Best Practices for Windows Server 2003 End-of-Support Migration: Part 4

We hope that you’ve been following along with this blog series so far, and that you’ve completed the Discovery phase of your migration planning.  Whether you are a Microsoft Partner or IT professional, you should now be at the point where you know the exact number of Windows Server 2003 instances running in your datacenter or in your customer’s environment, and you have a wonderful laundry list (or catalog) of applications and workloads that are going to need a new home come July 14, 2015.  If this description matches your current state, then you’re now ready to enter the assessment phase.  

The assessment phase is extremely crucial and requires you to analyze every workload and application - to identify the utilization, importance, and sustainability of each instance.  Through this process, you’ll probably find redundancies in your environment and service levels for availability that are mismatched.  Over time environments can be subject to "application sprawl" without the right level of IT controls, this is a great opportunity to address this and institute better controls.   Resources that were dedicated to what used to be a mainstream business critical project are no longer fully utilized but have resources dedicated to support a service level and level of availability that is no longer needed.  On the flip side, you’ll also identify truly vital and business critical applications and workloads that will need immediate attention and additional capacity.  You also may find cases where a business owner has "gone rogue" and established agreements with other vendors outside of the IT plan.  Assessment is the opportunity to target your efforts towards the migration and upgrade of the critical components of your datacenter, while making the most of scarce resources. 

In addition to technical evolution, an element of organizational change and business process evaluation is also important.  So this is an opportunity to meet with the business owner for each application to reconfirm the required service level, and to educate the business owner on the associated costs.  Most business stakeholders will always request 99.9% availability for their applications - but when educated on the actual costs a more productive conversation can occur, for example moving critical workloads to highly available cloud alternatives and agreeing to keep non-critical applications in lower cost/lower availability environments.  Some organizations also take this opportunity to institute internal chargeback models for IT infrastructure, or just "showback" where there is increased transparency on the actual infrastructure costs for each business owner or business unit.  As a Microsoft Partner advising a customer, or as an IT professional within and organization, this is a great opportunity to directly impact the bottom line by optimizing capital and operational expenditures.

This phase requires you to look closely at your catalog of applications and workloads.  There isn’t a tool or automation process that can assist you with this, as the effort requires detailed analysis of the relevance of individual workloads and applications to the business.  Depending on the number of items that you need to assess, this phase can take a substantial amount of time and will need inputs from the business in terms of what new capabilities they need, how much they need to expand, and where they plan to grow geographically..  You’ll need to identify the owners for each workload and application, and identify the impact of each.  In order to streamline the process, we suggest that you start to inventory and organize each workload and application by Type and criticality, as well as complexity and risk. 


  • By Type:

Bucketing your workloads and applications in this manner will allow you to engage with the correct individuals to determine your migration approach.  For example, if you have numerous databases currently running on Windows Server 2003, then you will need to engage with the applications team to discuss an upgrade of that database to a supported version.

• By Criticality: 

What departments or customers use these resources today?  Do they fit the business goals of your organization?  Who uses this anymore? What availability do they need and how much downtime is acceptable? This categorization will reveal some potential opportunities, as well as potential issues as shown in the diagram below: 

  • By Complexity and Risk: 

The complexity and risk categories will indicate which migrations might be the easiest and quickest to accomplish.  A critical consideration to keep top of mind is the dependencies that may exist, as there are chain reactions to retiring an application or database that is still connected to a separate workload.  A cross-category analysis provides even more insight.  For example, an important application with low complexity and only medium risk may be a good candidate for an early migration.  

After you’ve completed this phase, you should have successfully uncovered the truly important workloads and applications that require your undivided focus.  Likewise, the assessment will assist you with identifying the more easily migrated, as well as those that should be retired. 

Setting up a spreadsheet view on a share will assist you and your team with ensuring that a singular truth regarding owners, and the final categorization of each workload and application is clearly communicated. 


Setting up this spreadsheet early will also assist you with identifying the future ‘Target’ or ‘Destination’ for your workloads and applications.  (We’ll talk about those in our upcoming posts.) 

As we mentioned, you’ll need to coordinate between the various teams and business owners who are impacted.  As this will take time, having a well-thought out strategy prior to meeting is key to ensuring your migration doesn’t get stuck in a circular discussion that goes nowhere.  You’re leading this migration, so make sure you have your assessment as complete as possible, as well as a suggested approach for each application and workload.

Until next time, keep moving forward with your migration process, as of this post there are only nine months remaining to Windows Server 2003 EOS.  We’re here to help, so visit the Microsoft Windows Server 2003 migration page or reach out to one of our partners to assist you with this phase of your migration.  Until the next post!

Comments (2)

  1. Jasper says:

    Please tag the previous three blogs as well. Makes it a little difficult to read them completely in one go when they are not tagged together.

  2. Jasper says:

    Please tag the previous three blogs as well. Makes it a little difficult to read them completely in one go when they are not tagged together.

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