In Zambia, as elsewhere throughout sub-Saharan Africa, orphaned and vulnerable children (OVC) face multiple physical, emotional, social and psychological challenges which often negatively affect opportunities for educational attainment. REPSSI (Regional Psychosocial Support Initiative), in collaboration with, the University of Cape Town and other African academic institutions, developed the Teachers’ Diploma Program as part of the Mainstreaming Psychosocial Care and Support into Education Systems to provide teachers and school administrators with the knowledge and skills to provide needed support to students and enhance their learning environments. During initial implementation of the Teachers’ Diploma Program in Zambia (2013-2016), qualitative data was collected as a part of larger outcomes and process evaluation. In the current paper, these qualitative data are presented to describe baseline challenges and strengths within the Zambian government school system and early indicators of change during the first ten months of program implementation. These in-depth data provide both teachers’ and students’ experiences and perspectives and are being utilized to further strengthen the Teachers’ Diploma Program as the Zambian Ministry of Education, Science, Vocational Training and Early Childhood moves forward with plans to implement the training at a national level in colleges of teacher education.