Abstract This study explores questions around the abilities of social enterprises (SEs) to obtain market-based revenues in the context of a middle-income country with significant institutional and economic constraints (Egypt). Our main research question focuses on analyzing the reasons why SEs in this context are unable to obtain their desired level of market-based revenues. Through the analysis of 22 SEs with some degree of a mixed revenue model, we draw three major conclusions that contribute to both academic theory and SE practice: (a) the importance of investing in new cohorts of SE employees, (b) ways to increase SEs’ ability to respond to institutional barriers, and (c) the promotion of adaptive organizational models able to respond to changing external conditions. The study makes several contributions to the literature. Most importantly, it seeks to add findings to discussion around how SEs operate within constraints by providing real-life empirical data from a context that faces significant institutional and resource barriers. It adds to the current literature by offering insights on organizational capacity, institutions, legitimacy, and adaptability that can be applied to other countries with similar socio-economic contexts. Methodologically, it also makes an effort to move beyond biases of studying only successful SEs, to offer micro-level qualitative analysis of SEs, and to hear unique and potentially alternative perspectives to academic narratives rooted in concept and theory by better understanding how social entrepreneurs themselves perceive their own work and practices.