Recently, new approaches to organizational level sustainability management and reporting have emerged in the form of software and web-based applications. At first glance, it appears that such software and web-tools are applicable in small and medium-sized enterprises since they offer user-friendly and cost-effective alternatives to implement, manage and report on company-wide sustainability activities. Nevertheless, it remains academically and practically uncertain if such technologies will be adopted by a great number of SMEs. Using the Technology-Organization-Environment (TOE) model as a theoretical framework and empirical data from a recent survey with 1,250 German SMEs, this paper investigates various firm-internal and external factors that might influence managers’ decisions to adopt or reject this new technology. As a result, this paper can help determine which factors play a role in the adoption of sustainability management software and web-tools in SMEs.