Breaking up with Windows Server 2003? 5 Essential Steps Before Migrating

Microsoft officially stopped supporting Windows Server 2003 (the announcement had been made well in time) starting Jul 2015. If you, as an organization, are still using Windows Server 2003, without the knowledge of the serious risks of doing so, it’s probably time to have a tough talk with your CIO.

It’s Time to Move On

Just like organizations found it terrible to move on from Windows XP (its end of life happened in April 2014), IT departments are still holding on to Windows Server 2003, because they’ve spent years stabilizing their server infrastructure based on the tight and power packed Windows Server 2003 OS. However, it’s important to move on now, particularly when it’s already several months after the end of life of Windows Server 2003, and with cyber sphere already buzzing with stories of server outages occurring in organizations still clinging on to Windows Server 2003.

Some Key Facts to Absorb, Before You Migrate

  • Windows Server 2003’s replacements come aplenty – there’s Windows Server 2008, Windows Server 2012, Windows Sever 2008 R2, and Windows Server 2012 R2.
  • Windows Server 2012 R2 offers substantial compatibility of applications with Windows Server 2003, which makes migration easier.
  • Integrated virtualization, extensive scalability, and better security are the major improvements that Windows Server 2012 R2 brings to the table for an IT department.
  • Continuing beyond the end of life for Windows Server 2003 means exposing your organization’s databases to hackers and cybercriminals with uncovered vulnerabilities, and staying aloof from the latest from the world of server operating systems.
  • With simplified licensing and deployments attuned to a virtualization empowered IT environment, this migration offers the opportunity of adopting long term CAPEX savings.

Guide to Move from Windows Server 2013 – Five Essential Steps 

Step 1 – Step Back and Envisage the Broad IT Spectrum

Understanding the current state of your organization’s servers, the ideal state your IT department envisages, and a reasonably attainable end state for the same. You need to understand and express your IT goals in terms of server infrastructure.

Step 2 – Take Stock of the Current Server OS Utilization

  • Consult with your server administrator and get a good idea of the current state of Windows 2003 environment in your server centre. Get a decent idea of the real workloads being tackled by Windows Server 2003. Need help in mapping your datacenter workloads? Check out a few low cost or no cost applications –
    • Microsoft Assessment and Planning [MAP] Toolkit
    • OpenManage Server Administrator [OMSA] and ChangeBASE), from Dell
    • HP Asset Manager software
  • Find out the accurate number of Windows Server 2003 systems operating on your network. Spend time to extract details regarding CPU, disk space, and memory profile of each system. Identify systems with less than 50% utilizations (these are good candidates for virtualization). Take stock of systems that can be decommissioned; for instance, systems that have always lain unused, or can be retired without business impact.
  • Plus, Microsoft has handled the post end of life consultancy particularly well, which means you will still be able to talk to Microsoft MVPs (most valuable professionals) to get help on the best way forward.

Step 3 – Prepare Inventory Lists

The third step is about parsing applications, services, and workloads into different buckets. Here’s an actionable guide –

  • Displaceable Workloads – Standardized service offerings can be leveraged to displace workloads that can be replaced on-premise using OS services.
  • Minimal Hassle Apps – Applications that can be migrated from Windows Server 2003 to a newer version such as Server 2008 or Server 2012 with minimal time investment need to be recorded.
  • Moderate Effort Apps – These are applications that will need moderate time investment to be migrated.
  • Problem Apps – These are the apps that might need deeper analyses in terms of migration risks, cutover efforts, and could even pose challenges as huge as complete re-architecting.
  • Apps to be Retired – Understand the target server OS features, and look to discard the old applications running on Windows Server 2003 that these features can replace.

Step 4 – Look to Virtualize What You Can

  • Internal applications need to be tackled on a ‘virtualization first’ philosophy, to maximize the benefits of the server OS migration.
  • Look to leverage virtualization as a tool for facilitating quicker, cost effective, and secure transition from Windows Server 2003 to a newer version.
  • Consider the strategy of deploying Windows Server 2012 VMs first and downgrading to Windows Server 2003 as an intermediary step.
  • Look to move apps to PaaS (platform as a service) or IaaS (infrastructure as a service) cloud models. Generally, customer facing and web facing apps are good candidates of being migrated on cloud. Check out Microsoft’s established partners covered under the Cloud OS Initiative of 2013, which offers several viable options of Windows IaaS migrations for existing users of Windows Server 2003.

Step 5 – Risk Assessment

  • Take stock of the mission critical apps; the best way to do so is to envisage your IT infrastructure and business process without the app under consideration. If there is no replacement and has high impact on business, the app falls under ‘critical’ list, and you need to be extra careful for its migration, with a backup plan.
  • To bring down the risks associated with the migration, it’s advisable to begin with P2V migrations, and ensure that all migration activity is recorded. Ensure that snapshot version is running during the migration to ensure that the app functionality is available in case the migration activities are disrupted.

Remember, your love for Windows Server 2003 can never surpass the sense of duty you have for your organization. If you are the CIO or Chief Technology Officer of an SMB still using Windows Server 2003, it’s time to question other senior leaders if they prefer the board of directors and shareholders knowing that the company is running on server OS that will not get any security upgrades, which effectively puts the company’s intellectual properties and digital assets at a huge risk.

Author: Rahul Sharma
Image Courtesy: Microsoft