Through our phones and other personal devices, governments have an unprecedented ability to collect data on our whereabouts, conversations, habits, purchases, and connections. Many are concerned that this new level of surveillance will impede free speech and the ability of social movements to organize. At the same time, however, illegal groups and networks use these same devices to organize, recruit, and do harm. Surveillance of these “dark networks” can do much to protect society at large. This conversation grapples with how a democratic society strives to achieve an acceptable tradeoff between individual privacy rights, the rights of free speech, and national security.