This article draws attention to staffing and retention challenges that teachers face in rural schools in Eswatini. Despite policies and strategies developed by the Ministry of Education and Training, retention and staffing challenges continue unabated in rural schools. The continuing challenges indicate that limited success is achieved with the implementation of staffing and retention strategies. Drawing on staffing and retention literature, coupled with empirical data derived from teachers and head teachers in the Lubombo Region in Eswatini, this article proposes an alternative, multifaceted contextual approach to reducing staffing and retention challenges. A focus on lived rural and teaching experiences at rural schools offsets the abstract and one-dimensional universal approach to staffing and retaining teachers adopted by the office of the Teaching Service Commission in the Ministry of Education and Training in Eswatini. The article recommends that the office of the Teaching Service Commission should follow a context-specific differentiated approach based on thick analysis of staffing and retention challenges of teachers in rural schools.