In recent years, a number of reviews have generated evidence on the potential of community health insurance (CHI) to increase access to care and offer financial protection against the cost of illness for poor people excluded from formal insurance systems. Field experience, however, shows that in sub-Saharan Africa (SSA), a series of operational difficulties still hampers the successful development of CHI, yielding negative effects on potential progress towards increased access to care and improved financial protection. Through a careful assessment of the existing literature, including peer-reviewed articles, books, consultancy reports, and manuscripts from international organizations, we produce an analytical review of such difficulties. Our aim is to provide policy makers with the necessary knowledge on the problems at stake and with policy propositions to offset such problems, strengthening CHI and enhancing its role within SSA health systems. Our review of the literature reveals that the major difficulties currently faced by CHI in SSA are operational in nature and cluster around five areas: (i) lack of clear legislative and regulatory framework; (ii) low enrolment rates; (iii) insufficient risk management measures; (iv) weak managerial capacity; and (v) high overhead costs. Consequently, our review calls for appropriate policy interventions, specifically: (i) greater commitment towards the development of adequate legislation in support of CHI; (ii) increasing uptake of measures to expand equitable enrolment; (iii) the adoption of adequate risk management measures in all schemes; (iv) substantial investments from host countries as well as from sponsoring agencies to improve managerial capacity; and (v) collective efforts to contain overhead costs.