Cybersecurity is often portrayed as a ‘cat and mouse’ game testing the relative technical prowess of the attacker and the defender. However, it can equally be considered a battle of social wits. Negotiation in the cyber realm presents a significantly different dynamic from person-to-person negotiations typical of the boardroom, since there is no chance to read the face of the other side. You may have limited opportunity to negotiate in real time and, you probably will have no ability to ascertain the culture or values of the hacker. With critical infrastructure being under constant attack by hackers – both state sponsored and hobbyists, operators and managers must be prepared to negotiate with cyber terrorists. Our research involves work with managers of critical urban infrastructure to simulate attacks and help them develop a cyber negotiation playbook. This research is supported by MIT’s Internet Policy Research Initiative (IPRI).