This study was undertaken to investigate the links between a Master of TESOL program and its graduates' diverse teaching contexts through a questionnaire. It was discovered from the participants' responses which courses were the most contributing, which were irrelevant yet valuable to their teaching, what adjustments were needed as gaps were discovered between what they had learned and their real teaching contexts, whether they believed the outcomes had changed their teaching and contributed to their confidence in teaching, and their comments on their choices. Based on the findings and discussions, a processing model of forging these links is established. In addition, the article also discusses reasons associated with the results, and provides suggestions of solutions for possible implementations of future programs.