Classroom settings provide many obstacles for anxious students, from academic evaluations to social interactions. Although protective factors such as positive classroom climate and teacher support benefit anxious students, there are still at-risk students who continue to excel in the worst of circumstances. Despite the odds, some highly anxious students are also high achieving students. The characteristics of these anxious-and-achieving students will be discussed in terms of the Programme for International Student Assessment (PISA) 2012 Canadian sample. In particular, the inter-associations among subtypes of student engagement (perseverance, work habits, values, interests, and belonging) will be explored along with the impact of classroom (climate, teacher-student relationships, teacher support) and family factors (socioeconomic status, family resources). Implications for future work, including the role of socio-emotional learning will be discussed.