From 9abcc3365aed51aef4496b5139f1f99488ea9583 Mon Sep 17 00:00:00 2001 From: aeris Date: Sun, 29 Jan 2017 16:59:00 +0100 Subject: [PATCH] Generate crypto material for tests --- Makefile | 6 +- bin/generate-test-material.rb | 144 +++++++++++++++++++++++ disable_digest_check.path | 76 ++++++++++++ spec/resources/ca.crt | 21 ++-- spec/resources/custom.crt | 13 -- spec/resources/ecdsa-brainpoolP256r1.crt | 12 ++ spec/resources/ecdsa-brainpoolP384r1.crt | 13 ++ spec/resources/ecdsa-brainpoolP512r1.crt | 14 +++ spec/resources/ecdsa-prime192v1.crt | 12 ++ spec/resources/ecdsa-prime256v1.crt | 12 ++ spec/resources/ecdsa-secp256k1.crt | 12 ++ spec/resources/ecdsa-secp384r1.crt | 13 ++ spec/resources/ecdsa-secp521r1.crt | 14 +++ spec/resources/ecdsa-sect283k1.crt | 12 ++ spec/resources/ecdsa-sect283r1.crt | 12 ++ spec/resources/ecdsa-sect409k1.crt | 13 ++ spec/resources/ecdsa-sect409r1.crt | 13 ++ spec/resources/ecdsa-sect571k1.crt | 14 +++ spec/resources/ecdsa-sect571r1.crt | 14 +++ spec/resources/intermediate.crt | 21 ++-- spec/resources/md5.crt | 12 ++ spec/resources/must-staple.crt | 13 ++ spec/resources/rsa-1024.crt | 14 +++ spec/resources/rsa-1024.pem | 26 ++-- spec/resources/rsa-2048.crt | 16 +++ spec/resources/rsa-3072.crt | 19 +++ spec/resources/rsa-4096.crt | 22 ++++ spec/resources/rsa-512.crt | 12 ++ spec/resources/rsa-768.crt | 13 ++ spec/resources/self-signed.crt | 21 ++-- spec/resources/sha1.crt | 12 ++ 31 files changed, 581 insertions(+), 60 deletions(-) create mode 100755 bin/generate-test-material.rb create mode 100644 disable_digest_check.path delete mode 100644 spec/resources/custom.crt create mode 100644 spec/resources/ecdsa-brainpoolP256r1.crt create mode 100644 spec/resources/ecdsa-brainpoolP384r1.crt create mode 100644 spec/resources/ecdsa-brainpoolP512r1.crt create mode 100644 spec/resources/ecdsa-prime192v1.crt create mode 100644 spec/resources/ecdsa-prime256v1.crt create mode 100644 spec/resources/ecdsa-secp256k1.crt create mode 100644 spec/resources/ecdsa-secp384r1.crt create mode 100644 spec/resources/ecdsa-secp521r1.crt create mode 100644 spec/resources/ecdsa-sect283k1.crt create mode 100644 spec/resources/ecdsa-sect283r1.crt create mode 100644 spec/resources/ecdsa-sect409k1.crt create mode 100644 spec/resources/ecdsa-sect409r1.crt create mode 100644 spec/resources/ecdsa-sect571k1.crt create mode 100644 spec/resources/ecdsa-sect571r1.crt create mode 100644 spec/resources/md5.crt create mode 100644 spec/resources/must-staple.crt create mode 100644 spec/resources/rsa-1024.crt create mode 100644 spec/resources/rsa-2048.crt create mode 100644 spec/resources/rsa-3072.crt create mode 100644 spec/resources/rsa-4096.crt create mode 100644 spec/resources/rsa-512.crt create mode 100644 spec/resources/rsa-768.crt create mode 100644 spec/resources/sha1.crt diff --git a/Makefile b/Makefile index ad2579b..c0888bc 100644 --- a/Makefile +++ b/Makefile @@ -44,6 +44,7 @@ build/$(OPENSSL_NAME).tar.gz: | build/ $(OPENSSL_DIR)/: build/$(OPENSSL_NAME).tar.gz build/chacha-poly.patch tar -C build -xf build/$(OPENSSL_NAME).tar.gz patch -d $(OPENSSL_DIR) -p1 < build/chacha-poly.patch + patch -d $(OPENSSL_DIR) -p1 < disable_digest_check.path $(OPENSSL_DIR)/Makefile: | $(OPENSSL_DIR)/ #cd $(OPENSSL_DIR) && ./Configure enable-ssl2 enable-ssl3 enable-weak-ssl-ciphers enable-zlib enable-rc5 enable-rc2 enable-gost enable-md2 enable-mdc2 enable-shared linux-x86_64 @@ -91,10 +92,13 @@ $(RUBY_OPENSSL_EXT_DIR)/Makefile: libs | $(RUBY_DIR)/ patch -d $(RUBY_DIR)/ -p1 < multiple_certs.patch cd $(RUBY_OPENSSL_EXT_DIR) && ruby extconf.rb -$(RUBY_OPENSSL_EXT_DIR)/openssl.so: $(LIBS) #$(RUBY_OPENSSL_EXT_DIR)/Makefile +$(RUBY_OPENSSL_EXT_DIR)/openssl.so: $(LIBS) $(RUBY_OPENSSL_EXT_DIR)/Makefile top_srcdir=../.. $(MAKE) -C $(RUBY_OPENSSL_EXT_DIR) lib/openssl.so: $(RUBY_OPENSSL_EXT_DIR)/openssl.so cp $< $@ ext: lib/openssl.so + +test-material: + bin/generate-test-material.rb diff --git a/bin/generate-test-material.rb b/bin/generate-test-material.rb new file mode 100755 index 0000000..4de1278 --- /dev/null +++ b/bin/generate-test-material.rb @@ -0,0 +1,144 @@ +#!/usr/bin/env ruby +$:.unshift File.expand_path File.join File.dirname(__FILE__), '../lib' +require 'rubygems' +require 'bundler/setup' +require 'openssl' +require 'socket' +require 'cryptcheck' + +LOG = ::CryptCheck::Logger +LOG.level = ENV['LOG'] || :info + +OpenSSL::PKey::EC.send :alias_method, :private?, :private_key? + +CA_KEY_USAGE = %w(keyCertSign cRLSign) +CA_EXTENDED_KEY_USAGE = [] +CA_NETSCAPE_CERT_TYPE = %w(sslCA) +RSA_KEY_USAGE = %w(digitalSignature) +ECDSA_KEY_USAGE = %w(digitalSignature) +CERT_EXTENDED_KEY_USAGE = %w(serverAuth) +CERT_NETSCAPE_CERT_TYPE = %w(server) + + +def certificate(key, subject, san: %w(DNS:localhost), + from: Time.utc(2000, 1, 1), to: Time.utc(2001, 1, 1), + issuer: nil, ca: false, + key_usage: ECDSA_KEY_USAGE, extended_key_usage: CERT_EXTENDED_KEY_USAGE, + netscape_cert_type: CERT_NETSCAPE_CERT_TYPE, + hash: OpenSSL::Digest::SHA512, extensions: []) + cert = OpenSSL::X509::Certificate.new + cert.version = 3 + cert.serial = rand 2**63 .. 2**64 + cert.not_before = from if from + cert.not_after = to if to + + cert.public_key = case key + when OpenSSL::PKey::EC + curve = key.group.curve_name + public = OpenSSL::PKey::EC.new curve + public.public_key = key.public_key + public + else + key.public_key + end + + name = OpenSSL::X509::Name.parse subject + cert.subject = name + + issuer = { cert: cert, key: key } unless issuer + cert.issuer = issuer[:cert].subject + + extension_factory = OpenSSL::X509::ExtensionFactory.new nil, cert + extension_factory.subject_certificate = cert + extension_factory.issuer_certificate = issuer[:cert] + + cert.add_extension extension_factory.create_extension 'basicConstraints', "CA:#{ca.to_s.upcase}", true + cert.add_extension extension_factory.create_extension 'keyUsage', key_usage.uniq.join(','), true unless key_usage.empty? + cert.add_extension extension_factory.create_extension 'extendedKeyUsage', extended_key_usage.uniq.join(','), true unless extended_key_usage.empty? + cert.add_extension extension_factory.create_extension 'nsCertType', netscape_cert_type.uniq.join(',') unless netscape_cert_type.empty? + cert.add_extension extension_factory.create_extension 'subjectKeyIdentifier', 'hash' + cert.add_extension extension_factory.create_extension 'authorityKeyIdentifier', 'keyid:always' + cert.add_extension extension_factory.create_extension 'subjectAltName', san.uniq.join(',') unless san.empty? + + extensions.each { |e| cert.add_extension e } + + cert.sign issuer[:key], hash.new + + cert +end + +def generate_dh(size) + filename = "spec/resources/dh-#{size}.pem" + return if File.exist? filename + LOG.info "Generate dh-#{size}" + File.write filename, OpenSSL::PKey::DH.new(size).to_pem +end + +def generate_material(name, key, cert) + key_file = "spec/resources/#{name}.pem" + key = if File.exists?(key_file) + OpenSSL::PKey.read File.read key_file + else + LOG.info "Generate #{name} key" + key = key.call + File.write key_file, key.to_pem + key + end + + cert_file = "spec/resources/#{name}.crt" + cert = if File.exist?(cert_file) + OpenSSL::X509::Certificate.new File.read cert_file + else + LOG.info "Generate #{name} cert" + cert = cert.call key + File.write cert_file, cert.to_pem + cert + end + + [key, cert] +end + +ca_key, ca_cert = generate_material 'ca', + -> () { OpenSSL::PKey::EC.new('secp384r1').generate_key }, + -> (k) { certificate k, '/CN=ca', ca: true, key_usage: CA_KEY_USAGE, extended_key_usage: CA_EXTENDED_KEY_USAGE, netscape_cert_type: CA_NETSCAPE_CERT_TYPE } + +intermediate_key, intermediate_cert = generate_material 'intermediate', + -> () { OpenSSL::PKey::EC.new('secp384r1').generate_key }, + -> (key) { certificate key, '/CN=intermediate', ca: true, issuer: { cert: ca_cert, key: ca_key }, key_usage: CA_KEY_USAGE, extended_key_usage: CA_EXTENDED_KEY_USAGE, netscape_cert_type: CA_NETSCAPE_CERT_TYPE } +issuer = { cert: intermediate_cert, key: intermediate_key } + +[512, 768, 1024, 2048, 3072, 4096].each do |s| + generate_material "rsa-#{s}", + -> () { OpenSSL::PKey::RSA.new s }, + -> (key) { certificate key, "/CN=rsa-#{s}", issuer: issuer, key_usage: RSA_KEY_USAGE } + generate_dh s +end + +CryptCheck::Tls::Curve.each do |c| + c = c.name + generate_material "ecdsa-#{c}", + -> () { OpenSSL::PKey::EC.new(c).generate_key }, + -> (key) { certificate key, "/CN=ecdsa-#{c}", issuer: issuer } +end + +generate_material 'self-signed', + -> { OpenSSL::PKey::EC.new('prime256v1').generate_key }, + -> (key) { certificate key, '/CN=self-signed', ca: true, + key_usage: CA_KEY_USAGE+ECDSA_KEY_USAGE, + extended_key_usage: CA_EXTENDED_KEY_USAGE + CERT_EXTENDED_KEY_USAGE, + netscape_cert_type: CA_NETSCAPE_CERT_TYPE + CERT_NETSCAPE_CERT_TYPE } + +# Require patched OpenSSL to be able to issue MD5 certificates +generate_material 'md5', + -> { OpenSSL::PKey::EC.new('prime256v1').generate_key }, + -> (key) { certificate key, '/CN=md5', issuer: issuer, hash: OpenSSL::Digest::MD5 } + +# Require patched OpenSSL to be able to issue SHA1 certificates +generate_material 'sha1', + -> { OpenSSL::PKey::EC.new('prime256v1').generate_key }, + -> (key) { certificate key, '/CN=sha1', issuer: issuer, hash: OpenSSL::Digest::SHA1 } + +must_staple = OpenSSL::X509::Extension.new '1.3.6.1.5.5.7.1.24', '0', true +generate_material 'must-staple', + -> () { OpenSSL::PKey::EC.new('prime256v1').generate_key }, + -> (key) { certificate key, '/CN=must-staple', issuer: issuer, extensions: [must_staple] } diff --git a/disable_digest_check.path b/disable_digest_check.path new file mode 100644 index 0000000..297ae83 --- /dev/null +++ b/disable_digest_check.path @@ -0,0 +1,76 @@ +diff --git a/crypto/dsa/dsa_pmeth.c b/crypto/dsa/dsa_pmeth.c +index 42b8bb0..baaa76f 100644 +--- a/crypto/dsa/dsa_pmeth.c ++++ b/crypto/dsa/dsa_pmeth.c +@@ -174,26 +174,26 @@ static int pkey_dsa_ctrl(EVP_PKEY_CTX *ctx, int type, int p1, void *p2) + return 1; + + case EVP_PKEY_CTRL_DSA_PARAMGEN_MD: +- if (EVP_MD_type((const EVP_MD *)p2) != NID_sha1 && +- EVP_MD_type((const EVP_MD *)p2) != NID_sha224 && +- EVP_MD_type((const EVP_MD *)p2) != NID_sha256) { +- DSAerr(DSA_F_PKEY_DSA_CTRL, DSA_R_INVALID_DIGEST_TYPE); +- return 0; +- } ++ // if (EVP_MD_type((const EVP_MD *)p2) != NID_sha1 && ++ // EVP_MD_type((const EVP_MD *)p2) != NID_sha224 && ++ // EVP_MD_type((const EVP_MD *)p2) != NID_sha256) { ++ // DSAerr(DSA_F_PKEY_DSA_CTRL, DSA_R_INVALID_DIGEST_TYPE); ++ // return 0; ++ // } + dctx->md = p2; + return 1; + + case EVP_PKEY_CTRL_MD: +- if (EVP_MD_type((const EVP_MD *)p2) != NID_sha1 && +- EVP_MD_type((const EVP_MD *)p2) != NID_dsa && +- EVP_MD_type((const EVP_MD *)p2) != NID_dsaWithSHA && +- EVP_MD_type((const EVP_MD *)p2) != NID_sha224 && +- EVP_MD_type((const EVP_MD *)p2) != NID_sha256 && +- EVP_MD_type((const EVP_MD *)p2) != NID_sha384 && +- EVP_MD_type((const EVP_MD *)p2) != NID_sha512) { +- DSAerr(DSA_F_PKEY_DSA_CTRL, DSA_R_INVALID_DIGEST_TYPE); +- return 0; +- } ++ // if (EVP_MD_type((const EVP_MD *)p2) != NID_sha1 && ++ // EVP_MD_type((const EVP_MD *)p2) != NID_dsa && ++ // EVP_MD_type((const EVP_MD *)p2) != NID_dsaWithSHA && ++ // EVP_MD_type((const EVP_MD *)p2) != NID_sha224 && ++ // EVP_MD_type((const EVP_MD *)p2) != NID_sha256 && ++ // EVP_MD_type((const EVP_MD *)p2) != NID_sha384 && ++ // EVP_MD_type((const EVP_MD *)p2) != NID_sha512) { ++ // DSAerr(DSA_F_PKEY_DSA_CTRL, DSA_R_INVALID_DIGEST_TYPE); ++ // return 0; ++ // } + dctx->md = p2; + return 1; + +diff --git a/crypto/ec/ec_pmeth.c b/crypto/ec/ec_pmeth.c +index b767490..70eea17 100644 +--- a/crypto/ec/ec_pmeth.c ++++ b/crypto/ec/ec_pmeth.c +@@ -379,15 +379,15 @@ static int pkey_ec_ctrl(EVP_PKEY_CTX *ctx, int type, int p1, void *p2) + return dctx->kdf_ukmlen; + + case EVP_PKEY_CTRL_MD: +- if (EVP_MD_type((const EVP_MD *)p2) != NID_sha1 && +- EVP_MD_type((const EVP_MD *)p2) != NID_ecdsa_with_SHA1 && +- EVP_MD_type((const EVP_MD *)p2) != NID_sha224 && +- EVP_MD_type((const EVP_MD *)p2) != NID_sha256 && +- EVP_MD_type((const EVP_MD *)p2) != NID_sha384 && +- EVP_MD_type((const EVP_MD *)p2) != NID_sha512) { +- ECerr(EC_F_PKEY_EC_CTRL, EC_R_INVALID_DIGEST_TYPE); +- return 0; +- } ++ // if (EVP_MD_type((const EVP_MD *)p2) != NID_sha1 && ++ // EVP_MD_type((const EVP_MD *)p2) != NID_ecdsa_with_SHA1 && ++ // EVP_MD_type((const EVP_MD *)p2) != NID_sha224 && ++ // EVP_MD_type((const EVP_MD *)p2) != NID_sha256 && ++ // EVP_MD_type((const EVP_MD *)p2) != NID_sha384 && ++ // EVP_MD_type((const EVP_MD *)p2) != NID_sha512) { ++ // ECerr(EC_F_PKEY_EC_CTRL, EC_R_INVALID_DIGEST_TYPE); ++ // return 0; ++ // } + dctx->md = p2; + return 1; + diff --git a/spec/resources/ca.crt b/spec/resources/ca.crt index 7882709..c94b9b9 100644 --- a/spec/resources/ca.crt +++ b/spec/resources/ca.crt @@ -1,13 +1,12 @@ -----BEGIN CERTIFICATE----- -MIIB7zCCAXWgAwIBAgIJAKFu2k3vOIffMAoGCCqGSM49BAMEMBIxEDAOBgNVBAMM -B3Rlc3QtY2EwHhcNMTcwMTIyMTg1NTUxWhcNMTgwMTIyMTg1NTUxWjASMRAwDgYD -VQQDDAd0ZXN0LWNhMHYwEAYHKoZIzj0CAQYFK4EEACIDYgAEhVE2pSx4GG922yqA -z0W0usG8dFdY4qtTD5mwwBzRhu9NegzQmaE5oHNzQrQE8v0/ShrSHNdID6Phty9K -lPYoenUmpH0sdJDqQ5cVUDkmw0+f+XpROtCiBcN8kTmiVXQ5o4GWMIGTMA8GA1Ud -EwEB/wQFMAMBAf8wCwYDVR0PBAQDAgL0MB0GA1UdJQQWMBQGCCsGAQUFBwMBBggr -BgEFBQcDAjAdBgNVHQ4EFgQU2saIfk29nr+adaNemnS2AaNjXJEwHwYDVR0jBBgw -FoAU2saIfk29nr+adaNemnS2AaNjXJEwFAYDVR0RBA0wC4IJbG9jYWxob3N0MAoG -CCqGSM49BAMEA2gAMGUCMQCzxeexb5HauoM8OQPBK7MWxzganLfVoi1GCsbvjUQy -AB8AAVijIPwT/MGcigge4z8CMFimJXl934AtL8iM+Jd9ykvNXXxzSn9YRm9aLD3K -w6vam+k+gA4sdijDbRC/Tc/3NQ== +MIIBwzCCAUqgAwIBAwIJAKlvU4MMj9FAMAoGCCqGSM49BAMEMA0xCzAJBgNVBAMM +AmNhMB4XDTAwMDEwMTAwMDAwMFoXDTAxMDEwMTAwMDAwMFowDTELMAkGA1UEAwwC +Y2EwdjAQBgcqhkjOPQIBBgUrgQQAIgNiAASeQcdqy/n+tsyX4MIFD2kA/6T/IMOV +tuJIHFUdWa6hOvozb0O18EXP7ZKxIn5WzOOsLMZRk/hxPTmrKxDL9taeZUHw+UGT +KIU8ECJ2WtIvMsySPZGPM50Y9MA3Plizby2jdjB0MA8GA1UdEwEB/wQFMAMBAf8w +DgYDVR0PAQH/BAQDAgEGMBEGCWCGSAGG+EIBAQQEAwICBDAdBgNVHQ4EFgQURRb1 +3Y5HR1QFOXMFZykLelX/p1AwHwYDVR0jBBgwFoAURRb13Y5HR1QFOXMFZykLelX/ +p1AwCgYIKoZIzj0EAwQDZwAwZAIwJ7SSvTdCuvmX2WUjNboVgELYt//kLc1vYED5 +R9U2z+9b4ZixtnA5y+o+uUzDI/4kAjAUpyGlrM8ts/NNSdCe8f12llg7VUPgFZ7g +aasnq3YijB+lawuzV3sVVzWp+VDdHcw= -----END CERTIFICATE----- diff --git a/spec/resources/custom.crt b/spec/resources/custom.crt deleted file mode 100644 index f6ef235..0000000 --- a/spec/resources/custom.crt +++ /dev/null @@ -1,13 +0,0 @@ ------BEGIN CERTIFICATE----- -MIIB6jCCAXCgAwIBAgIJAKyx4KGEOyVdMAoGCCqGSM49BAMEMBwxGjAYBgNVBAMM -EXRlc3QtaW50ZXJtZWRpYXRlMB4XDTE3MDEyMjE4NTU1MVoXDTE4MDEyMjE4NTU1 -MVowFDESMBAGA1UEAwwJdGVzdC1sZWFmMHYwEAYHKoZIzj0CAQYFK4EEACIDYgAE -kZFi7jp4Z+3m1lR/aIHuNalLQtjaCErIgrWhFL7oUjzWMN1dR3nAmmosKlCSRc7A -Xazs+CC0QB1LgsZCFFPhPqUd5456iwCHaSVQ3maESrZtzJo78v/fE9HRuuh5fFiL -o4GFMIGCMAsGA1UdDwQEAwIE8DAdBgNVHSUEFjAUBggrBgEFBQcDAQYIKwYBBQUH -AwIwHQYDVR0OBBYEFB54cEd+wLKHpMKYkYCxmSgWERrQMB8GA1UdIwQYMBaAFMgN -6Mqlnk3ZRmp4RrAXXKeC3yVHMBQGA1UdEQQNMAuCCWxvY2FsaG9zdDAKBggqhkjO -PQQDBANoADBlAjEAwbhbwXjekyl3esK9ywh+jKCVhf7BzaF4H7LAxUE1PmXTORrZ -tqz2MXK3/zYfe1bXAjAuan+xZ4d5zCgBvnFO2/LMEX07SFQJT3l1hKAZjpbdNm/K -MY23IR6iLWkPlG1u+Wo= ------END CERTIFICATE----- diff --git a/spec/resources/ecdsa-brainpoolP256r1.crt b/spec/resources/ecdsa-brainpoolP256r1.crt new file mode 100644 index 0000000..1047c00 --- /dev/null +++ b/spec/resources/ecdsa-brainpoolP256r1.crt @@ -0,0 +1,12 @@ +-----BEGIN CERTIFICATE----- +MIIBzDCCAVKgAwIBAwIJAPr1Hn25EiltMAoGCCqGSM49BAMEMBcxFTATBgNVBAMM +DGludGVybWVkaWF0ZTAeFw0wMDAxMDEwMDAwMDBaFw0wMTAxMDEwMDAwMDBaMBAx +DjAMBgNVBAMMBWVjZHNhMFowFAYHKoZIzj0CAQYJKyQDAwIIAQEHA0IABHFxLQty +7xhy4VNRwiEDQKZsW7LJtCLyTjdRWhouxNloIYipXMlS37km9UEdrsd42FDFDfTt +KG6uCEVEGZzBoCWjgYwwgYkwDAYDVR0TAQH/BAIwADAOBgNVHQ8BAf8EBAMCB4Aw +FgYDVR0lAQH/BAwwCgYIKwYBBQUHAwEwEQYJYIZIAYb4QgEBBAQDAgZAMB0GA1Ud +DgQWBBR83waQCLiJ+QFYrLsXxHS2CYzYODAfBgNVHSMEGDAWgBQAeFKgmR+RS4S6 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