This is an instrumental case study of 1 novice and 1 experienced secondary social studies teachers' concurrent assessment practices within tightly structured, standardized-tested curricula and flexible elective curricula. It is anchored by 2 questions: (1) How did the teachers' assessment stances and practices manifest across the 2 course contexts? and (2) How did they mediate the influences of high-stakes tests and other curriculum controls in the process of deciding what assessment practices to pursue? Findings suggest that the teachers' assessment experiences in their elective contexts strengthened their critiques of and adaptations to standardized assessment pressures in their tested courses and invigorated their assessment dialogues with students across both. These findings are significant because they illustrate how the productive tensions of teaching across discrepant curricular contexts can be generative for thinking and making decisions about assessing students' learning amid the current culture of test-based accountability.