We advocate for a paradigm shift in supporting the information needs of developers, centered around the concept of automated on-demand developer documentation. Currently, developer information needs are fulfilled by asking experts or consulting documentation. Unfortunately, traditional documentation practices are inefficient because of, among others, the manual nature of its creation and the gap between the creators and consumers. We discuss the major challenges we face in realizing such a paradigm shift, highlight existing research that can be leveraged to this end, and promote opportunities for increased convergence in research on software documentation.