This study examines how three bilingual education teachers engaged with a transitional bilingual policy while balancing the demands of monolingual high-stakes assessments in ways that contributed to advocacy on behalf of their bilingual learners. The consequences of high-stakes accountability can be exacerbated in bilingual settings, because in these contexts often contradictory assessment policies and language policies interact. In this interaction, bilingual educators can become susceptible to enacting policies that largely fail their bilingual students and ultimately promote the status quo. Applying a Figured Worlds theoretical framing (Holland, Lachicotte, Skinner & Cain, 1998) in a vertical comparison case study design (Bartlett & Vavrus, 2016), the author explores the teacher's policy work from an improvisation lens. Findings reveal that the teachers engaged in both overt and improvisational policy work. The costs associated with the teachers' overt policy work suggests that improvisational agency offers great potential as a strategic and sustainable form of advocacy for bilingual students.