--- type: Whitepaper title: Using Frankencerts for Automated Adversarial Testing of Certificate Validation in SSL/TLS Implementations description: Generates frankencerts by randomly mutating parts of millions of real X.509 certificates, then differentially tests eight SSL/TLS libraries against each other so that any disagreement flags a validation bug. Found 208 discrepancies, including MatrixSSL and GnuTLS accepting any valid X.509v1 certificate as a CA, which enables man-in-the-middle attacks. resource: "https://www.ieee-security.org/TC/SP2014/papers/UsingFrankencertsforAutomatedAdversarialTestingofCertificateValidationinSSL_s_TLSImplementations.pdf" tags: [whitepaper, webseclist-reference, parser-differential, fuzzing, tls, https, auth-bypass, dynamic-analysis, tooling, owasp-a01-2021, owasp-a02-2021] generated: by: webseclist-refs/1 at: "2026-08-14T21:00:52+00:00" status: stable stale_after: 2027-08-14 sources: - id: original resource: "https://www.ieee-security.org/TC/SP2014/papers/UsingFrankencertsforAutomatedAdversarialTestingofCertificateValidationinSSL_s_TLSImplementations.pdf" title: Using Frankencerts for Automated Adversarial Testing of Certificate Validation in SSL/TLS Implementations author: Chad Brubaker, Suman Jana, Baishakhi Ray, Sarfraz Khurshid, Vitaly Shmatikov also_at: [] authors: - Chad Brubaker - Suman Jana - Baishakhi Ray - Sarfraz Khurshid - Vitaly Shmatikov canonical_url: "" cited_by: - "2014.md:63" commit: "" content_sha256: 5002395d218bf15e8126a9cb311d0275da2faf1d113b523c430f9ee78f55a75e depth: full depth_reason: default kind: whitepaper language: "" licence: unknown original_url: "https://www.ieee-security.org/TC/SP2014/papers/UsingFrankencertsforAutomatedAdversarialTestingofCertificateValidationinSSL_s_TLSImplementations.pdf" published: "" publisher: "" publisher_english: "" raw_sha256: 923b08580469dd0367cdb7268566784da9d8b46d12b8cbe68260b15a50fb2d0c retrieved_from: "https://www.ieee-security.org/TC/SP2014/papers/UsingFrankencertsforAutomatedAdversarialTestingofCertificateValidationinSSL_s_TLSImplementations.pdf" retrieved_kind: stored retrieved_utc: "2026-08-14T21:00:52+00:00" slug: using-frankencerts-automated-adversarial-testing-certificate-implementations snapshot: "" title_english: "" translation_file: "" translation_of: "" --- # Using Frankencerts for Automated Adversarial Testing of Certificate Validation in SSL/TLS Implementations **Using Frankencerts for Automated Adversarial Testing of Certificate Validation in SSL/TLS Implementations** - Chad Brubaker, Suman Jana, Baishakhi Ray, Sarfraz Khurshid, Vitaly Shmatikov, Publisher not stated. - Published: date not stated - Original: - Preserved from: https://www.ieee-security.org/TC/SP2014/papers/UsingFrankencertsforAutomatedAdversarialTestingofCertificateValidationinSSL_s_TLSImplementations.pdf (stored) on 2026-08-14 - Licence: unknown Rights remain with the original author and publisher. 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Using Frankencerts for Automated Adversarial Testing of Certificate Validation in SSL/TLS Implementations Chad Brubaker ∗ † Suman Jana† Baishakhi Ray‡ Sarfraz Khurshid† Vitaly Shmatikov† ∗ Google † The University of Texas at Austin ‡ University of California, Davis Abstract—Modern network security rests on the Secure Sock- many open-source implementations of SSL/TLS are available ets Layer (SSL) and Transport Layer Security (TLS) protocols. for developers who need to incorporate SSL/TLS into their Distributed systems, mobile and desktop applications, embedded software: OpenSSL, NSS, GnuTLS, CyaSSL, PolarSSL, Ma- devices, and all of secure Web rely on SSL/TLS for protection trixSSL, cryptlib, and several others. Several Web browsers against network attacks. This protection critically depends on include their own, proprietary implementations. whether SSL/TLS clients correctly validate X.509 certificates presented by servers during the SSL/TLS handshake protocol. In this paper, we focus on server authentication, which We design, implement, and apply the first methodology for is the only protection against man-in-the-middle and other large-scale testing of certificate validation logic in SSL/TLS server impersonation attacks, and thus essential for HTTPS implementations. Our first ingredient is “frankencerts,” synthetic and virtually any other application of SSL/TLS. Server authen- certificates that are randomly mutated from parts of real cer- tication in SSL/TLS depends entirely on a single step in the tificates and thus include unusual combinations of extensions handshake protocol. As part of its “Server Hello” message, and constraints. Our second ingredient is differential testing: if the server presents an X.509 certificate with its public key. one SSL/TLS implementation accepts a certificate while another The client must validate this certificate. Certificate validation rejects the same certificate, we use the discrepancy as an oracle involves verifying the chain of trust consisting of one or for finding flaws in individual implementations. more certificate authorities, checking whether the certificate is Differential testing with frankencerts uncovered 208 dis- valid for establishing SSL/TLS keys, certificate validity dates, crepancies between popular SSL/TLS implementations such as various extensions, and many other checks. OpenSSL, NSS, CyaSSL, GnuTLS, PolarSSL, MatrixSSL, etc. Many of them are caused by serious security vulnerabilities. For Systematically testing correctness of the certificate val- example, any server with a valid X.509 version 1 certificate can act idation logic in SSL/TLS implementations is a formidable as a rogue certificate authority and issue fake certificates for any challenge. We explain the two main hurdles below. domain, enabling man-in-the-middle attacks against MatrixSSL and GnuTLS. Several implementations also accept certificate First problem: generating test inputs. The test inputs, i.e., authorities created by unauthorized issuers, as well as certificates X.509 certificates, are structurally complex data with intricate not intended for server authentication. semantic and syntactic constraints. The underlying input space We also found serious vulnerabilities in how users are warned is huge with only a tiny fraction of the space consisting of about certificate validation errors. When presented with an actual certificates. A simple automated technique, such as expired, self-signed certificate, NSS, Safari, and Chrome (on random fuzzing, is unlikely to produce more than a handful of Linux) report that the certificate has expired—a low-risk, often useful inputs since a random string is overwhelmingly unlikely ignored error—but not that the connection is insecure against a to even be parsable as a certificate. man-in-the-middle attack. Some test certificates can be created manually, but writing These results demonstrate that automated adversarial testing with frankencerts is a powerful methodology for discovering just a small suite of such complex inputs requires considerable security flaws in SSL/TLS implementations. effort; manually creating a high-quality suite is simply infea- sible. Furthermore, the testing must include “corner cases”: I. I NTRODUCTION certificates with unusual combinations of features and exten- sions that do not occur in any currently existing certificate but Secure Sockets Layer (SSL) and its descendant Transport may be crafted by an attacker. Layer Security (TLS) protocols are the cornerstone of Internet security. They are the basis of HTTPS and are pervasively Second problem: interpreting the results of testing. Given a used by Web, mobile, enterprise, and embedded software to test certificate and an SSL/TLS implementation, we can record provide end-to-end confidentiality, integrity, and authentication whether the certificate has been accepted or rejected, but that for communication over insecure networks. does not answer the main question: is the implementation correct, i.e., is the accepted certificate valid? And, if the SSL/TLS is a big, complex protocol, described semi- certificate is rejected, is the reason given for rejection correct? formally in dozens of RFCs. Implementing it correctly is a daunting task for an application programmer. Fortunately, Manually characterizing test certificates as valid or invalid and writing the corresponding assertions for analyzing the frankencerts because it is not triggered by any real certificate outputs observed during testing does not scale. A naive ap- from our corpus (but, of course, a man-in-the-middle attacker proach to automate this characterization essentially requires could craft a malicious certificate to exploit this vulnerability). re-implementing certificate validation, which is impractical and has high potential for bugs of its own. Interpreting the results Many vulnerabilities are caused by incorrect or missing of large-scale testing requires an oracle for certificate validity. checks on the restrictions that root CAs impose on lower-level CAs. MatrixSSL does not check path length constraints. If Our contributions. We design, implement, and evaluate the a restricted CA (e.g., a corporate CA whose authority only first approach for systematically testing certificate validation extends to a particular enterprise) creates a new intermediate logic in SSL/TLS implementations. It solves both challenges: CA, who then issues certificates for any Internet domain, (1) automatically generating test certificates, and (2) automat- these certificates will be accepted by MatrixSSL. GnuTLS, ically detecting when some of the implementations do not CyaSSL, and PolarSSL do not check key usage constraints. As validate these certificates correctly. a consequence, an attacker who compromises the code signing key of some company can use it to spoof that company’s The first step of our approach is adversarial input gen- servers in TLS connections. Most of these flaws could not eration. By design, our generator synthesizes test certificates have been discovered without frankencerts because incorrect that are syntactically well-formed but may violate many of the validation logic is only triggered by certificates of a certain complex constraints and internal dependencies that a valid cer- form, not by “normal” certificates. tificate must satisfy. This enables us to test whether SSL/TLS implementations check these constraints and dependencies. Even if an SSL/TLS implementation correctly rejects a certificate, the reason given to the user is very important To “seed” the generator, we built a corpus of 243,246 because Web browsers and other interactive applications often real SSL/TLS certificates by scanning the Internet. Our gen- allow the user to override the warning. For example, if the erator broke them down into parts, then generated over 8 warning is that the certificate expired yesterday, this may million frankencerts by mutating random combinations of indicate a lazy system administrator but does not imply that these parts and artificial parts synthesized using the ASN.1 the connection is insecure. Because the risk is low, the user grammar for X.509. By construction, frankencerts are parsable may click through the warning. If, on the other hand, the as certificates, yet may violate X.509 semantics. They include certificate is not issued by a legitimate certificate authority, unusual combinations of critical and non-critical extensions, this means that the server could have been impersonated and rare extension values, strange key usage constraints, odd the connection may be insecure. certificate authorities, etc. Testing SSL/TLS implementations with frankencerts exercises code paths that rarely get executed Our differential testing uncovered serious vulnerabilities in when validating normal certificates and helps elicit behaviors how SSL/TLS implementations report errors. When presented that do not manifest during conventional testing. with an expired, self-signed certificate, NSS reports that the certificate has expired but not that the issuer is invalid. This Our second insight is that multiple, independent imple- vulnerability found its way into Web browsers such as Chrome mentations of X.509 certificate validation—the very same on Linux and Safari. Since users tend to click through expired- implementations that we are testing—can be used as an oracle certificate warnings—and are advised to do so [1]—this flaw to detect flaws in validation logic. For each frankencert, we gives attackers an easily exploitable vector for man-in-the- compare the answers produced by OpenSSL, NSS, GnuTLS, middle attacks against all users of these Web browsers. CyaSSL, PolarSSL, MatrixSSL, OpenJDK, and Bouncy Castle. These SSL/TLS libraries are supposed to implement the same In summary, adversarial test input generation and differen- certificate validation algorithm and, therefore, should agree tial mutation testing on millions of “frankencerts” synthesized on every certificate. Differences in the implementations of from parts of real certificates is a powerful new technique functionality left unspecified by the X.509 standard may cause for uncovering deep semantic errors in the implementations a “benign” discrepancy, but most discrepancies mean that some of SSL/TLS, the most important network security protocol. of the disagreeing SSL/TLS implementations are incorrect. II. R ELATED W ORK Our differential mutation testing of SSL/TLS implementa- tions on 8,127,600 frankencerts uncovered 208 discrepancies A. Security of SSL/TLS implementations between the implementations, many of which are caused by We are not aware of any prior work on systematic, auto- serious flaws. For example, MatrixSSL silently accepts X.509 mated discovery of certificate validation vulnerabilities in the version 1 certificates, making all MatrixSSL-based applications implementations of SSL/TLS clients. vulnerable to man-in-the-middle attacks: anyone with a valid version 1 certificate can pretend to be an intermediate certifi- Moxie Marlinspike demonstrated several flaws in the im- cate authority (CA), issue a fake certificate for any Internet plementations of SSL/TLS certificate validation [55, 56, 57], domain, and that certificate will be accepted by MatrixSSL. including the lack of CA bit checking in Microsoft’s Cryp- toAPI as of 2002 [54]. More recently, the same vulnerability In GnuTLS, our testing discovered a subtle bug in the was discovered in the SSL implementation on Apple iOS [40]. handling of X.509 version 1 certificates. Due to a mismatch between two flags, the code that intends to accept only locally Georgiev et al. carried out a study of certificate validation trusted version 1 root certificates is actually accepting any vulnerabilities caused by the incorrect use of SSL/TLS APIs, version 1 CA certificate, including fake ones from mali- as opposed to flaws in the implementations of these APIs [31]. cious servers. This bug could not have been found without Georgiev et al. focus primarily on the incorrect validation of hostnames in server certificates at a different level in the tations. The implementation of the SSL/TLS handshake in software stack—in applications, transport libraries, and Web- Mac OS and iOS accidentally did not check whether the key services middleware. Fahl et al. analyzed incorrect usage of used to sign the server’s key exchange messages matches the SSL in Android apps [29]. The class of certificate validation public key in the certificate presented by the server, leaving this vulnerabilities analyzed in this paper is complementary to and implementation vulnerable to server impersonation [49] (this has little overlap with the vulnerabilities discovered in [29, 31]. vulnerability is not caused by incorrect certificate validation). Unlike [29, 31], we developed an automated technique for In GnuTLS, certain errors during certificate parsing were discovering certificate validation vulnerabilities. accidentally interpreted as successful validation, thus enabling server impersonation [33]. We discuss the latter vulnerability A survey of security issues in SSL/TLS can be found in more detail in Section VIII. in [16]. Cryptographic flaws in SSL/TLS implementations and the protocol itself—including compression, initialization, padding of cipher modes and message authentication codes, B. Software testing etc.—can be exploited to attack confidentiality, especially Our work introduces a novel black-box testing ap- when the protocol is used for HTTPS (HTTP over SSL) [3, proach to address two foundational software testing prob- 24, 72]. By contrast, this paper is about authentication flaws. lems—generation of test inputs and validation of program Flaws in SSL server implementations can be exploited outputs (aka the “oracle” problem)—in the context of find- for chosen-ciphertext attacks, resulting in private key compro- ing security bugs, specifically in SSL/TLS implementations. mise [8, 9]. Flaws in pseudo-random number generation can Researchers have extensively studied these two problems produce SSL/TLS keys that are easy to compromise [38, 50]. over the last few decades in a number of contexts and de- veloped various automated techniques to address them. For Hash collisions [77] and certificate parsing discrepancies example, techniques using grammars [48, 52, 58, 75, 79], between certificate authorities (CAs) and Web browsers [44] constraints [13, 53], dedicated generators [18], fuzzing [36], can trick a CA into issuing a valid leaf certificate with the symbolic execution [12, 35, 45, 47, 74], and genetic algo- wrong subject name, or even a rogue intermediate CA cer- rithms [7] provide automated generation of inputs for black- tificate. By contrast, we focus on verifying whether SSL/TLS box and white-box testing, while techniques using correctness implementations correctly handle invalid certificates. specifications [15], differential testing [59], and metamorphic Large-scale surveys of SSL certificates “in the wild” can be testing [14] provide automated validation of program outputs. found in [19, 25, 27, 78]. Because their objective is to collect Differential black-box testing has been successfully used to and analyze certificates, not to find certificate validation errors find parsing discrepancies between antivirus tools that can help in SSL/TLS implementations, they are complementary to this malware evade detection [42]. paper: for example, their certificate corpi can be used to “seed” The use of grammars in testing dates back to the frankencert generation (Section VII). Delignat-Lavaud et al. 1970s [62] and has provided the basis for randomized [52, 58, note that GnuTLS ignores unsupported critical extensions [19], 75, 79] and systematic [48] techniques for finding application matching what we found with automated testing. bugs. The most closely related work to ours is Yang et Akhawe et al. surveyed SSL warnings in Web browsers [1]. al.’s Csmith framework, which used random grammar-based One of their recommendations is to accept recently expired generation of C programs to discover many bugs in production certificates. As we show in Section IX, several Web browsers C compilers [79]. The key difference between Csmith and our show just the “Expired certificate” warning even if the expired work is input generation. Csmith uses purely grammar-based certificate is not issued by a trusted CA and the connection is generation without actual C programs and hence only produces thus insecure. Akhawe and Felt performed a large-scale user input programs with language features that are explicitly study of the effectiveness of browser security warnings [2]. supported by its generation algorithm. Moreover, the design One of their findings is that users are less likely to click goal of Csmith is to generate safe programs that have a unique through an “Expired certificate” warning than through an meaning and no undefined behaviors. This allows Csmith to “Untrusted issuer” warning, possibly because the former tend use a straightforward test oracle that performs identity compar- to occur at websites that previously did not produce any ison on outputs for differential testing. By contrast, our goal is warnings. Amann et al. demonstrated that certain signs of man- to explore behaviors of SSL/TLS implementations that are not in-the-middle attacks, such as certificates never seen before for exercised by valid certificates and thus more likely to contain a given domain or issued by an unusual CA, can be caused security bugs. Hence, our test generator does not need to by benign changes in the CA infrastructure [4]. SSL security ensure that test outputs conform to a restricted form. To detect indicators in mobile Web browsers were studied in [5, 6]. validation errors, we cluster certificates into “buckets” based on the outputs produced by each SSL/TLS implementation The focus of this paper is on server certificate authentica- when presented with a given certificate, with each bucket tion, which is the most common usage pattern for SSL certifi- representing a discrepancy between the implementations. As cates. The other direction, i.e., client certificate authentication, explained in Section IX, multiple discrepancies may be caused was analyzed in [21, 60]. Our adversarial testing techniques for by the same underlying implementation error (in our testing, finding bugs in the client-side validation of server certificates 15 root causes led to 208 discrepancies). can also be applied to the implementations of server-side validation of client certificates. Clustering test executions is a well-explored area, e.g., to diagnose the causes of failed executions by reducing the Several recent high-profile vulnerabilities highlighted the number of failures to inspect [32, 41, 43, 61] or to distinguish need for thorough security analysis of SSL/TLS implemen- failing and passing executions in the context of a single implementation [20]. We use clustering and differential testing both the parsing code and the certificate validation code hidden in tandem to identify incorrect behavior in the context of deep inside the program. SSL certificates are structurally more multiple implementations tested together. complex than HTTP and NTP inputs, and, crucially, the certifi- cate validation logic lies deeper in SSL/TLS implementations Our test input generator combines parts of existing real than the X.509 parsing code. For example, a MiniWeb server certificates and also injects synthetic artificial parts using responding to a GET /index.html request (one of the case operations that resemble combination and mutation in genetic studies in [10]) executes 246,910 instructions. By contrast, the algorithms [39]. In principle, it may be possible to define simplest of our test cases—an OpenSSL client processing a a genetic algorithm for certificate generation by customizing certificate chain of length 1 with zero extensions—executes genetic combination and mutation with respect to the SSL 27,901,961 instructions. certificate grammar, fields, their values, extensions, etc. The main challenge for effective genetic search is how to define an An interesting avenue for future research is to explore appropriate fitness function, which must measure the potential whether the two approaches could be used in conjunction and, usefulness of a candidate input. Genetic search, as well as other in particular, whether generation of test SSL certificates can heuristics for test input generation, can complement systematic benefit from the fact that the technique of [10] performs a exploration using guided sampling [7]. directed search for likely behavioral differences. The classic idea of symbolic execution [47] as well as More recent work by Ramos and Engler on UC-KLEE [63], its more recent variants, e.g., where concrete inputs guide which integrates KLEE [11] and lazy initialization [45], ap- symbolic execution [12, 35, 74], enable a form of white-box plies more comprehensive symbolic execution over a bounded test input generation that has received much recent attention exhaustive execution space to check code equivalence; UC- for finding security bugs [36, 37, 46, 73]. Godefroid et KLEE has been effective in finding bugs in different tools, al.’s SAGE [36] introduced white-box fuzzing that executes including itself. In principle, such goal-directed approaches a given suite of inputs, monitors their execution paths, and are very powerful: they integrate the spirit of differential builds symbolic path condition constraints, which are sys- testing with symbolic analysis to create formulas that explic- tematically negated to explore their neighboring paths. SAGE itly capture behavioral differences of interest. However, the found several new bugs in Windows applications, including resulting formulas in the context of structurally complex data media players and image processors. Grammar-based whitebox can be exceedingly complex since they represent destructive fuzzing [34] uses a grammar to enumerate valid string inputs updates in imperative code using a stateless logic. Scaling such by solving constraints over symbolic grammar tokens. A approaches to SSL/TLS implementations is an open problem. security-focused application using a context-free fragment of In summary, while approaches based on symbolic execu- the JavaScript grammar to test the code generation module of tion have been successful in finding bugs in many applications, the Internet Explorer 7 JavaScript interpreter showed that the their central requirement—the need to solve constraints for use of the grammar provides enhanced code coverage. Similar each execution path explored in symbolic execution—is the but independent work on CESE [51] uses symbolic grammars basic bottleneck that limits their scalability and applicability with symbolic execution to create higher-coverage suites for for programs that operate on complex data types, such as select UNIX tools, albeit in a non-security setting. the structurally complex SSL certificates, and have complex Kiezun et al.’s Ardilla [46] uses concolic execution to path conditions that can be impractical to solve. By contrast, generate test inputs that drive its dynamic taint analysis and our test generation algorithm is not sensitive to the mutates the inputs using a library of attack patterns to create implementation-level complexity of the programs being SQL injection and cross-site scripting attacks. Halfond et tested. Instead, it focuses on the systematic exploration of al. [37] show how symbolic execution can more precisely the space of likely useful inputs and thus reduces the overall identify parameter values that define the interfaces of Web problem complexity by de-coupling the complexity of the input applications, and facilitate finding vulnerabilities. Saxena et space from that of the SSL/TLS implementations. al.’s Kudzu [73] uses a symbolic execution framework based Srivastava et al. [76] use static differential analysis, which on a customized string constraint language and solver to find does not perform test generation or execution, to analyze code injection vulnerabilities in JavaScript clients. consistency between different implementations of the Java Brumley et al. [10] proposed a white-box symbolic analysis Class Library API and use the discrepancies as an oracle technique to guide differential testing [59]. Their analysis to find flaws in the implementations of access-control logic. is driven by concrete executions in the spirit of dynamic While static analysis and dynamic analysis, such as testing, symbolic (aka concolic) execution [12, 35, 74]. They use are well-known to have complementary strengths, they can also weakest preconditions [23] over select execution paths together be applied in synergy [28]. For example, for testing SSL/TLS with constraint solving to compute inputs that likely cause implementations, static dataflow analysis could potentially parsing discrepancies between different implementations of reduce the space of candidate inputs for the test generator by protocols such as HTTP and NTP. focusing it to exercise fewer values or fewer combinations of values for certain certificate extensions. There are two basic differences between our methodology and that of [10]. First, our black-box approach does not require III. OVERVIEW OF SSL/TLS analyzing either the source, or the binary code. Second, the A. SSL/TLS protocol need to solve path constraints limits the scalability of the approach described in [10]. Generating even a single test The Secure Sockets Layers (SSL) Protocol Version 3.0 [70] certificate using their technique requires symbolic analysis of and its descendants, Transport Layer Security (TLS) Protocol Version 1.0 [64], Version 1.1 [67], and Version 1.2 [68], are the “de facto” standard for secure Internet communications. The primary goal of the SSL/TLS protocol is to provide privacy and data integrity between two communicating applications. In this paper, we focus on a particular security guarantee promised by SSL/TLS: server authentication. Server authen- tication is essential for security against network attackers. For example, when SSL/TLS is used to protect HTTP communi- cations (HTTPS), server authentication ensures that the client (e.g., Web browser) is not mistaken about the identity of the Web server it is connecting to. Without server authentication, SSL/TLS connections are insecure against man-in-the-middle attacks, which can be launched by malicious Wi-Fi access points, compromised routers, etc. The SSL/TLS protocol comprises the handshake protocol and the record protocol. Server authentication is performed entirely in the handshake protocol. As part of the hand- shake, the server presents an X.509 certificate with its public key [69]. The client must validate this certificate as described Fig. 1: A sample X509 certificate chain. in Section IV. If the certificate is not validated correctly, authentication guarantees of SSL/TLS do not hold. Certificate validation in SSL/TLS critically depends on certificate authorities (CAs). Consequently, we analyze the SSL/TLS. Therefore, we extend our testing to Web browsers, correctness of SSL/TLS implementations under the assumption all of which must support HTTPS: Firefox, Chrome, Internet that the CAs trusted by the client correctly verify the identities Explorer, Safari, Opera, and WebKit (the latter is a browser of the servers to whom they issue certificates. If this assump- “engine” rather than a standalone browser). Web browsers tion does not hold—e.g., a trusted CA has been compromised typically contain proprietary implementations of SSL/TLS, or tricked into issuing false certificates [17, 22]—SSL/TLS is some of which are derived from the libraries listed above. not secure regardless of whether the client is correct or not. For example, Firefox and Chrome use a version of NSS, while In summary, we aim to test if the implementations of WebKit has a GnuTLS-based HTTPS back end, among others. SSL/TLS clients correctly authenticate SSL/TLS servers in the presence of a standard “network attacker,” who can control any IV. C ERTIFICATE VALIDATION IN SSL/TLS part of the network and run his own servers, possibly with their own certificates, but does not control legitimate servers The only mechanism for server authentication in SSL/TLS and cannot forge their certificates. is the client’s validation of the server’s X.509 public-key certificate presented during the handshake protocol. Client B. SSL/TLS implementations authentication is less common (in a typical HTTPS browsing session, only the server is authenticated). It involves symmetric In this paper, we focus primarily on testing open-source steps on the server side to validate the client’s certificate. implementations of SSL/TLS. Our testing methodology can be successfully applied to closed-source implementations, too (as X.509 certificate validation is an extremely complex pro- illustrated by our testing of Web browsers), but having access cedure, described in several semi-formal RFCs [64, 65, 66, 67, to the source code makes it easier to identify the root causes 68, 69, 70, 71]. Below, we give a very brief, partial overview of the flaws and vulnerabilities uncovered by our testing. of some of the key steps. We tested the following SSL/TLS implementations: Chain of trust verification. Each SSL/TLS client trusts a OpenSSL, NSS, CyaSSL, GnuTLS, PolarSSL, MatrixSSL, number of certificate authorities (CAs), whose X.509 certifi- cryptlib, OpenJDK, and Bouncy Castle. These implementa- cates are stored in the client’s local “root of trust.” We will tions are distributed as open-source software libraries so that refer to these trusted certificate authorities as root CAs, and they can be incorporated into applications that need SSL/TLS to their certificates as root certificates. The list of root CAs for secure network communications. varies from application to application and from OS to OS. Many vulnerabilities stem from the fact that applications For example, the Firefox Web browser ships with 144 root use these libraries incorrectly [31], especially when some certificates pre-installed, while the Chrome Web browser on critical part of SSL/TLS functionality such as verifying the Linux and MacOS relies on the OS’s list of root certificates. server’s hostname is delegated by the SSL/TLS library to the Each X.509 certificate has an “issuer” field that contains application. In this paper, however, we focus on flaws within the name of the certificate authority (CA) that issued the the libraries, not in the applications that use them, with one certificate. The certificate presented by the server (we’ll call it exception—Web browsers. the leaf certificate) should be accompanied by the certificate HTTPS, the protocol for protecting Web sessions from of the issuing CA and, if the issuing CA is not a root CA, the network attackers, is perhaps the most important application of certificates of higher-level CAs all the way to a root CA. As part of certificate validation, the client must construct a If a certificate contains a Certificate Revocation List (CRL) valid chain of certificates starting from the leaf certificate and distribution points extension, the client should obtain CRL ending in a root certificate (see an example in Fig. 1). Below, information as specified by this extension. we list some of the checks involved in validating the chain. These brief synopses are very informal and incomplete, please The above list omits many important checks and subtleties refer to RFC 5280 [69] for the full explanation. of certificate validation. For example, CA certificates may contain policy constraints that limit their authority in various Each certificate in the chain must be signed by the CA ways [69, 4.2.1.11]. Policy constraints extension should be immediately above it and the root (“anchor”) of the chain must marked as critical, although in practice few SSL/TLS imple- be one of the client’s trusted root CAs. mentations understand policy constraints. The current time must be later than the value of each Hostname verification. After the chain of trust has been val- certificate’s “not valid before” field and earlier than the value idated, the client must verify the server’s identity by checking of each certificate’s “not valid after” field, in the time zone if the fully qualified DNS name of the server it wants to talk to specified in these fields. If no time zone is specified, then matches one of the names in the “SubjectAltNames” extension Greenwich Mean Time (GMT) should be used. or the “Common Name” field of the leaf certificate. Some SS- If a CA certificate in an X.509 version 1 or version 2 L/TLS implementations perform hostname verification, while certificate, then the client must either verify that it is indeed others delegate it to higher-level applications (see Table IX). a CA certificate through out-of-band means or reject the certificate [69, 6.1.4(k)]. The following checks apply only to V. C URRENT TESTING PRACTICES FOR SSL/TLS IMPLEMENTATIONS X.509 version 3 certificates. Most SSL/TLS implementations analyzed in this paper For each CA certificate in the chain, the client must verify ship with several pre-generated X.509 certificates intended for the basic constraints extension: testing (Table I). These certificates differ only in a few fields, • The “CA bit” must be set. If the CA bit is not set, then such as hashing algorithms (SHA-1, MD5, etc.), algorithms the current certificate cannot act as a root or intermediate for public-key cryptography (DSA, RSA, Diffie-Hellman, etc.), certificate in a certificate chain. The chain is not valid. and the sizes of public keys (512 bits, 1024 bits, etc.). • If the CA certificate contains a “path length” constraint, OpenSSL uses a total of 2 certificates to test client and server the number of intermediate CAs between the leaf certifi- authentication, respectively; the rest are intended to test other cate and the current certificate must be less than the path functionalities such as certificate parsing. length. For example, if the CA certificate has path length of 0, it can be used only to issue leaf certificates. TABLE I: Number of SSL/TLS certificates used by different Every extension in a certificate is designated as critical implementations for testing or non-critical. A certificate with a critical extension that the client does not recognize or understand must be rejected. Implementation Certificate count NSS 64 GnuTLS 51 If a CA certificate in the chain contains a name constraints OpenSSL 44 extension, then the subject name in the immediately following PolarSSL 18 certificate in the chain must satisfy the listed name constraints. CyaSSL 9 MatrixSSL 9 Name constraints are used to limit the subjects that a CA can issue certificates for, by listing permitted or excluded subjects. This extension is critical. Testing with a handful of valid certificates is unlikely to uncover vulnerabilities, omissions, and implementation flaws If a certificate in the chain contains a key usage extension, in the certificate validation logic. For example, we found that the value of this extension must include the purpose that the GnuTLS mistakenly accepts all versions 1 certificates even certificate is being used for. For example, the key usage of though the default flag is set to accept only locally trusted an intermediate certificate must include keyCertSign (it version 1 root certificates (see Section IX). This vulnerability must also have the CA bit set in the basic constraints, as would have never been discovered with their existing test suite described above). If a leaf certificate contains the server’s because it only contains version 3 certificates. RSA public key that will be used to encrypt a session key, its key usage extension must include keyEncipherment. Automated adversarial testing is rarely, if ever, performed CAs should mark this extension as critical. for SSL/TLS implementations. As we demonstrate in this paper, systematic testing with inputs that do not satisfy the Similar to key usage, if a certificate contains an extended protocol specification significantly improves the chances of key usage extension, the value of this extension must include uncovering subtle implementation flaws. the purpose that the certificate is being used for, e.g., server authentication in the case of a leaf certificate. Several of the SSL/TLS implementations in our study, in- cluding OpenSSL, NSS, and MatrixSSL, have been tested and If a certificate contains an Authority Key Identifier (AKI) certified according to FIPS 140-2 [30], the U.S. government extension, then its value—containing the key identifier and/or computer security standard for cryptographic modules. As the issuer and serial number—should be used to locate the public results of our testing demonstrate, FIPS certification does not key for validating the certificate. This extension is used when mean that an implementation performs authentication correctly the certificate issuer has multiple public keys. or is secure against man-in-the-middle attacks. TABLE II: 20 most common issuers in our corpus TABLE III: 10 most common issuers of X.509 version 1 certificates Common Name (CN) Occurrences Cybertrust Public SureServer SV CA 30066 Go Daddy Secure Certification Authority 13300 Common Name (CN) Occurrences localhost.localdomain 7179 BMS 4877 GeoTrust SSL CA 7171 Parallels Panel 2003 COMODO SSL CA 7114 localhost 1668 RapidSSL CA 6358 brutus.neuronio.pt 1196 COMODO SSL CA 2 5326 plesk 1163 BMS 4878 remotewd.com 1120 DigiCert High Assurance CA-3 4341 UBNT 1094 Hitron Technologies Cable Modem Root Certificate Authority 4013 localdomain 986 VeriSign Class 3 Secure Server CA - G3 3837 192.168.1.1 507 COMODO High-Assurance Secure Server CA 3681 ZTE Corporation 501 PositiveSSL CA 2 2724 Entrust Certification Authority - L1C 2719 Daniel 2639 Vodafone (Secure Networks) 2634 192.168.168.168 2417 GeoTrust DV SSL CA 2174 localhost 2142 Parallels Panel 2084 TABLE IV: Extensions observed in our corpus VI. C OLLECTING C ERTIFICATES Name or OID Occurrences Unique values We used ZMap [26] to scan the Internet and attempt an basicConstraints 161723 13 authorityKeyIdentifier 161572 21990 SSL connection to every host listening on port 443. If the subjectKeyIdentifier 151823 72496 connection was successful, the certificate presented by the keyUsage 132970 54 extendedKeyUsage 131453 83 server was saved along with the IP of the host. crlDistributionPoints 126579 4851 subjectAltName 101622 59767 This scan yielded a corpus of 243,246 unique certificates. authorityInfoAccess 89005 3864 23.5% of the collected certificates were already expired at the certificatePolicies 81264 418 nsCertType 63913 21 time they were presented by their servers, and 0.02% were not nsComment 5870 185 yet valid. The certificates in our corpus were issued by 33,837 1.3.6.1.4.1.311.20.2 2897 11 unique issuers, identified by the value of their CN (“Common issuerAltName 1519 115 1.3.6.1.5.5.7.1.12 1474 2 Name”) field. Table II shows the 20 most common issuers. SMIME-CAPS 915 4 1.3.6.1.4.1.311.21.10 875 16 23,698 of the certificates are X.509 version 1 (v1) cer- 1.3.6.1.4.1.311.21.7 873 312 tificates, 4,974 of which are expired. This is important be- privateKeyUsagePeriod 871 798 2.5.29.1 175 133 cause—as our testing has uncovered—any v1 certificate issued nsRevocationUrl 112 39 by a trusted CA can be used for man-in-the-middle attacks nsCaRevocationUrl 104 52 against several SSL/TLS implementations (see Section IX). nsCaPolicyUrl 74 32 nsSslServerName 73 17 nsBaseUrl 63 31 20,391 v1 certificates are self-signed. Table III shows 1.2.840.113533.7.65.0 59 6 the 10 most common issuers of the other 3,307 certificates. 2.16.840.1.113719.1.9.4.1 54 26 localhost, localdomain, and 192.168.1.1 are all self-issued nsRenewalUrl 33 7 2.5.29.80 10 10 certificate chains, but many v1 certificates have been issued by qcStatements 8 2 trusted issuers, especially manufacturers of embedded devices. 2.5.29.7 7 7 2.16.840.1.113733.1.6.15 6 6 For example, Remotewd.com is used for remote control of 2.5.29.10 5 1 Western Digital Smart TVs, while UBNT and ZTE make 1.3.6.1.4.1.3401.8.1.1 4 4 networking equipment. As we show in Section IX, SSL/TLS freshestCRL 4 3 subjectDirectoryAttributes 4 2 implementations that specifically target embedded devices han- 1.3.6.1.4.1.311.10.11.11 3 3 dle v1 certificates incorrectly and are thus vulnerable to man- 2.5.29.3 2 1 in-the-middle attacks using these certificates. 2.16.840.1.113733.1.6.7 2 2 1.3.6.1.4.4324.33 2 2 1.3.6.1.4.4324.36 2 2 437 certificates in our corpus have version 4, even though 1.3.6.1.4.4324.34 2 2 there is no X.509 version 4. 434 of them are self-signed, the 1.3.6.1.4.4324.35 2 1 other 3 are issued by Cyberoam, a manufacturer of hardware 1.2.40.0.10.1.1.1 2 2 1.3.6.1.4.1.311.21.1 2 1 “security appliances.” We conjecture that the cause is an off- 1.3.6.1.4.1.7650.1 1 1 by-one bug in the certificate issuance software: the version field 1.3.6.1.4.1.311.10.11.87 1 1 1.3.6.1.4.1.311.10.11.26 1 1 in the certificate is zero-indexed, and if set to 3 by the issuer, 1.3.6.1.4.1.8173.2.3.6 1 1 it is interpreted as version 4 by SSL/TLS implementations. 1.2.40.0.10.1.1.2 1 1 2.5.29.4 1 1 Table IV shows the number of times various extensions 1.2.250.1.71.1.2.5 1 1 1.3.6.1.4.1.6334.2.2 1 1 show up in our corpus and how many unique values we observed for each extension. Extensions are labeled by short names if known, otherwise by their object identifiers (OID). VII. G ENERATING F RANKENCERTS intermediate certificate may violate a name constraint which limits the set of subjects it is allowed to certify. The key challenge in generating test inputs for SSL/TLS implementations is how to create strings that (1) are parsed Algorithm 1 Generating a single frankencert as X.509 certificates by the implementations, but (2) exercise parts of their functionality that are rarely or never executed 1: procedure F RANKENCERT (certs, exts, issuer) when processing normal certificates. 2: new cert ← Create a blank cert 3: for all f ield ∈ new cert do We use our corpus of real certificates (see Section VI) as 4: if f ield =“key” then the source of syntactically valid certificate parts. Our algorithm 5: new cert.key ← Create a random key them assembles these parts into random combinations we 6: else if f ield =“issuer” then call frankencerts. One limitation of the certificates in our 7: new cert.issuer ← issuer corpus is that they all conform to the X.509 specification. To 8: else test how SSL/TLS implementations behave when faced with 9: random cert ← CHOICE(certs) syntactically valid certificates that do not conform to X.509, 10: new cert.f ield ← random cert.f ield we also synthesize artificial certificate parts and add them to 11: end if the inputs of the frankencerts generator (see Section VII-B). 12: end for 13: num exts ←RANDOM(0, 10) 14: for i ∈ 1..num exts do A. Generating frankencerts 15: random id ←CHOICE(exts) Algorithm 1 describes the generation of a single 16: random val ←CHOICE(exts[random id]) frankencert. Our prototype implementation of Frankencert 17: new cert.extensions[i].id ← random id is based on OpenSSL. It uses parts randomly selected from 18: new cert.extensions[i].val ← random val the corpus, with two exceptions: it generates a new RSA key 19: if RANDOM < 0.05 then and changes the issuer so that it can create chains where the 20: F LIP( new cert.extensions[i].critical) generated frankencert acts as an intermediate certificate. The 21: end if issuer field of each frankencert must be equal to the subject of 22: end for the certificate one level higher in the chain, or else all tested 23: S IGN(new cert, issuer.key) implementations fail to follow the chain and do not attempt 24: return new cert to validate any other part of the certificate. For every other 25: end procedure field, the generator picks the value from a randomly chosen certificate in the corpus (a different certificate for each field). Algorithm 2 Generating a chain of frankencerts Extensions are set as follows. The generator chooses a 1: procedure F RANKENCHAIN (certs, ca, length) random number of extensions from among all extensions 2: issuer ← ca observed in the corpus (Table IV). For each extension, it 3: chain ← ∅ randomly chooses a value from the set of all observed values 4: exts ←G ETEXTENSIONS(certs) for that extension. Each value, no matter how common or rare, 5: for i ∈ 1..length do has an equal probability of appearing in a frankencert. 6: chain[i] ←F RANKENCERT(certs, exts, issuer) We use two CAs as roots of trust, with an X.509 version 1 7: issuer ← chain[i] certificate and an X.509 version 3 certificate, respectively. For 8: end for the purposes of testing, both root CAs are installed in the local 9: return chain root of trust and thus trusted by all tested SSL/TLS clients. 10: end procedure Each frankencert is a well-formed X.509 certificate signed by a locally trusted CA, but it may be invalid for a number of B. Generating synthetic mutations reasons. By design, the frankencert generator does not respect the constraints on X.509 extensions. It also randomly desig- The purpose of synthetic certificate parts is to test how nates extensions as critical or non-critical in each generated SSL/TLS implementations react to extension values that follow frankencert, violating the requirement that certain extensions the ASN.1 grammar for X.509 but do not conform to the X.509 must be critical (Section IV). This allows us to test whether specification. SSL/TLS implementations reject certificates with unknown critical extensions, as required by the X.509 RFC [69]. Taking a frankencert as input, we first parse all extensions present in the certificate using OpenSSL. For certificate chains, we use between 0 and 3 frankencerts. The critical bit and the rest of the extension value Each intermediate certificate uses the previous certificate’s are extracted using X509 EXTENSION get critical() and (randomly chosen) subject as its issuer and is signed by the X509 EXTENSION get data(), respectively. Then, for each previous certificate, creating a chain that SSL/TLS implemen- of these extensions, the extension value is replaced with a tations can follow. These chains are well-formed, but may randomly generated ASN.1 string and a null character (0) still be invalid because of the contents of random frankencerts is probabilistically injected into this string. Because most of acting as intermediate certificates. For example, the key us- the SSL/TLS implementations in our testing are written in age extension of an intermediate certificate may not include C, and C strings are terminated by a null character, this step keyCertSign, as required by the X.509 RFC [69], or an helps verify whether implementations parse extension values Algorithm 3 Extracting unique extensions from a corpus of the slowest. The browser scripts are much slower: 0.6-1.0 certificates seconds for Firefox and 1.1-1.4 seconds for Chrome. 1: procedure G ET E XTENSIONS (certs) 2: uniq exts ← ∅ Differential testing. For differential testing of multiple SS- 3: for all cert ∈ certs do L/TLS implementations, we implemented a Python script that 4: for all ext ∈ cert.extensions do generates frankencerts and executes all clients against each 5: id ← ext.id frankencert. The entire script is 367 lines of code, including 6: val ← ext.val 102 lines for certificate generation and 163 lines for parallel 7: if id ∈ / uniq exts then execution of clients. Certificates are generated in batches of 8: uniq exts[id] ← ∅ 200; executing all clients on a single batch takes 25 seconds. 9: end if If a certificate causes disagreement between the clients (i.e., 10: if val ∈ / uniq exts[id] then the clients produce different error codes when presented with 11: uniq exts[id] ← uniq exts[id] ∪ val this certificate), the certificate is indexed by its SHA-1 hash 12: end if and stored into the appropriate bucket. Buckets are defined by 13: end for the tuples of error codes returned by each client. For example, 14: end for if client A accepts the certificate, client B rejects it with error 15: return uniq exts code 34, and client C rejects it with error code 1, the certificate 16: end procedure is stored into the 0-34-1 bucket. The size of each bucket is capped at 512 certificates. correctly. Finally, the extension is randomly marked as critical In total, we tested our clients on 8,127,600 frankencerts. or non-critical. It is not computationally feasible to exhaustively generate certificates with all possible combinations of extension values VIII. T ESTING SSL/TLS I MPLEMENTATIONS from Table IV, but every value of every extension appeared in at least one of the frankencerts used in the testing. We tested open-source SSL/TLS libraries and several Web browsers. The tested libraries are OpenSSL 1.0.1e, PolarSSL Our testing yielded 208 distinct discrepancies be- 1.2.8, GnuTLS 3.1.9.1, CyaSSL 2.7.0, MatrixSSL 3.4.2, NSS tween SSL/TLS implementations, with a total of 62,022 3.15.2, cryptlib 3.4.0-r1, OpenJDK 1.7.0 09-b30, and Bouncy frankencerts triggering these discrepancies. Castle 1.49. The tested browsers are Firefox 20.0, Chrome 30.0.1599.114 p1, WebKitGTK 1.10.2-r300, Opera 12.0, Sa- Analysis of the results. All SSL/TLS implementations we fari 7.0, and IE 10.0. tested are supposed to implement the same protocol and, in par- ticular, exactly the same certificate validation logic. Whenever Testing was done in parallel on 3 machines: an Ubuntu one implementation accepts a certificate and another rejects the Linux machine with two Intel Xeon E5420 (2.5Ghz) CPUs same certificate, their implementations of the X.509 standard and 16 GB of RAM, an Ubuntu Linux machine with an Intel must be semantically different. In other words, differential i7-2600K (4.0Ghz) CPU and 16GB of RAM, and a Gentoo testing has no false positives. This is very important when Linux machine with an Intel i5-3360M (2.8Ghz) CPU with testing on over 8 million inputs, because any non-negligible 8GB of RAM. Each machine generated and tested frankencerts false-positive rate would have resulted in an overwhelming independently, with the results merged later. The average speed number of false positives. of generating a frankencert chain with 3 certificates is 11.7ms. While all discrepancies found by differential testing indi- SSL/TLS clients. We implemented a simple client for each cate genuine differences between implementations, not every SSL/TLS library. Each client takes three arguments (host, port, difference implies a security vulnerability. For each discrep- path to the file with trusted root certificates) and makes an ancy, we manually analyzed the source code of the disagreeing SSL 3.0 connection to the host/port. The server presents a implementations to identify the root cause of the disagreement frankencert. The client records the answer reported by the and find the flaw (if any) in the certificate validation logic of library, including error codes if any. When implementing these one or more implementations. Because some parts of the X.509 clients, we used the documentation provided by the libraries standard are left to the discretion of the implementation, a few and followed the sample code in the documentation as closely of the discrepancies turned out to be benign. For example, as possible. We expect that most application developers using the differing treatments of the Authority Key Identifier (AKI) the library would follow the same procedure. extension (Section IX-E) fall into this category. For testing Web browsers, we created scripts with the Differential testing with frankencerts suffers from false same input/output format as our clients for the libraries, al- negatives and can miss security flaws. SSL/TLS implemen- lowing straightforward integration of browsers into our testing tations may contain code paths that are not exercised by a framework. For Firefox, we used Xulrunner to make an SSL given set of frankencerts. An example of this is the recently connection and print the output without bringing up a Firefox discovered certificate validation bug in GnuTLS [33], which is window. For Chrome, we could not find an easy way to avoid only triggered by syntactically malformed certificates. It was launching the window. Therefore, we used a JavaScript file to not found by our testing because all frankencerts we generated make the connection and record the results. comply with the X.509 grammar. Similarly, frankencerts will Each execution of a library client takes between 0.04 and not trigger flaws on the code paths responsible for processing 0.10 seconds, with OpenSSL being the fastest and PolarSSL extensions that do not occur in the certificate corpus from which these frankencerts are constructed, or the paths executed man-in-the-middle attacks. In MatrixSSL, the following code only for certain versions and modes of SSL/TLS, etc. silently skips the basic constraints check for any certificate whose version field is 0 or 1 (encoding X.509 version 1 or 2, Further, if all implementations make the same mistake, it respectively, because the version field is zero-indexed): will not manifest as a discrepancy. Finally, an implementation /* Certificate authority constraint only available in may reject an invalid certificate for the wrong reason(s). To version 3 certs */ reduce false negatives in the latter case, we also analyzed the discrepancies between the reported validation errors. if ((ic->version > 1) && (ic->extensions.bc.ca<= 0)) { psTraceCrypto("Issuer does not have basicConstraint CA permissions\n"); Analysis of error reporting. Proper error reporting is critical sc->authStatus = PS_CERT_AUTH_FAIL_BC; for SSL/TLS implementations because a trivial, low-risk warn- return PS_CERT_AUTH_FAIL_BC; } ing (e.g., expired certificate) may accidentally hide or mask a severe problem (e.g., invalid certificate issuer). GnuTLS, on the other hand, contains a very subtle error. Not every SSL/TLS implementation produces fine-grained This error could not have been uncovered without frankencerts error codes that are easy to translate into a human- because none of the real certificate chains in our corpus contain understandable reason for rejection. Many simply reject the v1 intermediate certificates. certificate and return a generic error. If the certificate is invalid for multiple reasons, all libraries except GnuTLS return only GnuTLS has three flags that an application can set one error value, but some allow the application to extract more to customize the library’s treatment of v1 CA certifi- error codes through additional function calls. This is fraught cates: GNUTLS_VERIFY_ALLOW_X509_V1_CA_CRT (only accept v1 with peril because the application may forget to make these root certificates), GNUTLS_VERIFY_ALLOW_ANY_X509_V1_CA_CRT (ac- additional calls and thus allow a less severe error to mask a cept v1 certificates for root and intermediate CAs), and GNUTLS_VERIFY_DO_NOT_ALLOW_X509_V1_CA_CRT (reject all v1 CA serious problem with the certificate. certificates). Only GNUTLS_VERIFY_ALLOW_X509_V1_CA_CRT is set by Therefore, we limited our differential testing of error default. The intention is good: the application may locally trust reporting to Web browsers, OpenSSL, NSS, GnuTLS, and a v1 root CA, but, to prevent other customers of that root CA OpenJDK. For this testing, each output was mapped to one of from acting as CAs themselves, no v1 intermediate certificates the following reasons: “Accepted,” “Invalid issuer,” “Expired,” should be accepted. “Not yet valid,” and “Unknown or invalid critical extension.” The relevant part of GnuTLS certificate validation code For Web browsers, we also included “Hostname in the certifi- is shown below (adapted from lib/x509/verify.c). After a cate does not match the server.” root v1 certificate has been accepted, GnuTLS needs to prevent any further v1 certificates from being accepted. To IX. R ESULTS this end, it clears the GNUTLS_VERIFY_ALLOW_X509_V1_CA_CRT flag Depending on the combination of mutations in a on line 12 before calling _gnutls_verify_certificate2. The frankencert, the same flaw in a given implementation of X.509 latter function accepts v1 certificates unless a different flag, certificate validation can produce different results. We analyzed GNUTLS_VERIFY_DO_NOT_ALLOW_X509_V1_CA_CRT is set (line 25). 208 discrepancies between the implementations found by our 1 unsigned int _gnutls_x509_verify_certificate(...) testing and attributed them to 15 distinct root causes. 2 { 3 ... 4 Table V summarizes the results. As the second column 5 /* verify the certificate path (chain) */ shows, most of the issues could not have been discovered 6 for (i = clist_size - 1; i > 0; i--) without frankencerts because the certificates triggering these 7 { 8 /* note that here we disable this V1 CA flag. So issues do not exist in our corpus (but, of course, can be crafted that no version 1 by the adversary to exploit the corresponding flaw). 9 * certificates can exist in a supplied chain. 10 * / 11 if (!(flags & A. Incorrect checking of basic constraints GNUTLS_VERIFY_ALLOW_ANY_X509_V1_CA_CRT)) 12 flags &= ˜(GNUTLS_VERIFY_ALLOW_X509_V1_CA_CRT); Basic constraints, described in Section IV, are an essential 13 if ((ret = _gnutls_verify_certificate2 (...)) == 0) part of CA certificates. Every X.509 version 3 CA certificate 14 { must have the CA bit set, otherwise any domain with a 15 /* return error */ valid leaf certificate could act as a rogue CA and issue fake 16 } 17 } certificates for other domains. 18 ... 19 } Untrusted version 1 intermediate certificate. Before version 20 21 int _gnutls_verify_certificate2(...) 3, X.509 certificates did not have basic constraints, making it 22 { impossible to check whether a certificate in the chain belongs 23 ... to a valid CA except via out-of-band means. If an SSL/TLS 24 if (!(flags & GNUTLS_VERIFY_DISABLE_CA_SIGN) && 25 ((flags & implementation encounters a version 1 (v1) CA certificate that GNUTLS_VERIFY_DO_NOT_ALLOW_X509_V1_CA_CRT) cannot be validated out of band, it must reject it [69, 6.1.4(k)]. 26 || issuer_version != 1)) 27 { Both MatrixSSL and GnuTLS accept chains containing 28 if (check_if_ca (cert, issuer, flags) == 0) 29 { v1 certificates. As we explain below, this can make any 30 /*return error*/ application based on MatrixSSL or GnuTLS vulnerable to 31 ... TABLE V: Semantic discrepancies in certificate validation (incorrect answers in bold) Problem Certificates OpenSSL PolarSSL GnuTLS CyaSSL MatrixSSL NSS OpenJDK, Browsers triggering Bouncy the problem Castle occur in the original corpus Untrusted version 1 intermediate CA No reject reject accept reject accept reject reject reject certificate Untrusted version 2 intermediate CA No reject reject reject reject accept reject reject reject certificate Version 1 certificate with valid basic No accept reject accept accept accept reject reject Firefox: reject constraints Opera, Chrome: accept Intermediate CA not authorized to is- No reject reject reject reject accept reject reject reject sue further intermediate CA certifi- cates, but followed in the chain by an intermediate CA certificate . . . followed by a leaf CA certificate No reject reject accept reject accept reject reject reject Intermediate CA not authorized to is- No reject reject accept accept accept reject reject reject sue certificates for server’s hostname Certificate not yet valid Yes reject accept reject reject reject reject reject reject Certificate expired in its timezone Yes reject accept reject reject accept reject reject reject CA certificate not authorized for sign- No reject reject accept accept accept reject reject reject ing other certificates Server certificate not authorized for Yes reject accept accept accept accept reject reject reject use in SSL/TLS handshake Server certificate not authorized for Yes reject accept accept accept accept reject reject reject server authentication Certificate with unknown critical ex- No reject reject accept accept accept reject reject reject tension Certificate with malformed extension No accept reject accept accept accept reject reject reject value Certificate with the same issuer and No reject reject accept reject accept reject reject reject subject and a valid chain of trust Issuer name does not match AKI No reject accept accept accept accept reject reject reject Issuer serial number does not match No reject accept reject accept accept reject reject reject AKI 32 } returns the actual version, not the version field, and the 33 } following check blocks version 2 certificates: 34 /*perform other checks*/ 35 ... issuer_version = gnutls_x509_crt_get_version (issuer); 36 } // ... if (!(flags & GNUTLS_VERIFY_DISABLE_CA_SIGN) && ((flags & There is an interesting dependency between the two GNUTLS_VERIFY_DO_NOT_ALLOW_X509_V1_CA_CRT) flags. To prevent intermediate v1 certificates from being ac- || issuer_version != 1)) cepted, GNUTLS_VERIFY_ALLOW_X509_V1_CA_CRT must be false and { // ... GNUTLS_VERIFY_DO_NOT_ALLOW_X509_V1_CA_CRT must be true. The } calling function sets the former, but not the latter. Therefore, although by default GnuTLS is only intended to accept root v1 certificates, in reality it accepts any v1 certificate. Version 1 certificate with valid basic constraints. Basic The consequences of this bug are not subtle. If an ap- constraints were added only in X.509 version 3, but several plication based on GnuTLS trusts a v1 root CA certificate, SSL/TLS implementations always verify basic constraints if then any server certified by the same root can act as a present in the certificate regardless of its version field. rogue CA, issuing fake certificates for any Internet domain Some of our frankencert chains include version 1 interme- and launching man-in-the-middle attacks against this GnuTLS- diate certificates with correct basic constraints (obviously, such based application. Unfortunately, trusting v1 root certificates is certificates do not exist “in the wild”). OpenSSL, GnuTLS, very common. For example, Gentoo Linux by default has 13 v1 MatrixSSL, CyaSSL, Opera, and Chrome accept them, Open- root CA certificates, Mozilla has 9, and we observed thousands JDK and Bouncy Castle reject them, NSS and Firefox fail with of CA-issued v1 leaf certificates “in the wild” (Section VI). a generic Security library failure error. Neither choice appears to lead to a security vulnerability. Untrusted version 2 intermediate certificate. We never observed X.509 version 2 certificates “in the wild,” but, for Intermediate CA not authorized to issue further intermediate the purposes of testing, did generate version 2 frankencerts. CA certificates. When a higher-level CA certifies a lower- As explained above, MatrixSSL silently accepts all CA level CA, it can impose various restrictions on the latter. For certificates whose version field is less than 2 (i.e., version example, it can limit the number of intermediate certificates number less than 3). In GnuTLS, gnutls_x509_crt_get_version that may follow the lower-level CA’s certificate in a certificate chain. This is done by setting the pathLenConstraint field in the MatrixSSL does not perform any time checks of its own basic constraints extension of the lower-level CA’s certificate. and delegates this responsibility to the applications. The sam- ple application code included with MatrixSSL checks the day, For example, if path length is set to zero, then the lower- but not the hours and minutes of the notAfter field, and uses level CA is authorized to issue only leaf certificates, but not local time, not GMT or the time zone specified in the field. intermediate CA certificates. This is good security practice: a CA delegates its authority to a lower-level CA, but prevents the latter from delegating it any further. We observed 17 CA D. Incorrect checking of key usage certificates with path length constraints in our corpus. SSL/TLS clients must check the key usage and, if present, MatrixSSL ignores path length constraints. This can be extended key usage extensions to verify that the certificates exploited by a malicious or compromised CA to evade restric- are authorized for their purpose. Leaf certificates must be tions imposed by a higher-level CA. For example, suppose authorized for key encipherment or key agreement, while CA that a trusted root CA authorized a lower-level CA—call it certificates must be authorized to sign other certificates. EnterpriseCA—but prohibited it from creating other CAs (via CA certificate not authorized for signing other certificates. path length constraints) and from issuing certificates for any All CA certificates in the chain must include keyCertSign domain other than enterprise.com (via name constraints—see in their key usage. GnuTLS, CyaSSL, and MatrixSSL do Section IX-B). This provides a degree of protection if Enter- not check the key usage extension in CA certificates. An priseCA is compromised. If the attacker uses EnterpriseCA to attacker who compromises any CA key, even a key that is issue a certificate for, say, google.com, this certificate should not intended or used for certificate issuance, can use it to be rejected by any SSL/TLS implementation because it violates forge certificates and launch man-in-the-middle attacks against the constraints expressed in EnterpriseCA’s own certificate. applications based on these libraries. This attack will succeed, however, against any application based on MatrixSSL. The impact of this vulnerability may be Server certificate not authorized for use in SSL/TLS hand- amplified by the fact that MatrixSSL targets embedded devices, shake. PolarSSL, GnuTLS, CyaSSL, and MatrixSSL do not whose manufacturers are the kind of organizations that are check the key usage extension in leaf certificates. This is likely to obtain CA certificates with restricted authority. a serious security vulnerability. For example, if an attacker compromises some company’s code signing certificate, which There is an interesting discrepancy in how the implemen- is only intended for authenticating code, he will be able tations react when an intermediate CA whose path length is to impersonate that company’s network and Web servers to zero is followed by a leaf certificate that also happens to be a any application based on the above SSL/TLS libraries, vastly CA certificate. In our testing, only MatrixSSL and GnuTLS ac- increasing the impact of the attack. cepted this chain. All other SSL/TLS implementations rejected it because they do not allow any CA certificate to follow an Server certificate not authorized for server authentication. intermediate CA whose path length is zero. This interpretation PolarSSL, gnuTLS, CyaSSL and MatrixSSL do not check the is incorrect. The X.509 standard explicitly permits a leaf CA extended key usage extension. Given a certificate with key certificate to follow an intermediate CA whose path length is usage that allows all operations and extended key usage that zero [69, Section 4.2.1.9], but only GnuTLS implements this only allows it to be used for TLS client authentication (or any part of the standard correctly. purpose other than server authentication), these libraries accept the certificate for server authentication. B. Incorrect checking of name constraints E. Other discrepancies in extension checks The higher-level CA may restrict the ability of a lower- level CA to issue certificates for arbitrary domains by including Unknown critical extensions. If an SSL/TLS implementation a name constraint in the lower-level’s CA’s certificate. For does not recognize an extension that is marked as critical, it example, if the issuing CA wants to allow the lower-level CA must reject the certificate. GnuTLS, CyaSSL, and MatrixSSL to certify only the subdomains of foo.com, it can add a name accept certificates with unknown critical extensions. constraint *.foo.com to the lower-level CA’s certificate. GnuTLS, MatrixSSL, and CyaSSL ignore name constraints Malformed extension values. Given a certificate with a known and accept the server’s certificate even if it has been issued by non-critical extension whose value is syntactically well-formed a CA that is not authorized to issue certificates for that server. ASN.1 but not a valid value for that extension, OpenSSL, GnuTLS, CyaSSL, and MatrixSSL accept it, while the other libraries and all browsers reject it. C. Incorrect checking of time Every X.509 certificate has the notBefore and notAfter Inconsistencies in the definition of self-signed. Self-issued timestamp fields. The SSL/TLS client must verify that the certificates are CA certificates in which the issuer and subject current date and time in GMT (or the time zone specified in are the same entity [69]. Nevertheless, given a (very odd) these fields) is within the range of these timestamps. certificate whose subject is the same as issuer but that also has a valid chain of trust, GnuTLS and MatrixSSL accept it. PolarSSL ignores the notBefore timestamp and thus accepts certificates that are not yet valid. When verifying the notAfter Inconsistencies between the certificate’s Authority Key Iden- field, it uses local time instead of GMT or the time zone tifier and its issuer. The Authority Key Identifier (AKI) specified in the field. extension differentiates between multiple certificates of the same issuer. When an AKI is present in a certificate issued I is the most severe error. It implies that the connection is by CA whose name is A, but the AKI points to a certificate insecure and must be reported to the user. On the other hand, whose subject name is B, some libraries reject, others accept. E is a common, relatively low-risk error. If the serial number field is absent in the AKI, then Table VI shows the results. For these tests, we extended GnuTLS accepts. But if this field is present and does not match our client suite with common Web browsers, since they are the issuer’s serial number, then GnuTLS rejects. directly responsible for interpreting the reasons for certificate rejection and presenting error warnings to human users. F. “Users. . . don’t go for the commercial CA racket” Most SSL/TLS implementations and Web browsers return only one error code even if the certificate is invalid for multiple We planned to include cryptlib in our testing, but then reasons. What is especially worrisome is that some browsers discovered that it does not verify certificate chains. We let the choose to report the less severe reason. In effect, they hide a following code snippet, taken from session/ssl_cli.c, speak severe security problem under a low-risk warning. These for itself (there is no code inside the if block): cases are highlighted in bold in Table VI. /* If certificate verification hasn’t been disabled For example, if a network attacker—say, a malicious Wi- , make sure that the Fi access point—presents a self-signed, very recently expired server’s certificate verifies */ certificate for gmail.com or any other important domain to if( !( verifyFlags & SSL_PFLAG_DISABLE_CERTVERIFY ) a user of Safari 7 or Chrome 30 (on Linux), the only error ) { warning the user will see is “Expired certificate.” 1 Many /* This is still too risky to enable by default users will click through this low-risk warning—even though because most users outside of web browsing don’t go for the commercial CA racket */ authentication has failed and the server has been spoofed! } This vulnerability is generic in all NSS-based applications: if the certificate is expired, that’s the only reported error code return( CRYPT_OK ); regardless of any other problems with the certificate. A related problem (not reflected in Table VI) is caused G. Security problems in error reporting by “Weak Key” warnings. When presented with a certificate containing a 512-bit RSA key, Firefox and Chrome accept it, Rejection of an invalid certificate is not the end of the while Opera warns that the key is weak. If the certificate is story. Web browsers and other interactive applications generate invalid, Opera still produces the same “Weak Key” warning, a warning based on the reason for rejection, show this warning masking other problems with the certificate, e.g., invalid issuer. to the user, and, in many cases, allow the user to override the The other warnings are available in the details tab of the error dialog and proceed. dialog, assuming Opera users know to look there. Different errors have different security implications. A re- Finally, if Firefox encounters two certs issued by the same cently expired, but otherwise valid certificate may be evidence CA that have the same serial number, it shows an error of a sloppy system administrator who forgot to install a new message describing the problem. This message masks all other certificate, but does not imply that the SSL/TLS connection warnings, but there is no way for the user to override it and will be insecure. “Expired certificate” warnings are sufficiently proceed, so this behavior is safe. common that users have learned to ignore them and browser developers are even advised to suppress them [1]. H. Other checks If, on the other hand, the certificate issuer is not valid, this Weak cryptographic hash functions. Digital signatures on means that the server cannot be authenticated and the con- SSL/TLS certificates can use a variety of cryptographic hash nection is not secure against man-in-the-middle attacks. If the (aka message digest) functions. As Table VII shows, only server’s hostname does not match the subject of the certificate, NSS, GnuTLS, and Chrome reject MD5 certificates, which the user may inspect both names and decide whether to proceed are known to be vulnerable to prefix-collision attacks [77]. or not. For example, if the hostname (e.g., bar.foo.com) is a subdomain of the common name in the certificate (e.g., Short keys. Table VIII shows that virtually all tested imple- foo.com), the user may chalk the discrepancy up to a minor mentations support short keys (512 bits for RSA) and unusual misconfiguration and proceed. key sizes (1023 bits, chosen because it occurs 87 times in our certificate corpus). To test whether SSL/TLS implementations report certificate errors correctly, we performed differential testing on leaf Additional checks. Table IX summarizes which SSL/TLS certificates with all combinations of the following: libraries perform additional checks, such as Certification Re- • Expired (E): Current time is later than the notAfter vocation Lists (CRL), subject alternative name, and hostname. timestamp in the certificate. The latter check is critically important for security against • Bad issuer (I): There is no valid chain of trust from the man-in-the-middle attacks [31], but often delegated by libraries certificate’s issuer to a trusted root CA. to higher-level applications. • Bad name (N): Neither the common name, nor the sub- 1 As this paper was being prepared, the same bug was reported in ject alternative name in the certificate match the server’s http://news.netcraft.com/archives/2013/10/16/us-government-aiding-spying- hostname. against-itself.html TABLE VI: Error code(s) returned by Web browsers and SSL/TLS libraries for certificates with various combinations of Bad Issuer (I), Expired (E), and Bad Name (N). Security vulnerabilities are highlighted in bold. Certs Firefox 20 Chrome 30 Opera 12 Opera 20 Safari 7 Chrome 30 IE 10 OpenSSL PolarSSL GnuTLS CyaSSL MatrixSSL NSS (Linux) (Linux) (Mac) (Mac) E E E E !E !E E E E E E E E E I I I I !I !I I I I I I I ** I IE IE E I# * !E * * I I IE ** ** E- IN IN I I# !I !I I IN I- I- I- I- *- I- IEN IEN N I# * !E * * I- IE- **- **- **- E- N N N N + !N N N - - - - - - NE NE N E# !E !E N NE E- **- E- E- E- E- * is a generic “invalid certificate” warning without a specific error message; the user cannot override this warning + is a generic “invalid certificate” warning without a specific error message; the user can override this warning ** is a generic “invalid certificate” error code # all errors are shown after the user clicks the details tab ! shows a generic error message first; the reported error is shown after user clicks the details button - the hostname check was not enabled for any of the tested clients TABLE VII: Support for cryptographic hash algorithms in certificate signatures Algorithm OpenSSL PolarSSL GnuTLS CyaSSL MatrixSSL NSS OpenJDK BouncyCastle Chrome Firefox WebKit Opera SHA-1 accept accept accept accept accept accept accept accept accept accept accept accept SHA-256 accept accept accept accept reject (u) accept accept accept accept accept accept accept SHA-512 accept accept accept reject (u) reject (u) accept accept accept accept accept accept accept MD2 reject reject reject reject reject reject reject reject reject reject reject reject MD4 reject reject reject reject reject reject reject (d) reject reject reject reject reject MD5 accept accept reject (w) accept accept reject (w) accept accept reject (w) accept accept accept reject (u) : reject because hash function is unknown reject (w) : reject because hash function is weak reject (d) : reject under default settings TABLE VIII: Support for short keys and unusual key sizes Key size OpenSSL PolarSSL GnuTLS CyaSSL MatrixSSL NSS OpenJDK BouncyCastle Chrome Firefox WebKit Opera 512-bit RSA accept accept accept accept accept accept accept accept accept accept accept warning 1023-bit RSA accept accept accept accept accept accept accept accept accept accept accept accept TABLE IX: Verification of extra certificate fields independently reported that GnuTLS does not reject certificates with unknown critical extensions. According to GnuTLS, re- Library CRL subjectAltName Host name jecting such certificates may allow certain corporations to lock MatrixSSL * No No out GnuTLS by issuing certificates with custom extensions PolarSSL Yes Yes Yes and thus forcing developers to use the corporation’s own SSL CyaSSL * Yes Yes library instead of GnuTLS. GnuTLS Yes Yes Yes NSS Yes Yes Yes OpenSSL * * * MatrixSSL plans to reject version 1 intermediate CAs and * not verified by default, application must explicitly enable check path length constraints starting from the next release. In general, MatrixSSL only performs basic checks on the certificate and depends on the application-provided callbacks X. D EVELOPER R ESPONSES to check key usage, extended key usage, expiration timestamps, etc. To facilitate these checks, MatrixSSL will parse the critical We notified the developers of all affected SSL/TLS imple- flags and the extended key usage extension. Since MatrixSSL mentations about the issues discovered by our testing. primarily targets embedded devices, which do not always have GnuTLS has fixed the bug involving version 1 intermediate the time zone information, in most cases the notBefore and CA certificates (starting from version 3.2.11) and also created notAfter timestamps in the certificate will have to be checked a patch for older versions. A security advisory (CVE-2014- against the available local time. 1959) has been issued for this bug. GnuTLS used to check the keyUsage field in earlier versions, but removed these checks CyaSSL is fixing all reported issues. The fixes will be part after getting bug reports from developers who were using of CyaSSL 3.0.0, expected to be released in April 2014. certificates with incorrect keyUsage fields.2 This was necessary for compatibility with several other SSL/TLS implementations PolarSSL is currently working on the fixes. that do not check this field. Delignat-Lavaud et al. [19] cryptlib does not support certificate chain validation to 2 http://www.gnutls.org/faq.html avoid validation failures for the users who run their own CA hierarchy or do not use certificates. The cryptlib manual3 rec- [3] N. AlFardan and K. Paterson. Lucky thirteen: Breaking the TLS ommends other techniques for authenticating the server, such and DTLS record protocols. In S&P, 2013. as matching key fingerprints. In addition, it strongly recom- [4] B. Amann, R. Sommer, M. Vallentin, and S. Hall. No attack necessary: The surprising dynamics of SSL trust relationships. mends using the PSK cipher suites for mutual authentication In ACSAC, 2013. of both the client and server. The manual also provides an [5] C. Amrutkar, K. Singh, A. Verma, and P. Traynor. Vulner- outline for the application writers who want to use certificates ableMe: Measuring systemic weaknesses in mobile browser on how to perform certificate validation on their own. security. In ICISS, 2012. [6] C. Amrutkar, P. Traynor, and P. van Oorschot. An empirical NSS developers informed us that all Mozilla products use evaluation of security indicators in mobile Web browsers. IEEE a glue layer called Personal Security Manager (PSM) over Trans. Mobile Computing, 2013. NSS instead of using NSS directly. The PSM certificate valida- [7] S. Anand, E. Burke, T. Chen, J. Clark, M. Cohen, W. Grieskamp, tion routine, CERT_VerifyCertificate, takes an argument named M. Harman, M. Harrold, and P. McMinn. An orchestrated survey CERTVerifyLog that, if not set to NULL, returns a list of all of methodologies for automated software test case generation. certificate validation errors. An example usage of the function Journal of Systems and Software, 86(8):1978–2001, 2013. can be found at http://mxr.mozilla.org/mozilla-central/source/ [8] D. Bleichenbacher. Chosen ciphertext attacks against protocols security/manager/ssl/src/SSLServerCertVerification.cpp#622 based on the RSA encryption standard PKCS #1. In CRYPTO, 1996. As of this writing, we are still talking to Web-browser [9] D. Brumley and D. Boneh. Remote timing attacks are practical. developers about user warnings generated by their browsers In USENIX Security, 2003. when certificate validation fails. [10] D. Brumley, J. Caballero, Z. Liang, J. Newsome, and D. Song. Towards automatic discovery of deviations in binary imple- mentations with applications to error detection and fingerprint XI. C ONCLUSIONS generation. In USENIX Security, 2007. We designed, implemented, and applied the first automated [11] C. Cadar, D. Dunbar, and D. Engler. KLEE: Unassisted and method for large-scale adversarial testing of certificate vali- automatic generation of high-coverage tests for complex systems dation logic in SSL/TLS implementations. Our key technical programs. In OSDI, 2008. innovation is “frankencerts,” synthetic certificates randomly [12] C. Cadar and D. Engler. Execution generated test cases: How mutated from parts of real certificates. Frankencerts are syn- to make systems code crash itself. In SPIN, 2005. [13] B. Chandrasekhar, S. Khurshid, and D. Marinov. Korat: Auto- tactically well-formed, but may violate the X.509 specification mated testing based on Java predicates. In ISSTA, 2002. and thus exercise rarely tested functionality in SSL/TLS im- [14] T. Chen, S. Cheung, and S. Yiu. Metamorphic testing: A plementations. Our testing uncovered multiple flaws in popular new approach for generating next test cases. Technical Re- SSL/TLS libraries and Web browsers, including security vul- port HKUST-CS98-01, Department of Computer Science, Hong nerabilities that break server authentication guarantees and can Kong University of Science and Technology, 1998. be exploited for stealthy man-in-the-middle attacks. [15] Y. Cheon and G. Leavens. A simple and practical approach to unit testing: The JML and JUnit way. In ECOOP, 2002. Certificate validation is only one part of the SSL/TLS hand- [16] J. Clark and P. van Oorschot. SoK: SSL and HTTPS: Revisiting shake. Bugs in other parts of the handshake—e.g., accidentally past challenges and evaluating certificate trust model enhance- omitting to check that the server’s messages are signed with the ments. In S&P, 2013. key that matches the certificate [49]—and incorrect usage of [17] Comodo report of incident. http://www.comodo.com/Comodo- SSL/TLS implementations by higher-level software [29, 31] Fraud-Incident-2011-03-23.html, 2011. can completely disable authentication and leave applications [18] B. Daniel, D. Dig, K. Garcia, and D. Marinov. Automated vulnerable to man-in-the-middle attacks. Development of auto- testing of refactoring engines. In FSE, 2007. mated methods that can analyze the entire SSL/TLS software [19] A. Delignat-Lavaud, M. Abadi, A. Birrell, I. Mironov, T. Wob- ber, and Y. Xie. Web PKI: Closing the gap between guidelines stack and prove that it has been implemented securely and and practices. In NDSS, 2014. correctly remains an open challenge. [20] W. Dickinson, D. Leon, and A. Podgurski. Finding failures by cluster analysis of execution profiles. In ICSE, 2001. Acknowledgments. We are grateful to Rui Qiu for partic- [21] M. Dietz, A. Czeskis, D. Balfanz, and D. Wallach. Origin-bound ipating in the initial exploration of the ideas that led to certificates: A fresh approach to strong client authentication for this work, and to our Oakland shepherd Matthew Smith the Web. In USENIX Security, 2012. for helping smooth ruffled feathers. This work was partially [22] Diginotar issues dodgy SSL certificates for Google services supported by the NSF grants CNS-0746888, CCF-0845628, after break-in. http://www.theinquirer.net/inquirer/news/ and CNS-1223396, a Google research award, NIH grant R01 2105321/diginotar-issues-dodgy-ssl-certificates-google- LM011028-01 from the National Library of Medicine, and services-break, 2011. Google PhD Fellowship to Suman Jana. [23] E. Dijkstra. A Discipline of Programming. 1976. [24] T. Duong and J. Rizzo. Here come the ⊕ ninjas. http:// nerdoholic.org/uploads/dergln/beast part2/ssl jun21.pdf, 2011. R EFERENCES [25] Z. Durumeric, J. Kasten, M. Bailey, and A. Halderman. Analysis [1] D. Akhawe, B. Amann, M. Vallentin, and R. Sommer. Here’s of the HTTPS certificate ecosystem. In IMC, 2013. my cert, so trust me, maybe? Understanding TLS errors on the [26] Z. Durumeric, E. Wustrow, and A. Halderman. ZMap: Fast Web. In WWW, 2013. Internet-wide scanning and its security applications. In USENIX [2] D. Akhawe and A. Felt. Alice in Warningland: A large- Security, 2013. scale field study of browser security warning effectiveness. In [27] P. Eckersley and J. Burns. An observatory for the SSLiverse. USENIX Security, 2013. In DEFCON, 2010. [28] M. Ernst. Static and dynamic analysis: Synergy and duality. In 3 http://www.cryptlib.com/downloads/manual.pdf, page 118 WODA, 2003. [29] S. Fahl, M. Harbach, T. Muders, and M. Smith. Why Eve [54] M. Marlinspike. IE SSL vulnerability. http://www.thoughtcrime. and Mallory love Android: An analysis of SSl (in)security on org/ie-ssl-chain.txt, 2002. Android. In CCS, 2012. [55] M. Marlinspike. More tricks for defeating SSL in practice. [30] FIPS PUB 140-2: Security requirements for cryptographic mod- DEFCON, 2009. ules. http://csrc.nist.gov/publications/fips/fips140-2/fips1402. [56] M. Marlinspike. New tricks for defeating SSL in practice. Black pdf, 2001. Hat DC, 2009. [31] M. Georgiev, S. Iyengar, S. Jana, R. Anubhai, D. Boneh, and [57] M. Marlinspike. Null prefix attacks against SSL/TLS certifi- V. Shmatikov. The most dangerous code in the world: Validating cates. http://www.thoughtcrime.org/papers/null-prefix-attacks. SSL certificates in non-browser software. In CCS, 2012. pdf, 2009. [32] M. Gligoric, F. Behrang, Y. Li, J. Overbey, M. Hafiz, and [58] P. Maurer. Generating test data with enhanced context-free D. Marinov. Systematic testing of refactoring engines on real grammars. IEEE Software, 7(4):50–55, 1990. software projects. In ECOOP, 2013. [59] W. McKeeman. Differential testing for software. Digital [33] CVE-2014-0092. https://bugzilla.redhat.com/show bug.cgi?id= Technical Journal, 10(1):100–107, 1998. 1069865, 2014. [60] A. Parsovs. Practical issues with TLS client certificate authen- [34] P. Godefroid, A. Kiezun, and M. Levin. Grammar-based tication. In NDSS, 2014. whitebox fuzzing. In PLDI, 2008. [61] A. Podgurski, D. Leon, P. Francis, W. Masri, M. Minch, J. Sun, [35] P. Godefroid, N. Klarlund, and K. Sen. DART: Directed and B. Wang. Automated support for classifying software failure automated random testing. In PLDI, 2005. reports. In ICSE, 2003. [36] P. Godefroid, M. Levin, and D. Molnar. Automated whitebox [62] P. Purdom. A sentence generator for testing parsers. BIT fuzz testing. In NDSS, 2008. Numerical Mathematics, 12:366–375, 1972. [37] W. Halfond, S. Anand, and A. Orso. Precise interface identifi- [63] D. Ramos and D. Engler. Practical, low-effort equivalence cation to improve testing and analysis of web applications. In verification of real code. In CAV, 2011. ISSTA, 2009. [64] The TLS protocol version 1.0. http://tools.ietf.org/html/rfc2246, [38] N. Heninger, Z. Durumeric, E. Wustrow, and A. Halderman. 1999. Mining your Ps and Qs: Detection of widespread weak keys in [65] Internet X.509 public key infrastructure certificate policy network devices. In USENIX Security, 2012. and certification practices framework. http://www.ietf.org/rfc/ [39] J. H. Holland. Adaptation in Natural and Artificial Systems. rfc2527.txt, 1999. University of Michigan Press, 1975. Second edition, 1992. [66] HTTP over TLS. http://www.ietf.org/rfc/rfc2818.txt, 2000. [40] CVE-2011-0228. http://cve.mitre.org/cgi-bin/cvename.cgi? [67] The Transport Layer Security (TLS) protocol version 1.1. http: name=CVE-2011-0228, 2011. //tools.ietf.org/html/rfc4346, 2006. [41] V. Jagannath, Y. Lee, B. Daniel, and D. Marinov. Reducing the [68] The Transport Layer Security (TLS) protocol version 1.2. http: costs of bounded-exhaustive testing. In FASE, 2009. //tools.ietf.org/html/rfc5246, 2008. [42] S. Jana and V. Shmatikov. Abusing file processing in malware [69] Internet X.509 public key infrastructure certificate and certificate detectors for fun and profit. In S&P, 2012. revocation list (CRL) profile. http://tools.ietf.org/html/rfc5280, [43] J. Jones, J. Bowring, and M. Harrold. Debugging in parallel. In 2008. ISSTA, 2007. [70] The Secure Sockets Layer (SSL) protocol version 3.0. http: [44] D. Kaminsky, M. Patterson, and L. Sassaman. PKI layer cake: //tools.ietf.org/html/rfc6101, 2011. New collision attacks against the global X.509 infrastructure. In [71] Representation and verification of domain-based application FC, 2010. service identity within Internet public key infrastructure using [45] S. Khurshid, C. Pasareanu, and W. Visser. Generalized symbolic X.509 (PKIX) certificates in the context of Transport Layer execution for model checking and testing. In TACAS, 2003. Security (TLS). http://tools.ietf.org/html/rfc6125, 2011. [46] A. Kiezun, P. Guo, K. Jayaraman, and M. Ernst. Automatic [72] J. Rizzo and T. Duong. The CRIME attack. In Ekoparty, 2012. creation of SQL injection and cross-site scripting attacks. In [73] P. Saxena, D. Akhawe, S. Hanna, F. Mao, S. McCamant, and ICSE, 2009. D. Song. A symbolic execution framework for JavaScript. In [47] J. King. Symbolic execution and program testing. Commun. S&P, 2010. ACM, 19(7), 1976. [74] K. Sen, D. Marinov, and G. Agha. CUTE: A concolic unit [48] R. Lammel and W. Schulte. Controllable combinatorial coverage testing engine for C. In FSE, 2005. in grammar-based testing. In Testing of Communicating Systems, [75] E. Sirer and B. Bershad. Using production grammars in software Lecture Notes in Computer Science, pages 19–38. 2006. testing. In Proc. 2nd Conference on Domain-specific Languages, [49] A. Langley. Apple’s SSL/TLS bug. https://www.imperialviolet. 1999. org/2014/02/22/applebug.html, 2014. [76] V. Srivastava, M. Bond, K. McKinley, and V. Shmatikov. A [50] A. Lenstra, J. Hughes, M. Augier, J. Bos, T. Kleinjung, and security policy oracle: Detecting security holes using multiple C. Wachter. Ron was wrong, Whit is right. http://eprint.iacr. API implementations. In PLDI, 2011. org/2012/064, 2012. [77] M. Stevens, A. Sotirov, J. Appelbaum, A. Lenstra, D. Molnar, [51] R. Majumdar and R. Xu. Directed test generation using D. Osvik, and B. Weger. Short chosen-prefix collisions for MD5 symbolic grammars. In ASE, 2007. and the creation of a rogue CA certificate. In CRYPTO, 2009. [52] B. Malloy and J. Power. An interpretation of Purdom’s algorithm [78] N. Vratonjic, J. Freudiger, V. Bindschaedler, and J.-P. Hubaux. for automatic generation of test cases. In ICIS, 2001. The inconvenient truth about Web certificates. In WEIS, 2011. [53] D. Marinov and S. Khurshid. TestEra: A novel framework for [79] X. Yang, Y. Chen, E. Eide, and J. Regehr. Finding and automated testing of Java programs. In ASE, 2001. understanding bugs in C compilers. In PLDI, 2011.