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VPNs (Virtual Private Networks) have become an essential privacy-enhancing technology, particularly for at-risk users like dissidents, journalists, NGOs, and others vulnerable to targeted threats. While previous research investigating VPN security has focused on cryptographic strength or traffic leakages, there remains a gap in understanding how lower-level primitives fundamental to VPN operations, like connection tracking, might undermine the security and privacy that VPNs are intended to provide.In this paper, we examine the connection tracking frameworks used in common operating systems, identifying a novel exploit primitive that we refer to as the port shadow. We use the port shadow to build four attacks against VPNs that allow an attacker to intercept and redirect encrypted traffic, de-anonymize a VPN peer, or even portscan a VPN peer behind the VPN server. We build a formal model of modern connection tracking frameworks and identify that the root cause of the port shadow lies in five shared, limited resources. Through bounded model checking, we propose and verify six mitigations in terms of enforcing process isolation. We hope our work leads to more attention on the security aspects of lower-level systems and the implications of integrating them into security-critical applications. 

Information flow tracking was proposed more than 40 years ago to address the limitations of access control mechanisms to guarantee the confidentiality and integrity of information flowing within a system, but has not yet been widely applied in practice for security solutions. Here, we survey and systematize literature on dynamic information flow tracking (DIFT) to discover challenges and opportunities to make it practical and effective for security solutions. We focus on common knowledge in the literature and lingering research gaps from two dimensions— (i) the layer of abstraction where DIFT is implemented (software, software/hardware, or hardware) and (ii) the security goal (confidentiality and/or integrity). We observe that two major limitations hinder the practical application of DIFT for on-the-fly security applications: (i) high implementation overhead and (ii) incomplete information flow tracking (low accuracy). We posit, after review of the literature, that addressing these major impedances via hardware parallelism can potentially unleash DIFT’s great potential for systems security, as it can allow security policies to be implemented in a built-in and standardized fashion. Furthermore, we provide recommendations for the next generation of practical and efficient DIFT systems with an eye towards hardware-supported implementations.