The integrity of the content a user is exposed to when browsing the web relies on a plethora of non-web technologies and an infrastructure of interdependent hosts, communication technologies, and trust relations. Incidents like the Chinese Great Cannon or the MyEtherWallet attack make it painfully clear: the security of end users hinges on the security of the surrounding infrastructure: routing, DNS, content delivery, and the PKI. There are many competing, but isolated proposals to increase security, from the network up to the application layer. So far, researchers have focused on analyzing attacks and defenses on specific layers. We still lack an evaluation of how, given the status quo of the web, these proposals can be combined, how effective they are, and at what cost the increase of security comes. In this work, we propose a graph-based analysis based on Stackelberg planning that considers a rich attacker model and a multitude of proposals from IPsec to DNSSEC and SRI. Our threat model considers the security of billions of users against attackers ranging from small hacker groups to nation-state actors. Analyzing the infrastructure of the Top 5k Alexa domains, we discover that the security mechanisms currently deployed are ineffective and that some infrastructure providers have a comparable threat potential to nations. We find a considerable increase of security (up to 13% protected web visits) is possible at a relatively modest cost, due to the effectiveness of mitigations at the application and transport layer, which dominate expensive infrastructure enhancements such as DNSSEC and IPsec.

Stackelberg planning is a recent framework where a leader and a follower each choose a plan in the same planning task, the leader's objective being to maximize plan cost for the follower. This formulation naturally captures security-related (leader=defender, follower=attacker) as well as robustness-related (leader=adversarial event, follower=agent) scenarios. Solving Stackelberg planning tasks requires solving many related planning tasks at the follower level (in the worst case, one for every possible leader plan). Here we introduce new methods to tackle this source of complexity, through sharing information across follower tasks. Our evaluation shows that these methods can significantly reduce both the time needed to solve follower tasks and the number of follower tasks that need to be solved in the first place.

Inspired by work on Stackelberg security games, we introduce Stackelberg planning, where a leader player in a classical planning task chooses a minimum-cost action sequence aimed at maximizing the plan cost of a follower player in the same task. Such Stackelberg planning can provide useful analyses not only in planning-based security applications like network penetration testing, but also to measure robustness against perturbances in more traditional planning applications (e. g. with a leader sabotaging road network connections in transportation-type domains). To identify all equilibria---exhibiting the leader’s own-cost-vs.-follower-cost trade-off---we design leader-follower search, a state space search at the leader level which calls in each state an optimal planner at the follower level. We devise simple heuristic guidance, branch-and-bound style pruning, and partial-order reduction techniques for this setting. We run experiments on Stackelberg variants of IPC and pentesting benchmarks. In several domains, Stackelberg planning is quite feasible in practice.

Security in the Internet has historically been added post-hoc, leaving services like email, which, after all, is used by 3.7 billion users, vulnerable to large-scale surveillance. For email alone, there is a multitude of proposals to mitigate known vulnerabilities, ranging from the introduction of completely new protocols to modifications of the communication paths used by big providers. Deciding which measures to deploy requires a deep understanding of the induced benefits, the cost and the resulting effects. This paper proposes the first automated methodology for making formal deployment assessments. Our planning algorithm analyses the impact and cost-efficiency of different known mitigation strategies against an attacker in a formal threat model. This novel formalisation of an infrastructure attacker includes routing, name resolution and application level weaknesses. We apply the methodology to a large-scale scan of the Internet, and assess how protocols like IPsec, DNSSEC, DANE, SMTP STS, SMTP over TLS and other mitigation techniques like server relocation can be combined to improve the confidentiality of email users in 45 combinations of attacker and defender countries and nine cost scenarios. This is the first deployment analysis for mitigation techniques at this scale.