Optimization of BGP Convergence and Prefix Security in IP/MPLS Networks

Multi-Protocol Label Switching-based networks are the backbone of the operation of the Internet, that communicates through the use of the Border Gateway Protocol which connects distinct networks, referred to as Autonomous Systems, together. As the technology matures, so does the challenges caused by the extreme growth rate of the Internet. The amount of BGP prefixes required to facilitate such an increase in connectivity introduces multiple new critical issues, such as with the scalability and the security of the aforementioned Border Gateway Protocol. Illustration of an implementation of an IP/MPLS core transmission network is formed through the introduction of the four main pillars of an Autonomous System: Multi-Protocol Label Switching, Border Gateway Protocol, Open Shortest Path First and the Resource Reservation Protocol. The symbiosis of these technologies is used to introduce the practicalities of operating an IP/MPLS-based ISP network with traffic engineering and fault-resilience at heart. The first research objective of this thesis is to determine whether the deployment of a new BGP feature, which is referred to as BGP Prefix Independent Convergence (PIC), within AS16086 would be a worthwhile endeavour. This BGP extension aims to reduce the convergence delay of BGP Prefixes inside of an IP/MPLS Core Transmission Network, thus improving the networks resilience against faults. Simultaneously, the second research objective was to research the available mechanisms considering the protection of BGP Prefixes, such as with the implementation of the Resource Public Key Infrastructure and the Artemis BGP Monitor for proactive and reactive security of BGP prefixes within AS16086. The future prospective deployment of BGPsec is discussed to form an outlook to the future of IP/MPLS network design. As the trust-based nature of BGP as a protocol has become a distinct vulnerability, thus necessitating the use of various technologies to secure the communications between the Autonomous Systems that form the network to end all networks, the Internet

BGP Routing Information Authentication

Import 05/08/2014Diplomová práce se zabývá prozkoumáním a zdokumentováním „problematiky“ standardizace a implementace infrastruktury Secure BGP a RPKI pro autorizaci síťových prefixů ze zdrojových autonomních systémů. Tato standardizace si klade za cíl zlepšit zabezpečení BGP infrastruktury pomocí certifikace přidělených čísel autonomních systémů rozsahů IP adres jednotlivým držitelům těchto zdrojů. Další dílčí částí této diplomové práce je ověření a nasazení vyhledaných nástrojů pro implementaci infrastruktury RPKI, které jsou dále porovnány z hlediska rychlosti validace jednotlivých sítí.This thesis deals with analyze and documenting problem of standardization and implementation SecureBGP and RPKI infrastructure for authorization of network prefixes from source autonomous systems. Aim of this standardization is improve security of BGP infrastructure by using certification of autonomous system numbers and ranges of IP addresses allocated to each holder these resources. Other part of this thesis is verified and deployment of matching tools for implementing RPKI infrastructure and then these tools are compared in terms of speed validation of networks prefixes.460 - Katedra informatikyvelmi dobř

Novel architectures and strategies for security offloading

Internet has become an indispensable and powerful tool in our modern society. Its ubiquitousness, pervasiveness and applicability have fostered paradigm changes around many aspects of our lives. This phenomena has positioned the network and its services as fundamental assets over which we rely and trust. However, Internet is far from being perfect. It has considerable security issues and vulnerabilities that jeopardize its main core functionalities with negative impact over its players. Furthermore, these vulnerabilities¿ complexities have been amplified along with the evolution of Internet user mobility. In general, Internet security includes both security for the correct network operation and security for the network users and endpoint devices. The former involves the challenges around the Internet core control and management vulnerabilities, while the latter encompasses security vulnerabilities over end users and endpoint devices. Similarly, Internet mobility poses major security challenges ranging from routing complications, connectivity disruptions and lack of global authentication and authorization. The purpose of this thesis is to present the design of novel architectures and strategies for improving Internet security in a non-disruptive manner. Our novel security proposals follow a protection offloading approach. The motives behind this paradigm target the further enhancement of the security protection while minimizing the intrusiveness and disturbance over the Internet routing protocols, its players and users. To accomplish such level of transparency, the envisioned solutions leverage on well-known technologies, namely, Software Defined Networks, Network Function Virtualization and Fog Computing. From the Internet core building blocks, we focus on the vulnerabilities of two key routing protocols that play a fundamental role in the present and the future of the Internet, i.e., the Border Gateway Protocol (BGP) and the Locator-Identifier Split Protocol (LISP). To this purpose, we first investigate current BGP vulnerabilities and countermeasures with emphasis in an unresolved security issue defined as Route Leaks. Therein, we discuss the reasons why different BGP security proposals have failed to be adopted, and the necessity to propose innovative solutions that minimize the impact over the already deployed routing solution. To this end, we propose pragmatic security methodologies to offload the protection with the following advantages: no changes to the BGP protocol, neither dependency on third party information nor on third party security infrastructure, and self-beneficial. Similarly, we research the current LISP vulnerabilities with emphasis on its control plane and mobility support. We leverage its by-design separation of control and data planes to propose an enhanced location-identifier registration process of end point identifiers. This proposal improves the mobility of end users with regards on securing a dynamic traffic steering over the Internet. On the other hand, from the end user and devices perspective we research new paradigms and architectures with the aim of enhancing their protection in a more controllable and consolidated manner. To this end, we propose a new paradigm which shifts the device-centric protection paradigm toward a user-centric protection. Our proposal focus on the decoupling or extending of the security protection from the end devices toward the network edge. It seeks the homogenization of the enforced protection per user independently of the device utilized. We further investigate this paradigm in a mobility user scenario. Similarly, we extend this proposed paradigm to the IoT realm and its intrinsic security challenges. Therein, we propose an alternative to protect both the things, and the services that leverage from them by consolidating the security at the network edge. We validate our proposal by providing experimental results from prof-of-concepts implementations.Internet se ha convertido en una poderosa e indispensable herramienta para nuestra sociedad moderna. Su omnipresencia y aplicabilidad han promovido grandes cambios en diferentes aspectos de nuestras vidas. Este fenómeno ha posicionado a la red y sus servicios como activos fundamentales sobre los que contamos y confiamos. Sin embargo, Internet está lejos de ser perfecto. Tiene considerables problemas de seguridad y vulnerabilidades que ponen en peligro sus principales funcionalidades. Además, las complejidades de estas vulnerabilidades se han ampliado junto con la evolución de la movilidad de usuarios de Internet y su limitado soporte. La seguridad de Internet incluye tanto la seguridad para el correcto funcionamiento de la red como la seguridad para los usuarios y sus dispositivos. El primero implica los desafíos relacionados con las vulnerabilidades de control y gestión de la infraestructura central de Internet, mientras que el segundo abarca las vulnerabilidades de seguridad sobre los usuarios finales y sus dispositivos. Del mismo modo, la movilidad en Internet plantea importantes desafíos de seguridad que van desde las complicaciones de enrutamiento, interrupciones de la conectividad y falta de autenticación y autorización globales. El propósito de esta tesis es presentar el diseño de nuevas arquitecturas y estrategias para mejorar la seguridad de Internet de una manera no perturbadora. Nuestras propuestas de seguridad siguen un enfoque de desacople de la protección. Los motivos detrás de este paradigma apuntan a la mejora adicional de la seguridad mientras que minimizan la intrusividad y la perturbación sobre los protocolos de enrutamiento de Internet, sus actores y usuarios. Para lograr este nivel de transparencia, las soluciones previstas aprovechan nuevas tecnologías, como redes definidas por software (SDN), virtualización de funciones de red (VNF) y computación en niebla. Desde la perspectiva central de Internet, nos centramos en las vulnerabilidades de dos protocolos de enrutamiento clave que desempeñan un papel fundamental en el presente y el futuro de Internet, el Protocolo de Puerta de Enlace Fronterizo (BGP) y el Protocolo de Separación Identificador/Localizador (LISP ). Para ello, primero investigamos las vulnerabilidades y medidas para contrarrestar un problema no resuelto en BGP definido como Route Leaks. Proponemos metodologías pragmáticas de seguridad para desacoplar la protección con las siguientes ventajas: no cambios en el protocolo BGP, cero dependencia en la información de terceros, ni de infraestructura de seguridad de terceros, y de beneficio propio. Del mismo modo, investigamos las vulnerabilidades actuales sobre LISP con énfasis en su plano de control y soporte de movilidad. Aprovechamos la separacçón de sus planos de control y de datos para proponer un proceso mejorado de registro de identificadores de ubicación y punto final, validando de forma segura sus respectivas autorizaciones. Esta propuesta mejora la movilidad de los usuarios finales con respecto a segurar un enrutamiento dinámico del tráfico a través de Internet. En paralelo, desde el punto de vista de usuarios finales y dispositivos investigamos nuevos paradigmas y arquitecturas con el objetivo de mejorar su protección de forma controlable y consolidada. Con este fin, proponemos un nuevo paradigma hacia una protección centrada en el usuario. Nuestra propuesta se centra en el desacoplamiento o ampliación de la protección de seguridad de los dispositivos finales hacia el borde de la red. La misma busca la homogeneización de la protección del usuario independientemente del dispositivo utilizado. Además, investigamos este paradigma en un escenario con movilidad. Validamos nuestra propuesta proporcionando resultados experimentales obtenidos de diferentes experimentos y pruebas de concepto implementados.Postprint (published version

Novel architectures and strategies for security offloading

Internet has become an indispensable and powerful tool in our modern society. Its ubiquitousness, pervasiveness and applicability have fostered paradigm changes around many aspects of our lives. This phenomena has positioned the network and its services as fundamental assets over which we rely and trust. However, Internet is far from being perfect. It has considerable security issues and vulnerabilities that jeopardize its main core functionalities with negative impact over its players. Furthermore, these vulnerabilities¿ complexities have been amplified along with the evolution of Internet user mobility. In general, Internet security includes both security for the correct network operation and security for the network users and endpoint devices. The former involves the challenges around the Internet core control and management vulnerabilities, while the latter encompasses security vulnerabilities over end users and endpoint devices. Similarly, Internet mobility poses major security challenges ranging from routing complications, connectivity disruptions and lack of global authentication and authorization. The purpose of this thesis is to present the design of novel architectures and strategies for improving Internet security in a non-disruptive manner. Our novel security proposals follow a protection offloading approach. The motives behind this paradigm target the further enhancement of the security protection while minimizing the intrusiveness and disturbance over the Internet routing protocols, its players and users. To accomplish such level of transparency, the envisioned solutions leverage on well-known technologies, namely, Software Defined Networks, Network Function Virtualization and Fog Computing. From the Internet core building blocks, we focus on the vulnerabilities of two key routing protocols that play a fundamental role in the present and the future of the Internet, i.e., the Border Gateway Protocol (BGP) and the Locator-Identifier Split Protocol (LISP). To this purpose, we first investigate current BGP vulnerabilities and countermeasures with emphasis in an unresolved security issue defined as Route Leaks. Therein, we discuss the reasons why different BGP security proposals have failed to be adopted, and the necessity to propose innovative solutions that minimize the impact over the already deployed routing solution. To this end, we propose pragmatic security methodologies to offload the protection with the following advantages: no changes to the BGP protocol, neither dependency on third party information nor on third party security infrastructure, and self-beneficial. Similarly, we research the current LISP vulnerabilities with emphasis on its control plane and mobility support. We leverage its by-design separation of control and data planes to propose an enhanced location-identifier registration process of end point identifiers. This proposal improves the mobility of end users with regards on securing a dynamic traffic steering over the Internet. On the other hand, from the end user and devices perspective we research new paradigms and architectures with the aim of enhancing their protection in a more controllable and consolidated manner. To this end, we propose a new paradigm which shifts the device-centric protection paradigm toward a user-centric protection. Our proposal focus on the decoupling or extending of the security protection from the end devices toward the network edge. It seeks the homogenization of the enforced protection per user independently of the device utilized. We further investigate this paradigm in a mobility user scenario. Similarly, we extend this proposed paradigm to the IoT realm and its intrinsic security challenges. Therein, we propose an alternative to protect both the things, and the services that leverage from them by consolidating the security at the network edge. We validate our proposal by providing experimental results from prof-of-concepts implementations.Internet se ha convertido en una poderosa e indispensable herramienta para nuestra sociedad moderna. Su omnipresencia y aplicabilidad han promovido grandes cambios en diferentes aspectos de nuestras vidas. Este fenómeno ha posicionado a la red y sus servicios como activos fundamentales sobre los que contamos y confiamos. Sin embargo, Internet está lejos de ser perfecto. Tiene considerables problemas de seguridad y vulnerabilidades que ponen en peligro sus principales funcionalidades. Además, las complejidades de estas vulnerabilidades se han ampliado junto con la evolución de la movilidad de usuarios de Internet y su limitado soporte. La seguridad de Internet incluye tanto la seguridad para el correcto funcionamiento de la red como la seguridad para los usuarios y sus dispositivos. El primero implica los desafíos relacionados con las vulnerabilidades de control y gestión de la infraestructura central de Internet, mientras que el segundo abarca las vulnerabilidades de seguridad sobre los usuarios finales y sus dispositivos. Del mismo modo, la movilidad en Internet plantea importantes desafíos de seguridad que van desde las complicaciones de enrutamiento, interrupciones de la conectividad y falta de autenticación y autorización globales. El propósito de esta tesis es presentar el diseño de nuevas arquitecturas y estrategias para mejorar la seguridad de Internet de una manera no perturbadora. Nuestras propuestas de seguridad siguen un enfoque de desacople de la protección. Los motivos detrás de este paradigma apuntan a la mejora adicional de la seguridad mientras que minimizan la intrusividad y la perturbación sobre los protocolos de enrutamiento de Internet, sus actores y usuarios. Para lograr este nivel de transparencia, las soluciones previstas aprovechan nuevas tecnologías, como redes definidas por software (SDN), virtualización de funciones de red (VNF) y computación en niebla. Desde la perspectiva central de Internet, nos centramos en las vulnerabilidades de dos protocolos de enrutamiento clave que desempeñan un papel fundamental en el presente y el futuro de Internet, el Protocolo de Puerta de Enlace Fronterizo (BGP) y el Protocolo de Separación Identificador/Localizador (LISP ). Para ello, primero investigamos las vulnerabilidades y medidas para contrarrestar un problema no resuelto en BGP definido como Route Leaks. Proponemos metodologías pragmáticas de seguridad para desacoplar la protección con las siguientes ventajas: no cambios en el protocolo BGP, cero dependencia en la información de terceros, ni de infraestructura de seguridad de terceros, y de beneficio propio. Del mismo modo, investigamos las vulnerabilidades actuales sobre LISP con énfasis en su plano de control y soporte de movilidad. Aprovechamos la separacçón de sus planos de control y de datos para proponer un proceso mejorado de registro de identificadores de ubicación y punto final, validando de forma segura sus respectivas autorizaciones. Esta propuesta mejora la movilidad de los usuarios finales con respecto a segurar un enrutamiento dinámico del tráfico a través de Internet. En paralelo, desde el punto de vista de usuarios finales y dispositivos investigamos nuevos paradigmas y arquitecturas con el objetivo de mejorar su protección de forma controlable y consolidada. Con este fin, proponemos un nuevo paradigma hacia una protección centrada en el usuario. Nuestra propuesta se centra en el desacoplamiento o ampliación de la protección de seguridad de los dispositivos finales hacia el borde de la red. La misma busca la homogeneización de la protección del usuario independientemente del dispositivo utilizado. Además, investigamos este paradigma en un escenario con movilidad. Validamos nuestra propuesta proporcionando resultados experimentales obtenidos de diferentes experimentos y pruebas de concepto implementados

A pragmatic approach toward securing inter-domain routing

Internet security poses complex challenges at different levels, where even the basic requirement of availability of Internet connectivity becomes a conundrum sometimes. Recent Internet service disruption events have made the vulnerability of the Internet apparent, and exposed the current limitations of Internet security measures as well. Usually, the main cause of such incidents, even in the presence of the security measures proposed so far, is the unintended or intended exploitation of the loop holes in the protocols that govern the Internet. In this thesis, we focus on the security of two different protocols that were conceived with little or no security mechanisms but play a key role both in the present and the future of the Internet, namely the Border Gateway Protocol (BGP) and the Locator Identifier Separation Protocol (LISP). The BGP protocol, being the de-facto inter-domain routing protocol in the Internet, plays a crucial role in current communications. Due to lack of any intrinsic security mechanism, it is prone to a number of vulnerabilities that can result in partial paralysis of the Internet. In light of this, numerous security strategies were proposed but none of them were pragmatic enough to be widely accepted and only minor security tweaks have found the pathway to be adopted. Even the recent IETF Secure Inter-Domain Routing (SIDR) Working Group (WG) efforts including, the Resource Public Key Infrastructure (RPKI), Route Origin authorizations (ROAs), and BGP Security (BGPSEC) do not address the policy related security issues, such as Route Leaks (RL). Route leaks occur due to violation of the export routing policies among the Autonomous Systems (ASes). Route leaks not only have the potential to cause large scale Internet service disruptions but can result in traffic hijacking as well. In this part of the thesis, we examine the route leak problem and propose pragmatic security methodologies which a) require no changes to the BGP protocol, b) are neither dependent on third party information nor on third party security infrastructure, and c) are self-beneficial regardless of their adoption by other players. Our main contributions in this part of the thesis include a) a theoretical framework, which, under realistic assumptions, enables a domain to autonomously determine if a particular received route advertisement corresponds to a route leak, and b) three incremental detection techniques, namely Cross-Path (CP), Benign Fool Back (BFB), and Reverse Benign Fool Back (R-BFB). Our strength resides in the fact that these detection techniques solely require the analytical usage of in-house control-plane, data-plane and direct neighbor relationships information. We evaluate the performance of the three proposed route leak detection techniques both through real-time experiments as well as using simulations at large scale. Our results show that the proposed detection techniques achieve high success rates for countering route leaks in different scenarios. The motivation behind LISP protocol has shifted over time from solving routing scalability issues in the core Internet to a set of vital use cases for which LISP stands as a technology enabler. The IETF's LISP WG has recently started to work toward securing LISP, but the protocol still lacks end-to-end mechanisms for securing the overall registration process on the mapping system ensuring RLOC authorization and EID authorization. As a result LISP is unprotected against different attacks, such as RLOC spoofing, which can cripple even its basic functionality. For that purpose, in this part of the thesis we address the above mentioned issues and propose practical solutions that counter them. Our solutions take advantage of the low technological inertia of the LISP protocol. The changes proposed for the LISP protocol and the utilization of existing security infrastructure in our solutions enable resource authorizations and lay the foundation for the needed end-to-end security

Improving the accuracy of spoofed traffic inference in inter-domain traffic

Ascertaining that a network will forward spoofed traffic usually requires an active probing vantage point in that network, effectively preventing a comprehensive view of this global Internet vulnerability. We argue that broader visibility into the spoofing problem may lie in the capability to infer lack of Source Address Validation (SAV) compliance from large, heavily aggregated Internet traffic data, such as traffic observable at Internet Exchange Points (IXPs). The key idea is to use IXPs as observatories to detect spoofed packets, by leveraging Autonomous System (AS) topology knowledge extracted from Border Gateway Protocol (BGP) data to infer which source addresses should legitimately appear across parts of the IXP switch fabric. In this thesis, we demonstrate that the existing literature does not capture several fundamental challenges to this approach, including noise in BGP data sources, heuristic AS relationship inference, and idiosyncrasies in IXP interconnec- tivity fabrics. We propose Spoofer-IX, a novel methodology to navigate these challenges, leveraging Customer Cone semantics of AS relationships to guide precise classification of inter-domain traffic as In-cone, Out-of-cone ( spoofed ), Unverifiable, Bogon, and Unas- signed. We apply our methodology on extensive data analysis using real traffic data from two distinct IXPs in Brazil, a mid-size and a large-size infrastructure. In the mid-size IXP with more than 200 members, we find an upper bound volume of Out-of-cone traffic to be more than an order of magnitude less than the previous method inferred on the same data, revealing the practical importance of Customer Cone semantics in such analysis. We also found no significant improvement in deployment of SAV in networks using the mid-size IXP between 2017 and 2019. In hopes that our methods and tools generalize to use by other IXPs who want to avoid use of their infrastructure for launching spoofed-source DoS attacks, we explore the feasibility of scaling the system to larger and more diverse IXP infrastructures. To promote this goal, and broad replicability of our results, we make the source code of Spoofer-IX publicly available. This thesis illustrates the subtleties of scientific assessments of operational Internet infrastructure, and the need for a community focus on reproducing and repeating previous methods.A constatação de que uma rede encaminhará tráfego falsificado geralmente requer um ponto de vantagem ativo de medição nessa rede, impedindo efetivamente uma visão abrangente dessa vulnerabilidade global da Internet. Isto posto, argumentamos que uma visibilidade mais ampla do problema de spoofing pode estar na capacidade de inferir a falta de conformidade com as práticas de Source Address Validation (SAV) a partir de dados de tráfego da Internet altamente agregados, como o tráfego observável nos Internet Exchange Points (IXPs). A ideia chave é usar IXPs como observatórios para detectar pacotes falsificados, aproveitando o conhecimento da topologia de sistemas autônomos extraído dos dados do protocolo BGP para inferir quais endereços de origem devem aparecer legitimamente nas comunicações através da infra-estrutura de um IXP. Nesta tese, demonstramos que a literatura existente não captura diversos desafios fundamentais para essa abordagem, incluindo ruído em fontes de dados BGP, inferência heurística de relacionamento de sistemas autônomos e características específicas de interconectividade nas infraestruturas de IXPs. Propomos o Spoofer-IX, uma nova metodologia para superar esses desafios, utilizando a semântica do Customer Cone de relacionamento de sistemas autônomos para guiar com precisão a classificação de tráfego inter-domínio como In-cone, Out-of-cone ( spoofed ), Unverifiable, Bogon, e Unassigned. Aplicamos nossa metodologia em análises extensivas sobre dados reais de tráfego de dois IXPs distintos no Brasil, uma infraestrutura de médio porte e outra de grande porte. No IXP de tamanho médio, com mais de 200 membros, encontramos um limite superior do volume de tráfego Out-of-cone uma ordem de magnitude menor que o método anterior inferiu sob os mesmos dados, revelando a importância prática da semântica do Customer Cone em tal análise. Além disso, não encontramos melhorias significativas na implantação do Source Address Validation (SAV) em redes usando o IXP de tamanho médio entre 2017 e 2019. Na esperança de que nossos métodos e ferramentas sejam aplicáveis para uso por outros IXPs que desejam evitar o uso de sua infraestrutura para iniciar ataques de negação de serviço através de pacotes de origem falsificada, exploramos a viabilidade de escalar o sistema para infraestruturas IXP maiores e mais diversas. Para promover esse objetivo e a ampla replicabilidade de nossos resultados, disponibilizamos publicamente o código fonte do Spoofer-IX. Esta tese ilustra as sutilezas das avaliações científicas da infraestrutura operacional da Internet e a necessidade de um foco da comunidade na reprodução e repetição de métodos anteriores

Security Implications of Insecure DNS Usage in the Internet

The Domain Name System (DNS) provides domain-to-address lookup-services used by almost all internet applications. Because of this ubiquitous use of the DNS, attacks against the DNS have become more and more critical. However, in the past, studies of DNS security have been mostly conducted against individual protocols and applications. In this thesis, we perform the first comprehensive evaluation of DNS-based attacks against a wide range of internet applications, ranging from time-synchronisation via NTP over internet resource management to security mechanisms. We show how to attack those applications by exploiting various weaknesses in the DNS. These attacks are based on both, already known weaknesses which are adapted to new attacks, as well as previously unknown attack vectors which have been found during the course of this thesis. We evaluate our attacks and provide the first taxonomy of DNS applications, to show how adversaries can systematically develop attacks exploiting the DNS. We analyze the attack surface created by our attacks in the internet and find that a significant number of applications and systems can be attacked. We work together with the developers of the vulnerable applications to develop patches and general countermeasures which can be applied by various parties to block our attacks. We also provide conceptual insights into the root causes allowing our attacks to help with the development of new applications and standards. The findings of this thesis are published in in 4 full-paper publications and 2 posters at international academic conferences. Additionally, we disclose our finding to developers which has lead to the registration of 8 Common Vulnerabilities and Exposures identifiers (CVE IDs) and patches in 10 software implementations. To raise awareness, we also presented our findings at several community meetings and via invited articles

Deniable Key Exchanges for Secure Messaging

Despite our increasing reliance on digital communication, much of our online discourse lacks any security or privacy protections. Almost no email messages sent today provide end-to-end security, despite privacy-enhancing technologies being available for decades. Recent revelations by Edward Snowden of government surveillance have highlighted this disconnect between the importance of our digital communications and the lack of available secure messaging tools. In response to increased public awareness and demand, the market has recently been flooded with new applications claiming to provide security and privacy guarantees. Unfortunately, the urgency with which these tools are being developed and marketed has led to inferior or insecure products, grandiose claims of unobtainable features, and widespread confusion about which schemes can be trusted. Meanwhile, there remains disagreement in the academic community over the definitions and desirability of secure messaging features. This incoherent vision is due in part to the lack of a broad perspective of the literature. One of the most contested properties is deniability—the plausible assertion that a user did not send a message or participate in a conversation. There are several subtly different definitions of deniability in the literature, and no available secure messaging scheme meets all definitions simultaneously. Deniable authenticated key exchanges (DAKEs), the primary cryptographic tool responsible for deniability in a secure messaging scheme, are also often unsuitable for use in emerging applications such as smartphone communications due to unreasonable resource or network requirements. In this thesis, we provide a guide for a practitioner seeking to implement deniable secure messaging systems. We examine dozens of existing secure messaging protocols, both proposed and implemented, and find that they achieve mixed results in terms of security. This systematization of knowledge serves as a resource for understanding the current state-of-the-art approaches. We survey formalizations of deniability in the secure messaging context, as well as the properties of existing DAKEs. We construct several new practical DAKEs with the intention of providing deniability in modern secure messaging environments. Notably, we introduce Spawn, the first non-interactive DAKE that offers forward secrecy and achieves deniability against both offline and online judges; Spawn can be used to improve the deniability properties of the popular TextSecure secure messaging application. We prove the security of our new constructions in the generalized universal composability (GUC) framework. To demonstrate the practicality of our protocols, we develop and compare open-source instantiations that remain secure without random oracles