Front-line public servants are charged with profoundly difficult tasks, often enacting roles characterized by complex rule sets in difficult and dynamic situations. These situations, though sometimes routine or standardized, may test the completeness and efficacy of those rules. Adding to this variability, those receiving services by these street-level workers—citizens, clients, or patients—span all possible types of individual, demographic, and economic categories. Though assumptions of appropriate and fair treatment across categories pervade these functions, both the incompleteness of policy and necessary flexibility to account for situational factors remain. This resulting uncertainty and room for discretion allows other factors to emerge as important, including perceptions of service recipients. In some cases surface characteristics and situational factors may impact assessment of service recipient need, interpretation of rules, and discretionary decision-making. Front-line worker behavior, then, is centrally linked to ideas about recipient deservingness of services. Previous research has identified responsibility for the current condition and individual behaviors in response to those conditions as determinants of deservingness. These issues are particularly important in emergency medical services (EMS), a function in which patient deservingness may be invisible and particularly difficult to assess. We use survey data collected in November and December 2017 from paramedics in Pennsylvania to investigate the impact of empathy and expertise on deservingness. Results indicate that, though expertise does not have a direct relationship with deservingness, it has a positive relationship with empathy which, in turn, has a positive impact on perceptions of patient deservingness. Concluding comments and implications for theory and practice are provided.