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This paper investigates how retailers at different stages of e-commerce maturity evaluate their entry to e-commerce activities. The study was conducted using qualitative approach interviewing 16 retailers in Saudi Arabia. It comes up with 22 factors that are believed the most influencing factors for retailers in Saudi Arabia. Interestingly, there seem to be differences between retailers in companies at different maturity stages in terms of having different attitudes regarding the issues of using e-commerce. The businesses that have reached a high stage of e-commerce maturity provide practical evidence of positive and optimistic attitudes and practices regarding use of e-commerce, whereas the businesses that have not reached higher levels of maturity provide practical evidence of more negative and pessimistic attitudes and practices. The study, therefore, should contribute to efforts leading to greater e-commerce development in Saudi Arabia and other countries with similar context.