Namibia and South Africa share land and maritime borders and the interrelated structural challenges of poverty and socio-economic inequalities amidst progressive economic growth that are rooted in their apartheid past and contemporary economic development trajectories. Such inequalities are defined along racial, class, gender and other social locations that either grant privilege, power and access to socio-economic opportunities or result in marginalisation, oppression and resource deprivation. The rationale for this article is linked to the historic call for social work to intensify efforts in promoting social and economic equality. Despite Namibia and South Africa’s geographical proximity and their intertwined histories, there is a dearth of social work studies that offer a comparative critical social work perspective on structural inequalities in these former apartheid strongholds. While social work should actively engage in contesting the structural contradictions of poverty and inequalities amidst abundant resources, the reality is often that of the uncritical acceptance of existing socio-political inequalities, such that the profession’s enunciated commitment to social justice becomes perimetric. Thus, the article argues for the inclusion of critical social work approaches in social work education and practice against a backdrop of ideological divides, political trends and contextual factors that limit social workers’ critical and structural level engagement.