A Smart Strategy for Windows Server 2003

A Necessary but Overwhelming Project

Microsoft Windows Server 2003 will reach its end-of-life by July 2015, servers will no longer be receiving security updates, leaving critical business systems vulnerable to attacks. The server operating system has run for many years and there are many customers, who have Windows Server 2003 in production today and some will continue to do so until end-of life of Windows Server 2003 for different reasons. If you are still using Windows Server 2003, now is the time to consider your options. The place to start is to develop a business case around operating system migration. A migration project requires many resources and will take some time and planning.

Some common concerns will reverberate through the organization. For example:

IT will be concerned about the process:

  • Do I need to touch every server in the company?
  • How do we handle servers in the branch office?
  • And more.....

At the top of the company, the CIO/CFO will be concerned about time and cost:

  • Do we have to migrate now?
  • How much hardware will we need to replace or upgrade?
  • How do we keep end users productive during and after the migration?
  • And so on.....

As you can imagine there will be lots of questions. And, indeed, a migration project contains pain points and, in its entirety, is a challenge across the whole organization.

In the end, the decision to upgrade rests on one question: How will Windows Server 2012 improve productivity and positively influence your company’s bottom line? Windows Server 2003 is a 10-year-old technology. Microsoft has made substantial improvements over the years to help businesses compete in today’s complex enterprise environments. Outdated servers open datacenters to higher security risks, inefficiency and increased maintenance cost. Upgrading to Windows Server 2012 enables organizations to modernize and standardize IT infrastructure. Results can include:

  • Reduced operational costs and increased efficiencies
  • Improved employee productivity
  • Ability to be cloud-ready
  • Increased business agility and ability to scale to accommodate business growth
  • Improved system availability
  • Ability to implement cost-effective backup and disaster recovery solutions

Better performance means less time waiting for the system to respond, resulting in more output in a given amount of time. Better reliability means less downtime due to problems and crashes, both increasing productivity and reducing administrative and tech support overhead.

The key to making the business case for switching to Windows Server 2012 lies in:

  • Demonstrating how the new OS can be more easily managed and thus make IT’s job easier and reduce operating expenses
  • Showing how new OS reliability and security features can result in less downtime and save the company money

There is an additional reason to migrate to Windows Server 2012: Microsoft will terminate support for Windows 2003 Server in July 2015.

Migrating to Windows Server 2012 is the kind of project that keeps IT managers awake at night. Why? It requires migrating hundreds and maybe even thousands of server applications. With so many applications and so much diversity, there’s no doubt that compatibility issues will arise. It may be necessary to make changes to either the installer or even the application for it to work properly on Windows Server 2012.

Identifying and fixing compatibility issues for your application portfolio is a huge undertaking.

Compatibility issues crop up in a number of different areas. Here are but a few examples:

  • Windows Server 2012 folder locations are different than Windows Server 2003, even more so for those upgrading from a 32-bit edition of Windows Server 2003
  • Windows Server 2012 User Account Control (UAC) causes applications that require administrator rights or check for administrator privileges to behave differently
  • Windows Server 2012 Resources Protection (WRP) can cause installation problems for custom installations that were not set up by Windows Server 2012
  • Many applications check the version of the operating system and behave differently or fail to run when they detect an unrecognized version number such as Windows Server 2012
  • Windows Server 2012 requires Internet Explorer 10 or later and these newer browsers may cause problems with both your browser-based and Web applications
  • Windows Server 2012 only supports Internet Information Services (IIS) 8 or later, which has been completely rewritten since IIS 6 for Windows Server 2003.

Next to technical issues, organizational or business subjects need to be taken under consideration. Will we change by departments to minimize impact on the organization in cases of failures, or will we change by client type or what else? What is the best timing? What server changes come along with Windows Server 2012? What training do we have to do before we can start? What internal documentation needs to be adjusted for administrators? Does the change imply changes in your internal standards as well, such as packaging guidelines? Are you combining the upgrade of the operating system with a switch to hardware virtualization, or even a paradigm shift towards cloud infrastructure?

The list may seem endless. Just determining all the issues to look for is in itself a daunting task, let alone testing the applications and fixing the issues. And that’s not all. You may have legacy applications that have to be converted first to Windows Installer (MSI) packages before migrating them to Windows Server 2012.

Another factor to consider is application virtualization. Many organizations look at a Windows Server 2012 migration project as an opportunity to also take advantage of application virtualization. While virtualization won’t solve application to operating system incompatibilities, it does solve problems between applications. The benefits are compelling and include cost savings through higher resource utilization and greater agility in meeting the demands of the business. Virtualization also paves the way for cloud computing.

But application virtualization brings even more tasks. You have to test applications for suitability to virtualization. Then you have to virtualize them. Performing all the migration and virtualization tasks manually can take thousands of man-hours to complete. What’s more, it could introduce errors that expose your organization to considerable risk. To master this part of the migration you need an industrially designed process capable of packaging and virtualizing your software to the highest automated degree possible while keeping control about the progress and quality of your work, since it will directly impact the quality of the overall migration project.

Microsoft provides some degree of migration assistance with the free Microsoft Application Compatibility Toolkit (ACT). The toolkit includes an agent that runs on current PCs and detects potential Windows Server 2012 compatibility issues as the applications execute. While providing valuable insight into compatibility issues, ACT does not offer comprehensive testing and remediation nor does it offer the industrial strength that larger organizations need to tackle a Windows Server 2012 migration.

Formulating A Strategy

You need to develop and implement a smart strategy for a Windows Server migration, one that simplifies and speeds the migration process without exposing your organization to risk. This strategy must encompass the entire migration process. The Application Readiness process provides a standardized approach to desktop and server migration.

This is an excerpt. Download the entire pdf: A Smart Strategy for Windows Server 2003