Language policy in education is influenced by the perceptions of the role and status of languages on the part of policymakers, with languages being promoted or neglected for explicit or implicit political reasons. With globalisation, choices have to be made regarding international, national and local languages, with concomitant tensions concerning linguistic hegemony, identity and social equity. These tensions are exacerbated in many Asian settings, because of historical experiences of imperialism and colonialism. But what happens to policies when political influences are mixed with educational goals? Are the chances for successful implementation enhanced or diminished? This chapter focuses on Hong Kong in the immediate postcolonial era. Using the Ferguson Tollefson Matrix (FTM), developed by Kan (2011) to facilitate language policy analysis and outcome predictions, we analyse Hong Kong’s language policies since the 1997 handover, as the language policies in the territory have undergone substantial changes, most notably in the medium of instruction (MoI) for secondary schools. Chinese MoI (CMI) policies initiated in 1998 proved unpopular with the majority of parents, leading the government to make a policy revision, known as the “Fine-tuning”, which took effect from the school year 2010–2011. Applying the FTM on the policy and analysing it against subsequent official reviews, we argue that political dimensions of a policy are not conducive to successful implementation.