Healthcare today provides an especially rich context for the intertwined transformation of work and the technologies of work, which need to be understood in tandem. Advances in artificial intelligence, robotics, the internet of things, and computational science promise to transform healthcare. The slow speed of organizational and professional change compared to the rapid innovation of healthcare technology makes it a compelling context for engaged scholarship. Sorting through the promise, hype, and reality of the datafication and automation of health and healthcare presents challenges that communication scholarship can help address. In this essay, I share my own healthcare paperwork and information technology story and discuss implications for the study of health information technology, automation, and healthcare work.