In the last three decades, the nature of technology incorporation into career and technical education (CTE) training has changed. Technology used in the field has been supplemented by technology used in training per se. Technology has increasingly infiltrated into today’s social arena, workplace, and education. In response, the use of technology in CTE reflects both educational philosophy and societal context. Teaching about technology differs from teaching with technology; the former focuses on content, and the latter focuses on process. The nature of CTE, instruction as a whole, and technology in particular, have shaped how CTE faculty teach with technology over the past three decades. In this period, technology-enhanced CTE instruction has moved from top-down to broad-based, from one-directional to two- and multi-directional communication, from static to dynamic, from programmer-dependent to content-dependent, and from administrative- to learning-oriented. Representative practices and a model of CTE technology-enhanced instruction are discussed.