Small to medium-sized enterprises (SMEs) have limited power in the Supply Chain Management Network (SCMN), as they come with limited resources to invest in advanced planning systems. This makes it difficult for them to cope with the latest challenges such as mass customization, which places higher demands on the company’s ability to attune its production planning to customers’ wishes and their suppliers in supply chain management. This chapter discusses the challenges (barriers and risks) that SMEs face today based on the findings of a survey that examined the extent of e-commerce adoption in Australia and New Zealand. The findings revealed how technical issues impact two groups of adopters, namely leaders and followers. Leaders refer to businesses that are willing to take risks and invest in IT, whereas followers refer to businesses that were more conscious of their IT investments. We conclude the chapter with key findings and implications to practice.