This paper unpacks how the everyday work-care realities and familial dynamics constrain Jua Kali women’s entrepreneurship in Rural Kenya. Drawing on 40 in-depth semi-structured interviews with Jua Kali rural women entrepreneurs and direct observation captured in field photographs, the findings reveal that Jua Kali women negotiate everyday work-care responsibilities for both for their immediate and extended families. They are often constrained by urgent and pressing familial needs –– related to education, health care, welfare for elderly and aging, and childcare costs which leads to a frequent and massive diversion of enterprise funds. When examined through a feminist intersectional analysis, the findings reveal an interplay of gender and class dynamics, with underlying structural, institutional arrangements and multiple societal structures, simultaneously intersecting with other categories of difference in individual women’s lives which further hinder their entrepreneurial activity. The paper extends the critical entrepreneurialism debate and contextualising entrepreneurship research by exposing the work-care realities of women’s entrepreneurs and unmasking the ‘dark side’ of African extended family system from under-explored contexts in the Global South, extend the feminist intersectional perspective and further proposes recommendations and implication for policy. The study proposes implications for policy for holistic and expansive approach to enterprise policy by having sectoral welfare policies (education, healthcare, elderly welfare, and childcare) to solve pressing socio-economic circumstances facing women which curtail their entrepreneurial potential and outcomes.