The introduction of the subject Mathematical Literacy (ML) as part of the education reform process, led to the development of many large scale in-service programmes designed to train practising teachers to teach the new subject. The purpose of the study is to examine the challenges associated with providing in-service training for teachers of ML, by focusing on one district. We present a case study of one programme that was offered by two different universities in three large-scale funded cohorts in the province of KwaZulu-Natal (KZN). Data for the study was generated by student records, questionnaires and follow up surveys with each school in the district. By considering the success rate as the number of actual qualified teachers in relation to the number that was needed, we quantified the rate at 13%. Some of the factors which were responsible for this low rate are related to the processes of recruitment and selection of the appropriate teachers for the programme; the low pass rate as well as the deployment and management of the graduates at the end of the programme. It is recommended that future large scale teacher training initiatives be jointly managed by the universities and the education authorities, to ensure higher rates of success.