Researchers travel on paths of knowledge throughout life and the outcomes of rigorous scientific investigation result in contributions of new knowledge to the world. The Information Systems (IS) discipline is particularly suited for contributing to digital innovations and the corresponding knowledge growth. IS research develops not only knowledge in the form of understanding and designing digital technologies but also the implementation and use of actual socio-technical systems. In this review, the authors integrate the current thinking in the design science research (DSR) literature around the conceptual and methodological foundations of these high-level topics into a conceptual knowledge path framework. The authors position DSR at the intersection of science and technology where the interplay of descriptive and prescriptive knowledge is most active. They delineate the various forms of prescriptive design knowledge and examine the knowledge paths that utilize and produce the varied forms of knowledge in a DSR project. They define, analyze, and expand the ideas of knowledge gaps and journeys and argue that more attention to design postulates in DSR along the outlined knowledge paths can contribute to an increase in actionable and sustainable digital innovations within the IS discipline. By doing so, the authors aim to guide and inspire design-oriented IS researchers to actively and deliberately consider and incorporate a greater variety of existing knowledge into their designs, reflect even more thoroughly and systematically on their knowledge usage and contributions, and explicate and document these reflections in their publications.