Abstract In spite of the significance of uncertainty and risk in strategy, there is still a general lack of attention to their explicit consideration in strategic planning processes. This lack of attention is also obvious in roadmapping in its application to strategic and innovation planning. This paper introduces and explores the concept of risk-aware roadmapping, which explicitly manages uncertainty and risk in roadmapping, and sheds light on what such a process will entail given the factors that influence it. The study adopts a qualitative approach involving in-depth interviews with roadmapping experts and case studies of roadmapping exercises. This paper contributes to knowledge by providing a process that adds three significant steps to the standard risk management process, to suit roadmapping and strategic front-end innovation planning and identifying the risk of missing valuable innovation opportunities, which is very often overlooked in practice. Theoretical implications for organisational sensemaking are identified especially in the use and management of constraints for sensemaking activities such as innovation planning.