Abstract This paper extends the current understanding of the time‐sensitivity of intent and usage following large‐scale IT implementation. Our study focuses on perceived system misfit with organizational processes in tandem with the availability of system circumvention opportunities. Case study comparisons and controlled experiments are used to support the theoretical unpacking of organizational and technical contingencies and their relationship to shifts in user intentions and variation in work‐processing tactics over time. Findings suggest that managers and users may retain strong intentions to circumvent systems in the presence of perceived task‐technology misfit. The perceived ease with which this circumvention is attainable factors significantly into the timeframe within which it is attempted, and subsequently impacts the onset of deviation from prescribed practice and anticipated dynamics.
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