Street-level bureaucrats set the terms for policy implementation and often operate under limited oversight. In American elections, poll workers are the street-level bureaucrats tasked with implementing a jurisdiction’s laws for verifying voter eligibility. Using in-depth interviews with 24 poll workers from the city of Chicago, this article assesses how poll workers make decisions about voter eligibility under Illinois’ signature-matching law. Respondents discussed a range of considerations used when they examine voter eligibility. The evidence I present suggests they rely on personal perspectives and experiences in their evaluations. Respondents also offered a range of responses for how they would proceed in the instance of a mismatching signature—including requesting voters provide identification even though it is not a requirement in Illinois unless a voter is challenged. Broadly, these results illustrate how poll workers’ subjective interpretations of election law shape their decisions and can lead to idiosyncratic applications of election law.