Well-trained judicial officers contribute to the effective administration of justice and the rule of law, both of which are sine qua non for sustainable development. The quality of justice in any nation depends on the governance environment and the professional quality of its judicial officers and legal professionals. The Kenyan and Ugandan judiciaries have established judicial training institutes (JTIs) to provide judicial officers with continuous legal training in various areas of law, including gender equality and gender justice. This chapter examines the extent to which the JTIs have focused on providing training that addresses discrimination and unfair treatment of women and other vulnerable groups (gender training) and the potential impact this training may have had on judicial officers’ judgments. Despite favorable constitutions and progressive laws, some gender-biased court decisions are still issued in both countries due to deeply rooted cultural and social biases. Although the gender training is inadequate, and mechanisms for assessing its potential impact are lacking, there is evidence linking some progressive decisions to this limited training. Ongoing robust monitoring and evaluation strategies on the performance of the two JTIs and the gender training are needed to justify continued investment in both.