This chapter examines the legal, institutional and philosophical impediments the Chinese community penal system has to face in the process of replacing administrative detention. It argues that while China endeavours to prompt the socialisation of administrative offenders in the community, the legal deficiencies of community approaches create a general obstacle for this practice to be fully implemented in China. The difficulty of imposing community penalty on minor offenders also lies on the characteristic features of China's contemporary socio-economic landscape. In particular, institutional conflict with the hukou system, shortage of community resources and lack of social recognition shape the most disturbing factors that discourage this new instrument from functioning as a well-operated program centring on education and persuasion. To understand the difficulty of remoulding administrative offenders in Chinese communities, one needs to carefully look into the factors that impede this practice in an interdisciplinary perspective that spanning socio-legal and eco-cultural contexts.