Following the availability of antiretrovirals (ARVs) for the treatment of HIV in the public sector from 2004 to 2008, thousands of multidisciplinary health care workers were trained by RHRU on HIV care and ARVs on behalf of the South African Department of Health. To ascertain if, and to what extent, transfer of learning had occurred, a case study approach was used involving a sample of seventy alumni. Data was collected via questionnaire, interview and observation tools. Data collected suggests that transfer of learning took place at some level for most alumni but was weakest with non clinical staff in ARV sites and ward based staff, many of whom did not feel that they treated HIV patients. The study concludes that the ‘one size fits all’ approach preferred by the Department of Health did not support effective transfer of learning for all alumni mainly due to the subsequent inappropriate training design for many participants and the impact of this on motivation and connection to a less enabling transfer climate. To optimize the possibility of transfer, therefore, HIV training should be specifically designed for the learning needs of each cadre of health care worker with clear expected changes to practice for participants, linked to supporting transfer environments post training.