In a globalized world with increasing international migration and encounters of difference, education is presented with new challenges and opportunities regarding diversity, including "teacher diversity." This paper focuses on teachers with immigrant backgrounds and explores how they potentially add constructive diversity to the receiving country's education system. The empirical setting of this paper is Singapore, an Asian city-state seldom featured in teacher diversity research. Drawing from a broader study involving online surveys and qualitative interviews, this article examines the discourses of five immigrant teachers chosen for their insightful perspectives. We found that the teachers consciously engaged their foreigner/outsider identities by drawing on their biographical and educational backgrounds; they sought to add value to aspects of the Singapore school system which they perceived to be lacking, while negotiating with dominant values and teaching practices. Their negotiations, however, remain delimited in significant ways. The paper argues that immigrant teachers represent an undertapped and underappreciated resource for greater educational diversity in Singapore and beyond.