Since the public inauguration of the URP (Urban and Regional Planning) Bill in 2009, which is now law (The Urban and Regional Planning Act No. 3 of 2015), urban planning in Zambia has undergone changes. In partnership with the Volunteer Service Overseas (VSO) Federation, the Zambian parliament put into effect pilot urban planning assistance programs to assist districts around the country, including Chipata District in 2011, transition to a more decentralized, integrated and locally-defined approach to urban planning. However, the presence of discrimination, corruption, and negative attitudes towards urban planning engagement, social maladies prominently displayed in Zambian society, pose challenges to implementing the ideal goals of the 2009 URP Bill. The extreme, widespread poverty in Zambia merely exacerbates the propensity towards corrupt and discriminatory behavior, and influences poor attitudes toward urban planning engagement. This paper describes the projects undertaken by the VSO volunteer from the USA between 2011 and 2012 in the light of the specific urban problems facing Chipata District, and discusses the ways the social maladies play out in Zambian society to pose challenges to implementing the recommended changes to the planning system scribed in the 2009 URP Bill.