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The research assesses the challenges deterring the progress of women’s small-scale businesses in Rwanda. It was guided by the following specific objectives: identify challenges faced by women’s small-scale businesses in Rwanda and assess how those challenges affect women’s small-scale businesses' progress. Findings were collected from 109 respondents who have been running small-scale businesses over a period ranging from one to three years. Results were collected through a questionnaire and desk review and quantitatively analyzed. The findings shed light on the challenges which small-scale women entrepreneurs face namely family expenses (53.2%), drunkenness (67%), family conflicts (93.6%), financial illiteracy (100%), and poverty (100%). The above-mentioned challenges affect small-scale businesses in that women entrepreneurs find themselves mixing up businesses and family expenses. Family conflicts were also highlighted to be another cause of business failure in that women who conflict with their husbands cannot easily prosper in their businesses. In addition, financial illiteracy makes them unable to assess their profit and find their businesses stagnant or closing. Thus, there is a need to provide support to small-scale businesswomen about how to assess business progress, and calculate their interest rate so that they may come up with financial skills. This would enable them to align their daily family expenses with their business interest. Once properly implemented, it would decrease the business failure rate.