The ability to effectively interrogate our society’s power structure — a key function of a free press — increasingly requires technological understanding. Major digital platforms have deeply affected our economy and our public discourse. Government and corporate surveillance has transformed our sense of privacy and our system of justice. Security flaws put businesses, personal data and even our democratic process at risk.Journalists and technologists have traditionally operated in separate spheres, but collaborative work can enable a more accurate public understanding of these problems and can bring more accountability for privacy and security problems. Technologists have a crucial role to play in advancing journalistic investigations in the digital age, particularly by contributing empirical evidence to a narrative structure.This talk will draw on examples of successful joint work in explaining how to work with reporters to bring privacy and security issues to the public’s attention.