One of the ongoing global projects remains how to deliver basic services for the less privileged and marginalized groups around the world who are exposed to all manners of social vices. Arguments have evolved around using social enterprises to tackle this development as it has been suggested that the enterprise is fundamental to any country's economic prosperity, employment creation, poverty alleviation, and sustainable development. Although, the social enterprise recognition is low while their performances remain not too encouraging in Nigeria. This study examined and evaluated the challenges facing social enterprises in Nigeria. These objectives were pursued through four social enterprises studied from different regions of Nigeria. The study adopted a qualitative method to gather data for the research purpose through multiple cases and interview means. Participants were the founders, staff, and beneficiaries of the social enterprises. With the aid of analysis, the findings revealed some of the factors that hampered social enterprises' performance in Nigeria such as insufficient funding, managerial deficiency, inadequate social facilities, corruption, lack of framework conditions, people's misconception about social enterprise, and improper application of digital technology. It was concluded that much is still required to be done in the space of social enterprises in Nigeria and based on this, the study recommends developmental programs in the area of regular orientation while the Government and policymakers should provide an enabling environment to encourage the performance of social enterprises.