Despite being the first Asian country (except for Hong Kong) to sign a film co-production agreement with China, Singapore’s film co-productions with China so far are few and far between, none of which have come under the official agreement. This raises wider questions about the policy making challenges of small nations when driving or facilitating regional collaborations with partners like China. Drawing on interviews with key interlocutors in the Singapore film industry, this article explores how Singapore’s filmmakers make sense of working with the Chinese film industry as collaborators and co-producers on joint film productions. Our main argument is that conventional models for understanding drivers of co-productions may not work for small partners collaborating with a dominant regional/global partner like China. Through exploring the political, economic, and cultural tensions in the Asia-Pacific region that emerge when Singapore engages in collaborative film work with China, we hope to contribute to the wider literature on ‘South-South’ collaborations between film industries (and nations) of vastly different sizes and power.