Despite being a high priority for most organisations the creation of an IT strategy is not guaranteed to deliver the expected business benefits. It is often the case that IT strategies do not evolve into business aligned plans and fail to add significant value to the organisation. Many influencing factors can be the cause of these failures, this article considers some of the key factors and suggests practical steps that can be taken to avoid them. The result of strategic failure can be wide ranging. This article explores the reasons why software implementations fail in the context of strategic alignment. From lack of executive sponsorship to rapidly changing technological landscape the article defines and suggests mitigation for the many of the most common issues.