Increasingly, organizations are adopting Enterprise Systems (ES) in an effort to increase productivity and reduce costs. Unfortunately, system-wide implementations such as these often fail to produce the outcomes desired by those that champion them. One noted reason for unsuccessful ES utilization rests in “workarounds”—the deviation or circumvention of the ES by users (employees) of the system. Our research question asks, “How do the outcomes of a workaround impact the downstream user and the system overall?” We assert that the motivation or why workarounds are employed is not as important as the outcomes these workarounds create. Using qualitative data from a longitudinal field study of a large organization in the U.S. Midwest, we categorize workarounds based on the outcomes they generate and consider the resultant effects these workaround outcomes have for the downstream user. In particular, we explore how workaround outcomes impact the effectiveness of accounting functions.