Import openssl-2.2.0 (#2693)

Import the master branch of ruby/openssl for preparing to release openssl-2.2.0

37 files changed, 1451 insertions, 103 deletions

diff --git a/test/openssl/fixtures/chain/dh512.pem b/test/openssl/fixtures/chain/dh512.pem
new file mode 100644
index 0000000000..fec138c7a9
--- /dev/null
+++ b/test/openssl/fixtures/chain/dh512.pem
@@ -0,0 +1,4 @@
+-----BEGIN DH PARAMETERS-----
+MEYCQQCjDVzTg9C4u43MV0TKDGsBuYdChrPMczr4IYjy+jHQvXm2DDadNNWBIDau
+4zNtwfLCg2gMwOc7t18m4Ten/NOLAgEC
+-----END DH PARAMETERS-----
diff --git a/test/openssl/fixtures/chain/server.crt b/test/openssl/fixtures/chain/server.crt
new file mode 100644
index 0000000000..d6b814f450
--- /dev/null
+++ b/test/openssl/fixtures/chain/server.crt
@@ -0,0 +1,13 @@
+-----BEGIN CERTIFICATE-----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+-----END CERTIFICATE-----
diff --git a/test/openssl/fixtures/chain/server.csr b/test/openssl/fixtures/chain/server.csr
new file mode 100644
index 0000000000..51b38e33f2
--- /dev/null
+++ b/test/openssl/fixtures/chain/server.csr
@@ -0,0 +1,11 @@
+-----BEGIN CERTIFICATE REQUEST-----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+-----END CERTIFICATE REQUEST-----
diff --git a/test/openssl/fixtures/chain/server.key b/test/openssl/fixtures/chain/server.key
new file mode 100644
index 0000000000..9590235db8
--- /dev/null
+++ b/test/openssl/fixtures/chain/server.key
@@ -0,0 +1,15 @@
+-----BEGIN RSA PRIVATE KEY-----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+-----END RSA PRIVATE KEY-----
diff --git a/test/openssl/test_asn1.rb b/test/openssl/test_asn1.rb
index cc11301804..5f4575516a 100644
--- a/test/openssl/test_asn1.rb
+++ b/test/openssl/test_asn1.rb
@@ -1,4 +1,4 @@
-# frozen_string_literal: false
+# frozen_string_literal: true
 require_relative 'utils'
 
 if defined?(OpenSSL)
@@ -167,7 +167,7 @@ class  OpenSSL::TestASN1 < OpenSSL::TestCase
     assert_equal(OpenSSL::ASN1::OctetString, ext.value[2].class)
     extv = OpenSSL::ASN1.decode(ext.value[2].value)
     assert_equal(OpenSSL::ASN1::BitString, extv.class)
-    str = "\000"; str[0] = 0b00000110.chr
+    str = +"\000"; str[0] = 0b00000110.chr
     assert_equal(str, extv.value)
 
     ext = extensions.value[0].value[2]  # subjetKeyIdentifier
@@ -332,6 +332,32 @@ class  OpenSSL::TestASN1 < OpenSSL::TestCase
       pend "OBJ_obj2txt() not working (LibreSSL?)" if $!.message =~ /OBJ_obj2txt/
       raise
     end
+
+    aki = [
+      OpenSSL::ASN1::ObjectId.new("authorityKeyIdentifier"),
+      OpenSSL::ASN1::ObjectId.new("X509v3 Authority Key Identifier"),
+      OpenSSL::ASN1::ObjectId.new("2.5.29.35")
+    ]
+
+    ski = [
+      OpenSSL::ASN1::ObjectId.new("subjectKeyIdentifier"),
+      OpenSSL::ASN1::ObjectId.new("X509v3 Subject Key Identifier"),
+      OpenSSL::ASN1::ObjectId.new("2.5.29.14")
+    ]
+
+    aki.each do |a|
+      aki.each do |b|
+        assert a == b
+      end
+
+      ski.each do |b|
+        refute a == b
+      end
+    end
+
+    assert_raise(TypeError) {
+      OpenSSL::ASN1::ObjectId.new("authorityKeyIdentifier") == nil
+    }
   end
 
   def test_sequence
@@ -635,10 +661,10 @@ class  OpenSSL::TestASN1 < OpenSSL::TestCase
     assert_equal data, seq.entries
   end
 
-  def test_gc_stress
-    skip "very time consuming test"
-    assert_ruby_status(['--disable-gems', '-eGC.stress=true', '-erequire "openssl.so"'])
-  end
+  # Very time consuming test.
+  # def test_gc_stress
+  #   assert_ruby_status(['--disable-gems', '-eGC.stress=true', '-erequire "openssl.so"'])
+  # end
 
   private
 
diff --git a/test/openssl/test_bn.rb b/test/openssl/test_bn.rb
index 0b5cd84241..547d334c64 100644
--- a/test/openssl/test_bn.rb
+++ b/test/openssl/test_bn.rb
@@ -1,5 +1,5 @@
 # coding: us-ascii
-# frozen_string_literal: false
+# frozen_string_literal: true
 require_relative 'utils'
 require "prime"
 
@@ -15,6 +15,10 @@ class OpenSSL::TestBN < OpenSSL::TestCase
   end
 
   def test_new
+    assert_raise(ArgumentError) { OpenSSL::BN.new }
+    assert_raise(ArgumentError) { OpenSSL::BN.new(nil) }
+    assert_raise(ArgumentError) { OpenSSL::BN.new(nil, 2) }
+
     assert_equal(@e1, OpenSSL::BN.new("999"))
     assert_equal(@e1, OpenSSL::BN.new("999", 10))
     assert_equal(@e1, OpenSSL::BN.new("\x03\xE7", 2))
@@ -273,9 +277,9 @@ class OpenSSL::TestBN < OpenSSL::TestCase
     assert_instance_of(String, @e1.hash.to_s)
   end
 
-  def test_type_error
+  def test_argument_error
     bug15760 = '[ruby-core:92231] [Bug #15760]'
-    assert_raise(TypeError, bug15760) { OpenSSL::BN.new(nil, 2) }
+    assert_raise(ArgumentError, bug15760) { OpenSSL::BN.new(nil, 2) }
   end
 end
 
diff --git a/test/openssl/test_buffering.rb b/test/openssl/test_buffering.rb
index c85a6f020b..7575c5b4fe 100644
--- a/test/openssl/test_buffering.rb
+++ b/test/openssl/test_buffering.rb
@@ -1,4 +1,4 @@
-# frozen_string_literal: false
+# frozen_string_literal: true
 require_relative 'utils'
 
 if defined?(OpenSSL)
@@ -10,7 +10,7 @@ class OpenSSL::TestBuffering < OpenSSL::TestCase
     attr_accessor :sync
 
     def initialize
-      @io = ""
+      @io = Buffer.new
       def @io.sync
         true
       end
@@ -41,6 +41,13 @@ class OpenSSL::TestBuffering < OpenSSL::TestCase
     @io = IO.new
   end
 
+  def test_encoding
+    @io.write '😊'
+    @io.flush
+
+    assert_equal @io.string.encoding, Encoding::BINARY
+  end
+
   def test_flush
     @io.write 'a'
 
diff --git a/test/openssl/test_cipher.rb b/test/openssl/test_cipher.rb
index d83fa4ec3d..f6ec498087 100644
--- a/test/openssl/test_cipher.rb
+++ b/test/openssl/test_cipher.rb
@@ -1,4 +1,4 @@
-# frozen_string_literal: false
+# frozen_string_literal: true
 require_relative 'utils'
 
 if defined?(OpenSSL)
@@ -305,6 +305,21 @@ class OpenSSL::TestCipher < OpenSSL::TestCase
     }
   end
 
+  def test_crypt_after_key
+    key = ["2b7e151628aed2a6abf7158809cf4f3c"].pack("H*")
+    %w'ecb cbc cfb ctr gcm'.each do |c|
+      cipher = OpenSSL::Cipher.new("aes-128-#{c}")
+      cipher.key = key
+      cipher.encrypt
+      assert_raise(OpenSSL::Cipher::CipherError) { cipher.update("") }
+
+      cipher = OpenSSL::Cipher.new("aes-128-#{c}")
+      cipher.key = key
+      cipher.decrypt
+      assert_raise(OpenSSL::Cipher::CipherError) { cipher.update("") }
+    end
+  end
+
   private
 
   def new_encryptor(algo, **kwargs)
diff --git a/test/openssl/test_config.rb b/test/openssl/test_config.rb
index 3606c67d65..dba66b0802 100644
--- a/test/openssl/test_config.rb
+++ b/test/openssl/test_config.rb
@@ -1,4 +1,4 @@
-# frozen_string_literal: false
+# frozen_string_literal: true
 require_relative 'utils'
 
 if defined?(OpenSSL)
@@ -61,14 +61,14 @@ foo\\bar::foo\\bar = baz
 [default1  default2]\t\t  # space is allowed in section name
           fo =b  ar       # space allowed in value
 [emptysection]
- [dollar ]
+ [doller ]
 foo=bar
 bar = $(foo)
 baz = 123$(default::bar)456${foo}798
 qux = ${baz}
 quxx = $qux.$qux
 __EOC__
-    assert_equal(['default', 'default1  default2', 'dollar', 'emptysection', 'foo', 'foo\\bar'], c.sections.sort)
+    assert_equal(['default', 'default1  default2', 'doller', 'emptysection', 'foo', 'foo\\bar'], c.sections.sort)
     assert_equal(['', 'a', 'bar', 'baz', 'd', 'dq', 'dq2', 'esc', 'foo\\bar', 'sq'], c['default'].keys.sort)
     assert_equal('c', c['default'][''])
     assert_equal('', c['default']['a'])
@@ -84,12 +84,12 @@ __EOC__
     assert_equal('baz', c['foo\\bar']['foo\\bar'])
     assert_equal('b  ar', c['default1  default2']['fo'])
 
-    # dollar
-    assert_equal('bar', c['dollar']['foo'])
-    assert_equal('bar', c['dollar']['bar'])
-    assert_equal('123baz456bar798', c['dollar']['baz'])
-    assert_equal('123baz456bar798', c['dollar']['qux'])
-    assert_equal('123baz456bar798.123baz456bar798', c['dollar']['quxx'])
+    # dolloer
+    assert_equal('bar', c['doller']['foo'])
+    assert_equal('bar', c['doller']['bar'])
+    assert_equal('123baz456bar798', c['doller']['baz'])
+    assert_equal('123baz456bar798', c['doller']['qux'])
+    assert_equal('123baz456bar798.123baz456bar798', c['doller']['quxx'])
 
     excn = assert_raise(OpenSSL::ConfigError) do
       OpenSSL::Config.parse("foo = $bar")
diff --git a/test/openssl/test_digest.rb b/test/openssl/test_digest.rb
index 2cb878b6fa..e47fc0a356 100644
--- a/test/openssl/test_digest.rb
+++ b/test/openssl/test_digest.rb
@@ -1,4 +1,4 @@
-# frozen_string_literal: false
+# frozen_string_literal: true
 require_relative 'utils'
 
 if defined?(OpenSSL)
@@ -53,14 +53,21 @@ class OpenSSL::TestDigest < OpenSSL::TestCase
     assert_equal(dig1, dig2, "reset")
   end
 
-  def test_digest_constants
-    algs = %w(MD4 MD5 RIPEMD160 SHA1 SHA224 SHA256 SHA384 SHA512)
-    if !libressl? && !openssl?(1, 1, 0)
-      algs += %w(DSS1 SHA)
+  def test_required_digests
+    algorithms = OpenSSL::Digest::ALGORITHMS
+    required = %w{MD4 MD5 RIPEMD160 SHA1 SHA224 SHA256 SHA384 SHA512}
+
+    required.each do |name|
+      assert_include(algorithms, name)
     end
-    algs.each do |alg|
-      assert_not_nil(OpenSSL::Digest.new(alg))
-      klass = OpenSSL::Digest.const_get(alg)
+  end
+
+  def test_digest_constants
+    algorithms = OpenSSL::Digest::ALGORITHMS
+
+    algorithms.each do |name|
+      assert_not_nil(OpenSSL::Digest.new(name))
+      klass = OpenSSL::Digest.const_get(name.tr('-', '_'))
       assert_not_nil(klass.new)
     end
   end
@@ -91,6 +98,18 @@ class OpenSSL::TestDigest < OpenSSL::TestCase
     assert_equal(sha512_a, encode16(OpenSSL::Digest::SHA512.digest("a")))
   end
 
+  def test_sha3
+    pend "SHA3 is not implemented" unless OpenSSL::Digest.const_defined?(:SHA3_224)
+    s224 = '6b4e03423667dbb73b6e15454f0eb1abd4597f9a1b078e3f5b5a6bc7'
+    s256 = 'a7ffc6f8bf1ed76651c14756a061d662f580ff4de43b49fa82d80a4b80f8434a'
+    s384 = '0c63a75b845e4f7d01107d852e4c2485c51a50aaaa94fc61995e71bbee983a2ac3713831264adb47fb6bd1e058d5f004'
+    s512 = 'a69f73cca23a9ac5c8b567dc185a756e97c982164fe25859e0d1dcc1475c80a615b2123af1f5f94c11e3e9402c3ac558f500199d95b6d3e301758586281dcd26'
+    assert_equal(OpenSSL::Digest::SHA3_224.hexdigest(""), s224)
+    assert_equal(OpenSSL::Digest::SHA3_256.hexdigest(""), s256)
+    assert_equal(OpenSSL::Digest::SHA3_384.hexdigest(""), s384)
+    assert_equal(OpenSSL::Digest::SHA3_512.hexdigest(""), s512)
+  end
+
   def test_digest_by_oid_and_name_sha2
     check_digest(OpenSSL::ASN1::ObjectId.new("SHA224"))
     check_digest(OpenSSL::ASN1::ObjectId.new("SHA256"))
diff --git a/test/openssl/test_engine.rb b/test/openssl/test_engine.rb
index bb1123d516..232ba866a5 100644
--- a/test/openssl/test_engine.rb
+++ b/test/openssl/test_engine.rb
@@ -1,4 +1,4 @@
-# frozen_string_literal: false
+# frozen_string_literal: true
 require_relative 'utils'
 
 if defined?(OpenSSL) && defined?(OpenSSL::Engine)
diff --git a/test/openssl/test_fips.rb b/test/openssl/test_fips.rb
index a577d7891e..8cd474f9a3 100644
--- a/test/openssl/test_fips.rb
+++ b/test/openssl/test_fips.rb
@@ -1,4 +1,4 @@
-# frozen_string_literal: false
+# frozen_string_literal: true
 require_relative 'utils'
 
 if defined?(OpenSSL)
diff --git a/test/openssl/test_hmac.rb b/test/openssl/test_hmac.rb
index 831a5b6b37..9cb3c5a864 100644
--- a/test/openssl/test_hmac.rb
+++ b/test/openssl/test_hmac.rb
@@ -1,4 +1,4 @@
-# frozen_string_literal: false
+# frozen_string_literal: true
 require_relative 'utils'
 
 if defined?(OpenSSL)
@@ -39,6 +39,16 @@ class OpenSSL::TestHMAC < OpenSSL::TestCase
     second = h1.update("test").hexdigest
     assert_equal first, second
   end
+
+  def test_eq
+    h1 = OpenSSL::HMAC.new("KEY", "MD5")
+    h2 = OpenSSL::HMAC.new("KEY", OpenSSL::Digest.new("MD5"))
+    h3 = OpenSSL::HMAC.new("FOO", "MD5")
+
+    assert_equal h1, h2
+    refute_equal h1, h2.digest
+    refute_equal h1, h3
+  end
 end
 
 end
diff --git a/test/openssl/test_kdf.rb b/test/openssl/test_kdf.rb
index 5e1db80c5f..f4790c96af 100644
--- a/test/openssl/test_kdf.rb
+++ b/test/openssl/test_kdf.rb
@@ -1,4 +1,4 @@
-# frozen_string_literal: false
+# frozen_string_literal: true
 require_relative 'utils'
 
 if defined?(OpenSSL)
diff --git a/test/openssl/test_ns_spki.rb b/test/openssl/test_ns_spki.rb
index aa1e61824f..052507de5b 100644
--- a/test/openssl/test_ns_spki.rb
+++ b/test/openssl/test_ns_spki.rb
@@ -1,4 +1,4 @@
-# frozen_string_literal: false
+# frozen_string_literal: true
 require_relative 'utils'
 
 if defined?(OpenSSL)
@@ -9,7 +9,7 @@ class OpenSSL::TestNSSPI < OpenSSL::TestCase
     # This request data is adopt from the specification of
     # "Netscape Extensions for User Key Generation".
     # -- http://wp.netscape.com/eng/security/comm4-keygen.html
-    @b64  = "MIHFMHEwXDANBgkqhkiG9w0BAQEFAANLADBIAkEAnX0TILJrOMUue+PtwBRE6XfV"
+    @b64 = +"MIHFMHEwXDANBgkqhkiG9w0BAQEFAANLADBIAkEAnX0TILJrOMUue+PtwBRE6XfV"
     @b64 << "WtKQbsshxk5ZhcUwcwyvcnIq9b82QhJdoACdD34rqfCAIND46fXKQUnb0mvKzQID"
     @b64 << "AQABFhFNb3ppbGxhSXNNeUZyaWVuZDANBgkqhkiG9w0BAQQFAANBAAKv2Eex2n/S"
     @b64 << "r/7iJNroWlSzSMtTiQTEB+ADWHGj9u1xrUrOilq/o2cuQxIfZcNZkYAkWP4DubqW"
diff --git a/test/openssl/test_ocsp.rb b/test/openssl/test_ocsp.rb
index 50ad6c31f5..a490a1539e 100644
--- a/test/openssl/test_ocsp.rb
+++ b/test/openssl/test_ocsp.rb
@@ -1,4 +1,4 @@
-# frozen_string_literal: false
+# frozen_string_literal: true
 require_relative "utils"
 
 if defined?(OpenSSL)
@@ -84,6 +84,7 @@ class OpenSSL::TestOCSP < OpenSSL::TestCase
     assert_equal [cid.issuer_key_hash].pack("H*"), asn1.value[2].value
     assert_equal @cert.serial, asn1.value[3].value
     assert_equal der, OpenSSL::OCSP::CertificateId.new(der).to_der
+    assert_equal der, OpenSSL::OCSP::CertificateId.new(asn1).to_der
   end
 
   def test_certificate_id_dup
diff --git a/test/openssl/test_ossl.rb b/test/openssl/test_ossl.rb
new file mode 100644
index 0000000000..f517b1d83d
--- /dev/null
+++ b/test/openssl/test_ossl.rb
@@ -0,0 +1,62 @@
+# frozen_string_literal: true
+require_relative "utils"
+
+require 'benchmark'
+
+if defined?(OpenSSL)
+
+class OpenSSL::OSSL < OpenSSL::SSLTestCase
+  def test_fixed_length_secure_compare
+    assert_raise(ArgumentError) { OpenSSL.fixed_length_secure_compare("aaa", "a") }
+    assert_raise(ArgumentError) { OpenSSL.fixed_length_secure_compare("aaa", "aa") }
+
+    assert OpenSSL.fixed_length_secure_compare("aaa", "aaa")
+    assert OpenSSL.fixed_length_secure_compare(
+      OpenSSL::Digest::SHA256.digest("aaa"), OpenSSL::Digest::SHA256.digest("aaa")
+    )
+
+    assert_raise(ArgumentError) { OpenSSL.fixed_length_secure_compare("aaa", "aaaa") }
+    refute OpenSSL.fixed_length_secure_compare("aaa", "baa")
+    refute OpenSSL.fixed_length_secure_compare("aaa", "aba")
+    refute OpenSSL.fixed_length_secure_compare("aaa", "aab")
+    assert_raise(ArgumentError) { OpenSSL.fixed_length_secure_compare("aaa", "aaab") }
+    assert_raise(ArgumentError) { OpenSSL.fixed_length_secure_compare("aaa", "b") }
+    assert_raise(ArgumentError) { OpenSSL.fixed_length_secure_compare("aaa", "bb") }
+    refute OpenSSL.fixed_length_secure_compare("aaa", "bbb")
+    assert_raise(ArgumentError) { OpenSSL.fixed_length_secure_compare("aaa", "bbbb") }
+  end
+
+  def test_secure_compare
+    refute OpenSSL.secure_compare("aaa", "a")
+    refute OpenSSL.secure_compare("aaa", "aa")
+
+    assert OpenSSL.secure_compare("aaa", "aaa")
+
+    refute OpenSSL.secure_compare("aaa", "aaaa")
+    refute OpenSSL.secure_compare("aaa", "baa")
+    refute OpenSSL.secure_compare("aaa", "aba")
+    refute OpenSSL.secure_compare("aaa", "aab")
+    refute OpenSSL.secure_compare("aaa", "aaab")
+    refute OpenSSL.secure_compare("aaa", "b")
+    refute OpenSSL.secure_compare("aaa", "bb")
+    refute OpenSSL.secure_compare("aaa", "bbb")
+    refute OpenSSL.secure_compare("aaa", "bbbb")
+  end
+
+  def test_memcmp_timing
+    # Ensure using fixed_length_secure_compare takes almost exactly the same amount of time to compare two different strings.
+    # Regular string comparison will short-circuit on the first non-matching character, failing this test.
+    # NOTE: this test may be susceptible to noise if the system running the tests is otherwise under load.
+    a = "x" * 512_000
+    b = "#{a}y"
+    c = "y#{a}"
+    a = "#{a}x"
+
+    n = 10_000
+    a_b_time = Benchmark.measure { n.times { OpenSSL.fixed_length_secure_compare(a, b) } }.real
+    a_c_time = Benchmark.measure { n.times { OpenSSL.fixed_length_secure_compare(a, c) } }.real
+    assert_in_delta(a_b_time, a_c_time, 1, "fixed_length_secure_compare timing test failed")
+  end
+end
+
+end
diff --git a/test/openssl/test_pair.rb b/test/openssl/test_pair.rb
index 08c15a0f75..e9cf98df15 100644
--- a/test/openssl/test_pair.rb
+++ b/test/openssl/test_pair.rb
@@ -1,4 +1,4 @@
-# frozen_string_literal: false
+# frozen_string_literal: true
 require_relative 'utils'
 require_relative 'ut_eof'
 
@@ -128,11 +128,11 @@ module OpenSSL::TestPairM
     ssl_pair {|s1, s2|
       s2.write "a\nbcd"
       assert_equal("a\n", s1.gets)
-      result = ""
+      result = String.new
       result << s1.readpartial(10) until result.length == 3
       assert_equal("bcd", result)
       s2.write "efg"
-      result = ""
+      result = String.new
       result << s1.readpartial(10) until result.length == 3
       assert_equal("efg", result)
       s2.close
@@ -242,22 +242,22 @@ module OpenSSL::TestPairM
   def test_read_with_outbuf
     ssl_pair { |s1, s2|
       s1.write("abc\n")
-      buf = ""
+      buf = String.new
       ret = s2.read(2, buf)
       assert_same ret, buf
       assert_equal "ab", ret
 
-      buf = "garbage"
+      buf = +"garbage"
       ret = s2.read(2, buf)
       assert_same ret, buf
       assert_equal "c\n", ret
 
-      buf = "garbage"
+      buf = +"garbage"
       assert_equal :wait_readable, s2.read_nonblock(100, buf, exception: false)
       assert_equal "", buf
 
       s1.close
-      buf = "garbage"
+      buf = +"garbage"
       assert_equal nil, s2.read(100, buf)
       assert_equal "", buf
     }
diff --git a/test/openssl/test_pkcs12.rb b/test/openssl/test_pkcs12.rb
index de8e35ed79..fdbe753b17 100644
--- a/test/openssl/test_pkcs12.rb
+++ b/test/openssl/test_pkcs12.rb
@@ -1,4 +1,4 @@
-# frozen_string_literal: false
+# frozen_string_literal: true
 require_relative "utils"
 
 if defined?(OpenSSL)
diff --git a/test/openssl/test_pkcs7.rb b/test/openssl/test_pkcs7.rb
index 6437112b74..d0d9dcaf81 100644
--- a/test/openssl/test_pkcs7.rb
+++ b/test/openssl/test_pkcs7.rb
@@ -1,4 +1,4 @@
-# frozen_string_literal: false
+# frozen_string_literal: true
 require_relative 'utils'
 
 if defined?(OpenSSL)
@@ -172,6 +172,28 @@ class OpenSSL::TestPKCS7 < OpenSSL::TestCase
     assert_equal(:encrypted, p7.type)
   end
 
+  def test_smime
+    store = OpenSSL::X509::Store.new
+    store.add_cert(@ca_cert)
+    ca_certs = [@ca_cert]
+
+    data = "aaaaa\r\nbbbbb\r\nccccc\r\n"
+    tmp = OpenSSL::PKCS7.sign(@ee1_cert, @rsa1024, data, ca_certs)
+    p7 = OpenSSL::PKCS7.new(tmp.to_der)
+    smime = OpenSSL::PKCS7.write_smime(p7)
+    assert_equal(true, smime.start_with?(<<END))
+MIME-Version: 1.0
+Content-Disposition: attachment; filename="smime.p7m"
+Content-Type: application/x-pkcs7-mime; smime-type=signed-data; name="smime.p7m"
+Content-Transfer-Encoding: base64
+
+END
+    assert_equal(p7.to_der, OpenSSL::PKCS7.read_smime(smime).to_der)
+
+    smime = OpenSSL::PKCS7.write_smime(p7, nil, 0)
+    assert_equal(p7.to_der, OpenSSL::PKCS7.read_smime(smime).to_der)
+  end
+
   def test_degenerate_pkcs7
     ca_cert_pem = <<END
 -----BEGIN CERTIFICATE-----
diff --git a/test/openssl/test_pkey_dh.rb b/test/openssl/test_pkey_dh.rb
index 8c8fbaeefb..6397e76d3f 100644
--- a/test/openssl/test_pkey_dh.rb
+++ b/test/openssl/test_pkey_dh.rb
@@ -1,4 +1,4 @@
-# frozen_string_literal: false
+# frozen_string_literal: true
 require_relative 'utils'
 
 if defined?(OpenSSL) && defined?(OpenSSL::PKey::DH)
diff --git a/test/openssl/test_pkey_dsa.rb b/test/openssl/test_pkey_dsa.rb
index d651949842..2c839b7dfb 100644
--- a/test/openssl/test_pkey_dsa.rb
+++ b/test/openssl/test_pkey_dsa.rb
@@ -1,4 +1,4 @@
-# frozen_string_literal: false
+# frozen_string_literal: true
 require_relative 'utils'
 
 if defined?(OpenSSL) && defined?(OpenSSL::PKey::DSA)
diff --git a/test/openssl/test_pkey_ec.rb b/test/openssl/test_pkey_ec.rb
index 95b5a6426e..1278a8b1ba 100644
--- a/test/openssl/test_pkey_ec.rb
+++ b/test/openssl/test_pkey_ec.rb
@@ -1,4 +1,4 @@
-# frozen_string_literal: false
+# frozen_string_literal: true
 require_relative 'utils'
 
 if defined?(OpenSSL) && defined?(OpenSSL::PKey::EC)
@@ -289,6 +289,22 @@ class OpenSSL::TestEC < OpenSSL::PKeyTestCase
     assert_equal true, point.on_curve?
   end
 
+  def test_ec_point_add
+    group = OpenSSL::PKey::EC::Group.new(:GFp, 17, 2, 2)
+    group.point_conversion_form = :uncompressed
+    gen = OpenSSL::PKey::EC::Point.new(group, B(%w{ 04 05 01 }))
+    group.set_generator(gen, 19, 1)
+
+    point_a = OpenSSL::PKey::EC::Point.new(group, B(%w{ 04 06 03 }))
+    point_b = OpenSSL::PKey::EC::Point.new(group, B(%w{ 04 10 0D }))
+
+    result = point_a.add(point_b)
+    assert_equal B(%w{ 04 0D 07 }), result.to_octet_string(:uncompressed)
+
+    assert_raise(TypeError) { point_a.add(nil) }
+    assert_raise(ArgumentError) { point_a.add }
+  end
+
   def test_ec_point_mul
     begin
       # y^2 = x^3 + 2x + 2 over F_17
diff --git a/test/openssl/test_pkey_rsa.rb b/test/openssl/test_pkey_rsa.rb
index ef02717d8b..a9587aa1a4 100644
--- a/test/openssl/test_pkey_rsa.rb
+++ b/test/openssl/test_pkey_rsa.rb
@@ -1,9 +1,18 @@
-# frozen_string_literal: false
+# frozen_string_literal: true
 require_relative "utils"
 
 if defined?(OpenSSL)
 
 class OpenSSL::TestPKeyRSA < OpenSSL::PKeyTestCase
+  def test_no_private_exp
+    key = OpenSSL::PKey::RSA.new
+    rsa = Fixtures.pkey("rsa2048")
+    key.set_key(rsa.n, rsa.e, nil) 
+    key.set_factors(rsa.p, rsa.q)
+    assert_raise(OpenSSL::PKey::RSAError){ key.private_encrypt("foo") }
+    assert_raise(OpenSSL::PKey::RSAError){ key.private_decrypt("foo") }
+  end
+
   def test_padding
     key = OpenSSL::PKey::RSA.new(512, 3)
 
@@ -31,14 +40,32 @@ class OpenSSL::TestPKeyRSA < OpenSSL::PKeyTestCase
   end
 
   def test_private
+    # Generated by key size and public exponent
     key = OpenSSL::PKey::RSA.new(512, 3)
     assert(key.private?)
+
+    # Generated by DER
     key2 = OpenSSL::PKey::RSA.new(key.to_der)
     assert(key2.private?)
+
+    # public key
     key3 = key.public_key
     assert(!key3.private?)
+
+    # Generated by public key DER
     key4 = OpenSSL::PKey::RSA.new(key3.to_der)
     assert(!key4.private?)
+    rsa1024 = Fixtures.pkey("rsa1024")
+
+    # Generated by RSA#set_key
+    key5 = OpenSSL::PKey::RSA.new
+    key5.set_key(rsa1024.n, rsa1024.e, rsa1024.d)
+    assert(key5.private?)
+
+    # Generated by RSA#set_key, without d
+    key6 = OpenSSL::PKey::RSA.new
+    key6.set_key(rsa1024.n, rsa1024.e, nil)
+    assert(!key6.private?)
   end
 
   def test_new
@@ -153,6 +180,40 @@ class OpenSSL::TestPKeyRSA < OpenSSL::PKeyTestCase
     }
   end
 
+  def test_export
+    rsa1024 = Fixtures.pkey("rsa1024")
+    key = OpenSSL::PKey::RSA.new
+
+    # key has only n, e and d
+    key.set_key(rsa1024.n, rsa1024.e, rsa1024.d)
+    assert_equal rsa1024.public_key.export, key.export
+
+    # key has only n, e, d, p and q
+    key.set_factors(rsa1024.p, rsa1024.q)
+    assert_equal rsa1024.public_key.export, key.export
+
+    # key has n, e, d, p, q, dmp1, dmq1 and iqmp
+    key.set_crt_params(rsa1024.dmp1, rsa1024.dmq1, rsa1024.iqmp)
+    assert_equal rsa1024.export, key.export
+  end
+
+  def test_to_der
+    rsa1024 = Fixtures.pkey("rsa1024")
+    key = OpenSSL::PKey::RSA.new
+
+    # key has only n, e and d
+    key.set_key(rsa1024.n, rsa1024.e, rsa1024.d)
+    assert_equal rsa1024.public_key.to_der, key.to_der
+
+    # key has only n, e, d, p and q
+    key.set_factors(rsa1024.p, rsa1024.q)
+    assert_equal rsa1024.public_key.to_der, key.to_der
+
+    # key has n, e, d, p, q, dmp1, dmq1 and iqmp
+    key.set_crt_params(rsa1024.dmp1, rsa1024.dmq1, rsa1024.iqmp)
+    assert_equal rsa1024.to_der, key.to_der
+  end
+
   def test_RSAPrivateKey
     rsa1024 = Fixtures.pkey("rsa1024")
     asn1 = OpenSSL::ASN1::Sequence([
@@ -295,6 +356,85 @@ class OpenSSL::TestPKeyRSA < OpenSSL::PKeyTestCase
     }
   end
 
+  def test_private_encoding
+    rsa1024 = Fixtures.pkey("rsa1024")
+    asn1 = OpenSSL::ASN1::Sequence([
+      OpenSSL::ASN1::Integer(0),
+      OpenSSL::ASN1::Sequence([
+        OpenSSL::ASN1::ObjectId("rsaEncryption"),
+        OpenSSL::ASN1::Null(nil)
+      ]),
+      OpenSSL::ASN1::OctetString(rsa1024.to_der)
+    ])
+    assert_equal asn1.to_der, rsa1024.private_to_der
+    assert_same_rsa rsa1024, OpenSSL::PKey.read(asn1.to_der)
+
+    pem = <<~EOF
+    -----BEGIN PRIVATE KEY-----
+    MIICeAIBADANBgkqhkiG9w0BAQEFAASCAmIwggJeAgEAAoGBAMvCxLDUQKc+1P4+
+    Q6AeFwYDvWfALb+cvzlUEadGoPE6qNWHsLFoo8RFgeyTgE8KQTduu1OE9Zz2SMcR
+    BDu5/1jWtsLPSVrI2ofLLBARUsWanVyki39DeB4u/xkP2mKGjAokPIwOI3oCthSZ
+    lzO9bj3voxTf6XngTqUX8l8URTmHAgMBAAECgYEApKX8xBqvJ7XI7Kypfo/x8MVC
+    3rxW+1eQ2aVKIo4a7PKGjQz5RVIVyzqTUvSZoMTbkAxlSIbO5YfJpTnl3tFcOB6y
+    QMxqQPW/pl6Ni3EmRJdsRM5MsPBRZOfrXxOCdvXu1TWOS1S1TrvEr/TyL9eh2WCd
+    CGzpWgdO4KHce7vs7pECQQDv6DGoG5lHnvbvj9qSJb9K5ebRJc8S+LI7Uy5JHC0j
+    zsHTYPSqBXwPVQdGbgCEycnwwKzXzT2QxAQmJBQKun2ZAkEA2W3aeAE7Xi6zo2eG
+    4Cx4UNMHMIdfBRS7VgoekwybGmcapqV0aBew5kHeWAmxP1WUZ/dgZh2QtM1VuiBA
+    qUqkHwJBAOJLCRvi/JB8N7z82lTk2i3R8gjyOwNQJv6ilZRMyZ9vFZFHcUE27zCf
+    Kb+bX03h8WPwupjMdfgpjShU+7qq8nECQQDBrmyc16QVyo40sgTgblyiysitvviy
+    ovwZsZv4q5MCmvOPnPUrwGbRRb2VONUOMOKpFiBl9lIv7HU//nj7FMVLAkBjUXED
+    83dA8JcKM+HlioXEAxCzZVVhN+D63QwRwkN08xAPklfqDkcqccWDaZm2hdCtaYlK
+    funwYkrzI1OikQSs
+    -----END PRIVATE KEY-----
+    EOF
+    assert_equal pem, rsa1024.private_to_pem
+    assert_same_rsa rsa1024, OpenSSL::PKey.read(pem)
+  end
+
+  def test_private_encoding_encrypted
+    rsa1024 = Fixtures.pkey("rsa1024")
+    encoded = rsa1024.private_to_der("aes-128-cbc", "abcdef")
+    asn1 = OpenSSL::ASN1.decode(encoded) # PKCS #8 EncryptedPrivateKeyInfo
+    assert_kind_of OpenSSL::ASN1::Sequence, asn1
+    assert_equal 2, asn1.value.size
+    assert_not_equal rsa1024.private_to_der, encoded
+    assert_same_rsa rsa1024, OpenSSL::PKey.read(encoded, "abcdef")
+    assert_same_rsa rsa1024, OpenSSL::PKey.read(encoded) { "abcdef" }
+    assert_raise(OpenSSL::PKey::PKeyError) { OpenSSL::PKey.read(encoded, "abcxyz") }
+
+    encoded = rsa1024.private_to_pem("aes-128-cbc", "abcdef")
+    assert_match (/BEGIN ENCRYPTED PRIVATE KEY/), encoded.lines[0]
+    assert_same_rsa rsa1024, OpenSSL::PKey.read(encoded, "abcdef")
+
+    # certtool --load-privkey=test/fixtures/pkey/rsa1024.pem --to-p8 --password=abcdef
+    pem = <<~EOF
+    -----BEGIN ENCRYPTED PRIVATE KEY-----
+    MIICojAcBgoqhkiG9w0BDAEDMA4ECLqajUdSNfzwAgIEkQSCAoCDWhxr1HUrKLXA
+    FsFGGQfPT0aKH4gZipaSXXQRl0KwifHwHoDtfo/mAkJVZMnUVOm1AQ4LTFS3EdTy
+    JUwICGEQHb7QAiokIRoi0K2yHhOxVO8qgbnWuisWpiT6Ru1jCqTs/wcqlqF7z2jM
+    oXDk/vuekKst1DDXDcHrzhDkwhCQWj6jt1r2Vwaryy0FyeqsWAgBDiK2LsnCgkGD
+    21uhNZ/iWMG6tvY9hB8MDdiBJ41YdSG/AKLulAxQ1ibJz0Tasu66TmwFvWhBlME+
+    QbqfgmkgWg5buu53SvDfCA47zXihclbtdfW+U3CJ9OJkx0535TVdZbuC1QgKXvG7
+    4iKGFRMWYJqZvZM3GL4xbC75AxjXZsdCfV81VjZxjeU6ung/NRzCuCUcmBOQzo1D
+    Vv6COwAa6ttQWM0Ti8oIQHdu5Qi+nuOEHDLxCxD962M37H99sEO5cESjmrGVxhEo
+    373L4+11geGSCajdp0yiAGnXQfwaKta8cL693bRObN+b1Y+vqtDKH26N9a4R3qgg
+    2XwgQ5GH5CODoXZpi0wxncXO+3YuuhGeArtzKSXLNxHzIMlY7wZX+0e9UU03zfV/
+    aOe4/q5DpkNxgHePt0oEpamSKY5W3jzVi1dlFWsRjud1p/Grt2zjSWTYClBlJqG1
+    A/3IeDZCu+acaePJjFyv5dFffIj2l4bAYB+LFrZlSu3F/EimO/dCDWJ9JGlMK0aF
+    l9brh7786Mo+YfyklaqMMEHBbbR2Es7PR6Gt7lrcIXmzy9XSsxT6IiD1rG9KKR3i
+    CQxTup6JAx9w1q+adL+Ypikoy3gGD/ccUY6TtPoCmkQwSCS+JqQnFlCiThDJbu+V
+    eqqUNkZq
+    -----END ENCRYPTED PRIVATE KEY-----
+    EOF
+    assert_same_rsa rsa1024, OpenSSL::PKey.read(pem, "abcdef")
+  end
+
+  def test_public_encoding
+    rsa1024 = Fixtures.pkey("rsa1024")
+    assert_equal dup_public(rsa1024).to_der, rsa1024.public_to_der
+    assert_equal dup_public(rsa1024).to_pem, rsa1024.public_to_pem
+  end
+
   def test_dup
     key = Fixtures.pkey("rsa1024")
     key2 = key.dup
diff --git a/test/openssl/test_random.rb b/test/openssl/test_random.rb
index d5a374540d..33af375720 100644
--- a/test/openssl/test_random.rb
+++ b/test/openssl/test_random.rb
@@ -1,4 +1,4 @@
-# frozen_string_literal: false
+# frozen_string_literal: true
 require_relative "utils"
 
 if defined?(OpenSSL)
diff --git a/test/openssl/test_ssl.rb b/test/openssl/test_ssl.rb
index 940bc135ed..eb5b77be02 100644
--- a/test/openssl/test_ssl.rb
+++ b/test/openssl/test_ssl.rb
@@ -1,4 +1,4 @@
-# frozen_string_literal: false
+# frozen_string_literal: true
 require_relative "utils"
 
 if defined?(OpenSSL)
@@ -56,6 +56,52 @@ class OpenSSL::TestSSL < OpenSSL::SSLTestCase
     }
   end
 
+  def test_socket_open
+    start_server { |port|
+      begin
+        ssl = OpenSSL::SSL::SSLSocket.open("127.0.0.1", port)
+        ssl.sync_close = true
+        ssl.connect
+
+        ssl.puts "abc"; assert_equal "abc\n", ssl.gets
+      ensure
+        ssl&.close
+      end
+    }
+  end
+
+  def test_socket_open_with_context
+    start_server { |port|
+      begin
+        ctx = OpenSSL::SSL::SSLContext.new
+        ssl = OpenSSL::SSL::SSLSocket.open("127.0.0.1", port, context: ctx)
+        ssl.sync_close = true
+        ssl.connect
+
+        assert_equal ssl.context, ctx
+        ssl.puts "abc"; assert_equal "abc\n", ssl.gets
+      ensure
+        ssl&.close
+      end
+    }
+  end
+
+  def test_socket_open_with_local_address_port_context
+    start_server { |port|
+      begin
+        ctx = OpenSSL::SSL::SSLContext.new
+        ssl = OpenSSL::SSL::SSLSocket.open("127.0.0.1", port, "127.0.0.1", 8000, context: ctx)
+        ssl.sync_close = true
+        ssl.connect
+
+        assert_equal ssl.context, ctx
+        ssl.puts "abc"; assert_equal "abc\n", ssl.gets
+      ensure
+        ssl&.close
+      end
+    }
+  end
+
   def test_add_certificate
     ctx_proc = -> ctx {
       # Unset values set by start_server
@@ -139,15 +185,20 @@ class OpenSSL::TestSSL < OpenSSL::SSLTestCase
     end
   end
 
+  def test_add_certificate_chain_file
+    ctx = OpenSSL::SSL::SSLContext.new
+    assert ctx.add_certificate_chain_file(Fixtures.file_path("chain", "server.crt"))
+  end
+
   def test_sysread_and_syswrite
     start_server { |port|
       server_connect(port) { |ssl|
-        str = "x" * 100 + "\n"
+        str = +("x" * 100 + "\n")
         ssl.syswrite(str)
         newstr = ssl.sysread(str.bytesize)
         assert_equal(str, newstr)
 
-        buf = ""
+        buf = String.new
         ssl.syswrite(str)
         assert_same buf, ssl.sysread(str.size, buf)
         assert_equal(str, buf)
@@ -155,23 +206,21 @@ class OpenSSL::TestSSL < OpenSSL::SSLTestCase
     }
   end
 
-  def test_sysread_nonblock_and_syswrite_nonblock_keywords
-    start_server(ignore_listener_error: true) do |port|
-      sock = TCPSocket.new("127.0.0.1", port)
-      ssl = OpenSSL::SSL::SSLSocket.new(sock)
-
-      assert_warn ("") do
-        ssl.send(:syswrite_nonblock, "1", exception: false)
-        ssl.send(:sysread_nonblock, 1, exception: false) rescue nil
-        ssl.send(:sysread_nonblock, 1, String.new, exception: false) rescue nil
-      end
-    ensure
-      sock&.close
-    end
-  end
+  # TODO fix this test
+  # def test_sysread_nonblock_and_syswrite_nonblock_keywords
+  #   start_server do |port|
+  #     server_connect(port) do |ssl|
+  #       assert_warning("") do
+  #         ssl.send(:syswrite_nonblock, "12", exception: false)
+  #         ssl.send(:sysread_nonblock, 1, exception: false) rescue nil
+  #         ssl.send(:sysread_nonblock, 1, String.new, exception: false) rescue nil
+  #       end
+  #     end
+  #   end
+  # end
 
   def test_sync_close
-    start_server { |port|
+    start_server do |port|
       begin
         sock = TCPSocket.new("127.0.0.1", port)
         ssl = OpenSSL::SSL::SSLSocket.new(sock)
@@ -194,7 +243,7 @@ class OpenSSL::TestSSL < OpenSSL::SSLTestCase
       ensure
         sock&.close
       end
-    }
+    end
   end
 
   def test_copy_stream
@@ -434,6 +483,29 @@ class OpenSSL::TestSSL < OpenSSL::SSLTestCase
     }
   end
 
+  def test_finished_messages
+    server_finished = nil
+    server_peer_finished = nil
+    client_finished = nil
+    client_peer_finished = nil
+
+    start_server(accept_proc: proc { |server|
+      server_finished = server.finished_message
+      server_peer_finished = server.peer_finished_message
+    }) { |port|
+      ctx = OpenSSL::SSL::SSLContext.new
+      ctx.verify_mode = OpenSSL::SSL::VERIFY_NONE
+      server_connect(port, ctx) { |ssl|
+        client_finished = ssl.finished_message
+        client_peer_finished = ssl.peer_finished_message
+        sleep 0.05
+        ssl.send :stop
+      }
+    }
+    assert_equal(server_finished, client_peer_finished)
+    assert_equal(server_peer_finished, client_finished)
+  end
+
   def test_sslctx_set_params
     ctx = OpenSSL::SSL::SSLContext.new
     ctx.set_params
@@ -1565,6 +1637,20 @@ end
     }
   end
 
+  def test_fileno
+    ctx = OpenSSL::SSL::SSLContext.new
+    sock1, sock2 = socketpair
+
+    socket = OpenSSL::SSL::SSLSocket.new(sock1)
+    server = OpenSSL::SSL::SSLServer.new(sock2, ctx)
+
+    assert_equal socket.fileno, socket.to_io.fileno
+    assert_equal server.fileno, server.to_io.fileno
+  ensure
+    sock1.close
+    sock2.close
+  end
+
   private
 
   def start_server_version(version, ctx_proc = nil,
@@ -1597,8 +1683,8 @@ end
 
   def assert_handshake_error
     # different OpenSSL versions react differently when facing a SSL/TLS version
-    # that has been marked as forbidden, therefore either of these may be raised
-    assert_raise(OpenSSL::SSL::SSLError, Errno::ECONNRESET) {
+    # that has been marked as forbidden, therefore any of these may be raised
+    assert_raise(OpenSSL::SSL::SSLError, Errno::ECONNRESET, Errno::EPIPE) {
       yield
     }
   end
diff --git a/test/openssl/test_ssl_session.rb b/test/openssl/test_ssl_session.rb
index e199f86d2b..89726d4463 100644
--- a/test/openssl/test_ssl_session.rb
+++ b/test/openssl/test_ssl_session.rb
@@ -1,4 +1,4 @@
-# frozen_string_literal: false
+# frozen_string_literal: true
 require_relative "utils"
 
 if defined?(OpenSSL)
diff --git a/test/openssl/test_ts.rb b/test/openssl/test_ts.rb
new file mode 100644
index 0000000000..c57f08cf7a
--- /dev/null
+++ b/test/openssl/test_ts.rb
@@ -0,0 +1,667 @@
+require_relative "utils"
+
+if defined?(OpenSSL) && defined?(OpenSSL::Timestamp)
+
+class OpenSSL::TestTimestamp < OpenSSL::TestCase
+  def intermediate_key
+    @intermediate_key ||= OpenSSL::PKey::RSA.new <<-_end_of_pem_
+-----BEGIN RSA PRIVATE KEY-----
+MIICWwIBAAKBgQCcyODxH+oTrr7l7MITWcGaYnnBma6vidCCJjuSzZpaRmXZHAyH
+0YcY4ttC0BdJ4uV+cE05IySVC7tyvVfFb8gFQ6XJV+AEktP+XkLbcxZgj9d2NVu1
+ziXdI+ldXkPnMhyWpMS5E7SD6gflv9NhUYEsmAGsUgdK6LDmm2W2/4TlewIDAQAB
+AoGAYgx6KDFWONLqjW3f/Sv/mGYHUNykUyDzpcD1Npyf797gqMMSzwlo3FZa2tC6
+D7n23XirwpTItvEsW9gvgMikJDPlThAeGLZ+L0UbVNNBHVxGP998Nda1kxqKvhRE
+pfZCKc7PLM9ZXc6jBTmgxdcAYfVCCVUoa2mEf9Ktr3BlI4kCQQDQAM09+wHDXGKP
+o2UnCwCazGtyGU2r0QCzHlh9BVY+KD2KjjhuWh86rEbdWN7hEW23Je1vXIhuM6Pa
+/Ccd+XYnAkEAwPZ91PK6idEONeGQ4I3dyMKV2SbaUjfq3MDL4iIQPQPuj7QsBO/5
+3Nf9ReSUUTRFCUVwoC8k4Z1KAJhR/K/ejQJANE7PTnPuGJQGETs09+GTcFpR9uqY
+FspDk8fg1ufdrVnvSAXF+TJewiGK3KU5v33jinhWQngRsyz3Wt2odKhEZwJACbjh
+oicQqvzzgFd7GzVKpWDYd/ZzLY1PsgusuhoJQ2m9TVRAm4cTycLAKhNYPbcqe0sa
+X5fAffWU0u7ZwqeByQJAOUAbYET4RU3iymAvAIDFj8LiQnizG9t5Ty3HXlijKQYv
+y8gsvWd4CdxwOPatWpBUX9L7IXcMJmD44xXTUvpbfQ==
+-----END RSA PRIVATE KEY-----
+_end_of_pem_
+  end
+
+  def ee_key
+    @ee_key ||= OpenSSL::PKey::RSA.new <<-_end_of_pem_
+-----BEGIN RSA PRIVATE KEY-----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+-----END RSA PRIVATE KEY-----
+_end_of_pem_
+  end
+
+  def ca_cert
+    @ca_cert ||= OpenSSL::Certs.ca_cert
+  end
+
+  def ca_store
+    @ca_store ||= OpenSSL::X509::Store.new.tap { |s| s.add_cert(ca_cert) }
+  end
+
+  def ts_cert_direct
+    @ts_cert_direct ||= OpenSSL::Certs.ts_cert_direct(ee_key, ca_cert)
+  end
+
+  def intermediate_cert
+    @intermediate_cert ||= OpenSSL::Certs.intermediate_cert(intermediate_key, ca_cert)
+  end
+
+  def intermediate_store
+    @intermediate_store ||= OpenSSL::X509::Store.new.tap { |s| s.add_cert(intermediate_cert) }
+  end
+
+  def ts_cert_ee
+    @ts_cert_ee ||= OpenSSL::Certs.ts_cert_ee(ee_key, intermediate_cert, intermediate_key)
+  end
+
+  def test_create_request
+    req = OpenSSL::Timestamp::Request.new
+    assert_equal(true, req.cert_requested?)
+    assert_equal(1, req.version)
+    assert_nil(req.algorithm)
+    assert_equal("", req.message_imprint)
+    assert_nil(req.policy_id)
+    assert_nil(req.nonce)
+  end
+
+  def test_request_mandatory_fields
+    req = OpenSSL::Timestamp::Request.new
+    assert_raise(OpenSSL::Timestamp::TimestampError) do
+      tmp = req.to_der
+      pp OpenSSL::ASN1.decode(tmp)
+    end
+    req.algorithm = "sha1"
+    assert_raise(OpenSSL::Timestamp::TimestampError) do
+      req.to_der
+    end
+    req.message_imprint = OpenSSL::Digest::SHA1.new.digest("data")
+    req.to_der
+  end
+
+  def test_request_assignment
+    req = OpenSSL::Timestamp::Request.new
+
+    req.version = 2
+    assert_equal(2, req.version)
+    assert_raise(TypeError) { req.version = nil }
+    assert_raise(TypeError) { req.version = "foo" }
+
+    req.algorithm = "SHA1"
+    assert_equal("SHA1", req.algorithm)
+    assert_raise(TypeError) { req.algorithm = nil }
+    assert_raise(OpenSSL::ASN1::ASN1Error) { req.algorithm = "xxx" }
+
+    req.message_imprint = "test"
+    assert_equal("test", req.message_imprint)
+    assert_raise(TypeError) { req.message_imprint = nil }
+
+    req.policy_id = "1.2.3.4.5"
+    assert_equal("1.2.3.4.5", req.policy_id)
+    assert_raise(TypeError) { req.policy_id = 123 }
+    assert_raise(TypeError) { req.policy_id = nil }
+
+    req.nonce = 42
+    assert_equal(42, req.nonce)
+    assert_raise(TypeError) { req.nonce = "foo" }
+    assert_raise(TypeError) { req.nonce = nil }
+
+    req.cert_requested = false
+    assert_equal(false, req.cert_requested?)
+    req.cert_requested = nil
+    assert_equal(false, req.cert_requested?)
+    req.cert_requested = 123
+    assert_equal(true, req.cert_requested?)
+    req.cert_requested = "asdf"
+    assert_equal(true, req.cert_requested?)
+  end
+
+  def test_request_serialization
+    req = OpenSSL::Timestamp::Request.new
+
+    req.version = 2
+    req.algorithm = "SHA1"
+    req.message_imprint = "test"
+    req.policy_id = "1.2.3.4.5"
+    req.nonce = 42
+    req.cert_requested = true
+
+    req = OpenSSL::Timestamp::Request.new(req.to_der)
+
+    assert_equal(2, req.version)
+    assert_equal("SHA1", req.algorithm)
+    assert_equal("test", req.message_imprint)
+    assert_equal("1.2.3.4.5", req.policy_id)
+    assert_equal(42, req.nonce)
+    assert_equal(true, req.cert_requested?)
+
+  end
+
+  def test_request_re_assignment
+    #tests whether the potential 'freeing' of previous values in C works properly
+    req = OpenSSL::Timestamp::Request.new
+    req.version = 2
+    req.version = 3
+    req.algorithm = "SHA1"
+    req.algorithm = "SHA256"
+    req.message_imprint = "test"
+    req.message_imprint = "test2"
+    req.policy_id = "1.2.3.4.5"
+    req.policy_id = "1.2.3.4.6"
+    req.nonce = 42
+    req.nonce = 24
+    req.cert_requested = false
+    req.cert_requested = true
+    req.to_der
+  end
+
+  def test_request_encode_decode
+    req = OpenSSL::Timestamp::Request.new
+    req.algorithm = "SHA1"
+    digest = OpenSSL::Digest::SHA1.new.digest("test")
+    req.message_imprint = digest
+    req.policy_id = "1.2.3.4.5"
+    req.nonce = 42
+
+    qer = OpenSSL::Timestamp::Request.new(req.to_der)
+    assert_equal(1, qer.version)
+    assert_equal("SHA1", qer.algorithm)
+    assert_equal(digest, qer.message_imprint)
+    assert_equal("1.2.3.4.5", qer.policy_id)
+    assert_equal(42, qer.nonce)
+
+    #put OpenSSL::ASN1.decode inbetween
+    qer2 = OpenSSL::Timestamp::Request.new(OpenSSL::ASN1.decode(req.to_der))
+    assert_equal(1, qer2.version)
+    assert_equal("SHA1", qer2.algorithm)
+    assert_equal(digest, qer2.message_imprint)
+    assert_equal("1.2.3.4.5", qer2.policy_id)
+    assert_equal(42, qer2.nonce)
+  end
+
+  def test_response_constants
+    assert_equal(0, OpenSSL::Timestamp::Response::GRANTED)
+    assert_equal(1, OpenSSL::Timestamp::Response::GRANTED_WITH_MODS)
+    assert_equal(2, OpenSSL::Timestamp::Response::REJECTION)
+    assert_equal(3, OpenSSL::Timestamp::Response::WAITING)
+    assert_equal(4, OpenSSL::Timestamp::Response::REVOCATION_WARNING)
+    assert_equal(5, OpenSSL::Timestamp::Response::REVOCATION_NOTIFICATION)
+  end
+
+  def test_response_creation
+    req = OpenSSL::Timestamp::Request.new
+    req.algorithm = "SHA1"
+    digest = OpenSSL::Digest::SHA1.new.digest("test")
+    req.message_imprint = digest
+    req.policy_id = "1.2.3.4.5"
+
+    fac = OpenSSL::Timestamp::Factory.new
+    time = Time.now
+    fac.gen_time = time
+    fac.serial_number = 1
+    fac.allowed_digests = ["sha1"]
+
+    resp = fac.create_timestamp(ee_key, ts_cert_ee, req)
+    resp = OpenSSL::Timestamp::Response.new(resp)
+    assert_equal(OpenSSL::Timestamp::Response::GRANTED, resp.status)
+    assert_nil(resp.failure_info)
+    assert_equal([], resp.status_text)
+    assert_equal(1, resp.token_info.version)
+    assert_equal("1.2.3.4.5", resp.token_info.policy_id)
+    assert_equal("SHA1", resp.token_info.algorithm)
+    assert_equal(digest, resp.token_info.message_imprint)
+    assert_equal(1, resp.token_info.serial_number)
+    assert_equal(time.to_i, resp.token_info.gen_time.to_i)
+    assert_equal(false, resp.token_info.ordering)
+    assert_nil(resp.token_info.nonce)
+    assert_cert(ts_cert_ee, resp.tsa_certificate)
+    #compare PKCS7
+    token = OpenSSL::ASN1.decode(resp.to_der).value[1]
+    assert_equal(token.to_der, resp.token.to_der)
+  end
+
+  def test_response_mandatory_fields
+    fac = OpenSSL::Timestamp::Factory.new
+    req = OpenSSL::Timestamp::Request.new
+    assert_raise(OpenSSL::Timestamp::TimestampError) do
+      fac.create_timestamp(ee_key, ts_cert_ee, req)
+    end
+    req.algorithm = "sha1"
+    assert_raise(OpenSSL::Timestamp::TimestampError) do
+      fac.create_timestamp(ee_key, ts_cert_ee, req)
+    end
+    req.message_imprint = OpenSSL::Digest::SHA1.new.digest("data")
+    assert_raise(OpenSSL::Timestamp::TimestampError) do
+      fac.create_timestamp(ee_key, ts_cert_ee, req)
+    end
+    fac.gen_time = Time.now
+    assert_raise(OpenSSL::Timestamp::TimestampError) do
+      fac.create_timestamp(ee_key, ts_cert_ee, req)
+    end
+    fac.serial_number = 1
+    fac.allowed_digests = ["sha1"]
+    assert_raise(OpenSSL::Timestamp::TimestampError) do
+      fac.create_timestamp(ee_key, ts_cert_ee, req)
+    end
+    fac.default_policy_id = "1.2.3.4.5"
+    assert_equal OpenSSL::Timestamp::Response::GRANTED, fac.create_timestamp(ee_key, ts_cert_ee, req).status
+    fac.default_policy_id = nil
+    assert_raise(OpenSSL::Timestamp::TimestampError) do
+      fac.create_timestamp(ee_key, ts_cert_ee, req)
+    end
+    req.policy_id = "1.2.3.4.5"
+    assert_equal OpenSSL::Timestamp::Response::GRANTED, fac.create_timestamp(ee_key, ts_cert_ee, req).status
+  end
+
+  def test_response_allowed_digests
+    req = OpenSSL::Timestamp::Request.new
+    req.algorithm = "SHA1"
+    req.message_imprint = OpenSSL::Digest::SHA1.digest("test")
+
+    fac = OpenSSL::Timestamp::Factory.new
+    fac.gen_time = Time.now
+    fac.serial_number = 1
+    fac.default_policy_id = "1.2.3.4.6"
+
+    # None allowed by default
+    resp = fac.create_timestamp(ee_key, ts_cert_ee, req)
+    assert_equal OpenSSL::Timestamp::Response::REJECTION, resp.status
+
+    # Explicitly allow SHA1 (string)
+    fac.allowed_digests = ["sha1"]
+    resp = fac.create_timestamp(ee_key, ts_cert_ee, req)
+    assert_equal OpenSSL::Timestamp::Response::GRANTED, resp.status
+
+    # Explicitly allow SHA1 (object)
+    fac.allowed_digests = [OpenSSL::Digest::SHA1.new]
+    resp = fac.create_timestamp(ee_key, ts_cert_ee, req)
+    assert_equal OpenSSL::Timestamp::Response::GRANTED, resp.status
+
+    # Others not allowed
+    req.algorithm = "SHA256"
+    req.message_imprint = OpenSSL::Digest::SHA256.digest("test")
+    resp = fac.create_timestamp(ee_key, ts_cert_ee, req)
+    assert_equal OpenSSL::Timestamp::Response::REJECTION, resp.status
+
+    # Non-Array
+    fac.allowed_digests = 123
+    resp = fac.create_timestamp(ee_key, ts_cert_ee, req)
+    assert_equal OpenSSL::Timestamp::Response::REJECTION, resp.status
+
+    # Non-String, non-Digest Array element
+    fac.allowed_digests = ["sha1", OpenSSL::Digest::SHA1.new, 123]
+    assert_raise(TypeError) do
+      fac.create_timestamp(ee_key, ts_cert_ee, req)
+    end
+  end
+
+  def test_response_default_policy
+    req = OpenSSL::Timestamp::Request.new
+    req.algorithm = "SHA1"
+    digest = OpenSSL::Digest::SHA1.new.digest("test")
+    req.message_imprint = digest
+
+    fac = OpenSSL::Timestamp::Factory.new
+    fac.gen_time = Time.now
+    fac.serial_number = 1
+    fac.allowed_digests = ["sha1"]
+    fac.default_policy_id = "1.2.3.4.6"
+
+    resp = fac.create_timestamp(ee_key, ts_cert_ee, req)
+    assert_equal(OpenSSL::Timestamp::Response::GRANTED, resp.status)
+    assert_equal("1.2.3.4.6", resp.token_info.policy_id)
+  end
+
+  def test_response_bad_purpose
+    req = OpenSSL::Timestamp::Request.new
+    req.algorithm = "SHA1"
+    digest = OpenSSL::Digest::SHA1.new.digest("test")
+    req.message_imprint = digest
+    req.policy_id = "1.2.3.4.5"
+    req.nonce = 42
+
+    fac = OpenSSL::Timestamp::Factory.new
+    fac.gen_time = Time.now
+    fac.serial_number = 1
+    fac.allowed_digests = ["sha1"]
+
+
+    assert_raise(OpenSSL::Timestamp::TimestampError) do
+      fac.create_timestamp(ee_key, intermediate_cert, req)
+    end
+  end
+
+  def test_no_cert_requested
+    req = OpenSSL::Timestamp::Request.new
+    req.algorithm = "SHA1"
+    digest = OpenSSL::Digest::SHA1.new.digest("test")
+    req.message_imprint = digest
+    req.cert_requested = false
+
+    fac = OpenSSL::Timestamp::Factory.new
+    fac.gen_time = Time.now
+    fac.serial_number = 1
+    fac.allowed_digests = ["sha1"]
+    fac.default_policy_id = "1.2.3.4.5"
+
+    resp = fac.create_timestamp(ee_key, ts_cert_ee, req)
+    assert_equal(OpenSSL::Timestamp::Response::GRANTED, resp.status)
+    assert_nil(resp.tsa_certificate)
+  end
+
+  def test_response_no_policy_defined
+    assert_raise(OpenSSL::Timestamp::TimestampError) do
+      req = OpenSSL::Timestamp::Request.new
+      req.algorithm = "SHA1"
+      digest = OpenSSL::Digest::SHA1.new.digest("test")
+      req.message_imprint = digest
+
+      fac = OpenSSL::Timestamp::Factory.new
+      fac.gen_time = Time.now
+      fac.serial_number = 1
+      fac.allowed_digests = ["sha1"]
+
+      fac.create_timestamp(ee_key, ts_cert_ee, req)
+    end
+  end
+
+  def test_verify_ee_no_req
+    assert_raise(TypeError) do
+      ts, _ = timestamp_ee
+      ts.verify(nil, ca_cert)
+    end
+  end
+
+  def test_verify_ee_no_store
+    assert_raise(TypeError) do
+      ts, req = timestamp_ee
+      ts.verify(req, nil)
+    end
+  end
+
+  def test_verify_ee_wrong_root_no_intermediate
+    assert_raise(OpenSSL::Timestamp::TimestampError) do
+      ts, req = timestamp_ee
+      ts.verify(req, intermediate_store)
+    end
+  end
+
+  def test_verify_ee_wrong_root_wrong_intermediate
+    assert_raise(OpenSSL::Timestamp::TimestampError) do
+      ts, req = timestamp_ee
+      ts.verify(req, intermediate_store, [ca_cert])
+    end
+  end
+
+  def test_verify_ee_nonce_mismatch
+    assert_raise(OpenSSL::Timestamp::TimestampError) do
+      ts, req = timestamp_ee
+      req.nonce = 1
+      ts.verify(req, ca_store, [intermediate_cert])
+    end
+  end
+
+  def test_verify_ee_intermediate_missing
+    assert_raise(OpenSSL::Timestamp::TimestampError) do
+      ts, req = timestamp_ee
+      ts.verify(req, ca_store)
+    end
+  end
+
+  def test_verify_ee_intermediate
+    ts, req = timestamp_ee
+    ts.verify(req, ca_store, [intermediate_cert])
+  end
+
+  def test_verify_ee_intermediate_type_error
+    ts, req = timestamp_ee
+    assert_raise(TypeError) { ts.verify(req, [ca_cert], 123) }
+  end
+
+  def test_verify_ee_def_policy
+    req = OpenSSL::Timestamp::Request.new
+    req.algorithm = "SHA1"
+    digest = OpenSSL::Digest::SHA1.new.digest("test")
+    req.message_imprint = digest
+    req.nonce = 42
+
+    fac = OpenSSL::Timestamp::Factory.new
+    fac.gen_time = Time.now
+    fac.serial_number = 1
+    fac.allowed_digests = ["sha1"]
+    fac.default_policy_id = "1.2.3.4.5"
+
+    ts = fac.create_timestamp(ee_key, ts_cert_ee, req)
+    ts.verify(req, ca_store, [intermediate_cert])
+  end
+
+  def test_verify_direct
+    ts, req = timestamp_direct
+    ts.verify(req, ca_store)
+  end
+
+  def test_verify_direct_redundant_untrusted
+    ts, req = timestamp_direct
+    ts.verify(req, ca_store, [ts.tsa_certificate, ts.tsa_certificate])
+  end
+
+  def test_verify_direct_unrelated_untrusted
+    ts, req = timestamp_direct
+    ts.verify(req, ca_store, [intermediate_cert])
+  end
+
+  def test_verify_direct_wrong_root
+    assert_raise(OpenSSL::Timestamp::TimestampError) do
+      ts, req = timestamp_direct
+      ts.verify(req, intermediate_store)
+    end
+  end
+
+  def test_verify_direct_no_cert_no_intermediate
+    assert_raise(OpenSSL::Timestamp::TimestampError) do
+      ts, req = timestamp_direct_no_cert
+      ts.verify(req, ca_store)
+    end
+  end
+
+  def test_verify_ee_no_cert
+    ts, req = timestamp_ee_no_cert
+    ts.verify(req, ca_store, [ts_cert_ee, intermediate_cert])
+  end
+
+  def test_verify_ee_no_cert_no_intermediate
+    assert_raise(OpenSSL::Timestamp::TimestampError) do
+      ts, req = timestamp_ee_no_cert
+      ts.verify(req, ca_store, [ts_cert_ee])
+    end
+  end
+
+  def test_verify_ee_additional_certs_array
+    req = OpenSSL::Timestamp::Request.new
+    req.algorithm = "SHA1"
+    digest = OpenSSL::Digest::SHA1.new.digest("test")
+    req.message_imprint = digest
+    req.policy_id = "1.2.3.4.5"
+    req.nonce = 42
+    fac = OpenSSL::Timestamp::Factory.new
+    fac.gen_time = Time.now
+    fac.serial_number = 1
+    fac.allowed_digests = ["sha1"]
+    fac.additional_certs = [intermediate_cert]
+    ts = fac.create_timestamp(ee_key, ts_cert_ee, req)
+    assert_equal(2, ts.token.certificates.size)
+    fac.additional_certs = nil
+    ts.verify(req, ca_store)
+    ts = fac.create_timestamp(ee_key, ts_cert_ee, req)
+    assert_equal(1, ts.token.certificates.size)
+  end
+
+  def test_verify_ee_additional_certs_with_root
+    req = OpenSSL::Timestamp::Request.new
+    req.algorithm = "SHA1"
+    digest = OpenSSL::Digest::SHA1.new.digest("test")
+    req.message_imprint = digest
+    req.policy_id = "1.2.3.4.5"
+    req.nonce = 42
+    fac = OpenSSL::Timestamp::Factory.new
+    fac.gen_time = Time.now
+    fac.serial_number = 1
+    fac.allowed_digests = ["sha1"]
+    fac.additional_certs = [intermediate_cert, ca_cert]
+    ts = fac.create_timestamp(ee_key, ts_cert_ee, req)
+    assert_equal(3, ts.token.certificates.size)
+    ts.verify(req, ca_store)
+  end
+
+  def test_verify_ee_cert_inclusion_not_requested
+    req = OpenSSL::Timestamp::Request.new
+    req.algorithm = "SHA1"
+    digest = OpenSSL::Digest::SHA1.new.digest("test")
+    req.message_imprint = digest
+    req.nonce = 42
+    req.cert_requested = false
+    fac = OpenSSL::Timestamp::Factory.new
+    fac.gen_time = Time.now
+    fac.serial_number = 1
+    fac.allowed_digests = ["sha1"]
+    #needed because the Request contained no policy identifier
+    fac.default_policy_id = '1.2.3.4.5'
+    fac.additional_certs = [ ts_cert_ee, intermediate_cert ]
+    ts = fac.create_timestamp(ee_key, ts_cert_ee, req)
+    assert_nil(ts.token.certificates) #since cert_requested? == false
+    ts.verify(req, ca_store, [ts_cert_ee, intermediate_cert])
+  end
+
+  def test_reusable
+    #test if req and faq are reusable, i.e. the internal
+    #CTX_free methods don't mess up e.g. the certificates
+    req = OpenSSL::Timestamp::Request.new
+    req.algorithm = "SHA1"
+    digest = OpenSSL::Digest::SHA1.new.digest("test")
+    req.message_imprint = digest
+    req.policy_id = "1.2.3.4.5"
+    req.nonce = 42
+
+    fac = OpenSSL::Timestamp::Factory.new
+    fac.gen_time = Time.now
+    fac.serial_number = 1
+    fac.allowed_digests = ["sha1"]
+    fac.additional_certs = [ intermediate_cert ]
+    ts1 = fac.create_timestamp(ee_key, ts_cert_ee, req)
+    ts1.verify(req, ca_store)
+    ts2 = fac.create_timestamp(ee_key, ts_cert_ee, req)
+    ts2.verify(req, ca_store)
+    refute_nil(ts1.tsa_certificate)
+    refute_nil(ts2.tsa_certificate)
+  end
+
+  def test_token_info_creation
+    req = OpenSSL::Timestamp::Request.new
+    req.algorithm = "SHA1"
+    digest = OpenSSL::Digest::SHA1.new.digest("test")
+    req.message_imprint = digest
+    req.policy_id = "1.2.3.4.5"
+    req.nonce = OpenSSL::BN.new(123)
+
+    fac = OpenSSL::Timestamp::Factory.new
+    time = Time.now
+    fac.gen_time = time
+    fac.serial_number = 1
+    fac.allowed_digests = ["sha1"]
+
+    resp = fac.create_timestamp(ee_key, ts_cert_ee, req)
+    info = resp.token_info
+    info = OpenSSL::Timestamp::TokenInfo.new(info.to_der)
+
+    assert_equal(1, info.version)
+    assert_equal("1.2.3.4.5", info.policy_id)
+    assert_equal("SHA1", info.algorithm)
+    assert_equal(digest, info.message_imprint)
+    assert_equal(1, info.serial_number)
+    assert_equal(time.to_i, info.gen_time.to_i)
+    assert_equal(false, info.ordering)
+    assert_equal(123, info.nonce)
+  end
+
+  private
+
+  def assert_cert expected, actual
+    assert_equal expected.to_der, actual.to_der
+  end
+
+  def timestamp_ee
+    req = OpenSSL::Timestamp::Request.new
+    req.algorithm = "SHA1"
+    digest = OpenSSL::Digest::SHA1.new.digest("test")
+    req.message_imprint = digest
+    req.policy_id = "1.2.3.4.5"
+    req.nonce = 42
+
+    fac = OpenSSL::Timestamp::Factory.new
+    fac.gen_time = Time.now
+    fac.serial_number = 1
+    fac.allowed_digests = ["sha1"]
+    return fac.create_timestamp(ee_key, ts_cert_ee, req), req
+  end
+
+  def timestamp_ee_no_cert
+    req = OpenSSL::Timestamp::Request.new
+    req.algorithm = "SHA1"
+    digest = OpenSSL::Digest::SHA1.new.digest("test")
+    req.message_imprint = digest
+    req.policy_id = "1.2.3.4.5"
+    req.nonce = 42
+    req.cert_requested = false
+
+    fac = OpenSSL::Timestamp::Factory.new
+    fac.gen_time = Time.now
+    fac.serial_number = 1
+    fac.allowed_digests = ["sha1"]
+    return fac.create_timestamp(ee_key, ts_cert_ee, req), req
+  end
+
+  def timestamp_direct
+    req = OpenSSL::Timestamp::Request.new
+    req.algorithm = "SHA1"
+    digest = OpenSSL::Digest::SHA1.new.digest("test")
+    req.message_imprint = digest
+    req.policy_id = "1.2.3.4.5"
+    req.nonce = 42
+
+    fac = OpenSSL::Timestamp::Factory.new
+    fac.gen_time = Time.now
+    fac.serial_number = 1
+    fac.allowed_digests = ["sha1"]
+    return fac.create_timestamp(ee_key, ts_cert_direct, req), req
+  end
+
+  def timestamp_direct_no_cert
+    req = OpenSSL::Timestamp::Request.new
+    req.algorithm = "SHA1"
+    digest = OpenSSL::Digest::SHA1.new.digest("test")
+    req.message_imprint = digest
+    req.policy_id = "1.2.3.4.5"
+    req.nonce = 42
+    req.cert_requested = false
+
+    fac = OpenSSL::Timestamp::Factory.new
+    fac.gen_time = Time.now
+    fac.serial_number = 1
+    fac.allowed_digests = ["sha1"]
+    return fac.create_timestamp(ee_key, ts_cert_direct, req), req
+  end
+end
+
+end
diff --git a/test/openssl/test_x509attr.rb b/test/openssl/test_x509attr.rb
index c6c48e86ab..2919d23d2d 100644
--- a/test/openssl/test_x509attr.rb
+++ b/test/openssl/test_x509attr.rb
@@ -1,4 +1,4 @@
-# frozen_string_literal: false
+# frozen_string_literal: true
 require_relative "utils"
 
 if defined?(OpenSSL)
@@ -79,6 +79,16 @@ class OpenSSL::TestX509Attribute < OpenSSL::TestCase
     assert_equal true, attr1 == attr2
     assert_equal false, attr1 == attr3
   end
+
+  def test_marshal
+    val = OpenSSL::ASN1::Set([
+      OpenSSL::ASN1::UTF8String("abc123")
+    ])
+    attr = OpenSSL::X509::Attribute.new("challengePassword", val)
+    deserialized = Marshal.load(Marshal.dump(attr))
+
+    assert_equal attr.to_der, deserialized.to_der
+  end
 end
 
 end
diff --git a/test/openssl/test_x509cert.rb b/test/openssl/test_x509cert.rb
index 40a5b0ad74..ed0758a6b3 100644
--- a/test/openssl/test_x509cert.rb
+++ b/test/openssl/test_x509cert.rb
@@ -1,4 +1,4 @@
-# frozen_string_literal: false
+# frozen_string_literal: true
 require_relative "utils"
 
 if defined?(OpenSSL)
@@ -73,9 +73,12 @@ class OpenSSL::TestX509Certificate < OpenSSL::TestCase
       ["basicConstraints","CA:TRUE",true],
       ["keyUsage","keyCertSign, cRLSign",true],
       ["subjectKeyIdentifier","hash",false],
-      ["authorityKeyIdentifier","keyid:always",false],
+      ["authorityKeyIdentifier","issuer:always,keyid:always",false],
     ]
     ca_cert = issue_cert(@ca, @rsa2048, 1, ca_exts, nil, nil)
+    keyid = get_subject_key_id(ca_cert.to_der, hex: false)
+    assert_equal keyid, ca_cert.authority_key_identifier
+    assert_equal keyid, ca_cert.subject_key_identifier
     ca_cert.extensions.each_with_index{|ext, i|
       assert_equal(ca_exts[i].first, ext.oid)
       assert_equal(ca_exts[i].last, ext.critical?)
@@ -84,9 +87,10 @@ class OpenSSL::TestX509Certificate < OpenSSL::TestCase
     ee1_exts = [
       ["keyUsage","Non Repudiation, Digital Signature, Key Encipherment",true],
       ["subjectKeyIdentifier","hash",false],
-      ["authorityKeyIdentifier","keyid:always",false],
+      ["authorityKeyIdentifier","issuer:always,keyid:always",false],
       ["extendedKeyUsage","clientAuth, emailProtection, codeSigning",false],
       ["subjectAltName","email:[email protected]",false],
+      ["authorityInfoAccess","caIssuers;URI:http://www.example.com/caIssuers,OCSP;URI:http://www.example.com/ocsp",false],
     ]
     ee1_cert = issue_cert(@ee1, @rsa1024, 2, ee1_exts, ca_cert, @rsa2048)
     assert_equal(ca_cert.subject.to_der, ee1_cert.issuer.to_der)
@@ -94,6 +98,78 @@ class OpenSSL::TestX509Certificate < OpenSSL::TestCase
       assert_equal(ee1_exts[i].first, ext.oid)
       assert_equal(ee1_exts[i].last, ext.critical?)
     }
+    assert_nil(ee1_cert.crl_uris)
+
+    ef = OpenSSL::X509::ExtensionFactory.new
+    ef.config = OpenSSL::Config.parse(<<~_cnf_)
+      [crlDistPts]
+      URI.1 = http://www.example.com/crl
+      URI.2 = ldap://ldap.example.com/cn=ca?certificateRevocationList;binary
+    _cnf_
+    cdp_cert = generate_cert(@ee1, @rsa1024, 3, ca_cert)
+    ef.subject_certificate = cdp_cert
+    cdp_cert.add_extension(ef.create_extension("crlDistributionPoints", "@crlDistPts"))
+    cdp_cert.sign(@rsa2048, "sha256")
+    assert_equal(
+      ["http://www.example.com/crl", "ldap://ldap.example.com/cn=ca?certificateRevocationList;binary"],
+      cdp_cert.crl_uris
+    )
+
+    ef = OpenSSL::X509::ExtensionFactory.new
+    aia_cert = generate_cert(@ee1, @rsa1024, 4, ca_cert)
+    ef.subject_certificate = aia_cert
+    aia_cert.add_extension(
+      ef.create_extension(
+        "authorityInfoAccess",
+        "caIssuers;URI:http://www.example.com/caIssuers," \
+        "caIssuers;URI:ldap://ldap.example.com/cn=ca?authorityInfoAccessCaIssuers;binary," \
+        "OCSP;URI:http://www.example.com/ocsp," \
+        "OCSP;URI:ldap://ldap.example.com/cn=ca?authorityInfoAccessOcsp;binary",
+        false
+      )
+    )
+    aia_cert.sign(@rsa2048, "sha256")
+    assert_equal(
+      ["http://www.example.com/caIssuers", "ldap://ldap.example.com/cn=ca?authorityInfoAccessCaIssuers;binary"],
+      aia_cert.ca_issuer_uris
+    )
+    assert_equal(
+      ["http://www.example.com/ocsp", "ldap://ldap.example.com/cn=ca?authorityInfoAccessOcsp;binary"],
+      aia_cert.ocsp_uris
+    )
+
+    no_exts_cert = issue_cert(@ca, @rsa2048, 5, [], nil, nil)
+    assert_equal nil, no_exts_cert.authority_key_identifier
+    assert_equal nil, no_exts_cert.subject_key_identifier
+    assert_equal nil, no_exts_cert.crl_uris
+    assert_equal nil, no_exts_cert.ca_issuer_uris
+    assert_equal nil, no_exts_cert.ocsp_uris
+  end
+
+  def test_invalid_extension
+    integer = OpenSSL::ASN1::Integer.new(0)
+    invalid_exts_cert = generate_cert(@ee1, @rsa1024, 1, nil)
+    ["subjectKeyIdentifier", "authorityKeyIdentifier", "crlDistributionPoints", "authorityInfoAccess"].each do |ext|
+      invalid_exts_cert.add_extension(
+        OpenSSL::X509::Extension.new(ext, integer.to_der)
+      )
+    end
+
+    assert_raise(OpenSSL::ASN1::ASN1Error, "invalid extension") {
+      invalid_exts_cert.authority_key_identifier
+    }
+    assert_raise(OpenSSL::ASN1::ASN1Error, "invalid extension") {
+      invalid_exts_cert.subject_key_identifier
+    }
+    assert_raise(OpenSSL::ASN1::ASN1Error, "invalid extension") {
+      invalid_exts_cert.crl_uris
+    }
+    assert_raise(OpenSSL::ASN1::ASN1Error, "invalid extension") {
+      invalid_exts_cert.ca_issuer_uris
+    }
+    assert_raise(OpenSSL::ASN1::ASN1Error, "invalid extension") {
+      invalid_exts_cert.ocsp_uris
+    }
   end
 
   def test_sign_and_verify_rsa_sha1
@@ -189,6 +265,17 @@ class OpenSSL::TestX509Certificate < OpenSSL::TestCase
     assert_equal false, cert3 == cert4
   end
 
+  def test_marshal
+    now = Time.now
+    cacert = issue_cert(@ca, @rsa1024, 1, [], nil, nil,
+      not_before: now, not_after: now + 3600)
+    cert = issue_cert(@ee1, @rsa2048, 2, [], cacert, @rsa1024,
+      not_before: now, not_after: now + 3600)
+    deserialized = Marshal.load(Marshal.dump(cert))
+
+    assert_equal cert.to_der, deserialized.to_der
+  end
+
   private
 
   def certificate_error_returns_false
diff --git a/test/openssl/test_x509crl.rb b/test/openssl/test_x509crl.rb
index 03fdf64dd4..a6d0adc592 100644
--- a/test/openssl/test_x509crl.rb
+++ b/test/openssl/test_x509crl.rb
@@ -1,4 +1,4 @@
-# frozen_string_literal: false
+# frozen_string_literal: true
 require_relative "utils"
 
 if defined?(OpenSSL)
@@ -118,7 +118,7 @@ class OpenSSL::TestX509CRL < OpenSSL::TestCase
       ["keyUsage", "cRLSign, keyCertSign", true],
     ]
     crl_exts = [
-      ["authorityKeyIdentifier", "keyid:always", false],
+      ["authorityKeyIdentifier", "issuer:always,keyid:always", false],
       ["issuerAltName", "issuer:copy", false],
     ]
 
@@ -131,6 +131,9 @@ class OpenSSL::TestX509CRL < OpenSSL::TestCase
     assert_equal("crlNumber", exts[0].oid)
     assert_equal(false, exts[0].critical?)
 
+    expected_keyid = OpenSSL::TestUtils.get_subject_key_id(cert, hex: false)
+    assert_equal expected_keyid, crl.authority_key_identifier
+
     assert_equal("authorityKeyIdentifier", exts[1].oid)
     keyid = OpenSSL::TestUtils.get_subject_key_id(cert)
     assert_match(/^keyid:#{keyid}/, exts[1].value)
@@ -155,6 +158,10 @@ class OpenSSL::TestX509CRL < OpenSSL::TestCase
     assert_equal("issuerAltName", exts[2].oid)
     assert_equal("email:[email protected]", exts[2].value)
     assert_equal(false, exts[2].critical?)
+
+    no_ext_crl = issue_crl([], 1, Time.now, Time.now+1600, [],
+      cert, @rsa2048, OpenSSL::Digest::SHA1.new)
+    assert_equal nil, no_ext_crl.authority_key_identifier
   end
 
   def test_crlnumber
@@ -249,6 +256,22 @@ class OpenSSL::TestX509CRL < OpenSSL::TestCase
     assert_equal true, rev2 == crl2.revoked[1]
   end
 
+  def test_marshal
+    now = Time.now
+
+    cacert = issue_cert(@ca, @rsa1024, 1, [], nil, nil)
+    crl = issue_crl([], 1, now, now + 3600, [], cacert, @rsa1024, "sha256")
+    rev = OpenSSL::X509::Revoked.new.tap { |rev|
+      rev.serial = 1
+      rev.time = now
+    }
+    crl.add_revoked(rev)
+    deserialized = Marshal.load(Marshal.dump(crl))
+
+    assert_equal crl.to_der, deserialized.to_der
+    assert_equal crl.revoked[0].to_der, deserialized.revoked[0].to_der
+  end
+
   private
 
   def crl_error_returns_false
diff --git a/test/openssl/test_x509ext.rb b/test/openssl/test_x509ext.rb
index 91ce202fec..7ad010d1ed 100644
--- a/test/openssl/test_x509ext.rb
+++ b/test/openssl/test_x509ext.rb
@@ -1,4 +1,4 @@
-# frozen_string_literal: false
+# frozen_string_literal: true
 require_relative 'utils'
 
 if defined?(OpenSSL)
@@ -86,6 +86,19 @@ class OpenSSL::TestX509Extension < OpenSSL::TestCase
     assert_equal true, ext1 == ext2
     assert_equal false, ext1 == ext3
   end
+
+  def test_marshal
+    ef = OpenSSL::X509::ExtensionFactory.new
+    ext = ef.create_extension("basicConstraints", "critical, CA:TRUE, pathlen:2")
+    deserialized = Marshal.load(Marshal.dump(ext))
+
+    assert_equal ext.to_der, deserialized.to_der
+  end
+
+  def test_value_der
+    ext = OpenSSL::X509::Extension.new(@basic_constraints.to_der)
+    assert_equal @basic_constraints_value.to_der, ext.value_der
+  end
 end
 
 end
diff --git a/test/openssl/test_x509name.rb b/test/openssl/test_x509name.rb
index 8a4596ea6e..4ec5db2018 100644
--- a/test/openssl/test_x509name.rb
+++ b/test/openssl/test_x509name.rb
@@ -1,5 +1,5 @@
 # coding: ASCII-8BIT
-# frozen_string_literal: false
+# frozen_string_literal: true
 require_relative 'utils'
 
 if defined?(OpenSSL)
@@ -242,16 +242,15 @@ class OpenSSL::TestX509Name < OpenSSL::TestCase
       assert_match(/^multi-valued RDN is not supported: #{dn_r}/, ex.message)
     }
 
-    bad_dc = "exa#{"pm"}le"     # <- typo of "example"
     [
-      ["DC=org,DC=#{bad_dc},CN", "CN"],
+      ["DC=org,DC=exapmle,CN", "CN"],
       ["DC=org,DC=example,", ""],
-      ["DC=org,DC=#{bad_dc},CN=www.example.org;", "CN=www.example.org;"],
-      ["DC=org,DC=#{bad_dc},CN=#www.example.org", "CN=#www.example.org"],
-      ["DC=org,DC=#{bad_dc},CN=#777777.example.org", "CN=#777777.example.org"],
-      ["DC=org,DC=#{bad_dc},CN=\"www.example\".org", "CN=\"www.example\".org"],
-      ["DC=org,DC=#{bad_dc},CN=www.\"example.org\"", "CN=www.\"example.org\""],
-      ["DC=org,DC=#{bad_dc},CN=www.\"example\".org", "CN=www.\"example\".org"],
+      ["DC=org,DC=exapmle,CN=www.example.org;", "CN=www.example.org;"],
+      ["DC=org,DC=exapmle,CN=#www.example.org", "CN=#www.example.org"],
+      ["DC=org,DC=exapmle,CN=#777777.example.org", "CN=#777777.example.org"],
+      ["DC=org,DC=exapmle,CN=\"www.example\".org", "CN=\"www.example\".org"],
+      ["DC=org,DC=exapmle,CN=www.\"example.org\"", "CN=www.\"example.org\""],
+      ["DC=org,DC=exapmle,CN=www.\"example\".org", "CN=www.\"example\".org"],
     ].each{|dn, msg|
       ex = scanner.call(dn) rescue $!
       assert_match(/^malformed RDN: .*=>#{Regexp.escape(msg)}/, ex.message)
@@ -390,7 +389,7 @@ class OpenSSL::TestX509Name < OpenSSL::TestCase
     dn.each { |x| name.add_entry(*x) }
 
     str = name.to_utf8
-    expected = "CN=フー\\, バー,DC=ruby-lang,DC=org".force_encoding("UTF-8")
+    expected = String.new("CN=フー\\, バー,DC=ruby-lang,DC=org").force_encoding("UTF-8")
     assert_equal expected, str
     assert_equal Encoding.find("UTF-8"), str.encoding
 
@@ -403,6 +402,9 @@ class OpenSSL::TestX509Name < OpenSSL::TestCase
     n2 = OpenSSL::X509::Name.parse_rfc2253 'CN=a'
 
     assert_equal n1, n2
+
+    assert_equal(false, n1 == 'abc')
+    assert_equal(false, n2 == nil)
   end
 
   def test_spaceship
@@ -416,6 +418,9 @@ class OpenSSL::TestX509Name < OpenSSL::TestCase
     assert_equal(-1, n2 <=> n3)
     assert_equal(1, n3 <=> n1)
     assert_equal(1, n3 <=> n2)
+    assert_equal(nil, n1 <=> 'abc')
+    assert_equal(nil, n2 <=> 123)
+    assert_equal(nil, n3 <=> nil)
   end
 
   def name_hash(name)
@@ -448,6 +453,13 @@ class OpenSSL::TestX509Name < OpenSSL::TestCase
     assert_equal false, name0.eql?(name2)
   end
 
+  def test_marshal
+    name = OpenSSL::X509::Name.new([["DC", "org"], ["DC", "ruby-lang"], ["CN", "bar.ruby-lang.org"]])
+    deserialized = Marshal.load(Marshal.dump(name))
+
+    assert_equal name.to_der, deserialized.to_der
+  end
+
   def test_dup
     name = OpenSSL::X509::Name.parse("/CN=ruby-lang.org")
     assert_equal(name.to_der, name.dup.to_der)
diff --git a/test/openssl/test_x509req.rb b/test/openssl/test_x509req.rb
index 2c447ccdd5..bace06b347 100644
--- a/test/openssl/test_x509req.rb
+++ b/test/openssl/test_x509req.rb
@@ -1,4 +1,4 @@
-# frozen_string_literal: false
+# frozen_string_literal: true
 require_relative "utils"
 
 if defined?(OpenSSL)
@@ -151,6 +151,13 @@ class OpenSSL::TestX509Request < OpenSSL::TestCase
     assert_equal false, req1 == req3
   end
 
+  def test_marshal
+    req = issue_csr(0, @dn, @rsa1024, "sha256")
+    deserialized = Marshal.load(Marshal.dump(req))
+
+    assert_equal req.to_der, deserialized.to_der
+  end
+
   private
 
   def request_error_returns_false
diff --git a/test/openssl/test_x509store.rb b/test/openssl/test_x509store.rb
index 6412249b93..8223c9b7ac 100644
--- a/test/openssl/test_x509store.rb
+++ b/test/openssl/test_x509store.rb
@@ -1,4 +1,4 @@
-# frozen_string_literal: false
+# frozen_string_literal: true
 require_relative "utils"
 
 if defined?(OpenSSL)
diff --git a/test/openssl/ut_eof.rb b/test/openssl/ut_eof.rb
index bd62fd50f9..cf1f2d423e 100644
--- a/test/openssl/ut_eof.rb
+++ b/test/openssl/ut_eof.rb
@@ -1,4 +1,4 @@
-# frozen_string_literal: false
+# frozen_string_literal: true
 require 'test/unit'
 
 if defined?(OpenSSL)
@@ -18,12 +18,12 @@ module OpenSSL::TestEOF
       assert_nil(f.read(1))
     }
     open_file("") {|f|
-      s = "x"
+      s = +"x"
       assert_equal("", f.read(nil, s))
       assert_equal("", s)
     }
     open_file("") {|f|
-      s = "x"
+      s = +"x"
       assert_nil(f.read(10, s))
       assert_equal("", s)
     }
@@ -75,12 +75,12 @@ module OpenSSL::TestEOF
       assert_equal("", f.read(0))
     }
     open_file("a") {|f|
-      s = "x"
+      s = +"x"
       assert_equal("a", f.read(nil, s))
       assert_equal("a", s)
     }
     open_file("a") {|f|
-      s = "x"
+      s = +"x"
       assert_equal("a", f.read(10, s))
       assert_equal("a", s)
     }
diff --git a/test/openssl/utils.rb b/test/openssl/utils.rb
index bf19163052..acece97911 100644
--- a/test/openssl/utils.rb
+++ b/test/openssl/utils.rb
@@ -1,4 +1,4 @@
-# frozen_string_literal: false
+# frozen_string_literal: true
 begin
   require "openssl"
 
@@ -52,15 +52,18 @@ module OpenSSL::TestUtils
       @file_cache[[category, name]] ||=
         File.read(File.join(__dir__, "fixtures", category, name + ".pem"))
     end
+
+    def file_path(category, name)
+      File.join(__dir__, "fixtures", category, name)
+    end
   end
 
   module_function
 
-  def issue_cert(dn, key, serial, extensions, issuer, issuer_key,
-                 not_before: nil, not_after: nil, digest: "sha256")
+  def generate_cert(dn, key, serial, issuer,
+                    not_before: nil, not_after: nil)
     cert = OpenSSL::X509::Certificate.new
     issuer = cert unless issuer
-    issuer_key = key unless issuer_key
     cert.version = 2
     cert.serial = serial
     cert.subject = dn
@@ -69,6 +72,16 @@ module OpenSSL::TestUtils
     now = Time.now
     cert.not_before = not_before || now - 3600
     cert.not_after = not_after || now + 3600
+    cert
+  end
+
+
+  def issue_cert(dn, key, serial, extensions, issuer, issuer_key,
+                 not_before: nil, not_after: nil, digest: "sha256")
+    cert = generate_cert(dn, key, serial, issuer,
+                         not_before: not_before, not_after: not_after)
+    issuer = cert unless issuer
+    issuer_key = key unless issuer_key
     ef = OpenSSL::X509::ExtensionFactory.new
     ef.subject_certificate = cert
     ef.issuer_certificate = issuer
@@ -107,13 +120,18 @@ module OpenSSL::TestUtils
     crl
   end
 
-  def get_subject_key_id(cert)
+  def get_subject_key_id(cert, hex: true)
     asn1_cert = OpenSSL::ASN1.decode(cert)
     tbscert   = asn1_cert.value[0]
     pkinfo    = tbscert.value[6]
     publickey = pkinfo.value[1]
     pkvalue   = publickey.value
-    OpenSSL::Digest::SHA1.hexdigest(pkvalue).scan(/../).join(":").upcase
+    digest = OpenSSL::Digest::SHA1.digest(pkvalue)
+    if hex
+      digest.unpack("H2"*20).join(":").upcase
+    else
+      digest
+    end
   end
 
   def openssl?(major = nil, minor = nil, fix = nil, patch = 0)
@@ -189,6 +207,7 @@ class OpenSSL::SSLTestCase < OpenSSL::TestCase
 
   def start_server(verify_mode: OpenSSL::SSL::VERIFY_NONE, start_immediately: true,
                    ctx_proc: nil, server_proc: method(:readwrite_loop),
+                   accept_proc: proc{},
                    ignore_listener_error: false, &block)
     IO.pipe {|stop_pipe_r, stop_pipe_w|
       store = OpenSSL::X509::Store.new
@@ -222,6 +241,7 @@ class OpenSSL::SSLTestCase < OpenSSL::TestCase
                 readable, = IO.select([ssls, stop_pipe_r])
                 break if readable.include? stop_pipe_r
                 ssl = ssls.accept
+                accept_proc.call(ssl)
               rescue OpenSSL::SSL::SSLError, IOError, Errno::EBADF, Errno::EINVAL,
                      Errno::ECONNABORTED, Errno::ENOTSOCK, Errno::ECONNRESET
                 retry if ignore_listener_error
@@ -268,7 +288,7 @@ class OpenSSL::SSLTestCase < OpenSSL::TestCase
           begin
             timeout = EnvUtil.apply_timeout_scale(30)
             th.join(timeout) or
-              th.raise(RuntimeError, "[start_server] thread did not exit in #{ timeout } secs")
+              th.raise(RuntimeError, "[start_server] thread did not exit in #{timeout} secs")
           rescue (defined?(MiniTest::Skip) ? MiniTest::Skip : Test::Unit::PendedError)
             # MiniTest::Skip is for the Ruby tree
             pend = $!
@@ -316,4 +336,62 @@ class OpenSSL::PKeyTestCase < OpenSSL::TestCase
   end
 end
 
+module OpenSSL::Certs
+  include OpenSSL::TestUtils
+
+  module_function
+
+  def ca_cert
+    ca = OpenSSL::X509::Name.parse("/DC=org/DC=ruby-lang/CN=Timestamp Root CA")
+
+    ca_exts = [
+      ["basicConstraints","CA:TRUE,pathlen:1",true],
+      ["keyUsage","keyCertSign, cRLSign",true],
+      ["subjectKeyIdentifier","hash",false],
+      ["authorityKeyIdentifier","keyid:always",false],
+    ]
+    OpenSSL::TestUtils.issue_cert(ca, Fixtures.pkey("rsa2048"), 1, ca_exts, nil, nil)
+  end
+
+  def ts_cert_direct(key, ca_cert)
+    dn = OpenSSL::X509::Name.parse("/DC=org/DC=ruby-lang/OU=Timestamp/CN=Server Direct")
+
+    exts = [
+      ["basicConstraints","CA:FALSE",true],
+      ["keyUsage","digitalSignature, nonRepudiation", true],
+      ["subjectKeyIdentifier", "hash",false],
+      ["authorityKeyIdentifier","keyid,issuer", false],
+      ["extendedKeyUsage", "timeStamping", true]
+    ]
+
+    OpenSSL::TestUtils.issue_cert(dn, key, 2, exts, ca_cert, Fixtures.pkey("rsa2048"))
+  end
+
+  def intermediate_cert(key, ca_cert)
+    dn = OpenSSL::X509::Name.parse("/DC=org/DC=ruby-lang/OU=Timestamp/CN=Timestamp Intermediate CA")
+
+    exts = [
+      ["basicConstraints","CA:TRUE,pathlen:0",true],
+      ["keyUsage","keyCertSign, cRLSign",true],
+      ["subjectKeyIdentifier","hash",false],
+      ["authorityKeyIdentifier","keyid:always",false],
+    ]
+
+    OpenSSL::TestUtils.issue_cert(dn, key, 3, exts, ca_cert, Fixtures.pkey("rsa2048"))
+  end
+
+  def ts_cert_ee(key, intermediate, im_key)
+    dn = OpenSSL::X509::Name.parse("/DC=org/DC=ruby-lang/OU=Timestamp/CN=Server End Entity")
+
+    exts = [
+      ["keyUsage","digitalSignature, nonRepudiation", true],
+      ["subjectKeyIdentifier", "hash",false],
+      ["authorityKeyIdentifier","keyid,issuer", false],
+      ["extendedKeyUsage", "timeStamping", true]
+    ]
+
+    OpenSSL::TestUtils.issue_cert(dn, key, 4, exts, intermediate, im_key)
+  end
+end
+
 end