endpoint security company Bit9 recommends several steps in the process:
Don't do it alone: A smooth transition to a new platform will require full buy-in and agreement from any and all impacted stakeholders. That means not just the IT department, but the business units impacted and the budgeting finance team.
Dedicate time for project scoping: The average migration project will take over 200 days to implement, from assessment, to migration, to debugging. You're not just copying files, there is much more to the migration. So find the potential pitfalls early on and not get tripped up during the migration.
Work within your budget: If you are not making the move for financial reasons, then you likely already have a good idea of your finances. You will need a clear picture of potential project risks, costs and buy-in for the necessary human resource requirements.
Set a realistic timeline: As said above, a migration takes on average 200 days. Some can be worse, others easier. Rushing will only make a mess. It will lead to mistakes, cost overruns and resource misallocation.
Microsoft is abandoning the OS but not the people who use it. It has prepared an entire site for Windows Server 2003 End of Service, all of which is dedicated to helping you plan your migration. Microsoft lays this out in a four-step migration process, which involves:
Discover: Discover and catalogue all the software and workloads that are running on Windows Server 2003/R2 at present. The site has a Microsoft Assessment and Planning toolkit you can download, which works with System Center to examine your infrastructure and identify all of the servers and apps running on them.
Assess: Now you have a list of servers and apps, it's time to categorize your apps and workloads by type, importance and complexity. This could mean having to rearchitect your infrastructure around Windows Server 2012 and System Center 2012, which have changed radically since Server 2012. It also means reimaging your Active Directory, network infrastructure and file server/storage options.
Target: This is where you the destination for each application and workload. Because of the variety of apps and workloads, Microsoft offers a number of free software trials to test out your apps and workloads. They include:
- Windows Server 2012 R2
- System Center 2012 R2
- Microsoft Azure
- SQL Server 2014
- Office 365
All come with 30 day free trials. "Those trials are really important. Use those 30 days to work on compatibility with all the apps, and make sure that when it's in your test environment that everything is stable and meets your needs," said Peter Tsai, content marketing manager with Spiceworks, makers of IT management software.
Migrate: This is where you build a migration plan, either to do on your own or with a partner. AppZero is probably the best-known of the Server 2003 migration consultancies and has a working agreement with Microsoft. There are other companies and services firms, like HP's services group, formerly EDS. Microsoft offers a Migration Planning Assistant which covers all four steps and has official training courses to help you with the migration.
Other Microsoft resources
Microsoft Virtual Academy: A massive collection of free study resources from Microsoft MVPs and other experts, including videos, slide decks and self-assessments. There are whole sections on migrating to Windows Server 2012 and Azure.
Windows Server 2003 Roles Migration Process: This is a very large printable poster that you can stick on a wall and use it to visualize and track the whole process.
Microsoft Deployment Toolkit: This is a collection of processes and practices, assistance tools and guidance for automating new desktop and server deployments.