It has been shown that national, regional, and local needs must be taken into account in successful IT (information technology) education. Educational programs need to be contextualized to utilize particular strengths of their context of deployment, and they need to meet particular educational, social, and workforce strategic objectives. Based on those premises, Tumaini University in Iringa, Tanzania, started a contextualized IT program in 2007. To date, two cohorts of students have graduated, and the program has somewhat stabilized. This joint paper reports participant observation over a time-span of four and a half years, as analyzed by the IT program’s four previous heads of department, ICT director of the college, and the college’s director for research and postgraduate studies. The paper identifies 8 major success factors and 40 SWOT analysis items for IT education development. Our analysis makes 18 pedagogical, administrative, curricular, technical, sociocultural, and financial recommendations for development of IT education in the Tanzanian context.