In many European countries, community entrepreneurship is increasingly considered as a means to initiate small-scale urban regeneration in the context of austerity policies and welfare state retrenchment. However, residents in deprived neighbourhoods are often viewed to lack key entrepreneurial attributes and skills. While there is research on community entrepreneurship support, most evidence is based on cross-sectional studies and overly focussed on support provided through government policies. This paper extends the current body of knowledge by reporting a unique national experiment in the Netherlands with nascent community enterprises which received start-up support from a private foundation. The paper aims is to investigate how active citizens perceive the benefits and drawbacks of this support. The approached used is unique because of its longitudinal nature right from the start of the experiment. The paper provides an in-depth analysis of transcriptions of repeated semi-structured interviews with the same respondents (panel design) from nascent community enterprises in a number of Dutch deprived neighbourhoods. While positive feedback on the support is found, the study provides strong evidence for a ‘support paradox’: the support that was intended to overcome a number of entry barriers and difficulties on the road to community entrepreneurship has in fact significantly hampered progress among several of the studied community enterprises.