The importance of individuals’ social environment as an explanation for the ‘happiness-income paradox’, but also accounting for the negative relationship between income inequality and subjective well-being in macro-comparative perspective is now widely recognized. At the same time, however, debates are still ongoing about the specific role local communities play in moderating the relationship between personal income and subjective well-being. This article adds to this literature by examining cross-level interactions between individual- and district-level determinants of self-rated happiness using multilevel mixed regression techniques. Our findings suggest that living in wealthier districts in Hong Kong is a ‘positive’ for individuals on lower personal incomes, whereas the effect on those with higher incomes is more in line with arguments underlining the role of local communities as a ‘negative’. While the overall effect of district-level poverty on self-reported happiness in Hong Kong is benign, this is not the case for individuals on low incomes who are most negatively affected if they live in districts featuring higher levels of deprivation. Governments across contemporary Asian global cities should recognize the important role of citizens’ social environment and tackle existing structural barriers to greater self-reported happiness accordingly.