Street-level bureaucrats interact directly with people on behalf of government agencies to perform a wide range of functions, including, for example, administering social services and policing. A key feature of street-level bureaucracy is that the civil servants, while tasked with implementing agency policy, are also granted significant discretion in how they choose to apply that policy in individual cases. Using that discretion could be beneficial, as it allows for exceptions to policies based on human interactions and evaluations, but it could also allow biases and inequities to seep into important domains of societal resource allocation. In this paper, we use machine learning techniques to understand street-level bureaucrats' behavior. We leverage a rich dataset that combines demographic and other information on households with information on which homelessness interventions they were assigned during a period when assignments were not formulaic. We find that caseworker decisions in this time are highly predictable overall, and some, but not all of this predictivity can be captured by simple decision rules. We theorize that the decisions not captured by the simple decision rules can be considered applications of caseworker discretion. These discretionary decisions are far from random in both the characteristics of such households and in terms of the outcomes of the decisions. Caseworkers typically only apply discretion to households that would be considered less vulnerable. When they do apply discretion to assign households to more intensive interventions, the marginal benefits to those households are significantly higher than would be expected if the households were chosen at random; there is no similar reduction in marginal benefit to households that are discretionarily allocated less intensive interventions, suggesting that caseworkers are using their knowledge and experience to improve outcomes for households experiencing homelessness.