openssl: import v2.1.0.beta2

Import Ruby/OpenSSL 2.1.0.beta2. The full commit log since commit
e72d960db262 which was imported by r60013 can be found at:

	https://github.com/ruby/openssl/compare/e72d960db262...v2.1.0.beta2

----------------------------------------------------------------
Kazuki Yamaguchi (26):
      bn: use ALLOCV() macro instead of xmalloc()
      appveyor.yml: remove 'openssl version' line
      test/test_ssl_session: skip tests for session_remove_cb
      x509ext: implement X509::Extension#==
      x509attr: implement X509::Attribute#==
      x509cert: implement X509::Certificate#==
      x509revoked: add missing X509::Revoked#to_der
      x509crl, x509revoked: implement X509::{CRL,Revoked}#==
      x509req: implement X509::Request#==
      ssl: extract rb_intern("call")
      cipher: disallow setting AAD for non-AEAD ciphers
      test/test_cipher: fix test_non_aead_cipher_set_auth_data failure
      ssl: fix conflict of options in SSLContext#set_params
      buffering: let #write accept multiple arguments
      pkey: make pkey_check_public_key() non-static
      x509cert, x509crl, x509req, ns_spki: check sanity of public key
      test/envutil: port assert_warning from Ruby trunk
      test/utils: remove a pointless .public_key call in issue_cert
      ssl: add SSLContext#add_certificate
      test/test_ssl: fix test_security_level
      Drop support for LibreSSL 2.4
      kdf: add HKDF support
      test/test_x509cert: fix flaky test
      test/test_x509crl: fix random failure
      History.md: fix a typo
      Ruby/OpenSSL 2.1.0.beta2

Mark Wright (1):
      Fix build failure against OpenSSL 1.1 built with no-deprecated Thanks rhenium for the code review and fixes.

Peter Karman (1):
      Add RSA sign_pss() and verify_pss() methods

aeris (1):
      TLS Fallback Signaling Cipher Suite Value

kazu (1):
      Use caller with length to reduce unused strings

git-svn-id: svn+ssh://ci.ruby-lang.org/ruby/trunk@60907 b2dd03c8-39d4-4d8f-98ff-823fe69b080e

32 files changed, 1020 insertions, 116 deletions

diff --git a/ext/openssl/History.md b/ext/openssl/History.md
index 4e12682c64..f83f523dcc 100644
--- a/ext/openssl/History.md
+++ b/ext/openssl/History.md
@@ -1,18 +1,21 @@
-Version 2.1.0.beta1
+Version 2.1.0.beta2
 ===================
 
 Notable changes
 ---------------
 
-* Support for OpenSSL versions before 1.0.1 is removed.
+* Support for OpenSSL versions before 1.0.1 and LibreSSL versions before 2.5
+  is removed.
   [[GitHub #86]](https://github.com/ruby/openssl/pull/86)
 * OpenSSL::BN#negative?, #+@, and #-@ are added.
 * OpenSSL::SSL::SSLSocket#connect raises a more informative exception when
   certificate verification fails.
   [[GitHub #99]](https://github.com/ruby/openssl/pull/99)
-* OpenSSL::KDF module is newly added. Support for scrypt is added.
+* OpenSSL::KDF module is newly added. In addition to PBKDF2-HMAC that has moved
+  from OpenSSL::PKCS5, scrypt and HKDF are supported.
   [[GitHub #109]](https://github.com/ruby/openssl/pull/109)
-* OpenSSL.fips_mode is added. We have had the setter, but not the getter.
+  [[GitHub #173]](https://github.com/ruby/openssl/pull/173)
+* OpenSSL.fips_mode is added. We had the setter, but not the getter.
   [[GitHub #125]](https://github.com/ruby/openssl/pull/125)
 * OpenSSL::OCSP::Request#signed? is added.
 * OpenSSL::ASN1 handles the indefinite length form better. OpenSSL::ASN1.decode
@@ -22,11 +25,31 @@ Notable changes
 * OpenSSL::X509::Name#add_entry now accepts two additional keyword arguments
   'loc' and 'set'.
   [[GitHub #94]](https://github.com/ruby/openssl/issues/94)
-* OpenSSL::SSL::SSLContext#min_version= and #max_version= are added.
+* OpenSSL::SSL::SSLContext#min_version= and #max_version= are added to replace
+  #ssl_version= that was built on top of the deprecated OpenSSL C API. Use of
+  that method and the constant OpenSSL::SSL::SSLContext::METHODS is now
+  deprecated.
   [[GitHub #142]](https://github.com/ruby/openssl/pull/142)
 * OpenSSL::X509::Name#to_utf8 is added.
   [[GitHub #26]](https://github.com/ruby/openssl/issues/26)
   [[GitHub #143]](https://github.com/ruby/openssl/pull/143)
+* OpenSSL::X509::{Extension,Attribute,Certificate,CRL,Revoked,Request} can be
+  compared with == operator.
+  [[GitHub #161]](https://github.com/ruby/openssl/pull/161)
+* TLS Fallback Signaling Cipher Suite Value (SCSV) support is added.
+  [[GitHub #165]](https://github.com/ruby/openssl/pull/165)
+* Build failure with OpenSSL 1.1 built with no-deprecated is fixed.
+  [[GitHub #160]](https://github.com/ruby/openssl/pull/160)
+* OpenSSL::Buffering#write accepts an arbitrary number of arguments.
+  [[Feature #9323]](https://bugs.ruby-lang.org/issues/9323)
+  [[GitHub #162]](https://github.com/ruby/openssl/pull/162)
+* OpenSSL::PKey::RSA#sign_pss and #verify_pss are added. They perform RSA-PSS
+  signature and verification.
+  [[GitHub #75]](https://github.com/ruby/openssl/issues/75)
+  [[GitHub #76]](https://github.com/ruby/openssl/pull/76)
+  [[GitHub #169]](https://github.com/ruby/openssl/pull/169)
+* OpenSSL::SSL::SSLContext#add_certificate is added.
+  [[GitHub #167]](https://github.com/ruby/openssl/pull/167)
 
 
 Version 2.0.6
@@ -201,7 +224,7 @@ Notable changes
   - A new option 'verify_hostname' is added to OpenSSL::SSL::SSLContext. When it
     is enabled, and the SNI hostname is also set, the hostname verification on
     the server certificate is automatically performed. It is now enabled by
-    OpenSSL::SSL::Context#set_params.
+    OpenSSL::SSL::SSLContext#set_params.
     [[GH ruby/openssl#60]](https://github.com/ruby/openssl/pull/60)
 
 Removals
diff --git a/ext/openssl/lib/openssl/buffering.rb b/ext/openssl/lib/openssl/buffering.rb
index f328c0007d..935f61f0ef 100644
--- a/ext/openssl/lib/openssl/buffering.rb
+++ b/ext/openssl/lib/openssl/buffering.rb
@@ -340,9 +340,10 @@ module OpenSSL::Buffering
   # converted using +.to_s+ method.  Returns the number of bytes written.
 
   def write(*s)
-    s = s.size == 1 ? s[0] : s.join("")
-    do_write(s)
-    s.bytesize
+    s.inject(0) do |written, str|
+      do_write(str)
+      written + str.bytesize
+    end
   end
 
   ##
diff --git a/ext/openssl/lib/openssl/x509.rb b/ext/openssl/lib/openssl/x509.rb
index 6d31b98c68..98358f90da 100644
--- a/ext/openssl/lib/openssl/x509.rb
+++ b/ext/openssl/lib/openssl/x509.rb
@@ -41,6 +41,11 @@ module OpenSSL
     end
 
     class Extension
+      def ==(other)
+        return false unless Extension === other
+        to_der == other.to_der
+      end
+
       def to_s # "oid = critical, value"
         str = self.oid
         str << " = "
@@ -160,6 +165,13 @@ module OpenSSL
       end
     end
 
+    class Attribute
+      def ==(other)
+        return false unless Attribute === other
+        to_der == other.to_der
+      end
+    end
+
     class StoreContext
       def cleanup
         warn "(#{caller.first}) OpenSSL::X509::StoreContext#cleanup is deprecated with no replacement" if $VERBOSE
@@ -178,5 +190,26 @@ module OpenSSL
         }
       end
     end
+
+    class CRL
+      def ==(other)
+        return false unless CRL === other
+        to_der == other.to_der
+      end
+    end
+
+    class Revoked
+      def ==(other)
+        return false unless Revoked === other
+        to_der == other.to_der
+      end
+    end
+
+    class Request
+      def ==(other)
+        return false unless Request === other
+        to_der == other.to_der
+      end
+    end
   end
 end
diff --git a/ext/openssl/openssl.gemspec b/ext/openssl/openssl.gemspec
index a8b21a561b..b60b5358d9 100644
--- a/ext/openssl/openssl.gemspec
+++ b/ext/openssl/openssl.gemspec
@@ -1,16 +1,16 @@
 # -*- encoding: utf-8 -*-
-# stub: openssl 2.1.0.beta1 ruby lib
+# stub: openssl 2.1.0.beta2 ruby lib
 # stub: ext/openssl/extconf.rb
 
 Gem::Specification.new do |s|
   s.name = "openssl".freeze
-  s.version = "2.1.0.beta1"
+  s.version = "2.1.0.beta2"
 
   s.required_rubygems_version = Gem::Requirement.new("> 1.3.1".freeze) if s.respond_to? :required_rubygems_version=
   s.metadata = { "msys2_mingw_dependencies" => "openssl" } if s.respond_to? :metadata=
   s.require_paths = ["lib".freeze]
   s.authors = ["Martin Bosslet".freeze, "SHIBATA Hiroshi".freeze, "Zachary Scott".freeze, "Kazuki Yamaguchi".freeze]
-  s.date = "2017-09-24"
+  s.date = "2017-11-25"
   s.description = "It wraps the OpenSSL library.".freeze
   s.email = ["ruby-core@ruby-lang.org".freeze]
   s.extensions = ["ext/openssl/extconf.rb".freeze]
@@ -20,7 +20,7 @@ Gem::Specification.new do |s|
   s.licenses = ["Ruby".freeze]
   s.rdoc_options = ["--main".freeze, "README.md".freeze]
   s.required_ruby_version = Gem::Requirement.new(">= 2.3.0".freeze)
-  s.rubygems_version = "2.6.13".freeze
+  s.rubygems_version = "2.7.2".freeze
   s.summary = "OpenSSL provides SSL, TLS and general purpose cryptography.".freeze
 
   if s.respond_to? :specification_version then
diff --git a/ext/openssl/openssl_missing.h b/ext/openssl/openssl_missing.h
index cc31f6ace7..debd25adea 100644
--- a/ext/openssl/openssl_missing.h
+++ b/ext/openssl/openssl_missing.h
@@ -209,6 +209,10 @@ IMPL_PKEY_GETTER(EC_KEY, ec)
 #  define X509_get0_notAfter(x) X509_get_notAfter(x)
 #  define X509_CRL_get0_lastUpdate(x) X509_CRL_get_lastUpdate(x)
 #  define X509_CRL_get0_nextUpdate(x) X509_CRL_get_nextUpdate(x)
+#  define X509_set1_notBefore(x, t) X509_set_notBefore(x, t)
+#  define X509_set1_notAfter(x, t) X509_set_notAfter(x, t)
+#  define X509_CRL_set1_lastUpdate(x, t) X509_CRL_set_lastUpdate(x, t)
+#  define X509_CRL_set1_nextUpdate(x, t) X509_CRL_set_nextUpdate(x, t)
 #endif
 
 #if !defined(HAVE_SSL_SESSION_GET_PROTOCOL_VERSION)
diff --git a/ext/openssl/ossl.c b/ext/openssl/ossl.c
index 93ecc7d414..245385e7da 100644
--- a/ext/openssl/ossl.c
+++ b/ext/openssl/ossl.c
@@ -1109,25 +1109,14 @@ Init_openssl(void)
     /*
      * Init all digests, ciphers
      */
-    /* CRYPTO_malloc_init(); */
-    /* ENGINE_load_builtin_engines(); */
+#if !defined(LIBRESSL_VERSION_NUMBER) && OPENSSL_VERSION_NUMBER >= 0x10100000
+    if (!OPENSSL_init_ssl(0, NULL))
+        rb_raise(rb_eRuntimeError, "OPENSSL_init_ssl");
+#else
     OpenSSL_add_ssl_algorithms();
     OpenSSL_add_all_algorithms();
     ERR_load_crypto_strings();
     SSL_load_error_strings();
-
-    /*
-     * FIXME:
-     * On unload do:
-     */
-#if 0
-    CONF_modules_unload(1);
-    destroy_ui_method();
-    EVP_cleanup();
-    ENGINE_cleanup();
-    CRYPTO_cleanup_all_ex_data();
-    ERR_remove_state(0);
-    ERR_free_strings();
 #endif
 
     /*
@@ -1149,7 +1138,11 @@ Init_openssl(void)
     /*
      * Version of OpenSSL the ruby OpenSSL extension is running with
      */
+#if !defined(LIBRESSL_VERSION_NUMBER) && OPENSSL_VERSION_NUMBER >= 0x10100000
+    rb_define_const(mOSSL, "OPENSSL_LIBRARY_VERSION", rb_str_new2(OpenSSL_version(OPENSSL_VERSION)));
+#else
     rb_define_const(mOSSL, "OPENSSL_LIBRARY_VERSION", rb_str_new2(SSLeay_version(SSLEAY_VERSION)));
+#endif
 
     /*
      * Version number of OpenSSL the ruby OpenSSL extension was built with
diff --git a/ext/openssl/ossl.h b/ext/openssl/ossl.h
index f08889b22e..5a15839cb4 100644
--- a/ext/openssl/ossl.h
+++ b/ext/openssl/ossl.h
@@ -35,6 +35,11 @@
 #if !defined(OPENSSL_NO_OCSP)
 #  include <openssl/ocsp.h>
 #endif
+#include <openssl/bn.h>
+#include <openssl/rsa.h>
+#include <openssl/dsa.h>
+#include <openssl/evp.h>
+#include <openssl/dh.h>
 
 /*
  * Common Module
diff --git a/ext/openssl/ossl_bn.c b/ext/openssl/ossl_bn.c
index d337d50961..4666ce6c2f 100644
--- a/ext/openssl/ossl_bn.c
+++ b/ext/openssl/ossl_bn.c
@@ -979,20 +979,20 @@ static VALUE
 ossl_bn_hash(VALUE self)
 {
     BIGNUM *bn;
-    VALUE hash;
+    VALUE tmp, hash;
     unsigned char *buf;
     int len;
 
     GetBN(self, bn);
     len = BN_num_bytes(bn);
-    buf = xmalloc(len);
+    buf = ALLOCV(tmp, len);
     if (BN_bn2bin(bn, buf) != len) {
-	xfree(buf);
-	ossl_raise(eBNError, NULL);
+	ALLOCV_END(tmp);
+	ossl_raise(eBNError, "BN_bn2bin");
     }
 
     hash = ST2FIX(rb_memhash(buf, len));
-    xfree(buf);
+    ALLOCV_END(tmp);
 
     return hash;
 }
diff --git a/ext/openssl/ossl_cipher.c b/ext/openssl/ossl_cipher.c
index bfa76c1aab..3038a76687 100644
--- a/ext/openssl/ossl_cipher.c
+++ b/ext/openssl/ossl_cipher.c
@@ -508,7 +508,7 @@ ossl_cipher_set_iv(VALUE self, VALUE iv)
     StringValue(iv);
     GetCipher(self, ctx);
 
-    if (EVP_CIPHER_CTX_flags(ctx) & EVP_CIPH_FLAG_AEAD_CIPHER)
+    if (EVP_CIPHER_flags(EVP_CIPHER_CTX_cipher(ctx)) & EVP_CIPH_FLAG_AEAD_CIPHER)
 	iv_len = (int)(VALUE)EVP_CIPHER_CTX_get_app_data(ctx);
     if (!iv_len)
 	iv_len = EVP_CIPHER_CTX_iv_length(ctx);
@@ -535,7 +535,7 @@ ossl_cipher_is_authenticated(VALUE self)
 
     GetCipher(self, ctx);
 
-    return (EVP_CIPHER_CTX_flags(ctx) & EVP_CIPH_FLAG_AEAD_CIPHER) ? Qtrue : Qfalse;
+    return (EVP_CIPHER_flags(EVP_CIPHER_CTX_cipher(ctx)) & EVP_CIPH_FLAG_AEAD_CIPHER) ? Qtrue : Qfalse;
 }
 
 /*
@@ -569,6 +569,8 @@ ossl_cipher_set_auth_data(VALUE self, VALUE data)
     in_len = RSTRING_LEN(data);
 
     GetCipher(self, ctx);
+    if (!(EVP_CIPHER_flags(EVP_CIPHER_CTX_cipher(ctx)) & EVP_CIPH_FLAG_AEAD_CIPHER))
+	ossl_raise(eCipherError, "AEAD not supported by this cipher");
 
     if (!ossl_cipher_update_long(ctx, NULL, &out_len, in, in_len))
         ossl_raise(eCipherError, "couldn't set additional authenticated data");
@@ -606,7 +608,7 @@ ossl_cipher_get_auth_tag(int argc, VALUE *argv, VALUE self)
 
     GetCipher(self, ctx);
 
-    if (!(EVP_CIPHER_CTX_flags(ctx) & EVP_CIPH_FLAG_AEAD_CIPHER))
+    if (!(EVP_CIPHER_flags(EVP_CIPHER_CTX_cipher(ctx)) & EVP_CIPH_FLAG_AEAD_CIPHER))
 	ossl_raise(eCipherError, "authentication tag not supported by this cipher");
 
     ret = rb_str_new(NULL, tag_len);
@@ -641,7 +643,7 @@ ossl_cipher_set_auth_tag(VALUE self, VALUE vtag)
     tag_len = RSTRING_LENINT(vtag);
 
     GetCipher(self, ctx);
-    if (!(EVP_CIPHER_CTX_flags(ctx) & EVP_CIPH_FLAG_AEAD_CIPHER))
+    if (!(EVP_CIPHER_flags(EVP_CIPHER_CTX_cipher(ctx)) & EVP_CIPH_FLAG_AEAD_CIPHER))
 	ossl_raise(eCipherError, "authentication tag not supported by this cipher");
 
     if (!EVP_CIPHER_CTX_ctrl(ctx, EVP_CTRL_AEAD_SET_TAG, tag_len, tag))
@@ -668,7 +670,7 @@ ossl_cipher_set_auth_tag_len(VALUE self, VALUE vlen)
     EVP_CIPHER_CTX *ctx;
 
     GetCipher(self, ctx);
-    if (!(EVP_CIPHER_CTX_flags(ctx) & EVP_CIPH_FLAG_AEAD_CIPHER))
+    if (!(EVP_CIPHER_flags(EVP_CIPHER_CTX_cipher(ctx)) & EVP_CIPH_FLAG_AEAD_CIPHER))
 	ossl_raise(eCipherError, "AEAD not supported by this cipher");
 
     if (!EVP_CIPHER_CTX_ctrl(ctx, EVP_CTRL_AEAD_SET_TAG, tag_len, NULL))
@@ -695,7 +697,7 @@ ossl_cipher_set_iv_length(VALUE self, VALUE iv_length)
     EVP_CIPHER_CTX *ctx;
 
     GetCipher(self, ctx);
-    if (!(EVP_CIPHER_CTX_flags(ctx) & EVP_CIPH_FLAG_AEAD_CIPHER))
+    if (!(EVP_CIPHER_flags(EVP_CIPHER_CTX_cipher(ctx)) & EVP_CIPH_FLAG_AEAD_CIPHER))
 	ossl_raise(eCipherError, "cipher does not support AEAD");
 
     if (!EVP_CIPHER_CTX_ctrl(ctx, EVP_CTRL_AEAD_SET_IVLEN, len, NULL))
@@ -786,7 +788,7 @@ ossl_cipher_iv_length(VALUE self)
     int len = 0;
 
     GetCipher(self, ctx);
-    if (EVP_CIPHER_CTX_flags(ctx) & EVP_CIPH_FLAG_AEAD_CIPHER)
+    if (EVP_CIPHER_flags(EVP_CIPHER_CTX_cipher(ctx)) & EVP_CIPH_FLAG_AEAD_CIPHER)
 	len = (int)(VALUE)EVP_CIPHER_CTX_get_app_data(ctx);
     if (!len)
 	len = EVP_CIPHER_CTX_iv_length(ctx);
diff --git a/ext/openssl/ossl_engine.c b/ext/openssl/ossl_engine.c
index d69b5dcac5..5ca0d4ca3f 100644
--- a/ext/openssl/ossl_engine.c
+++ b/ext/openssl/ossl_engine.c
@@ -46,13 +46,25 @@ VALUE eEngineError;
 /*
  * Private
  */
-#define OSSL_ENGINE_LOAD_IF_MATCH(x) \
+#if !defined(LIBRESSL_VERSION_NUMBER) && OPENSSL_VERSION_NUMBER >= 0x10100000
+#define OSSL_ENGINE_LOAD_IF_MATCH(engine_name, x) \
 do{\
-  if(!strcmp(#x, RSTRING_PTR(name))){\
-    ENGINE_load_##x();\
+  if(!strcmp(#engine_name, RSTRING_PTR(name))){\
+    if (OPENSSL_init_crypto(OPENSSL_INIT_ENGINE_##x, NULL))\
+      return Qtrue;\
+    else\
+      ossl_raise(eEngineError, "OPENSSL_init_crypto"); \
+  }\
+}while(0)
+#else
+#define OSSL_ENGINE_LOAD_IF_MATCH(engine_name, x)  \
+do{\
+  if(!strcmp(#engine_name, RSTRING_PTR(name))){\
+    ENGINE_load_##engine_name();\
     return Qtrue;\
   }\
 }while(0)
+#endif
 
 static void
 ossl_engine_free(void *engine)
@@ -94,55 +106,55 @@ ossl_engine_s_load(int argc, VALUE *argv, VALUE klass)
     StringValueCStr(name);
 #ifndef OPENSSL_NO_STATIC_ENGINE
 #if HAVE_ENGINE_LOAD_DYNAMIC
-    OSSL_ENGINE_LOAD_IF_MATCH(dynamic);
+    OSSL_ENGINE_LOAD_IF_MATCH(dynamic, DYNAMIC);
 #endif
 #if HAVE_ENGINE_LOAD_4758CCA
-    OSSL_ENGINE_LOAD_IF_MATCH(4758cca);
+    OSSL_ENGINE_LOAD_IF_MATCH(4758cca, 4758CCA);
 #endif
 #if HAVE_ENGINE_LOAD_AEP
-    OSSL_ENGINE_LOAD_IF_MATCH(aep);
+    OSSL_ENGINE_LOAD_IF_MATCH(aep, AEP);
 #endif
 #if HAVE_ENGINE_LOAD_ATALLA
-    OSSL_ENGINE_LOAD_IF_MATCH(atalla);
+    OSSL_ENGINE_LOAD_IF_MATCH(atalla, ATALLA);
 #endif
 #if HAVE_ENGINE_LOAD_CHIL
-    OSSL_ENGINE_LOAD_IF_MATCH(chil);
+    OSSL_ENGINE_LOAD_IF_MATCH(chil, CHIL);
 #endif
 #if HAVE_ENGINE_LOAD_CSWIFT
-    OSSL_ENGINE_LOAD_IF_MATCH(cswift);
+    OSSL_ENGINE_LOAD_IF_MATCH(cswift, CSWIFT);
 #endif
 #if HAVE_ENGINE_LOAD_NURON
-    OSSL_ENGINE_LOAD_IF_MATCH(nuron);
+    OSSL_ENGINE_LOAD_IF_MATCH(nuron, NURON);
 #endif
 #if HAVE_ENGINE_LOAD_SUREWARE
-    OSSL_ENGINE_LOAD_IF_MATCH(sureware);
+    OSSL_ENGINE_LOAD_IF_MATCH(sureware, SUREWARE);
 #endif
 #if HAVE_ENGINE_LOAD_UBSEC
-    OSSL_ENGINE_LOAD_IF_MATCH(ubsec);
+    OSSL_ENGINE_LOAD_IF_MATCH(ubsec, UBSEC);
 #endif
 #if HAVE_ENGINE_LOAD_PADLOCK
-    OSSL_ENGINE_LOAD_IF_MATCH(padlock);
+    OSSL_ENGINE_LOAD_IF_MATCH(padlock, PADLOCK);
 #endif
 #if HAVE_ENGINE_LOAD_CAPI
-    OSSL_ENGINE_LOAD_IF_MATCH(capi);
+    OSSL_ENGINE_LOAD_IF_MATCH(capi, CAPI);
 #endif
 #if HAVE_ENGINE_LOAD_GMP
-    OSSL_ENGINE_LOAD_IF_MATCH(gmp);
+    OSSL_ENGINE_LOAD_IF_MATCH(gmp, GMP);
 #endif
 #if HAVE_ENGINE_LOAD_GOST
-    OSSL_ENGINE_LOAD_IF_MATCH(gost);
+    OSSL_ENGINE_LOAD_IF_MATCH(gost, GOST);
 #endif
 #if HAVE_ENGINE_LOAD_CRYPTODEV
-    OSSL_ENGINE_LOAD_IF_MATCH(cryptodev);
+    OSSL_ENGINE_LOAD_IF_MATCH(cryptodev, CRYPTODEV);
 #endif
 #if HAVE_ENGINE_LOAD_AESNI
-    OSSL_ENGINE_LOAD_IF_MATCH(aesni);
+    OSSL_ENGINE_LOAD_IF_MATCH(aesni, AESNI);
 #endif
 #endif
 #ifdef HAVE_ENGINE_LOAD_OPENBSD_DEV_CRYPTO
-    OSSL_ENGINE_LOAD_IF_MATCH(openbsd_dev_crypto);
+    OSSL_ENGINE_LOAD_IF_MATCH(openbsd_dev_crypto, OPENBSD_DEV_CRYPTO);
 #endif
-    OSSL_ENGINE_LOAD_IF_MATCH(openssl);
+    OSSL_ENGINE_LOAD_IF_MATCH(openssl, OPENSSL);
     rb_warning("no such builtin loader for `%"PRIsVALUE"'", name);
     return Qnil;
 #endif /* HAVE_ENGINE_LOAD_BUILTIN_ENGINES */
@@ -160,7 +172,9 @@ ossl_engine_s_load(int argc, VALUE *argv, VALUE klass)
 static VALUE
 ossl_engine_s_cleanup(VALUE self)
 {
+#if defined(LIBRESSL_VERSION_NUMBER) || OPENSSL_VERSION_NUMBER < 0x10100000
     ENGINE_cleanup();
+#endif
     return Qnil;
 }
 
diff --git a/ext/openssl/ossl_kdf.c b/ext/openssl/ossl_kdf.c
index 9fa42e174a..ee124718b5 100644
--- a/ext/openssl/ossl_kdf.c
+++ b/ext/openssl/ossl_kdf.c
@@ -3,6 +3,9 @@
  * Copyright (C) 2007, 2017 Ruby/OpenSSL Project Authors
  */
 #include "ossl.h"
+#if OPENSSL_VERSION_NUMBER >= 0x10100000 && !defined(LIBRESSL_VERSION_NUMBER)
+# include <openssl/kdf.h>
+#endif
 
 static VALUE mKDF, eKDF;
 
@@ -138,6 +141,97 @@ kdf_scrypt(int argc, VALUE *argv, VALUE self)
 }
 #endif
 
+#if OPENSSL_VERSION_NUMBER >= 0x10100000 && !defined(LIBRESSL_VERSION_NUMBER)
+/*
+ * call-seq:
+ *    KDF.hkdf(ikm, salt:, info:, length:, hash:) -> String
+ *
+ * HMAC-based Extract-and-Expand Key Derivation Function (HKDF) as specified in
+ * {RFC 5869}[https://tools.ietf.org/html/rfc5869].
+ *
+ * New in OpenSSL 1.1.0.
+ *
+ * === Parameters
+ * _ikm_::
+ *   The input keying material.
+ * _salt_::
+ *   The salt.
+ * _info_::
+ *   The context and application specific information.
+ * _length_::
+ *   The output length in octets. Must be <= <tt>255 * HashLen</tt>, where
+ *   HashLen is the length of the hash function output in octets.
+ * _hash_::
+ *   The hash function.
+ */
+static VALUE
+kdf_hkdf(int argc, VALUE *argv, VALUE self)
+{
+    VALUE ikm, salt, info, opts, kwargs[4], str;
+    static ID kwargs_ids[4];
+    int saltlen, ikmlen, infolen;
+    size_t len;
+    const EVP_MD *md;
+    EVP_PKEY_CTX *pctx;
+
+    if (!kwargs_ids[0]) {
+	kwargs_ids[0] = rb_intern_const("salt");
+	kwargs_ids[1] = rb_intern_const("info");
+	kwargs_ids[2] = rb_intern_const("length");
+	kwargs_ids[3] = rb_intern_const("hash");
+    }
+    rb_scan_args(argc, argv, "1:", &ikm, &opts);
+    rb_get_kwargs(opts, kwargs_ids, 4, 0, kwargs);
+
+    StringValue(ikm);
+    ikmlen = RSTRING_LENINT(ikm);
+    salt = StringValue(kwargs[0]);
+    saltlen = RSTRING_LENINT(salt);
+    info = StringValue(kwargs[1]);
+    infolen = RSTRING_LENINT(info);
+    len = (size_t)NUM2LONG(kwargs[2]);
+    if (len > LONG_MAX)
+	rb_raise(rb_eArgError, "length must be non-negative");
+    md = ossl_evp_get_digestbyname(kwargs[3]);
+
+    str = rb_str_new(NULL, (long)len);
+    pctx = EVP_PKEY_CTX_new_id(EVP_PKEY_HKDF, NULL);
+    if (!pctx)
+	ossl_raise(eKDF, "EVP_PKEY_CTX_new_id");
+    if (EVP_PKEY_derive_init(pctx) <= 0) {
+	EVP_PKEY_CTX_free(pctx);
+	ossl_raise(eKDF, "EVP_PKEY_derive_init");
+    }
+    if (EVP_PKEY_CTX_set_hkdf_md(pctx, md) <= 0) {
+	EVP_PKEY_CTX_free(pctx);
+	ossl_raise(eKDF, "EVP_PKEY_CTX_set_hkdf_md");
+    }
+    if (EVP_PKEY_CTX_set1_hkdf_salt(pctx, (unsigned char *)RSTRING_PTR(salt),
+				    saltlen) <= 0) {
+	EVP_PKEY_CTX_free(pctx);
+	ossl_raise(eKDF, "EVP_PKEY_CTX_set_hkdf_salt");
+    }
+    if (EVP_PKEY_CTX_set1_hkdf_key(pctx, (unsigned char *)RSTRING_PTR(ikm),
+				   ikmlen) <= 0) {
+	EVP_PKEY_CTX_free(pctx);
+	ossl_raise(eKDF, "EVP_PKEY_CTX_set_hkdf_key");
+    }
+    if (EVP_PKEY_CTX_add1_hkdf_info(pctx, (unsigned char *)RSTRING_PTR(info),
+				    infolen) <= 0) {
+	EVP_PKEY_CTX_free(pctx);
+	ossl_raise(eKDF, "EVP_PKEY_CTX_set_hkdf_info");
+    }
+    if (EVP_PKEY_derive(pctx, (unsigned char *)RSTRING_PTR(str), &len) <= 0) {
+	EVP_PKEY_CTX_free(pctx);
+	ossl_raise(eKDF, "EVP_PKEY_derive");
+    }
+    rb_str_set_len(str, (long)len);
+    EVP_PKEY_CTX_free(pctx);
+
+    return str;
+}
+#endif
+
 void
 Init_ossl_kdf(void)
 {
@@ -162,6 +256,7 @@ Init_ossl_kdf(void)
      * * PKCS #5 PBKDF2 (Password-Based Key Derivation Function 2) in
      *   combination with HMAC
      * * scrypt
+     * * HKDF
      *
      * == Examples
      * === Generating a 128 bit key for a Cipher (e.g. AES)
@@ -218,4 +313,7 @@ Init_ossl_kdf(void)
 #if defined(HAVE_EVP_PBE_SCRYPT)
     rb_define_module_function(mKDF, "scrypt", kdf_scrypt, -1);
 #endif
+#if OPENSSL_VERSION_NUMBER >= 0x10100000 && !defined(LIBRESSL_VERSION_NUMBER)
+    rb_define_module_function(mKDF, "hkdf", kdf_hkdf, -1);
+#endif
 }
diff --git a/ext/openssl/ossl_ns_spki.c b/ext/openssl/ossl_ns_spki.c
index f17b9509c6..6f61e61bf5 100644
--- a/ext/openssl/ossl_ns_spki.c
+++ b/ext/openssl/ossl_ns_spki.c
@@ -208,12 +208,13 @@ static VALUE
 ossl_spki_set_public_key(VALUE self, VALUE key)
 {
     NETSCAPE_SPKI *spki;
+    EVP_PKEY *pkey;
 
     GetSPKI(self, spki);
-    if (!NETSCAPE_SPKI_set_pubkey(spki, GetPKeyPtr(key))) { /* NO NEED TO DUP */
-	ossl_raise(eSPKIError, NULL);
-    }
-
+    pkey = GetPKeyPtr(key);
+    ossl_pkey_check_public_key(pkey);
+    if (!NETSCAPE_SPKI_set_pubkey(spki, pkey))
+	ossl_raise(eSPKIError, "NETSCAPE_SPKI_set_pubkey");
     return key;
 }
 
@@ -307,17 +308,20 @@ static VALUE
 ossl_spki_verify(VALUE self, VALUE key)
 {
     NETSCAPE_SPKI *spki;
+    EVP_PKEY *pkey;
 
     GetSPKI(self, spki);
-    switch (NETSCAPE_SPKI_verify(spki, GetPKeyPtr(key))) { /* NO NEED TO DUP */
-    case 0:
+    pkey = GetPKeyPtr(key);
+    ossl_pkey_check_public_key(pkey);
+    switch (NETSCAPE_SPKI_verify(spki, pkey)) {
+      case 0:
+	ossl_clear_error();
 	return Qfalse;
-    case 1:
+      case 1:
 	return Qtrue;
-    default:
-	ossl_raise(eSPKIError, NULL);
+      default:
+	ossl_raise(eSPKIError, "NETSCAPE_SPKI_verify");
     }
-    return Qnil; /* dummy */
 }
 
 /* Document-class: OpenSSL::Netscape::SPKI
diff --git a/ext/openssl/ossl_pkey.c b/ext/openssl/ossl_pkey.c
index 23e2115409..2b96ece575 100644
--- a/ext/openssl/ossl_pkey.c
+++ b/ext/openssl/ossl_pkey.c
@@ -163,8 +163,8 @@ ossl_pkey_new_from_data(int argc, VALUE *argv, VALUE self)
     return ossl_pkey_new(pkey);
 }
 
-static void
-pkey_check_public_key(EVP_PKEY *pkey)
+void
+ossl_pkey_check_public_key(const EVP_PKEY *pkey)
 {
     void *ptr;
     const BIGNUM *n, *e, *pubkey;
@@ -172,7 +172,8 @@ pkey_check_public_key(EVP_PKEY *pkey)
     if (EVP_PKEY_missing_parameters(pkey))
 	ossl_raise(ePKeyError, "parameters missing");
 
-    ptr = EVP_PKEY_get0(pkey);
+    /* OpenSSL < 1.1.0 takes non-const pointer */
+    ptr = EVP_PKEY_get0((EVP_PKEY *)pkey);
     switch (EVP_PKEY_base_id(pkey)) {
       case EVP_PKEY_RSA:
 	RSA_get0_key(ptr, &n, &e, NULL);
@@ -352,7 +353,7 @@ ossl_pkey_verify(VALUE self, VALUE digest, VALUE sig, VALUE data)
     int siglen, result;
 
     GetPKey(self, pkey);
-    pkey_check_public_key(pkey);
+    ossl_pkey_check_public_key(pkey);
     md = ossl_evp_get_digestbyname(digest);
     StringValue(sig);
     siglen = RSTRING_LENINT(sig);
diff --git a/ext/openssl/ossl_pkey.h b/ext/openssl/ossl_pkey.h
index a87472ad09..2b17bf5368 100644
--- a/ext/openssl/ossl_pkey.h
+++ b/ext/openssl/ossl_pkey.h
@@ -44,6 +44,7 @@ int ossl_generate_cb_2(int p, int n, BN_GENCB *cb);
 void ossl_generate_cb_stop(void *ptr);
 
 VALUE ossl_pkey_new(EVP_PKEY *);
+void ossl_pkey_check_public_key(const EVP_PKEY *);
 EVP_PKEY *GetPKeyPtr(VALUE);
 EVP_PKEY *DupPKeyPtr(VALUE);
 EVP_PKEY *GetPrivPKeyPtr(VALUE);
diff --git a/ext/openssl/ossl_pkey_rsa.c b/ext/openssl/ossl_pkey_rsa.c
index 26397bd021..4800fb2710 100644
--- a/ext/openssl/ossl_pkey_rsa.c
+++ b/ext/openssl/ossl_pkey_rsa.c
@@ -538,6 +538,196 @@ ossl_rsa_private_decrypt(int argc, VALUE *argv, VALUE self)
 
 /*
  * call-seq:
+ *    rsa.sign_pss(digest, data, salt_length:, mgf1_hash:) -> String
+ *
+ * Signs _data_ using the Probabilistic Signature Scheme (RSA-PSS) and returns
+ * the calculated signature.
+ *
+ * RSAError will be raised if an error occurs.
+ *
+ * See #verify_pss for the verification operation.
+ *
+ * === Parameters
+ * _digest_::
+ *   A String containing the message digest algorithm name.
+ * _data_::
+ *   A String. The data to be signed.
+ * _salt_length_::
+ *   The length in octets of the salt. Two special values are reserved:
+ *   +:digest+ means the digest length, and +:max+ means the maximum possible
+ *   length for the combination of the private key and the selected message
+ *   digest algorithm.
+ * _mgf1_hash_::
+ *   The hash algorithm used in MGF1 (the currently supported mask generation
+ *   function (MGF)).
+ *
+ * === Example
+ *   data = "Sign me!"
+ *   pkey = OpenSSL::PKey::RSA.new(2048)
+ *   signature = pkey.sign_pss("SHA256", data, salt_length: :max, mgf1_hash: "SHA256")
+ *   pub_key = pkey.public_key
+ *   puts pub_key.verify_pss("SHA256", signature, data,
+ *                           salt_length: :auto, mgf1_hash: "SHA256") # => true
+ */
+static VALUE
+ossl_rsa_sign_pss(int argc, VALUE *argv, VALUE self)
+{
+    VALUE digest, data, options, kwargs[2], signature;
+    static ID kwargs_ids[2];
+    EVP_PKEY *pkey;
+    EVP_PKEY_CTX *pkey_ctx;
+    const EVP_MD *md, *mgf1md;
+    EVP_MD_CTX *md_ctx;
+    size_t buf_len;
+    int salt_len;
+
+    if (!kwargs_ids[0]) {
+	kwargs_ids[0] = rb_intern_const("salt_length");
+	kwargs_ids[1] = rb_intern_const("mgf1_hash");
+    }
+    rb_scan_args(argc, argv, "2:", &digest, &data, &options);
+    rb_get_kwargs(options, kwargs_ids, 2, 0, kwargs);
+    if (kwargs[0] == ID2SYM(rb_intern("max")))
+	salt_len = -2; /* RSA_PSS_SALTLEN_MAX_SIGN */
+    else if (kwargs[0] == ID2SYM(rb_intern("digest")))
+	salt_len = -1; /* RSA_PSS_SALTLEN_DIGEST */
+    else
+	salt_len = NUM2INT(kwargs[0]);
+    mgf1md = ossl_evp_get_digestbyname(kwargs[1]);
+
+    pkey = GetPrivPKeyPtr(self);
+    buf_len = EVP_PKEY_size(pkey);
+    md = ossl_evp_get_digestbyname(digest);
+    StringValue(data);
+    signature = rb_str_new(NULL, (long)buf_len);
+
+    md_ctx = EVP_MD_CTX_new();
+    if (!md_ctx)
+	goto err;
+
+    if (EVP_DigestSignInit(md_ctx, &pkey_ctx, md, NULL, pkey) != 1)
+	goto err;
+
+    if (EVP_PKEY_CTX_set_rsa_padding(pkey_ctx, RSA_PKCS1_PSS_PADDING) != 1)
+	goto err;
+
+    if (EVP_PKEY_CTX_set_rsa_pss_saltlen(pkey_ctx, salt_len) != 1)
+	goto err;
+
+    if (EVP_PKEY_CTX_set_rsa_mgf1_md(pkey_ctx, mgf1md) != 1)
+	goto err;
+
+    if (EVP_DigestSignUpdate(md_ctx, RSTRING_PTR(data), RSTRING_LEN(data)) != 1)
+	goto err;
+
+    if (EVP_DigestSignFinal(md_ctx, (unsigned char *)RSTRING_PTR(signature), &buf_len) != 1)
+	goto err;
+
+    rb_str_set_len(signature, (long)buf_len);
+
+    EVP_MD_CTX_free(md_ctx);
+    return signature;
+
+  err:
+    EVP_MD_CTX_free(md_ctx);
+    ossl_raise(eRSAError, NULL);
+}
+
+/*
+ * call-seq:
+ *    rsa.verify_pss(digest, signature, data, salt_length:, mgf1_hash:) -> true | false
+ *
+ * Verifies _data_ using the Probabilistic Signature Scheme (RSA-PSS).
+ *
+ * The return value is +true+ if the signature is valid, +false+ otherwise.
+ * RSAError will be raised if an error occurs.
+ *
+ * See #sign_pss for the signing operation and an example code.
+ *
+ * === Parameters
+ * _digest_::
+ *   A String containing the message digest algorithm name.
+ * _data_::
+ *   A String. The data to be signed.
+ * _salt_length_::
+ *   The length in octets of the salt. Two special values are reserved:
+ *   +:digest+ means the digest length, and +:auto+ means automatically
+ *   determining the length based on the signature.
+ * _mgf1_hash_::
+ *   The hash algorithm used in MGF1.
+ */
+static VALUE
+ossl_rsa_verify_pss(int argc, VALUE *argv, VALUE self)
+{
+    VALUE digest, signature, data, options, kwargs[2];
+    static ID kwargs_ids[2];
+    EVP_PKEY *pkey;
+    EVP_PKEY_CTX *pkey_ctx;
+    const EVP_MD *md, *mgf1md;
+    EVP_MD_CTX *md_ctx;
+    int result, salt_len;
+
+    if (!kwargs_ids[0]) {
+	kwargs_ids[0] = rb_intern_const("salt_length");
+	kwargs_ids[1] = rb_intern_const("mgf1_hash");
+    }
+    rb_scan_args(argc, argv, "3:", &digest, &signature, &data, &options);
+    rb_get_kwargs(options, kwargs_ids, 2, 0, kwargs);
+    if (kwargs[0] == ID2SYM(rb_intern("auto")))
+	salt_len = -2; /* RSA_PSS_SALTLEN_AUTO */
+    else if (kwargs[0] == ID2SYM(rb_intern("digest")))
+	salt_len = -1; /* RSA_PSS_SALTLEN_DIGEST */
+    else
+	salt_len = NUM2INT(kwargs[0]);
+    mgf1md = ossl_evp_get_digestbyname(kwargs[1]);
+
+    GetPKey(self, pkey);
+    md = ossl_evp_get_digestbyname(digest);
+    StringValue(signature);
+    StringValue(data);
+
+    md_ctx = EVP_MD_CTX_new();
+    if (!md_ctx)
+	goto err;
+
+    if (EVP_DigestVerifyInit(md_ctx, &pkey_ctx, md, NULL, pkey) != 1)
+	goto err;
+
+    if (EVP_PKEY_CTX_set_rsa_padding(pkey_ctx, RSA_PKCS1_PSS_PADDING) != 1)
+	goto err;
+
+    if (EVP_PKEY_CTX_set_rsa_pss_saltlen(pkey_ctx, salt_len) != 1)
+	goto err;
+
+    if (EVP_PKEY_CTX_set_rsa_mgf1_md(pkey_ctx, mgf1md) != 1)
+	goto err;
+
+    if (EVP_DigestVerifyUpdate(md_ctx, RSTRING_PTR(data), RSTRING_LEN(data)) != 1)
+	goto err;
+
+    result = EVP_DigestVerifyFinal(md_ctx,
+				   (unsigned char *)RSTRING_PTR(signature),
+				   RSTRING_LEN(signature));
+
+    switch (result) {
+      case 0:
+	ossl_clear_error();
+	EVP_MD_CTX_free(md_ctx);
+	return Qfalse;
+      case 1:
+	EVP_MD_CTX_free(md_ctx);
+	return Qtrue;
+      default:
+	goto err;
+    }
+
+  err:
+    EVP_MD_CTX_free(md_ctx);
+    ossl_raise(eRSAError, NULL);
+}
+
+/*
+ * call-seq:
  *   rsa.params => hash
  *
  * THIS METHOD IS INSECURE, PRIVATE INFORMATION CAN LEAK OUT!!!
@@ -731,6 +921,8 @@ Init_ossl_rsa(void)
     rb_define_method(cRSA, "public_decrypt", ossl_rsa_public_decrypt, -1);
     rb_define_method(cRSA, "private_encrypt", ossl_rsa_private_encrypt, -1);
     rb_define_method(cRSA, "private_decrypt", ossl_rsa_private_decrypt, -1);
+    rb_define_method(cRSA, "sign_pss", ossl_rsa_sign_pss, -1);
+    rb_define_method(cRSA, "verify_pss", ossl_rsa_verify_pss, -1);
 
     DEF_OSSL_PKEY_BN(cRSA, rsa, n);
     DEF_OSSL_PKEY_BN(cRSA, rsa, e);
diff --git a/ext/openssl/ossl_ssl.c b/ext/openssl/ossl_ssl.c
index 32ae2df557..8cdb9737b5 100644
--- a/ext/openssl/ossl_ssl.c
+++ b/ext/openssl/ossl_ssl.c
@@ -32,7 +32,7 @@ VALUE cSSLSocket;
 static VALUE eSSLErrorWaitReadable;
 static VALUE eSSLErrorWaitWritable;
 
-static ID ID_callback_state, id_tmp_dh_callback, id_tmp_ecdh_callback,
+static ID id_call, ID_callback_state, id_tmp_dh_callback, id_tmp_ecdh_callback,
 	  id_npn_protocols_encoded;
 static VALUE sym_exception, sym_wait_readable, sym_wait_writable;
 
@@ -205,7 +205,7 @@ ossl_call_client_cert_cb(VALUE obj)
     if (NIL_P(cb))
 	return Qnil;
 
-    ary = rb_funcall(cb, rb_intern("call"), 1, obj);
+    ary = rb_funcallv(cb, id_call, 1, &obj);
     Check_Type(ary, T_ARRAY);
     GetX509CertPtr(cert = rb_ary_entry(ary, 0));
     GetPrivPKeyPtr(key = rb_ary_entry(ary, 1));
@@ -248,8 +248,8 @@ ossl_call_tmp_dh_callback(struct tmp_dh_callback_args *args)
     cb = rb_funcall(args->ssl_obj, args->id, 0);
     if (NIL_P(cb))
 	return NULL;
-    dh = rb_funcall(cb, rb_intern("call"), 3,
-		    args->ssl_obj, INT2NUM(args->is_export), INT2NUM(args->keylength));
+    dh = rb_funcall(cb, id_call, 3, args->ssl_obj, INT2NUM(args->is_export),
+		    INT2NUM(args->keylength));
     pkey = GetPKeyPtr(dh);
     if (EVP_PKEY_base_id(pkey) != args->type)
 	return NULL;
@@ -374,12 +374,12 @@ ossl_call_session_get_cb(VALUE ary)
     cb = rb_funcall(ssl_obj, rb_intern("session_get_cb"), 0);
     if (NIL_P(cb)) return Qnil;
 
-    return rb_funcall(cb, rb_intern("call"), 1, ary);
+    return rb_funcallv(cb, id_call, 1, &ary);
 }
 
 /* this method is currently only called for servers (in OpenSSL <= 0.9.8e) */
 static SSL_SESSION *
-#if OPENSSL_VERSION_NUMBER >= 0x10100000L && !defined(LIBRESSL_VERSION_NUMBER)
+#if OPENSSL_VERSION_NUMBER >= 0x10100000 && !defined(LIBRESSL_VERSION_NUMBER)
 ossl_sslctx_session_get_cb(SSL *ssl, const unsigned char *buf, int len, int *copy)
 #else
 ossl_sslctx_session_get_cb(SSL *ssl, unsigned char *buf, int len, int *copy)
@@ -420,7 +420,7 @@ ossl_call_session_new_cb(VALUE ary)
     cb = rb_funcall(ssl_obj, rb_intern("session_new_cb"), 0);
     if (NIL_P(cb)) return Qnil;
 
-    return rb_funcall(cb, rb_intern("call"), 1, ary);
+    return rb_funcallv(cb, id_call, 1, &ary);
 }
 
 /* return 1 normal.  return 0 removes the session */
@@ -467,7 +467,7 @@ ossl_call_session_remove_cb(VALUE ary)
     cb = rb_attr_get(sslctx_obj, id_i_session_remove_cb);
     if (NIL_P(cb)) return Qnil;
 
-    return rb_funcall(cb, rb_intern("call"), 1, ary);
+    return rb_funcallv(cb, id_call, 1, &ary);
 }
 
 static void
@@ -533,7 +533,7 @@ ossl_call_servername_cb(VALUE ary)
     cb = rb_attr_get(sslctx_obj, id_i_servername_cb);
     if (NIL_P(cb)) return Qnil;
 
-    ret_obj = rb_funcall(cb, rb_intern("call"), 1, ary);
+    ret_obj = rb_funcallv(cb, id_call, 1, &ary);
     if (rb_obj_is_kind_of(ret_obj, cSSLContext)) {
         SSL *ssl;
         SSL_CTX *ctx2;
@@ -585,7 +585,7 @@ ssl_renegotiation_cb(const SSL *ssl)
     cb = rb_attr_get(sslctx_obj, id_i_renegotiation_cb);
     if (NIL_P(cb)) return;
 
-    (void) rb_funcall(cb, rb_intern("call"), 1, ssl_obj);
+    rb_funcallv(cb, id_call, 1, &ssl_obj);
 }
 
 #if !defined(OPENSSL_NO_NEXTPROTONEG) || \
@@ -635,7 +635,7 @@ npn_select_cb_common_i(VALUE tmp)
 	in += l;
     }
 
-    selected = rb_funcall(args->cb, rb_intern("call"), 1, protocols);
+    selected = rb_funcallv(args->cb, id_call, 1, &protocols);
     StringValue(selected);
     len = RSTRING_LEN(selected);
     if (len < 1 || len >= 256) {
@@ -1193,6 +1193,134 @@ ossl_sslctx_set_security_level(VALUE self, VALUE value)
     return value;
 }
 
+#ifdef SSL_MODE_SEND_FALLBACK_SCSV
+/*
+ * call-seq:
+ *    ctx.enable_fallback_scsv() => nil
+ *
+ * Activate TLS_FALLBACK_SCSV for this context.
+ * See RFC 7507.
+ */
+static VALUE
+ossl_sslctx_enable_fallback_scsv(VALUE self)
+{
+    SSL_CTX *ctx;
+
+    GetSSLCTX(self, ctx);
+    SSL_CTX_set_mode(ctx, SSL_MODE_SEND_FALLBACK_SCSV);
+
+    return Qnil;
+}
+#endif
+
+/*
+ * call-seq:
+ *    ctx.add_certificate(certiticate, pkey [, extra_certs]) -> self
+ *
+ * Adds a certificate to the context. _pkey_ must be a corresponding private
+ * key with _certificate_.
+ *
+ * Multiple certificates with different public key type can be added by
+ * repeated calls of this method, and OpenSSL will choose the most appropriate
+ * certificate during the handshake.
+ *
+ * #cert=, #key=, and #extra_chain_cert= are old accessor methods for setting
+ * certificate and internally call this method.
+ *
+ * === Parameters
+ * _certificate_::
+ *   A certificate. An instance of OpenSSL::X509::Certificate.
+ * _pkey_::
+ *   The private key for _certificate_. An instance of OpenSSL::PKey::PKey.
+ * _extra_certs_::
+ *   Optional. An array of OpenSSL::X509::Certificate. When sending a
+ *   certificate chain, the certificates specified by this are sent following
+ *   _certificate_, in the order in the array.
+ *
+ * === Example
+ *   rsa_cert = OpenSSL::X509::Certificate.new(...)
+ *   rsa_pkey = OpenSSL::PKey.read(...)
+ *   ca_intermediate_cert = OpenSSL::X509::Certificate.new(...)
+ *   ctx.add_certificate(rsa_cert, rsa_pkey, [ca_intermediate_cert])
+ *
+ *   ecdsa_cert = ...
+ *   ecdsa_pkey = ...
+ *   another_ca_cert = ...
+ *   ctx.add_certificate(ecdsa_cert, ecdsa_pkey, [another_ca_cert])
+ *
+ * === Note
+ * OpenSSL before the version 1.0.2 could handle only one extra chain across
+ * all key types. Calling this method discards the chain set previously.
+ */
+static VALUE
+ossl_sslctx_add_certificate(int argc, VALUE *argv, VALUE self)
+{
+    VALUE cert, key, extra_chain_ary;
+    SSL_CTX *ctx;
+    X509 *x509;
+    STACK_OF(X509) *extra_chain = NULL;
+    EVP_PKEY *pkey, *pub_pkey;
+
+    GetSSLCTX(self, ctx);
+    rb_scan_args(argc, argv, "21", &cert, &key, &extra_chain_ary);
+    rb_check_frozen(self);
+    x509 = GetX509CertPtr(cert);
+    pkey = GetPrivPKeyPtr(key);
+
+    /*
+     * The reference counter is bumped, and decremented immediately.
+     * X509_get0_pubkey() is only available in OpenSSL >= 1.1.0.
+     */
+    pub_pkey = X509_get_pubkey(x509);
+    EVP_PKEY_free(pub_pkey);
+    if (!pub_pkey)
+	rb_raise(rb_eArgError, "certificate does not contain public key");
+    if (EVP_PKEY_cmp(pub_pkey, pkey) != 1)
+	rb_raise(rb_eArgError, "public key mismatch");
+
+    if (argc >= 3)
+	extra_chain = ossl_x509_ary2sk(extra_chain_ary);
+
+    if (!SSL_CTX_use_certificate(ctx, x509)) {
+	sk_X509_pop_free(extra_chain, X509_free);
+	ossl_raise(eSSLError, "SSL_CTX_use_certificate");
+    }
+    if (!SSL_CTX_use_PrivateKey(ctx, pkey)) {
+	sk_X509_pop_free(extra_chain, X509_free);
+	ossl_raise(eSSLError, "SSL_CTX_use_PrivateKey");
+    }
+
+    if (extra_chain) {
+#if OPENSSL_VERSION_NUMBER >= 0x10002000 && !defined(LIBRESSL_VERSION_NUMBER)
+	if (!SSL_CTX_set0_chain(ctx, extra_chain)) {
+	    sk_X509_pop_free(extra_chain, X509_free);
+	    ossl_raise(eSSLError, "SSL_CTX_set0_chain");
+	}
+#else
+	STACK_OF(X509) *orig_extra_chain;
+	X509 *x509_tmp;
+
+	/* First, clear the existing chain */
+	SSL_CTX_get_extra_chain_certs(ctx, &orig_extra_chain);
+	if (orig_extra_chain && sk_X509_num(orig_extra_chain)) {
+	    rb_warning("SSL_CTX_set0_chain() is not available; " \
+		       "clearing previously set certificate chain");
+	    SSL_CTX_clear_extra_chain_certs(ctx);
+	}
+	while ((x509_tmp = sk_X509_shift(extra_chain))) {
+	    /* Transfers ownership */
+	    if (!SSL_CTX_add_extra_chain_cert(ctx, x509_tmp)) {
+		X509_free(x509_tmp);
+		sk_X509_pop_free(extra_chain, X509_free);
+		ossl_raise(eSSLError, "SSL_CTX_add_extra_chain_cert");
+	    }
+	}
+	sk_X509_free(extra_chain);
+#endif
+    }
+    return self;
+}
+
 /*
  *  call-seq:
  *     ctx.session_add(session) -> true | false
@@ -2261,6 +2389,7 @@ Init_ossl_ssl(void)
     rb_mWaitWritable = rb_define_module_under(rb_cIO, "WaitWritable");
 #endif
 
+    id_call = rb_intern("call");
     ID_callback_state = rb_intern("callback_state");
 
     ossl_ssl_ex_vcb_idx = SSL_get_ex_new_index(0, (void *)"ossl_ssl_ex_vcb_idx", 0, 0, 0);
@@ -2324,11 +2453,17 @@ Init_ossl_ssl(void)
 
     /*
      * Context certificate
+     *
+     * The _cert_, _key_, and _extra_chain_cert_ attributes are deprecated.
+     * It is recommended to use #add_certificate instead.
      */
     rb_attr(cSSLContext, rb_intern("cert"), 1, 1, Qfalse);
 
     /*
      * Context private key
+     *
+     * The _cert_, _key_, and _extra_chain_cert_ attributes are deprecated.
+     * It is recommended to use #add_certificate instead.
      */
     rb_attr(cSSLContext, rb_intern("key"), 1, 1, Qfalse);
 
@@ -2402,6 +2537,9 @@ Init_ossl_ssl(void)
     /*
      * An Array of extra X509 certificates to be added to the certificate
      * chain.
+     *
+     * The _cert_, _key_, and _extra_chain_cert_ attributes are deprecated.
+     * It is recommended to use #add_certificate instead.
      */
     rb_attr(cSSLContext, rb_intern("extra_chain_cert"), 1, 1, Qfalse);
 
@@ -2561,6 +2699,10 @@ Init_ossl_ssl(void)
     rb_define_method(cSSLContext, "ecdh_curves=", ossl_sslctx_set_ecdh_curves, 1);
     rb_define_method(cSSLContext, "security_level", ossl_sslctx_get_security_level, 0);
     rb_define_method(cSSLContext, "security_level=", ossl_sslctx_set_security_level, 1);
+#ifdef SSL_MODE_SEND_FALLBACK_SCSV
+    rb_define_method(cSSLContext, "enable_fallback_scsv", ossl_sslctx_enable_fallback_scsv, 0);
+#endif
+    rb_define_method(cSSLContext, "add_certificate", ossl_sslctx_add_certificate, -1);
 
     rb_define_method(cSSLContext, "setup", ossl_sslctx_setup, 0);
     rb_define_alias(cSSLContext, "freeze", "setup");
diff --git a/ext/openssl/ossl_x509cert.c b/ext/openssl/ossl_x509cert.c
index 003a9c1949..40542c4a78 100644
--- a/ext/openssl/ossl_x509cert.c
+++ b/ext/openssl/ossl_x509cert.c
@@ -440,7 +440,7 @@ ossl_x509_set_not_before(VALUE self, VALUE time)
 
     GetX509(self, x509);
     asn1time = ossl_x509_time_adjust(NULL, time);
-    if (!X509_set_notBefore(x509, asn1time)) {
+    if (!X509_set1_notBefore(x509, asn1time)) {
 	ASN1_TIME_free(asn1time);
 	ossl_raise(eX509CertError, "X509_set_notBefore");
     }
@@ -479,7 +479,7 @@ ossl_x509_set_not_after(VALUE self, VALUE time)
 
     GetX509(self, x509);
     asn1time = ossl_x509_time_adjust(NULL, time);
-    if (!X509_set_notAfter(x509, asn1time)) {
+    if (!X509_set1_notAfter(x509, asn1time)) {
 	ASN1_TIME_free(asn1time);
 	ossl_raise(eX509CertError, "X509_set_notAfter");
     }
@@ -508,18 +508,19 @@ ossl_x509_get_public_key(VALUE self)
 
 /*
  * call-seq:
- *    cert.public_key = key => key
+ *    cert.public_key = key
  */
 static VALUE
 ossl_x509_set_public_key(VALUE self, VALUE key)
 {
     X509 *x509;
+    EVP_PKEY *pkey;
 
     GetX509(self, x509);
-    if (!X509_set_pubkey(x509, GetPKeyPtr(key))) { /* DUPs pkey */
-	ossl_raise(eX509CertError, NULL);
-    }
-
+    pkey = GetPKeyPtr(key);
+    ossl_pkey_check_public_key(pkey);
+    if (!X509_set_pubkey(x509, pkey))
+	ossl_raise(eX509CertError, "X509_set_pubkey");
     return key;
 }
 
@@ -557,9 +558,9 @@ ossl_x509_verify(VALUE self, VALUE key)
     X509 *x509;
     EVP_PKEY *pkey;
 
-    pkey = GetPKeyPtr(key); /* NO NEED TO DUP */
     GetX509(self, x509);
-
+    pkey = GetPKeyPtr(key);
+    ossl_pkey_check_public_key(pkey);
     switch (X509_verify(x509, pkey)) {
       case 1:
 	return Qtrue;
@@ -684,6 +685,26 @@ ossl_x509_inspect(VALUE self)
 }
 
 /*
+ * call-seq:
+ *    cert1 == cert2 -> true | false
+ *
+ * Compares the two certificates. Note that this takes into account all fields,
+ * not just the issuer name and the serial number.
+ */
+static VALUE
+ossl_x509_eq(VALUE self, VALUE other)
+{
+    X509 *a, *b;
+
+    GetX509(self, a);
+    if (!rb_obj_is_kind_of(other, cX509Cert))
+	return Qfalse;
+    GetX509(other, b);
+
+    return !X509_cmp(a, b) ? Qtrue : Qfalse;
+}
+
+/*
  * INIT
  */
 void
@@ -821,4 +842,5 @@ Init_ossl_x509cert(void)
     rb_define_method(cX509Cert, "extensions=", ossl_x509_set_extensions, 1);
     rb_define_method(cX509Cert, "add_extension", ossl_x509_add_extension, 1);
     rb_define_method(cX509Cert, "inspect", ossl_x509_inspect, 0);
+    rb_define_method(cX509Cert, "==", ossl_x509_eq, 1);
 }
diff --git a/ext/openssl/ossl_x509crl.c b/ext/openssl/ossl_x509crl.c
index 5ecd7ea0b2..b0badf45c4 100644
--- a/ext/openssl/ossl_x509crl.c
+++ b/ext/openssl/ossl_x509crl.c
@@ -226,7 +226,7 @@ ossl_x509crl_set_last_update(VALUE self, VALUE time)
 
     GetX509CRL(self, crl);
     asn1time = ossl_x509_time_adjust(NULL, time);
-    if (!X509_CRL_set_lastUpdate(crl, asn1time)) {
+    if (!X509_CRL_set1_lastUpdate(crl, asn1time)) {
 	ASN1_TIME_free(asn1time);
 	ossl_raise(eX509CRLError, "X509_CRL_set_lastUpdate");
     }
@@ -257,7 +257,7 @@ ossl_x509crl_set_next_update(VALUE self, VALUE time)
 
     GetX509CRL(self, crl);
     asn1time = ossl_x509_time_adjust(NULL, time);
-    if (!X509_CRL_set_nextUpdate(crl, asn1time)) {
+    if (!X509_CRL_set1_nextUpdate(crl, asn1time)) {
 	ASN1_TIME_free(asn1time);
 	ossl_raise(eX509CRLError, "X509_CRL_set_nextUpdate");
     }
@@ -359,9 +359,12 @@ static VALUE
 ossl_x509crl_verify(VALUE self, VALUE key)
 {
     X509_CRL *crl;
+    EVP_PKEY *pkey;
 
     GetX509CRL(self, crl);
-    switch (X509_CRL_verify(crl, GetPKeyPtr(key))) {
+    pkey = GetPKeyPtr(key);
+    ossl_pkey_check_public_key(pkey);
+    switch (X509_CRL_verify(crl, pkey)) {
       case 1:
 	return Qtrue;
       case 0:
diff --git a/ext/openssl/ossl_x509req.c b/ext/openssl/ossl_x509req.c
index 9f20dba311..2c20042a92 100644
--- a/ext/openssl/ossl_x509req.c
+++ b/ext/openssl/ossl_x509req.c
@@ -293,11 +293,10 @@ ossl_x509req_set_public_key(VALUE self, VALUE key)
     EVP_PKEY *pkey;
 
     GetX509Req(self, req);
-    pkey = GetPKeyPtr(key); /* NO NEED TO DUP */
-    if (!X509_REQ_set_pubkey(req, pkey)) {
-	ossl_raise(eX509ReqError, NULL);
-    }
-
+    pkey = GetPKeyPtr(key);
+    ossl_pkey_check_public_key(pkey);
+    if (!X509_REQ_set_pubkey(req, pkey))
+	ossl_raise(eX509ReqError, "X509_REQ_set_pubkey");
     return key;
 }
 
@@ -328,7 +327,8 @@ ossl_x509req_verify(VALUE self, VALUE key)
     EVP_PKEY *pkey;
 
     GetX509Req(self, req);
-    pkey = GetPKeyPtr(key); /* NO NEED TO DUP */
+    pkey = GetPKeyPtr(key);
+    ossl_pkey_check_public_key(pkey);
     switch (X509_REQ_verify(req, pkey)) {
       case 1:
 	return Qtrue;
diff --git a/ext/openssl/ossl_x509revoked.c b/ext/openssl/ossl_x509revoked.c
index 85489efdb2..5fe6853430 100644
--- a/ext/openssl/ossl_x509revoked.c
+++ b/ext/openssl/ossl_x509revoked.c
@@ -249,6 +249,26 @@ ossl_x509revoked_add_extension(VALUE self, VALUE ext)
     return ext;
 }
 
+static VALUE
+ossl_x509revoked_to_der(VALUE self)
+{
+    X509_REVOKED *rev;
+    VALUE str;
+    int len;
+    unsigned char *p;
+
+    GetX509Rev(self, rev);
+    len = i2d_X509_REVOKED(rev, NULL);
+    if (len <= 0)
+	ossl_raise(eX509RevError, "i2d_X509_REVOKED");
+    str = rb_str_new(NULL, len);
+    p = (unsigned char *)RSTRING_PTR(str);
+    if (i2d_X509_REVOKED(rev, &p) <= 0)
+	ossl_raise(eX509RevError, "i2d_X509_REVOKED");
+    ossl_str_adjust(str, p);
+    return str;
+}
+
 /*
  * INIT
  */
@@ -276,4 +296,5 @@ Init_ossl_x509revoked(void)
     rb_define_method(cX509Rev, "extensions", ossl_x509revoked_get_extensions, 0);
     rb_define_method(cX509Rev, "extensions=", ossl_x509revoked_set_extensions, 1);
     rb_define_method(cX509Rev, "add_extension", ossl_x509revoked_add_extension, 1);
+    rb_define_method(cX509Rev, "to_der", ossl_x509revoked_to_der, 0);
 }
diff --git a/test/openssl/test_cipher.rb b/test/openssl/test_cipher.rb
index d87dedf73c..56061741bc 100644
--- a/test/openssl/test_cipher.rb
+++ b/test/openssl/test_cipher.rb
@@ -295,6 +295,13 @@ class OpenSSL::TestCipher < OpenSSL::TestCase
     assert_equal tag1, tag2
   end
 
+  def test_non_aead_cipher_set_auth_data
+    assert_raise(OpenSSL::Cipher::CipherError) {
+      cipher = OpenSSL::Cipher.new("aes-128-cfb").encrypt
+      cipher.auth_data = "123"
+    }
+  end
+
   private
 
   def new_encryptor(algo, **kwargs)
diff --git a/test/openssl/test_kdf.rb b/test/openssl/test_kdf.rb
index d91fa3cf5d..5e1db80c5f 100644
--- a/test/openssl/test_kdf.rb
+++ b/test/openssl/test_kdf.rb
@@ -131,6 +131,48 @@ class OpenSSL::TestKDF < OpenSSL::TestCase
     assert_equal(expected, OpenSSL::KDF.scrypt(pass, salt: salt, N: n, r: r, p: p, length: dklen))
   end
 
+  def test_hkdf_rfc5869_test_case_1
+    pend "HKDF is not implemented" unless OpenSSL::KDF.respond_to?(:hkdf) # OpenSSL >= 1.1.0
+    hash = "sha256"
+    ikm = B("0b0b0b0b0b0b0b0b0b0b0b0b0b0b0b0b0b0b0b0b0b0b")
+    salt = B("000102030405060708090a0b0c")
+    info = B("f0f1f2f3f4f5f6f7f8f9")
+    l = 42
+
+    okm = B("3cb25f25faacd57a90434f64d0362f2a" \
+            "2d2d0a90cf1a5a4c5db02d56ecc4c5bf" \
+            "34007208d5b887185865")
+    assert_equal(okm, OpenSSL::KDF.hkdf(ikm, salt: salt, info: info, length: l, hash: hash))
+  end
+
+  def test_hkdf_rfc5869_test_case_3
+    pend "HKDF is not implemented" unless OpenSSL::KDF.respond_to?(:hkdf) # OpenSSL >= 1.1.0
+    hash = "sha256"
+    ikm = B("0b0b0b0b0b0b0b0b0b0b0b0b0b0b0b0b0b0b0b0b0b0b")
+    salt = B("")
+    info = B("")
+    l = 42
+
+    okm = B("8da4e775a563c18f715f802a063c5a31" \
+            "b8a11f5c5ee1879ec3454e5f3c738d2d" \
+            "9d201395faa4b61a96c8")
+    assert_equal(okm, OpenSSL::KDF.hkdf(ikm, salt: salt, info: info, length: l, hash: hash))
+  end
+
+  def test_hkdf_rfc5869_test_case_4
+    pend "HKDF is not implemented" unless OpenSSL::KDF.respond_to?(:hkdf) # OpenSSL >= 1.1.0
+    hash = "sha1"
+    ikm = B("0b0b0b0b0b0b0b0b0b0b0b")
+    salt = B("000102030405060708090a0b0c")
+    info = B("f0f1f2f3f4f5f6f7f8f9")
+    l = 42
+
+    okm = B("085a01ea1b10f36933068b56efa5ad81" \
+            "a4f14b822f5b091568a9cdd4f155fda2" \
+            "c22e422478d305f3f896")
+    assert_equal(okm, OpenSSL::KDF.hkdf(ikm, salt: salt, info: info, length: l, hash: hash))
+  end
+
   private
 
   def B(ary)
diff --git a/test/openssl/test_ocsp.rb b/test/openssl/test_ocsp.rb
index 9d48496de5..50ad6c31f5 100644
--- a/test/openssl/test_ocsp.rb
+++ b/test/openssl/test_ocsp.rb
@@ -122,12 +122,12 @@ class OpenSSL::TestOCSP < OpenSSL::TestCase
 
     assert_equal true, req.verify([@cert], store, OpenSSL::OCSP::NOINTERN)
     ret = req.verify([@cert], store)
-    if ret || openssl?(1, 0, 2) || libressl?(2, 4, 2)
+    if ret || openssl?(1, 0, 2)
       assert_equal true, ret
     else
       # RT2560; OCSP_request_verify() does not find signer cert from 'certs' when
       # OCSP_NOINTERN is not specified.
-      # fixed by OpenSSL 1.0.1j, 1.0.2 and LibreSSL 2.4.2
+      # fixed by OpenSSL 1.0.1j, 1.0.2
       pend "RT2560: ocsp_req_find_signer"
     end
 
@@ -262,11 +262,6 @@ class OpenSSL::TestOCSP < OpenSSL::TestCase
     bres.add_status(cid2, OpenSSL::OCSP::V_CERTSTATUS_REVOKED, OpenSSL::OCSP::REVOKED_STATUS_UNSPECIFIED, -400, -300, nil, [])
     bres.add_status(cid2, OpenSSL::OCSP::V_CERTSTATUS_GOOD, nil, nil, Time.now + 100, nil, nil)
 
-    if bres.responses[2].check_validity # thisUpdate is in future; must fail
-      # LibreSSL bug; skip for now
-      pend "OCSP_check_validity() is broken"
-    end
-
     single1 = bres.responses[0]
     assert_equal false, single1.check_validity
     assert_equal false, single1.check_validity(30)
@@ -275,6 +270,8 @@ class OpenSSL::TestOCSP < OpenSSL::TestCase
     assert_equal true, single2.check_validity
     assert_equal true, single2.check_validity(0, 500)
     assert_equal false, single2.check_validity(0, 200)
+    single3 = bres.responses[2]
+    assert_equal false, single3.check_validity
   end
 
   def test_response
diff --git a/test/openssl/test_pair.rb b/test/openssl/test_pair.rb
index 55b62321b8..29d5c9bbb1 100644
--- a/test/openssl/test_pair.rb
+++ b/test/openssl/test_pair.rb
@@ -362,6 +362,15 @@ module OpenSSL::TestPairM
     }
   end
 
+  def test_write_multiple_arguments
+    ssl_pair {|s1, s2|
+      str1 = "foo"; str2 = "bar"
+      assert_equal 6, s1.write(str1, str2)
+      s1.close
+      assert_equal "foobar", s2.read
+    }
+  end
+
   def test_partial_tls_record_read_nonblock
     ssl_pair { |s1, s2|
       # the beginning of a TLS record
diff --git a/test/openssl/test_pkey_rsa.rb b/test/openssl/test_pkey_rsa.rb
index 49ab379251..d9bea1a622 100644
--- a/test/openssl/test_pkey_rsa.rb
+++ b/test/openssl/test_pkey_rsa.rb
@@ -113,6 +113,39 @@ class OpenSSL::TestPKeyRSA < OpenSSL::PKeyTestCase
     }
   end
 
+  def test_sign_verify_pss
+    key = Fixtures.pkey("rsa1024")
+    data = "Sign me!"
+    invalid_data = "Sign me?"
+
+    signature = key.sign_pss("SHA256", data, salt_length: 20, mgf1_hash: "SHA1")
+    assert_equal 128, signature.bytesize
+    assert_equal true,
+      key.verify_pss("SHA256", signature, data, salt_length: 20, mgf1_hash: "SHA1")
+    assert_equal true,
+      key.verify_pss("SHA256", signature, data, salt_length: :auto, mgf1_hash: "SHA1")
+    assert_equal false,
+      key.verify_pss("SHA256", signature, invalid_data, salt_length: 20, mgf1_hash: "SHA1")
+
+    signature = key.sign_pss("SHA256", data, salt_length: :digest, mgf1_hash: "SHA1")
+    assert_equal true,
+      key.verify_pss("SHA256", signature, data, salt_length: 32, mgf1_hash: "SHA1")
+    assert_equal true,
+      key.verify_pss("SHA256", signature, data, salt_length: :auto, mgf1_hash: "SHA1")
+    assert_equal false,
+      key.verify_pss("SHA256", signature, data, salt_length: 20, mgf1_hash: "SHA1")
+
+    signature = key.sign_pss("SHA256", data, salt_length: :max, mgf1_hash: "SHA1")
+    assert_equal true,
+      key.verify_pss("SHA256", signature, data, salt_length: 94, mgf1_hash: "SHA1")
+    assert_equal true,
+      key.verify_pss("SHA256", signature, data, salt_length: :auto, mgf1_hash: "SHA1")
+
+    assert_raise(OpenSSL::PKey::RSAError) {
+      key.sign_pss("SHA256", data, salt_length: 95, mgf1_hash: "SHA1")
+    }
+  end
+
   def test_RSAPrivateKey
     rsa1024 = Fixtures.pkey("rsa1024")
     asn1 = OpenSSL::ASN1::Sequence([
diff --git a/test/openssl/test_ssl.rb b/test/openssl/test_ssl.rb
index 4f3df9dd1d..b3f3143f4f 100644
--- a/test/openssl/test_ssl.rb
+++ b/test/openssl/test_ssl.rb
@@ -54,6 +54,87 @@ class OpenSSL::TestSSL < OpenSSL::SSLTestCase
     }
   end
 
+  def test_add_certificate
+    ctx_proc = -> ctx {
+      # Unset values set by start_server
+      ctx.cert = ctx.key = ctx.extra_chain_cert = nil
+      ctx.add_certificate(@svr_cert, @svr_key, [@ca_cert]) # RSA
+    }
+    start_server(ctx_proc: ctx_proc) do |port|
+      server_connect(port) { |ssl|
+        assert_equal @svr_cert.subject, ssl.peer_cert.subject
+        assert_equal [@svr_cert.subject, @ca_cert.subject],
+          ssl.peer_cert_chain.map(&:subject)
+      }
+    end
+  end
+
+  def test_add_certificate_multiple_certs
+    pend "EC is not supported" unless defined?(OpenSSL::PKey::EC)
+    pend "TLS 1.2 is not supported" unless tls12_supported?
+
+    # SSL_CTX_set0_chain() is needed for setting multiple certificate chains
+    add0_chain_supported = openssl?(1, 0, 2)
+
+    if add0_chain_supported
+      ca2_key = Fixtures.pkey("rsa1024")
+      ca2_exts = [
+        ["basicConstraints", "CA:TRUE", true],
+        ["keyUsage", "cRLSign, keyCertSign", true],
+      ]
+      ca2_dn = OpenSSL::X509::Name.parse_rfc2253("CN=CA2")
+      ca2_cert = issue_cert(ca2_dn, ca2_key, 123, ca2_exts, nil, nil)
+    else
+      # Use the same CA as @svr_cert
+      ca2_key = @ca_key; ca2_cert = @ca_cert
+    end
+
+    ecdsa_key = Fixtures.pkey("p256")
+    exts = [
+      ["keyUsage", "digitalSignature", false],
+    ]
+    ecdsa_dn = OpenSSL::X509::Name.parse_rfc2253("CN=localhost2")
+    ecdsa_cert = issue_cert(ecdsa_dn, ecdsa_key, 456, exts, ca2_cert, ca2_key)
+
+    if !add0_chain_supported
+      # Testing the warning emitted when 'extra' chain is replaced
+      tctx = OpenSSL::SSL::SSLContext.new
+      tctx.add_certificate(@svr_cert, @svr_key, [@ca_cert])
+      assert_warning(/set0_chain/) {
+        tctx.add_certificate(ecdsa_cert, ecdsa_key, [ca2_cert])
+      }
+    end
+
+    ctx_proc = -> ctx {
+      # Unset values set by start_server
+      ctx.cert = ctx.key = ctx.extra_chain_cert = nil
+      ctx.ecdh_curves = "P-256" unless openssl?(1, 0, 2)
+      ctx.add_certificate(@svr_cert, @svr_key, [@ca_cert]) # RSA
+      EnvUtil.suppress_warning do # !add0_chain_supported
+        ctx.add_certificate(ecdsa_cert, ecdsa_key, [ca2_cert])
+      end
+    }
+    start_server(ctx_proc: ctx_proc) do |port|
+      ctx = OpenSSL::SSL::SSLContext.new
+      ctx.max_version = :TLS1_2 # TODO: We need this to force certificate type
+      ctx.ciphers = "aECDSA"
+      server_connect(port, ctx) { |ssl|
+        assert_equal ecdsa_cert.subject, ssl.peer_cert.subject
+        assert_equal [ecdsa_cert.subject, ca2_cert.subject],
+          ssl.peer_cert_chain.map(&:subject)
+      }
+
+      ctx = OpenSSL::SSL::SSLContext.new
+      ctx.max_version = :TLS1_2
+      ctx.ciphers = "aRSA"
+      server_connect(port, ctx) { |ssl|
+        assert_equal @svr_cert.subject, ssl.peer_cert.subject
+        assert_equal [@svr_cert.subject, @ca_cert.subject],
+          ssl.peer_cert_chain.map(&:subject)
+      }
+    end
+  end
+
   def test_sysread_and_syswrite
     start_server { |port|
       server_connect(port) { |ssl|
@@ -1222,6 +1303,59 @@ end
     end
   end
 
+  def test_fallback_scsv
+    pend "Fallback SCSV is not supported" unless OpenSSL::SSL::SSLContext.method_defined?( :enable_fallback_scsv)
+
+    start_server do |port|
+      ctx = OpenSSL::SSL::SSLContext.new
+      ctx.max_version = OpenSSL::SSL::TLS1_2_VERSION
+      # Here is OK
+      # TLS1.2 supported and this is what we ask the first time
+      server_connect(port, ctx)
+    end
+
+    ctx_proc = proc { |ctx|
+      ctx.max_version = OpenSSL::SSL::TLS1_1_VERSION
+    }
+    start_server(ctx_proc: ctx_proc) do |port|
+      ctx = OpenSSL::SSL::SSLContext.new
+      ctx.enable_fallback_scsv
+      ctx.max_version = OpenSSL::SSL::TLS1_1_VERSION
+      # Here is OK too
+      # TLS1.2 not supported, fallback to TLS1.1 and signaling the fallback
+      # Server doesn't support better, so connection OK
+      server_connect(port, ctx)
+    end
+
+    # Here is not OK
+    # TLS1.2 is supported, fallback to TLS1.1 (downgrade attack) and signaling the fallback
+    # Server support better, so refuse the connection
+    sock1, sock2 = socketpair
+    begin
+      ctx1 = OpenSSL::SSL::SSLContext.new
+      s1 = OpenSSL::SSL::SSLSocket.new(sock1, ctx1)
+
+      ctx2 = OpenSSL::SSL::SSLContext.new
+      ctx2.enable_fallback_scsv
+      ctx2.max_version = OpenSSL::SSL::TLS1_1_VERSION
+      s2 = OpenSSL::SSL::SSLSocket.new(sock2, ctx2)
+      t = Thread.new {
+        assert_raise_with_message(OpenSSL::SSL::SSLError, /inappropriate fallback/) {
+          s2.connect
+        }
+      }
+
+      assert_raise_with_message(OpenSSL::SSL::SSLError, /inappropriate fallback/) {
+        s1.accept
+      }
+
+      assert t.join
+    ensure
+      sock1.close
+      sock2.close
+    end
+  end
+
   def test_dh_callback
     pend "TLS 1.2 is not supported" unless tls12_supported?
 
@@ -1336,11 +1470,24 @@ end
       return
     end
     assert_equal(1, ctx.security_level)
-    # assert_raise(OpenSSL::SSL::SSLError) { ctx.key = Fixtures.pkey("dsa512") }
-    # ctx.key = Fixtures.pkey("rsa1024")
-    # ctx.security_level = 2
-    # assert_raise(OpenSSL::SSL::SSLError) { ctx.key = Fixtures.pkey("rsa1024") }
-    pend "FIXME: SSLContext#key= currently does not raise because SSL_CTX_use_certificate() is delayed"
+
+    dsa512 = Fixtures.pkey("dsa512")
+    dsa512_cert = issue_cert(@svr, dsa512, 50, [], @ca_cert, @ca_key)
+    rsa1024 = Fixtures.pkey("rsa1024")
+    rsa1024_cert = issue_cert(@svr, rsa1024, 51, [], @ca_cert, @ca_key)
+
+    assert_raise(OpenSSL::SSL::SSLError) {
+      # 512 bit DSA key is rejected because it offers < 80 bits of security
+      ctx.add_certificate(dsa512_cert, dsa512)
+    }
+    assert_nothing_raised {
+      ctx.add_certificate(rsa1024_cert, rsa1024)
+    }
+    ctx.security_level = 2
+    assert_raise(OpenSSL::SSL::SSLError) {
+      # < 112 bits of security
+      ctx.add_certificate(rsa1024_cert, rsa1024)
+    }
   end
 
   def test_dup
diff --git a/test/openssl/test_x509attr.rb b/test/openssl/test_x509attr.rb
index 108162f407..c6c48e86ab 100644
--- a/test/openssl/test_x509attr.rb
+++ b/test/openssl/test_x509attr.rb
@@ -62,6 +62,23 @@ class OpenSSL::TestX509Attribute < OpenSSL::TestCase
     attr = OpenSSL::X509::Attribute.new("challengePassword", val)
     assert_equal(attr.to_der, attr.dup.to_der)
   end
+
+  def test_eq
+    val1 = OpenSSL::ASN1::Set([
+      OpenSSL::ASN1::UTF8String("abc123")
+    ])
+    attr1 = OpenSSL::X509::Attribute.new("challengePassword", val1)
+    attr2 = OpenSSL::X509::Attribute.new("challengePassword", val1)
+    ef = OpenSSL::X509::ExtensionFactory.new
+    val2 = OpenSSL::ASN1::Set.new([OpenSSL::ASN1::Sequence.new([
+      ef.create_extension("keyUsage", "keyCertSign", true)
+    ])])
+    attr3 = OpenSSL::X509::Attribute.new("extReq", val2)
+
+    assert_equal false, attr1 == 12345
+    assert_equal true, attr1 == attr2
+    assert_equal false, attr1 == attr3
+  end
 end
 
 end
diff --git a/test/openssl/test_x509cert.rb b/test/openssl/test_x509cert.rb
index 289994d17b..40a5b0ad74 100644
--- a/test/openssl/test_x509cert.rb
+++ b/test/openssl/test_x509cert.rb
@@ -169,6 +169,26 @@ class OpenSSL::TestX509Certificate < OpenSSL::TestCase
     }
   end
 
+  def test_eq
+    now = Time.now
+    cacert = issue_cert(@ca, @rsa1024, 1, [], nil, nil,
+                        not_before: now, not_after: now + 3600)
+    cert1 = issue_cert(@ee1, @rsa2048, 2, [], cacert, @rsa1024,
+                       not_before: now, not_after: now + 3600)
+    cert2 = issue_cert(@ee1, @rsa2048, 2, [], cacert, @rsa1024,
+                       not_before: now, not_after: now + 3600)
+    cert3 = issue_cert(@ee1, @rsa2048, 3, [], cacert, @rsa1024,
+                       not_before: now, not_after: now + 3600)
+    cert4 = issue_cert(@ee1, @rsa2048, 2, [], cacert, @rsa1024,
+                       digest: "sha512", not_before: now, not_after: now + 3600)
+
+    assert_equal false, cert1 == 12345
+    assert_equal true, cert1 == cert2
+    assert_equal false, cert1 == cert3
+    assert_equal false, cert1 == cert4
+    assert_equal false, cert3 == cert4
+  end
+
   private
 
   def certificate_error_returns_false
diff --git a/test/openssl/test_x509crl.rb b/test/openssl/test_x509crl.rb
index 1914a651cf..03fdf64dd4 100644
--- a/test/openssl/test_x509crl.rb
+++ b/test/openssl/test_x509crl.rb
@@ -197,6 +197,58 @@ class OpenSSL::TestX509CRL < OpenSSL::TestCase
     assert_equal(false, crl.verify(@dsa512))
   end
 
+  def test_revoked_to_der
+    # revokedCertificates     SEQUENCE OF SEQUENCE  {
+    #      userCertificate         CertificateSerialNumber,
+    #      revocationDate          Time,
+    #      crlEntryExtensions      Extensions OPTIONAL
+    #                               -- if present, version MUST be v2
+    #                           }  OPTIONAL,
+
+    now = Time.utc(2000, 1, 1)
+    rev1 = OpenSSL::X509::Revoked.new
+    rev1.serial = 123
+    rev1.time = now
+    ext = OpenSSL::X509::Extension.new("CRLReason", OpenSSL::ASN1::Enumerated(1))
+    rev1.extensions = [ext]
+    asn1 = OpenSSL::ASN1::Sequence([
+      OpenSSL::ASN1::Integer(123),
+      OpenSSL::ASN1::UTCTime(now),
+      OpenSSL::ASN1::Sequence([ext.to_der])
+    ])
+
+    assert_equal asn1.to_der, rev1.to_der
+  end
+
+  def test_eq
+    now = Time.now
+
+    cacert = issue_cert(@ca, @rsa1024, 1, [], nil, nil)
+    crl1 = issue_crl([], 1, now, now + 3600, [], cacert, @rsa1024, "sha256")
+    rev1 = OpenSSL::X509::Revoked.new.tap { |rev|
+      rev.serial = 1
+      rev.time = now
+    }
+    crl1.add_revoked(rev1)
+    crl2 = OpenSSL::X509::CRL.new(crl1.to_der)
+
+    # CRL
+    assert_equal false, crl1 == 12345
+    assert_equal true, crl1 == crl2
+    rev2 = OpenSSL::X509::Revoked.new.tap { |rev|
+      rev.serial = 2
+      rev.time = now
+    }
+    crl2.add_revoked(rev2)
+    assert_equal false, crl1 == crl2
+
+    # Revoked
+    assert_equal false, rev1 == 12345
+    assert_equal true, rev1 == crl2.revoked[0]
+    assert_equal false, rev1 == crl2.revoked[1]
+    assert_equal true, rev2 == crl2.revoked[1]
+  end
+
   private
 
   def crl_error_returns_false
diff --git a/test/openssl/test_x509ext.rb b/test/openssl/test_x509ext.rb
index f384a25e8c..91ce202fec 100644
--- a/test/openssl/test_x509ext.rb
+++ b/test/openssl/test_x509ext.rb
@@ -75,6 +75,17 @@ class OpenSSL::TestX509Extension < OpenSSL::TestCase
     assert_equal(@basic_constraints.to_der, ext.to_der)
     assert_equal(ext.to_der, ext.dup.to_der)
   end
+
+  def test_eq
+    ext1 = OpenSSL::X509::Extension.new(@basic_constraints.to_der)
+    ef = OpenSSL::X509::ExtensionFactory.new
+    ext2 = ef.create_extension("basicConstraints", "critical, CA:TRUE, pathlen:2")
+    ext3 = ef.create_extension("basicConstraints", "critical, CA:TRUE")
+
+    assert_equal false, ext1 == 12345
+    assert_equal true, ext1 == ext2
+    assert_equal false, ext1 == ext3
+  end
 end
 
 end
diff --git a/test/openssl/test_x509req.rb b/test/openssl/test_x509req.rb
index a21d45da19..2c447ccdd5 100644
--- a/test/openssl/test_x509req.rb
+++ b/test/openssl/test_x509req.rb
@@ -141,6 +141,16 @@ class OpenSSL::TestX509Request < OpenSSL::TestCase
     assert_equal(req.to_der, req.dup.to_der)
   end
 
+  def test_eq
+    req1 = issue_csr(0, @dn, @rsa1024, "sha1")
+    req2 = issue_csr(0, @dn, @rsa1024, "sha1")
+    req3 = issue_csr(0, @dn, @rsa1024, "sha256")
+
+    assert_equal false, req1 == 12345
+    assert_equal true, req1 == req2
+    assert_equal false, req1 == req3
+  end
+
   private
 
   def request_error_returns_false
diff --git a/test/openssl/utils.rb b/test/openssl/utils.rb
index f59d53b0d1..a359949061 100644
--- a/test/openssl/utils.rb
+++ b/test/openssl/utils.rb
@@ -67,7 +67,7 @@ module OpenSSL::TestUtils
     cert.serial = serial
     cert.subject = dn
     cert.issuer = issuer.subject
-    cert.public_key = key.public_key
+    cert.public_key = key
     now = Time.now
     cert.not_before = not_before || now - 3600
     cert.not_after = not_after || now + 3600