Countries in Southern Africa face many social, development, economic, trade, education, health, diplomatic, defense, security, and political challenges. These countries also have a history of colonialism, liberatory struggle, and independence. Although the language of business and schooling is English for most of the countries, there are still huge chunks of the population that are illiterate and functionally illiterate. People also speak one or more indigenous languages. The majority of the countries in this region have high levels of unemployment and poverty. Ensuring that psychological assessments are appropriate and fair in these contexts is a huge challenge. When this challenge occurs in a poorly resourced setting against the background of social inequality, practitioners need to be highly resourceful, as well as culturally sensitive and ethically aware. This chapter discusses the historical development of psychological assessment in South Africa, Zambia, Botswana, and Zimbabwe demonstrating how the social and contextual factors interacted with assessment.