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This paper considers the problems of evaluating the benefits of an investment in information technology and systems against a background of institutional change. It is based on a case study in the National Health Service and follows the progress of a project to introduce benefits realisation in NHS Trusts. The case illustrates the importance of personal, hands‐on attention to benefits management and calls attention to the different contingencies faced by managers in attempting to introduce evaluation or benefits realisation schemes. It concludes that, where managers face “certain” contingencies, formative evaluation will be beneficial, but where the contingencies are uncertain, structural changes in the organisation may be more effective in achieving benefits. The paper ends with a plea for evaluation activities to be re‐integrated into their organisational context.