To enable businesses to maximise value and achieve benefits from electronic commerce, it is imperative to identify, analyse and overcome challenges that lie ahead those engaging in conducting the business electronically. The research presented in this paper reports on the pitfalls – challenges of electronic commerce encountered among the top 500 Australian publicly listed companies. The results showed that the most encountered challenges among large corporations include a lack of e-commerce knowledge, technology cost, acquiring IT skilled people, a lack of e-commerce infrastructure, security, as well as making the business known to users, customer service, budgetary constraints, etc. It has also been established that participating companies from the industries with the highest response rate to the questionnaire have encountered similar challenges in their paths of implementation of electronic commerce. However, despite the fact that the encountered challenges among participating companies were similar, the analysis have shown that different industries have experienced different impacts from the challenges they met.