Research in education has long noted teachers' role in assisting social and ideological reproduction. Separately, scholarship has also investigated the use of extra-curricular activities in equipping disadvantaged students with social and cultural capital, to embark on social mobility. Positioned at the intersection of these two apparently disparate strands, this paper presents a case in which teachers' extra-curricular work is seen to simultaneously enact subtle socio-ideological reproduction, and the facilitation of social mobility attainment. Specifically, the paper draws on a study of how teachers in a lower-status junior college in Singapore prepare their students in applying for prestigious state-sponsored scholarships. Through teachers' extra-curricular work of "allying" and "aligning," social mobility and social reproduction are simultaneously made possible, yet also exist in some tension. Thus, this paper offers a unique sociological perspective on teachers' extra-curricular work and its significance for broader issues of meritocracy, social mobility, and social reproduction.