The middle grades are a critical transition period in students’ mathematics trajectories, as students move from arithmetic to the more complex and abstract concepts of algebra. Teachers’ and parents’ judgments of students’ math abilities in these years are important to instructional planning and decision making for teachers, and can advise parents and students on future course placement. This study specifically examined teacher and parent judgments of students’ performance and preparedness for the next grade level in 5th and 6th grades mathematics. Results demonstrate that teacher and parent perceptions of students’ abilities are not calibrated to national norms, but to local contexts. Our findings are similar to other work suggesting that high poverty school contexts may provide teachers and parents a false comparative context for judging how well students are mastering mathematical concepts.