/* Icinga 2 | (c) 2021 Icinga GmbH | GPLv2+ */ #include "test/base-tlsutility.hpp" #include "base/tlsutility.hpp" #include "base/utility.hpp" #include "remote/pkiutility.hpp" #include "test/remote-certificate-fixture.hpp" #include #include #include #include #include #include #include #include using namespace icinga; static const long l_2016 = 1480000000; // Thu Nov 24 15:06:40 UTC 2016 static const long l_2017 = 1490000000; // Mon Mar 20 08:53:20 UTC 2017 BOOST_AUTO_TEST_SUITE(base_tlsutility) BOOST_AUTO_TEST_CASE(sha1) { std::string allchars; for (size_t i = 0; i < 256; i++) { allchars.push_back(i); } std::vector> testdata = { {"", "da39a3ee5e6b4b0d3255bfef95601890afd80709"}, {"icinga", "f172c5e9e4d840a55356882a2b644846b302b216"}, {"Icinga", "b3bdae77f60d9065f6152c7e3bbd351fa65e6fab"}, {"ICINGA", "335da1d814abeef09b4623e2ce5169140c267a39"}, {"#rX|wlcM:.8)uVmxz", "99dc4d34caf36c6d6b08404135f1a7286211be1e"}, {"AgbM;Z8Tz1!Im,kecZWs", "aa793bef1ca307012980ae5ae046b7e929f6ed99"}, {"yLUA4vKQ~24W}ahI;i?NLLS", "5e1a5ee3bd9fae5150681ef656ad43d9cb8e7005"}, {allchars, "4916d6bdb7f78e6803698cab32d1586ea457dfc8"}, }; for (const auto& p : testdata) { const auto& input = p.first; const auto& expected = p.second; auto output = SHA1(input); BOOST_CHECK_MESSAGE(output == expected, "SHA1('" << input << "') should be " << expected << ", got " << output); } } static String GetOpenSSLError() { std::array errBuf; ERR_error_string_n(ERR_get_error(), errBuf.data(), errBuf.size()); return {errBuf.data()}; } static std::shared_ptr GetRsaPrivateKey(const String& keyfile) { std::shared_ptr cakeybio(BIO_new_file(keyfile.CStr(), "r"), BIO_free); BOOST_REQUIRE_MESSAGE(cakeybio, "BIO_new_file() for private key from '" << keyfile << "': " << GetOpenSSLError()); RSA* rsa = PEM_read_bio_RSAPrivateKey(cakeybio.get(), nullptr, nullptr, nullptr); BOOST_REQUIRE_MESSAGE(rsa, "PEM read bio RSA key from private key file '" << keyfile << "': " << GetOpenSSLError()); BOOST_CHECK_EQUAL(1, RSA_check_key(rsa)); // 1 == valid, 0 == invalid std::shared_ptr rsaKey(EVP_PKEY_new(), EVP_PKEY_free); EVP_PKEY_assign_RSA(rsaKey.get(), rsa); BOOST_CHECK_EQUAL(EVP_PKEY_RSA, EVP_PKEY_id(rsaKey.get())); return rsaKey; } /** * Creates a new certificate based on an existing one, with modified validity period. * * @param cert The existing certificate to base the new one on. * @param validFrom The start time of the new certificate's validity period (in seconds). * @param validFor The duration of the new certificate's validity period (in seconds). * @param caCert Whether the new certificate should be a CA certificate. * * @returns A shared pointer to the newly created X509 certificate. */ static auto NewCertFromExisting(const std::shared_ptr& cert, long validFrom, long validFor, bool caCert = false) { std::shared_ptr caPubKey(X509_get_pubkey(cert.get()), EVP_PKEY_free); return CreateCertIcingaCA(caPubKey.get(), X509_get_subject_name(cert.get()), validFrom, validFor, caCert); } /** * Creates an ASN1_TIME object representing the current time plus the specified number of seconds. * * @param seconds The number of seconds to add to the current time. * @returns A shared pointer to the ASN1_TIME object. */ static std::shared_ptr MakeASN1TimeFrom(long seconds) { auto now = time(nullptr); return {X509_time_adj_ex(nullptr, 0, seconds, &now), ASN1_TIME_free}; } /** * Formats an ASN1_TIME object as a human-readable string. * * @param t The ASN1_TIME object to format. * * @returns A string representation of the ASN1_TIME object. */ static std::string FormatAsn1Time(const ASN1_TIME* t) { std::shared_ptr bio(BIO_new(BIO_s_mem()), BIO_free); BOOST_REQUIRE_MESSAGE(bio, "BIO_new(BIO_s_mem()): " << GetOpenSSLError()); ASN1_TIME_print(bio.get(), t); char *data; long len = BIO_get_mem_data(bio.get(), &data); std::string result(data, data + len); return result; } // Asserts that verifying the given leaf certificate against the given CA certificate results in a certificate // expiration error. This macro is used so that when the assertion fails, the test output refers to the exact // line where the macro was invoked, rather than the line inside the lambda function, which can be everywhere. #define ASSERT_CERT_EXPIRED(ca, leaf) \ do { \ BOOST_CHECK_EXCEPTION( \ VerifyCertificate(ca, leaf, String()), \ openssl_error, \ [](const openssl_error& e) { \ const unsigned long* opensslCode = boost::get_error_info(e); \ BOOST_REQUIRE(opensslCode); \ BOOST_REQUIRE_EQUAL(*opensslCode, X509_V_ERR_CERT_HAS_EXPIRED); \ return *opensslCode == X509_V_ERR_CERT_HAS_EXPIRED; \ } \ ); \ } while (0) // Asserts that verifying the given leaf certificate against the given CA certificate results in a certificate // signature failure error. This macro serves the same purpose as ASSERT_CERT_EXPIRED. #define ASSERT_SIGNATURE_FAILURE(ca, leaf) \ do { \ BOOST_CHECK_EXCEPTION( \ VerifyCertificate(ca, leaf, String()), \ openssl_error, \ [](const openssl_error& e) { \ const unsigned long* opensslCode = boost::get_error_info(e); \ BOOST_REQUIRE(opensslCode); \ BOOST_REQUIRE_EQUAL(*opensslCode, X509_V_ERR_CERT_SIGNATURE_FAILURE); \ return *opensslCode == X509_V_ERR_CERT_SIGNATURE_FAILURE; \ } \ ); \ } while (0) BOOST_AUTO_TEST_CASE(verify_static_certs) { BOOST_CHECK(VerifyCertificate(StringToCertificate(l_IcingaCa), StringToCertificate(l_ExampleCrt), String())); ASSERT_CERT_EXPIRED(StringToCertificate(l_IcingaCa), StringToCertificate(l_ExpiredCrt)); ASSERT_CERT_EXPIRED(StringToCertificate(l_ExpiredCa), StringToCertificate(l_ExpiredCaLeaf)); // Signature failure test case with mismatched CA and leaf certificate. ASSERT_SIGNATURE_FAILURE(StringToCertificate(l_IcingaCa2), StringToCertificate(l_ExampleCrt)); } BOOST_AUTO_TEST_CASE(static_certs_uptodate) { BOOST_CHECK(IsCaUptodate(StringToCertificate(l_IcingaCa).get())); BOOST_CHECK(IsCaUptodate(StringToCertificate(l_IcingaCa2).get())); BOOST_CHECK(!IsCaUptodate(StringToCertificate(l_ExpiredCa).get())); BOOST_CHECK(IsCertUptodate(StringToCertificate(l_ExampleCrt))); BOOST_CHECK(IsCertUptodate(StringToCertificate(l_ExpiredCaLeaf))); // Its CA is expired, but not itself. BOOST_CHECK(!IsCertUptodate(StringToCertificate(l_ExpiredCrt))); } BOOST_FIXTURE_TEST_CASE(create_verify_ca, CertificateFixture) { auto cacert(GetX509Certificate(m_CaDir.string()+"/ca.crt")); if constexpr (OPENSSL_VERSION_NUMBER >= 0x10100000L) { // OpenSSL 1.1.x provides https://www.openssl.org/docs/man1.1.0/man3/X509_check_ca.html BOOST_CHECK(IsCa(cacert)); } else { BOOST_CHECK_THROW(IsCa(cacert), std::invalid_argument); } BOOST_CHECK(VerifyCertificate(cacert, cacert, String())); // Self-signed CA! BOOST_CHECK(IsCaUptodate(cacert.get())); // Is CA up-to-date after its creation? auto validUntil = MakeASN1TimeFrom(ROOT_VALID_FOR); BOOST_CHECK_MESSAGE(0 >= Asn1TimeCompare(X509_get_notAfter(cacert.get()), validUntil.get()), "CA should expire within " << std::quoted(FormatAsn1Time(validUntil.get())) << ", notAfter: " << std::quoted(FormatAsn1Time(X509_get_notAfter(cacert.get())))); // Set the CA certificate to expire in 100 days, i.e. less than the LEAF_VALID_FOR threshold of 397 days. cacert = NewCertFromExisting(cacert, 0, 100*24*60*60, true); BOOST_CHECK(!IsCaUptodate(cacert.get())); // Is CA outdated now? cacert = NewCertFromExisting(cacert, 0, LEAF_VALID_FOR-1, true); BOOST_CHECK(!IsCaUptodate(cacert.get())); // Still outdated, as it's less than LEAF_VALID_FOR. } BOOST_FIXTURE_TEST_CASE(create_verify_leaf_certs, CertificateFixture) { String caDir = m_CaDir.string(); String certsDir = m_CertsDir.string(); auto caprivatekey(GetRsaPrivateKey(caDir+"/ca.key")); auto cacert(GetX509Certificate(caDir+"/ca.crt")); BOOST_CHECK(IsCaUptodate(cacert.get())); BOOST_CHECK_EQUAL(1, X509_verify(cacert.get(), caprivatekey.get())); // 1 == equal, 0 == unequal, -1 == error auto certInfo = EnsureCertFor("example.com", true); // Generates example.com.{key,csr,crt} files. auto cert(GetX509Certificate(certInfo.crtFile)); if constexpr (OPENSSL_VERSION_NUMBER >= 0x10100000L) { BOOST_CHECK(!IsCa(cert)); } else { BOOST_CHECK_THROW(IsCa(cert), std::invalid_argument); } BOOST_CHECK(IsCertUptodate(cert)); // Is leaf up-to-date after its creation? BOOST_CHECK(VerifyCertificate(cacert, cert, String())); // Signed by our CA? auto validUntil = MakeASN1TimeFrom(LEAF_VALID_FOR); BOOST_CHECK_MESSAGE(0 >= Asn1TimeCompare(X509_get_notAfter(cert.get()), validUntil.get()), "Leaf certificate should expire within " << std::quoted(FormatAsn1Time(validUntil.get())) << ", notAfter: " << std::quoted(FormatAsn1Time(X509_get_notAfter(cert.get())))); // Set the certificate to expire in 20 days, i.e. less than the RENEW_THRESHOLD of 30 days. cert = NewCertFromExisting(cert, 0, 20*24*60*60); BOOST_CHECK(!IsCertUptodate(cert)); BOOST_CHECK(VerifyCertificate(cacert, cert, String())); // Verification should still work. // Check whether expired certificates are correctly detected and verification fails. cert = NewCertFromExisting(cert, -LEAF_VALID_FOR, -10*24*60*60); // Expire 10 days ago! validUntil = MakeASN1TimeFrom(-10*24*60*60); BOOST_CHECK_MESSAGE(0 >= Asn1TimeCompare(X509_get_notAfter(cert.get()), validUntil.get()), // Is certificate indeed expired? "Leaf certificate should have expired on " << std::quoted(FormatAsn1Time(validUntil.get())) << ", notAfter: " << std::quoted(FormatAsn1Time(X509_get_notAfter(cert.get())))); BOOST_CHECK(!IsCertUptodate(cert)); // It's already expired, so definitely not up-to-date. ASSERT_CERT_EXPIRED(cacert, cert); // Set the certificate validity start date to 2016, all certificates created before 2017 are considered outdated. cert = NewCertFromExisting(cert, -(time(nullptr)-l_2016), LEAF_VALID_FOR); BOOST_CHECK(!IsCertUptodate(cert)); // ... but verification should still work, as the certificate is still valid. BOOST_CHECK(VerifyCertificate(cacert, cert, String())); // Reset the certificate validity start date to the least acceptable value, i.e. 2017. cert = NewCertFromExisting(cert, -(time(nullptr)-l_2017), LEAF_VALID_FOR); BOOST_CHECK(IsCertUptodate(cert)); BOOST_CHECK(VerifyCertificate(cacert, cert, String())); cacert = NewCertFromExisting(cacert, -LEAF_VALID_FOR, -10*24*60*60, true); // Expire the CA 10 days ago. BOOST_CHECK_EQUAL(1, X509_verify(cacert.get(), caprivatekey.get())); // 1 == equal, 0 == unequal, -1 == error BOOST_CHECK(!IsCaUptodate(cacert.get())); ASSERT_CERT_EXPIRED(cacert, cert); // Generate a new CA certificate to simulate a renewal and check whether verification still works. auto newCACert = NewCertFromExisting(cacert, 0, ROOT_VALID_FOR, true); BOOST_REQUIRE(newCACert); BOOST_CHECK_EQUAL(1, X509_verify(newCACert.get(), caprivatekey.get())); // 1 == equal, 0 == unequal, -1 == error BOOST_CHECK(IsCaUptodate(newCACert.get())); BOOST_CHECK(VerifyCertificate(newCACert, newCACert, String())); BOOST_CHECK(VerifyCertificate(newCACert, cert, String())); auto assertIMMorDZSSC = [](const openssl_error& e) { // IMM = Issuer Mismatch, DZSSC = Depth Zero Self-Signed Cert const unsigned long* opensslCode = boost::get_error_info(e); BOOST_REQUIRE(opensslCode); #ifdef LIBRESSL_VERSION_NUMBER BOOST_REQUIRE_EQUAL(*opensslCode, X509_V_ERR_SUBJECT_ISSUER_MISMATCH); return *opensslCode == X509_V_ERR_SUBJECT_ISSUER_MISMATCH; #else BOOST_REQUIRE_EQUAL(*opensslCode, X509_V_ERR_DEPTH_ZERO_SELF_SIGNED_CERT); return *opensslCode == X509_V_ERR_DEPTH_ZERO_SELF_SIGNED_CERT; #endif }; //... but verifying the new CA with the old CA or vice versa should fail. BOOST_CHECK_EXCEPTION(VerifyCertificate(cacert, newCACert, String()), openssl_error, assertIMMorDZSSC); BOOST_CHECK_EXCEPTION(VerifyCertificate(newCACert, cacert, String()), openssl_error, assertIMMorDZSSC); cacert = newCACert; cert = NewCertFromExisting(cert, 0, LEAF_VALID_FOR); BOOST_CHECK(IsCertUptodate(cert)); BOOST_CHECK(VerifyCertificate(cacert, cert, String())); // Remove the previously generated CA before regenerating a new one, PkiUtility::NewCa() would fail otherwise. Utility::Remove(caDir+"/ca.crt"); Utility::Remove(caDir+"/ca.key"); BOOST_CHECK_EQUAL(0, PkiUtility::NewCa()); newCACert = GetX509Certificate(caDir+"/ca.crt"); auto newCAPrivateKey = GetRsaPrivateKey(caDir+"/ca.key"); BOOST_REQUIRE(newCACert); BOOST_CHECK_NE(0, ASN1_INTEGER_cmp(X509_get_serialNumber(cacert.get()), X509_get_serialNumber(newCACert.get()))); // 1 == equal, 0 == unequal but same type, -1 == different types (e.g. RSA vs. EC) and -2 == unsupported op. BOOST_CHECK_NE(1, EVP_PKEY_cmp(X509_get_pubkey(cacert.get()), X509_get_pubkey(newCACert.get()))); BOOST_CHECK_MESSAGE(1 == X509_verify(newCACert.get(), newCAPrivateKey.get()), "Failed to verify new CA certificate: " << GetOpenSSLError()); BOOST_CHECK_MESSAGE(1 > X509_verify(newCACert.get(), caprivatekey.get()), "New CA certificate should not be verifiable with the old private key"); BOOST_CHECK_MESSAGE(1 > X509_verify(cacert.get(), newCAPrivateKey.get()), "Old CA certificate should not be verifiable with the new private key"); BOOST_CHECK(IsCaUptodate(newCACert.get())); BOOST_CHECK(VerifyCertificate(newCACert, newCACert, String())); // Self-signed CA! // Verification should fail because the leaf certificate was signed by the old CA. ASSERT_SIGNATURE_FAILURE(newCACert, StringToCertificate(CertificateToString(cert))); // Renew the leaf certificate and check whether verification works with the new CA. auto newCert = NewCertFromExisting(cert, 0, LEAF_VALID_FOR, false); BOOST_CHECK(IsCertUptodate(newCert)); BOOST_CHECK(VerifyCertificate(newCACert, newCert, String())); // Verification should fail because the new leaf certificate was signed by the newly generated CA. ASSERT_SIGNATURE_FAILURE(cacert, StringToCertificate(CertificateToString(newCert))); } BOOST_AUTO_TEST_SUITE_END()