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Abstract In various organizations including hospitals, individuals are not forced to follow specific assignments, and thus, deviations from preferred task assignments are common. This is due to the conventional wisdom that professionals should be given the flexibility to deviate from preferred assignments as needed. It is unclear, however, whether and when this conventional wisdom is true. We use evidence on the assignments of generalist and specialists to patients in our partner hospital (a children’s hospital), and generate insights into whether and when hospital administrators should disallow such flexibility. We do so by identifying 73 top medical diagnoses and using detailed patient-level electronic medical record (EMR) data of more than 4,700 hospitalizations. In parallel, we conduct a survey of medical experts and utilized it to identify the preferred provider type that should have been assigned to each patient. Using these two sources of data, we examine the consequence of deviations from preferred provider assignments on three sets of performance measures: operational efficiency (measured by length of stay), quality of care (measured by 30-day readmissions and adverse events), and cost (measured by total charges). We find that deviating from preferred assignments is beneficial for task types (patients’ diagnosis in our setting) that are either (a) well-defined (improving operational efficiency and costs), or (b) require high contact (improving costs and adverse events, though at the expense of lower operational efficiency). For other task types (e.g., highly complex or resource-intensive tasks), we observe that deviations are either detrimental or yield no tangible benefits, and thus, hospitals should try to eliminate them (e.g., by developing and enforcing assignment guidelines). To understand the causal mechanism behind our results, we make use of mediation analysis and find that utilizing advanced imaging (e.g., MRIs, CT scans, or nuclear radiology) plays an important role in how deviations impact performance outcomes. Our findings also provide evidence for a “no free lunch” theorem: while for some task types, deviations are beneficial for certain performance outcomes, they can simultaneously degrade performance in terms of other dimensions. To provide clear recommendations for hospital administrators, we also consider counterfactual scenarios corresponding to imposing the preferred assignments fully or partially, and perform cost-effectiveness analyses. Our results indicate that enforcing the preferred assignments either for all tasks or only for resource-intensive tasks is cost-effective, with the latter being the superior policy. Finally, by comparing deviations during weekdays and weekends, early shifts and late shifts, and high congestion and low congestion periods, our results shed light on some environmental conditions under which deviations occur more in practice.