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As the production of knowledge moves from a linear innovation model in an explanations-oriented world to a networked innovation model in a solutions-oriented world, the practice of design in engineering and industry and the practice of research in academia are getting closer and closer. This proximity is calling for a renewal of the debates on the nature of academic research, on the epistemology of design, and on the relationship between research and design. This is particularly challenging as we concentrate on the specific field of information systems. It is, also, mostly enlightening as we look into the philosophical groundings of both the design disciplines and action research. This chapter attempts to escort the reader in the examination of these issues. It starts with a brief characterization of the two main modes of knowledge production, followed by a debate on the relationships between research and design. It then puts forward a simple philosophical framework that will be used to put in perspective the designerly ways of knowing, their relationship with action research, and the resulting implications on information systems research. The chapter closes with the re-examination, under this new perspective, of some recent debates on topics such as the rigor vs relevance dilemma and the ethical dimension of action research in information systems.