Conclusion: Windows XP will not stop working in April 2014 when Microsoft stops supporting this popular operating system. However, as time passes, this OS will become an increasing burden on organisations, due to third party support, security challenges, increasingly specialised skillsets, and perception. Windows XP will quickly become a legacy environment, with all the associated challenges. Consequently, CIOs should have a clear plan for any remaining Windows XP machines. The value of a clear plan is two-fold: firstly for common understanding within the IT department, but also for communicating to stakeholders.