Some historical and current trends in reflective practice (RP), artificial intelligence (AI), and engineering design (ED) are presented and compared. Human artistry, context, and connectionist approaches to knowledge are the common threads highlighted. ED is considered to be a type of RP and AI a part of RP. This is supported by an analysis of the transformation processes involved in each. AI and systems are presented as approaches for the formalization of RP at the technical and conceptual levels, respectively. Interconnectedness in a hierarchical fashion and purposeful process loops are defined as the key ingredients of a systems approach. AI techniques that could support a range of ED categories (case-based reasoning, decomposition, and transformation) are identified, as are the wider RP approaches that subsume those categories. The ED, AI, and RP categories are identified as spanning from routine to creative, connectionist to cognitivist, and intuitive to deliberate, respectively.