The Seal of Biliteracy (SoBL) is a language education policy adopted by states to recognize students' biliteracy. Originally implemented in high schools to recognize graduating seniors, the initiative also includes pathway awards, which can be implemented in earlier grades to promote lengthier language study and increase biliteracy attainment. This qualitative case study investigates the K-12 implementation of SoBL and pathway recognitions in the urban-intensive context of the Chicago Public Schools. Drawing from documentation and interviews with district- and school-level stakeholders, this research uncovers the nuanced policy work to promote, assess, and recognize biliteracy in a district with 322,000 students.