In recent years, the Malaysian teachers market makes such a compelling and profitable demographic segment for online business. However, little research has attempted to examine the purchase attitude and behaviour of the teachers. Thus, using the extended Technology Acceptance Model (TAM), this study aims to investigate the effect of perceived usefulness, perceived ease of use, perceived reputation, perceived security and perceived privacy on teachers' trust and consequently on teachers' online purchase intention. This study adopted quantitative approach. Data obtained from a sample of 150 teachers using a self-administered questionnaire, were analysed using Multiple Regression Analysis. The results reveal the perceived ease of use, perceived security and perceived privacy as significant predictors of online trust among teachers, and online trust positively affect the online purchase intention. The results provide empirical evidence on the role of additional constructs and applicability of the extended TAM. The results also offer valuable insights to marketers on how to better serve the huge market of teachers and induce them to purchase online.