Multichannel retailing has emerged as a key strategic issue for most retailers. Yet, while there are many drivers associated with retailers' going multichannel, so too are there technology-related obstacles. By using a multicase approach to understand the key drivers and technology-related obstacles associated with retailers' moving to multichannel retailing, our study makes two key contributions. First, we extend prior theory by providing novel empirical insights into the main drivers underpinning retailers' use of a multichannel strategy. We find that meeting customer needs and increasing sales are the primary drivers behind retailers' use of the strategy, although there is diversity in the way retailers respond to these motives. Second, we provide empirical support for a proposed theoretical framework that summarizes the key technology-related obstacles retailers encounter, by stage of implementation, when going multichannel. The framework reveals that retailers face technology-related obstacles when implementing a multichannel strategy due to the need to switch/acquire resources and achieve channel integration. Furthermore, the framework highlights that these resource and channel integration issues are often interrelated with one another and with other staff engagement and cultural issues, vary by retailer and stage of implementation, and pose greater obstacles to retailers' use of new and multiple channels than the extant literature suggests.