The IT Plan is generally seen as a cornerstone of the IS/IT presence in an organisation. Researchers have outlined various approaches to IT planning and many have suggested categorising such plans in terms of an evolutionary model detailing the degree of integration with organisational business plans. To determine how IT plans are developed in practice and the actual forces at play the study in this paper uses an evolutionary model to examine the development of the IT plan over a five year period in a large governmental organisation. The case study highlights some of the pain and disruption evident within the IT department of a large governmental organization as it moves through the various business stages of "corporatisation", "privatisation" and "down-sizing". The findings highlight that IT plans do not always evolve through stages of closer integration with the business plan; that the IT plan can be viewed as a political manifesto often with the intention of cementing the IT Department’s place in the organisation; and that an overly rational approach to planning appears to achieve very little. A complex interplay of structural and agency factors determine the success of IT plans at any particular stage and when both conspire in opposition a likely outcome is its complete obliteration.