Increased funding pressures on community development and reductions in governmental funding for community support suggest potent roles for philanthropy as a funding source, and the possibility of changing relationships between community development and philanthropy.Focusing on English community foundations and their implementation of the Canadian Vital Signs initiative, which is geared towards assessing communities' vitality and social priorities, our article explores whether, and how, such changes may be occurring.Using the literature on the respective value of 'unsettling' and 'settled' third sector organisations to community development, we reflect on the roles and contributions of community foundations to community development through community philanthropy. Vital Signs reports' content indicates donor-led community philanthropy associated with ameliorative rather than fundamental social change positions, as well as uncertainty surrounding community leadership in this context. We identify community foundations as 'settled' organisations within the community development spectrum and as reflecting the 'directed' community development form. In this instance, it appears that the philanthropycommunity development gap that we suggest is at best being partially bridged. Nevertheless, and paradoxically, these organisations' achievement of financial security through community donorship could also strengthen their community leadership roles in 'unsettling' ways, so doing more to lessen philanthropy and community development's separation.3