The Intelligence Community Studies Board of the National Academies of Sciences, Engineering, and Medicine convened a workshop on August 9-10, 2017 to examine challenges in machine generation of analytic products from multi-source data. Workshop speakers and participants discussed research challenges related to machine-based methods for generating analytic products and for automating the evaluation of these products, with special attention to learning from small data, using multi-source data, adversarial learning, and understanding the human-machine relationship. This publication summarizes the presentations and discussions from the workshop.