Windows Server 2003 Migration (Part 1) – coping when reality interferes with the plan.

Developer Support

In Part 1 of this 5 part series, Senior Application Development Manager, Chuck Goodspeed, shares insights and lessons from a large Windows Server 2003 migration.

July of 2015, Support for Microsoft Windows Server 2003 came to an end.

By this point of time, all of our customers should have migrated off of Windows Server 2003 to Windows 2008 R2 at minimum or preferably to Windows Server 2012 R2. These customers should be enjoying the benefits of an extensive reinvestment of knowledge, technology and modernization into their technology environments and mission critical applications. They are now planning their future, secure in their conviction that all Microsoft Products, 3rd Party Vender applications and custom applications have been updated and are current. Corporate domains and Active Directories have been updated with the latest security techniques. Prudent and vigilant detection systems have been adopted to protect secure customer information from the perils of hackers or other malicious users. These customers are now poised to migrate applications and services to private and public clouds integrating the best of mobile technology and social networks. steps to migration for Windows Server 2003

Why do so many customers remain on Windows Server 2003 today?

Today, many customers still remain on Windows Server 2003 and/or Windows XP. They have entered into costly Custom Support Agreements (CSA’s) to keep their mission critical environments under support. IT budgets, already under scrutiny, are having to absorb the higher support budget and defer new projects that are more cost effective and actually contribute significant return on investment. This dilemma is accompanied by a collective wringing of hands and a persistent lamenting on “why this massive migration must be done now?” After all, the current environments JUST WORK, precariously housed in corporate card houses and frantically sheltered from the winds of change.

Why do so many customers continue to postpone the inevitable? Is it because they don’t know what the steps are to migrate? Is it because they lack the skills, resources, support, or partners do get the process accomplished? Are budgetary constraints preventing the migration? While any one of these reasons can certainly impact the timing or methodology of the migration, the primary inhibiting factor is inertia! The process of “change” is daunting to most organizations. It is always easier to remain stationary then it is to move forward. The problems of the present are well known and legacy processes are in place to deal with any issues that arise. The “potential” problems of the future are unknown and the unknown promotes fear and trepidation in most organizations.

How does Premier help customers embrace change and benefit from the latest technologies?

The solution to overcoming any resistance to change is helping customers break down the migration process into succinct, manageable steps. Each step should be detailed. Each task should be objective, have an owner, and a timeline. Escalation processes should be outlined for any problems and right up front, there must be an acceptance that there will be some problems. Some will be simple to solve and others will challenge the resolve of the project and sometimes, the organization.

There must be a substantial commitment from customer management at the highest levels, so important decisions go well beyond Corporate IT. Line of Business (LOB) management must be prepared for the disruption to internal and external customers if the process is not handled correctly. Every corner that was cut and every short time decision that was made in the past will surface again during the migration. Problems long deferred must be addressed and solved. There will be pain! LOB’s will have enjoyed relative stability or at least manageable stability for years may be asked to REINVEST in old, but STABLE applications. Some of these applications will be long past original projected service life!

There must be an acceptance that this process will take time and resources must be properly allocated to do it right!

Premier is in a unique position to assist customers with these types of migrations. We are trusted advisers. Through our ongoing support relationship, we sometimes know our customer’s environments better than they do. We understand the technology of the past and live the technology of the future. We can help customers understand the benefits of completing a migration quickly. More importantly, we know how to overcome the problems that will arise!

Where does the migration start?

All migrations start from the beginning. They must have a start, a middle point and an end. They must be achievable! We build confidence with our customers that no matter how daunting a migration seems, that it is within their capability to succeed. The best way to do this is to provide examples of customers that have already undertaken this process successfully.

As an example I recently completed an 18 month engagement, as an ADM, assisting a large financial company in making this journey. They have emerged from the end of the migration process slightly bruised but certainly wiser for the experience. They chose to migrate from:

  • Windows 2003 Server to Windows Server 2008 R2 
  • Multiple Legacy SQL Server installations to SQL Server 2012
  • Legacy .NET applications from .NET 1.1 to .NET 4.5.2
  • Legacy web services to WCF Migrate
  • IIS 6 to IIS 7.5
  • IE 6 to IE9

We encountered:

  • Applications without source
  • 16 Bit Perl and other legacy script apps
  • Classic ASP apps
  • Unmanaged C++ apps
  • VB6 apps
  • Windows Media Applications
  • Windows Indexing Applications
  • What seemed to be a huge menagerie of one off “are you kidding me – you can’t still be using this” products still in use

As an ADM, I played the primary role in “Mr. Wizard”, “Stump the Star” and other enactments in my daily 90 minute Stand-Up meeting and daily 60 minute Triage Calls. I answered many questions using 30 years of experience and leaned on the vast array of Microsoft colleagues for the items that were beyond my reach, all within the scope of the Premier Support relationship. During the migration, we compiled a long list of problems encountered and the resolutions to each issue or problem.

I spent many hours onsite to help provide assistance and ease migration pains. I, along with my customer, gained experience from the journey. Through their choice, the nature of our engagement was primarily reactive despite my insistence at the beginning that they could benefit from proactive measures to help ease the transition. Hindsight is always 20/20! They learned from minor and major mistakes in the migration plan and are now working together to plan the next migration from Windows Server 2008 R2 to Windows Server 2012 R2 and beyond.

Going forward

Over the next 4-5 posts, I will:

  • Detail the plan steps 
  • Describe the successes and failures encountered in each step
  • Outline “our” solution to the issues
  • Suggest potential alternate courses of action  

There are many documents available that describe the migration process from a Microsoft point of view. As a long time manager, architect and developer, I know that there are many different ways to accomplish the same task. The challenge is to organize the material and processes succinctly within the detailed steps of the prescribed plan. I will organize each post to conform to the following recommendation format:

(Download Supporting Slides)

2003 Windows Server Migrate graphic 3

Therefore the next 4 posts will follow the 4 major steps defined in the presentation above

  1. Windows Server 2003 Migration: Discover – Catalog your software and workloads
  2. Windows Server 2003 Migration: Access – Categorize your software and workloads
  3. Windows Server 2003 Migration: : Target – Identify your destination(s)
  4. Windows Server 2003 Migration: Migrate – Make the move

In the 5th and final blog. I will summarize the results and lessons learned.


Premier Support for Developers provides strategic technology guidance, critical support coverage, and a range of essential services to help teams optimize development lifecycles and improve software quality.  Contact your Application Development Manager (ADM) or email us to learn more about what we can do for you.


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