openssl: import v2.1.3

Bring the local copy of ruby/openssl in sync with the upstream gem
release v2.1.3. The commits happened in the upstream repository can be
found at:

	https://github.com/ruby/openssl/compare/v2.1.2...v2.1.3

Note that many of these have already been applied to ruby.git and don't
appear in the file changes of this commit.

19 files changed, 439 insertions, 160 deletions

diff --git a/ext/openssl/History.md b/ext/openssl/History.md
index db5050014e..9e7ee53397 100644
--- a/ext/openssl/History.md
+++ b/ext/openssl/History.md
@@ -1,3 +1,39 @@
+Version 2.1.3
+=============
+
+Bug fixes
+---------
+
+* Fix deprecation warnings on Ruby 3.0.
+* Add ".include" directive support in `OpenSSL::Config`.
+  [[GitHub #216]](https://github.com/ruby/openssl/pull/216)
+* Fix handling of IPv6 address SANs.
+  [[GitHub #185]](https://github.com/ruby/openssl/pull/185)
+* Hostname verification failure with `OpenSSL::SSL::SSLContext#verify_hostname=`
+  sets a proper error code.
+  [[GitHub #350]](https://github.com/ruby/openssl/pull/350)
+* Fix crash with `OpenSSL::BN.new(nil, 2)`.
+  [[Bug #15760]](https://bugs.ruby-lang.org/issues/15760)
+* `OpenSSL::SSL::SSLSocket#sys{read,write}` prevent internal string buffers from
+  being modified by another thread.
+  [[GitHub #453]](https://github.com/ruby/openssl/pull/453)
+* Fix misuse of input record separator in `OpenSSL::Buffering` where it was
+  for output.
+* Fix wrong interger casting in `OpenSSL::PKey::EC#dsa_verify_asn1`.
+  [[GitHub #460]](https://github.com/ruby/openssl/pull/460)
+* `extconf.rb` explicitly checks that OpenSSL's version number is 1.0.1 or
+  newer but also less than 3.0. Ruby/OpenSSL v2.1.x and v2.2.x will not support
+  OpenSSL 3.0 API.
+  [[GitHub #458]](https://github.com/ruby/openssl/pull/458)
+* Activate `digest` gem correctly. `digest` library could go into an
+  inconsistent state if there are multiple versions of `digest` is installed
+  and `openssl` is `require`d before `digest`.
+  [[GitHub #463]](https://github.com/ruby/openssl/pull/463)
+* Fix GC.compact compatibility.
+  [[GitHub #464]](https://github.com/ruby/openssl/issues/464)
+  [[GitHub #465]](https://github.com/ruby/openssl/pull/465)
+
+
 Version 2.1.2
 =============
 
diff --git a/ext/openssl/extconf.rb b/ext/openssl/extconf.rb
index 264130bb51..7e817ae2da 100644
--- a/ext/openssl/extconf.rb
+++ b/ext/openssl/extconf.rb
@@ -37,9 +37,6 @@ if $mswin || $mingw
   have_library("ws2_32")
 end
 
-Logging::message "=== Checking for required stuff... ===\n"
-result = pkg_config("openssl") && have_header("openssl/ssl.h")
-
 def find_openssl_library
   if $mswin || $mingw
     # required for static OpenSSL libraries
@@ -90,19 +87,33 @@ def find_openssl_library
   return false
 end
 
-unless result
-  unless find_openssl_library
-    Logging::message "=== Checking for required stuff failed. ===\n"
-    Logging::message "Makefile wasn't created. Fix the errors above.\n"
-    raise "OpenSSL library could not be found. You might want to use " \
-      "--with-openssl-dir=<dir> option to specify the prefix where OpenSSL " \
-      "is installed."
-  end
+Logging::message "=== Checking for required stuff... ===\n"
+pkg_config_found = pkg_config("openssl") && have_header("openssl/ssl.h")
+
+if !pkg_config_found && !find_openssl_library
+  Logging::message "=== Checking for required stuff failed. ===\n"
+  Logging::message "Makefile wasn't created. Fix the errors above.\n"
+  raise "OpenSSL library could not be found. You might want to use " \
+    "--with-openssl-dir=<dir> option to specify the prefix where OpenSSL " \
+    "is installed."
 end
 
-unless checking_for("OpenSSL version is 1.0.1 or later") {
-    try_static_assert("OPENSSL_VERSION_NUMBER >= 0x10001000L", "openssl/opensslv.h") }
-  raise "OpenSSL >= 1.0.1 or LibreSSL is required"
+version_ok = if have_macro("LIBRESSL_VERSION_NUMBER", "openssl/opensslv.h")
+  is_libressl = true
+  checking_for("LibreSSL version >= 2.5.0") {
+    try_static_assert("LIBRESSL_VERSION_NUMBER >= 0x20500000L", "openssl/opensslv.h") }
+else
+  checking_for("OpenSSL version >= 1.0.1 and < 3.0.0") {
+    try_static_assert("OPENSSL_VERSION_NUMBER >= 0x10001000L", "openssl/opensslv.h") &&
+    !try_static_assert("OPENSSL_VERSION_MAJOR >= 3", "openssl/opensslv.h") }
+end
+unless version_ok
+  raise "OpenSSL >= 1.0.1, < 3.0.0 or LibreSSL >= 2.5.0 is required"
+end
+
+# Prevent wincrypt.h from being included, which defines conflicting macro with openssl/x509.h
+if is_libressl && ($mswin || $mingw)
+  $defs.push("-DNOCRYPT")
 end
 
 Logging::message "=== Checking for OpenSSL features... ===\n"
@@ -114,10 +125,6 @@ engines.each { |name|
   OpenSSL.check_func_or_macro("ENGINE_load_#{name}", "openssl/engine.h")
 }
 
-if ($mswin || $mingw) && have_macro("LIBRESSL_VERSION_NUMBER", "openssl/opensslv.h")
-  $defs.push("-DNOCRYPT")
-end
-
 # added in 1.0.2
 have_func("EC_curve_nist2nid")
 have_func("X509_REVOKED_dup")
diff --git a/ext/openssl/openssl.gemspec b/ext/openssl/openssl.gemspec
index 295379fb6c..c22eece7d6 100644
--- a/ext/openssl/openssl.gemspec
+++ b/ext/openssl/openssl.gemspec
@@ -1,29 +1,27 @@
-# -*- encoding: utf-8 -*-
+Gem::Specification.new do |spec|
+  spec.name          = "openssl"
+  spec.version       = "2.1.3"
+  spec.authors       = ["Martin Bosslet", "SHIBATA Hiroshi", "Zachary Scott", "Kazuki Yamaguchi"]
+  spec.email         = ["ruby-core@ruby-lang.org"]
+  spec.summary       = %q{OpenSSL provides SSL, TLS and general purpose cryptography.}
+  spec.description   = %q{It wraps the OpenSSL library.}
+  spec.homepage      = "https://github.com/ruby/openssl"
+  spec.license       = "Ruby"
 
-Gem::Specification.new do |s|
-  s.name = "openssl"
-  s.version = "2.1.2"
+  spec.files         = Dir["lib/**/*.rb", "ext/**/*.{c,h,rb}", "*.md", "BSDL", "LICENSE.txt"]
+  spec.require_paths = ["lib"]
+  spec.extensions    = ["ext/openssl/extconf.rb"]
 
-  s.required_rubygems_version = Gem::Requirement.new(">= 0") if s.respond_to? :required_rubygems_version=
-  s.metadata = { "msys2_mingw_dependencies" => "openssl" } if s.respond_to? :metadata=
-  s.require_paths = ["lib"]
-  s.authors = ["Martin Bosslet", "SHIBATA Hiroshi", "Zachary Scott", "Kazuki Yamaguchi"]
-  s.date = "2018-10-17"
-  s.description = "It wraps the OpenSSL library."
-  s.email = ["ruby-core@ruby-lang.org"]
-  s.extensions = ["ext/openssl/extconf.rb"]
-  s.extra_rdoc_files = ["README.md", "CONTRIBUTING.md", "History.md"]
-  s.files = ["BSDL", "CONTRIBUTING.md", "History.md", "LICENSE.txt", "README.md", "ext/openssl/deprecation.rb", "ext/openssl/extconf.rb", "ext/openssl/openssl_missing.c", "ext/openssl/openssl_missing.h", "ext/openssl/ossl.c", "ext/openssl/ossl.h", "ext/openssl/ossl_asn1.c", "ext/openssl/ossl_asn1.h", "ext/openssl/ossl_bio.c", "ext/openssl/ossl_bio.h", "ext/openssl/ossl_bn.c", "ext/openssl/ossl_bn.h", "ext/openssl/ossl_cipher.c", "ext/openssl/ossl_cipher.h", "ext/openssl/ossl_config.c", "ext/openssl/ossl_config.h", "ext/openssl/ossl_digest.c", "ext/openssl/ossl_digest.h", "ext/openssl/ossl_engine.c", "ext/openssl/ossl_engine.h", "ext/openssl/ossl_hmac.c", "ext/openssl/ossl_hmac.h", "ext/openssl/ossl_kdf.c", "ext/openssl/ossl_kdf.h", "ext/openssl/ossl_ns_spki.c", "ext/openssl/ossl_ns_spki.h", "ext/openssl/ossl_ocsp.c", "ext/openssl/ossl_ocsp.h", "ext/openssl/ossl_pkcs12.c", "ext/openssl/ossl_pkcs12.h", "ext/openssl/ossl_pkcs7.c", "ext/openssl/ossl_pkcs7.h", "ext/openssl/ossl_pkey.c", "ext/openssl/ossl_pkey.h", "ext/openssl/ossl_pkey_dh.c", "ext/openssl/ossl_pkey_dsa.c", "ext/openssl/ossl_pkey_ec.c", "ext/openssl/ossl_pkey_rsa.c", "ext/openssl/ossl_rand.c", "ext/openssl/ossl_rand.h", "ext/openssl/ossl_ssl.c", "ext/openssl/ossl_ssl.h", "ext/openssl/ossl_ssl_session.c", "ext/openssl/ossl_version.h", "ext/openssl/ossl_x509.c", "ext/openssl/ossl_x509.h", "ext/openssl/ossl_x509attr.c", "ext/openssl/ossl_x509cert.c", "ext/openssl/ossl_x509crl.c", "ext/openssl/ossl_x509ext.c", "ext/openssl/ossl_x509name.c", "ext/openssl/ossl_x509req.c", "ext/openssl/ossl_x509revoked.c", "ext/openssl/ossl_x509store.c", "ext/openssl/ruby_missing.h", "lib/openssl.rb", "lib/openssl/bn.rb", "lib/openssl/buffering.rb", "lib/openssl/cipher.rb", "lib/openssl/config.rb", "lib/openssl/digest.rb", "lib/openssl/pkcs5.rb", "lib/openssl/pkey.rb", "lib/openssl/ssl.rb", "lib/openssl/x509.rb"]
-  s.homepage = "https://github.com/ruby/openssl"
-  s.licenses = ["Ruby"]
-  s.rdoc_options = ["--main", "README.md"]
-  s.required_ruby_version = Gem::Requirement.new(">= 2.3.0")
-  s.rubygems_version = "3.0.0.beta1"
-  s.summary = "OpenSSL provides SSL, TLS and general purpose cryptography."
+  spec.extra_rdoc_files = Dir["*.md"]
+  spec.rdoc_options = ["--main", "README.md"]
 
-  s.add_runtime_dependency("ipaddr", [">= 0"])
-  s.add_development_dependency("rake", [">= 0"])
-  s.add_development_dependency("rake-compiler", [">= 0"])
-  s.add_development_dependency("test-unit", ["~> 3.0"])
-  s.add_development_dependency("rdoc", [">= 0"])
+  spec.required_ruby_version = ">= 2.3.0"
+
+  spec.add_runtime_dependency "ipaddr"
+  spec.add_development_dependency "rake"
+  spec.add_development_dependency "rake-compiler"
+  spec.add_development_dependency "test-unit", "~> 3.0"
+  spec.add_development_dependency "rdoc"
+
+  spec.metadata["msys2_mingw_dependencies"] = "openssl"
 end
diff --git a/ext/openssl/ossl.h b/ext/openssl/ossl.h
index 6af7ddd7d0..39699bd5e6 100644
--- a/ext/openssl/ossl.h
+++ b/ext/openssl/ossl.h
@@ -27,6 +27,7 @@
 #include <openssl/hmac.h>
 #include <openssl/rand.h>
 #include <openssl/conf.h>
+#include <openssl/conf_api.h>
 #include <openssl/crypto.h>
 #if !defined(OPENSSL_NO_ENGINE)
 #  include <openssl/engine.h>
diff --git a/ext/openssl/ossl_bn.c b/ext/openssl/ossl_bn.c
index 6f0064e966..e3846d2df9 100644
--- a/ext/openssl/ossl_bn.c
+++ b/ext/openssl/ossl_bn.c
@@ -400,7 +400,7 @@ ossl_bn_is_negative(VALUE self)
 	if (!(result = BN_new())) {			\
 	    ossl_raise(eBNError, NULL);			\
 	}						\
-	if (!BN_##func(result, bn, ossl_bn_ctx)) {	\
+	if (BN_##func(result, bn, ossl_bn_ctx) <= 0) {	\
 	    BN_free(result);				\
 	    ossl_raise(eBNError, NULL);			\
 	}						\
@@ -426,7 +426,7 @@ BIGNUM_1c(sqr)
 	if (!(result = BN_new())) {			\
 	    ossl_raise(eBNError, NULL);			\
 	}						\
-	if (!BN_##func(result, bn1, bn2)) {		\
+	if (BN_##func(result, bn1, bn2) <= 0) {		\
 	    BN_free(result);				\
 	    ossl_raise(eBNError, NULL);			\
 	}						\
@@ -459,7 +459,7 @@ BIGNUM_2(sub)
 	if (!(result = BN_new())) {				\
 	    ossl_raise(eBNError, NULL);				\
 	}							\
-	if (!BN_##func(result, bn1, bn2, ossl_bn_ctx)) {	\
+	if (BN_##func(result, bn1, bn2, ossl_bn_ctx) <= 0) {	\
 	    BN_free(result);					\
 	    ossl_raise(eBNError, NULL);				\
 	}							\
@@ -503,11 +503,21 @@ BIGNUM_2c(gcd)
 BIGNUM_2c(mod_sqr)
 
 /*
- * Document-method: OpenSSL::BN#mod_inverse
  * call-seq:
- *   bn.mod_inverse(bn2) => aBN
+ *    bn.mod_inverse(bn2) => aBN
  */
-BIGNUM_2c(mod_inverse)
+static VALUE
+ossl_bn_mod_inverse(VALUE self, VALUE other)
+{
+    BIGNUM *bn1, *bn2 = GetBNPtr(other), *result;
+    VALUE obj;
+    GetBN(self, bn1);
+    obj = NewBN(rb_obj_class(self));
+    if (!(result = BN_mod_inverse(NULL, bn1, bn2, ossl_bn_ctx)))
+        ossl_raise(eBNError, "BN_mod_inverse");
+    SetBN(obj, result);
+    return obj;
+}
 
 /*
  * call-seq:
@@ -556,7 +566,7 @@ ossl_bn_div(VALUE self, VALUE other)
 	if (!(result = BN_new())) {				\
 	    ossl_raise(eBNError, NULL);				\
 	}							\
-	if (!BN_##func(result, bn1, bn2, bn3, ossl_bn_ctx)) {	\
+	if (BN_##func(result, bn1, bn2, bn3, ossl_bn_ctx) <= 0) { \
 	    BN_free(result);					\
 	    ossl_raise(eBNError, NULL);				\
 	}							\
@@ -598,7 +608,7 @@ BIGNUM_3c(mod_exp)
     {							\
 	BIGNUM *bn;					\
 	GetBN(self, bn);				\
-	if (!BN_##func(bn, NUM2INT(bit))) {		\
+	if (BN_##func(bn, NUM2INT(bit)) <= 0) {		\
 	    ossl_raise(eBNError, NULL);			\
 	}						\
 	return self;					\
@@ -658,7 +668,7 @@ ossl_bn_is_bit_set(VALUE self, VALUE bit)
 	if (!(result = BN_new())) {			\
 		ossl_raise(eBNError, NULL);		\
 	}						\
-	if (!BN_##func(result, bn, b)) {		\
+	if (BN_##func(result, bn, b) <= 0) {		\
 		BN_free(result);			\
 		ossl_raise(eBNError, NULL);		\
 	}						\
@@ -688,7 +698,7 @@ BIGNUM_SHIFT(rshift)
 	int b;						\
 	b = NUM2INT(bits);				\
 	GetBN(self, bn);				\
-	if (!BN_##func(bn, bn, b))			\
+	if (BN_##func(bn, bn, b) <= 0)			\
 		ossl_raise(eBNError, NULL);		\
 	return self;					\
     }
@@ -727,7 +737,7 @@ BIGNUM_SELF_SHIFT(rshift)
 	if (!(result = BN_new())) {				\
 	    ossl_raise(eBNError, NULL);				\
 	}							\
-	if (!BN_##func(result, b, top, bottom)) {		\
+	if (BN_##func(result, b, top, bottom) <= 0) {		\
 	    BN_free(result);					\
 	    ossl_raise(eBNError, NULL);				\
 	}							\
@@ -756,7 +766,7 @@ BIGNUM_RAND(pseudo_rand)
 	if (!(result = BN_new())) {				\
 	    ossl_raise(eBNError, NULL);				\
 	}							\
-	if (!BN_##func##_range(result, bn)) {			\
+	if (BN_##func##_range(result, bn) <= 0) {		\
 	    BN_free(result);					\
 	    ossl_raise(eBNError, NULL);				\
 	}							\
diff --git a/ext/openssl/ossl_digest.c b/ext/openssl/ossl_digest.c
index 112ce33647..8674a3947c 100644
--- a/ext/openssl/ossl_digest.c
+++ b/ext/openssl/ossl_digest.c
@@ -313,8 +313,6 @@ ossl_digest_block_length(VALUE self)
 void
 Init_ossl_digest(void)
 {
-    rb_require("digest");
-
 #if 0
     mOSSL = rb_define_module("OpenSSL");
     eOSSLError = rb_define_class_under(mOSSL, "OpenSSLError", rb_eStandardError);
@@ -433,6 +431,12 @@ Init_ossl_digest(void)
      *   digest2 = sha256.digest(data2)
      *
      */
+
+    /*
+     * Digest::Class is defined by the digest library. rb_require() cannot be
+     * used here because it bypasses RubyGems.
+     */
+    rb_funcall(Qnil, rb_intern_const("require"), 1, rb_str_new_cstr("digest"));
     cDigest = rb_define_class_under(mOSSL, "Digest", rb_path2class("Digest::Class"));
     /* Document-class: OpenSSL::Digest::DigestError
      *
diff --git a/ext/openssl/ossl_pkcs7.c b/ext/openssl/ossl_pkcs7.c
index 28010c81fb..79ba0bdf48 100644
--- a/ext/openssl/ossl_pkcs7.c
+++ b/ext/openssl/ossl_pkcs7.c
@@ -803,9 +803,9 @@ ossl_pkcs7_decrypt(int argc, VALUE *argv, VALUE self)
     BIO *out;
     VALUE str;
 
-    rb_scan_args(argc, argv, "12", &pkey, &cert, &flags);
+    rb_scan_args(argc, argv, "21", &pkey, &cert, &flags);
     key = GetPrivPKeyPtr(pkey); /* NO NEED TO DUP */
-    x509 = NIL_P(cert) ? NULL : GetX509CertPtr(cert); /* NO NEED TO DUP */
+    x509 = GetX509CertPtr(cert); /* NO NEED TO DUP */
     flg = NIL_P(flags) ? 0 : NUM2INT(flags);
     GetPKCS7(self, p7);
     if(!(out = BIO_new(BIO_s_mem())))
diff --git a/ext/openssl/ossl_pkey_ec.c b/ext/openssl/ossl_pkey_ec.c
index 8bb611248b..b47678dc1d 100644
--- a/ext/openssl/ossl_pkey_ec.c
+++ b/ext/openssl/ossl_pkey_ec.c
@@ -653,15 +653,15 @@ static VALUE ossl_ec_key_dsa_verify_asn1(VALUE self, VALUE data, VALUE sig)
     StringValue(data);
     StringValue(sig);
 
-    switch (ECDSA_verify(0, (unsigned char *) RSTRING_PTR(data), RSTRING_LENINT(data), (unsigned char *) RSTRING_PTR(sig), (int)RSTRING_LEN(sig), ec)) {
-    case 1:	return Qtrue;
-    case 0:	return Qfalse;
-    default:	break;
+    switch (ECDSA_verify(0, (unsigned char *)RSTRING_PTR(data), RSTRING_LENINT(data),
+                         (unsigned char *)RSTRING_PTR(sig), RSTRING_LENINT(sig), ec)) {
+      case 1:
+        return Qtrue;
+      case 0:
+        return Qfalse;
+      default:
+        ossl_raise(eECError, "ECDSA_verify");
     }
-
-    ossl_raise(eECError, "ECDSA_verify");
-
-    UNREACHABLE;
 }
 
 /*
diff --git a/ext/openssl/ossl_ssl.c b/ext/openssl/ossl_ssl.c
index de0556f543..bfd80126c2 100644
--- a/ext/openssl/ossl_ssl.c
+++ b/ext/openssl/ossl_ssl.c
@@ -13,6 +13,12 @@
 
 #define numberof(ary) (int)(sizeof(ary)/sizeof((ary)[0]))
 
+#if !defined(TLS1_3_VERSION) && \
+    defined(LIBRESSL_VERSION_NUMBER) && \
+    LIBRESSL_VERSION_NUMBER >= 0x3020000fL
+#  define TLS1_3_VERSION 0x0304
+#endif
+
 #ifdef _WIN32
 #  define TO_SOCKET(s) _get_osfhandle(s)
 #else
@@ -33,7 +39,7 @@ static VALUE eSSLErrorWaitReadable;
 static VALUE eSSLErrorWaitWritable;
 
 static ID id_call, ID_callback_state, id_tmp_dh_callback, id_tmp_ecdh_callback,
-	  id_npn_protocols_encoded;
+	  id_npn_protocols_encoded, id_each;
 static VALUE sym_exception, sym_wait_readable, sym_wait_writable;
 
 static ID id_i_cert_store, id_i_ca_file, id_i_ca_path, id_i_verify_mode,
@@ -54,6 +60,13 @@ static int ossl_sslctx_ex_store_p;
 #endif
 
 static void
+ossl_sslctx_mark(void *ptr)
+{
+    SSL_CTX *ctx = ptr;
+    rb_gc_mark((VALUE)SSL_CTX_get_ex_data(ctx, ossl_sslctx_ex_ptr_idx));
+}
+
+static void
 ossl_sslctx_free(void *ptr)
 {
     SSL_CTX *ctx = ptr;
@@ -67,7 +80,7 @@ ossl_sslctx_free(void *ptr)
 static const rb_data_type_t ossl_sslctx_type = {
     "OpenSSL/SSL/CTX",
     {
-	0, ossl_sslctx_free,
+        ossl_sslctx_mark, ossl_sslctx_free,
     },
     0, 0, RUBY_TYPED_FREE_IMMEDIATELY,
 };
@@ -359,7 +372,14 @@ ossl_ssl_verify_callback(int preverify_ok, X509_STORE_CTX *ctx)
 	    rb_ivar_set(ssl_obj, ID_callback_state, INT2NUM(status));
 	    return 0;
 	}
-	preverify_ok = ret == Qtrue;
+        if (ret != Qtrue) {
+            preverify_ok = 0;
+#if defined(X509_V_ERR_HOSTNAME_MISMATCH)
+            X509_STORE_CTX_set_error(ctx, X509_V_ERR_HOSTNAME_MISMATCH);
+#else
+            X509_STORE_CTX_set_error(ctx, X509_V_ERR_CERT_REJECTED);
+#endif
+        }
     }
 
     return ossl_verify_cb_call(cb, preverify_ok, ctx);
@@ -609,7 +629,7 @@ static VALUE
 ssl_encode_npn_protocols(VALUE protocols)
 {
     VALUE encoded = rb_str_new(NULL, 0);
-    rb_iterate(rb_each, protocols, ssl_npn_encode_protocol_i, encoded);
+    rb_block_call(protocols, id_each, 0, 0, ssl_npn_encode_protocol_i, encoded);
     return encoded;
 }
 
@@ -679,7 +699,7 @@ static int
 ssl_npn_advertise_cb(SSL *ssl, const unsigned char **out, unsigned int *outlen,
 		     void *arg)
 {
-    VALUE protocols = (VALUE)arg;
+    VALUE protocols = rb_attr_get((VALUE)arg, id_npn_protocols_encoded);
 
     *out = (const unsigned char *) RSTRING_PTR(protocols);
     *outlen = RSTRING_LENINT(protocols);
@@ -897,7 +917,7 @@ ossl_sslctx_setup(VALUE self)
     if (!NIL_P(val)) {
 	VALUE encoded = ssl_encode_npn_protocols(val);
 	rb_ivar_set(self, id_npn_protocols_encoded, encoded);
-	SSL_CTX_set_next_protos_advertised_cb(ctx, ssl_npn_advertise_cb, (void *)encoded);
+	SSL_CTX_set_next_protos_advertised_cb(ctx, ssl_npn_advertise_cb, (void *)self);
 	OSSL_Debug("SSL NPN advertise callback added");
     }
     if (RTEST(rb_attr_get(self, id_i_npn_select_cb))) {
@@ -1516,6 +1536,14 @@ ssl_started(SSL *ssl)
 }
 
 static void
+ossl_ssl_mark(void *ptr)
+{
+    SSL *ssl = ptr;
+    rb_gc_mark((VALUE)SSL_get_ex_data(ssl, ossl_ssl_ex_ptr_idx));
+    rb_gc_mark((VALUE)SSL_get_ex_data(ssl, ossl_ssl_ex_vcb_idx));
+}
+
+static void
 ossl_ssl_free(void *ssl)
 {
     SSL_free(ssl);
@@ -1524,7 +1552,7 @@ ossl_ssl_free(void *ssl)
 const rb_data_type_t ossl_ssl_type = {
     "OpenSSL/SSL",
     {
-	0, ossl_ssl_free,
+        ossl_ssl_mark, ossl_ssl_free,
     },
     0, 0, RUBY_TYPED_FREE_IMMEDIATELY,
 };
@@ -1680,6 +1708,11 @@ ossl_start_ssl(VALUE self, int (*func)(), const char *funcname, VALUE opts)
             rb_io_wait_readable(fptr->fd);
             continue;
 	case SSL_ERROR_SYSCALL:
+#ifdef __APPLE__
+            /* See ossl_ssl_write_internal() */
+            if (errno == EPROTOTYPE)
+                continue;
+#endif
 	    if (errno) rb_sys_fail(funcname);
 	    ossl_raise(eSSLError, "%s SYSCALL returned=%d errno=%d state=%s", funcname, ret2, errno, SSL_state_string_long(ssl));
 #if defined(SSL_R_CERTIFICATE_VERIFY_FAILED)
@@ -1836,26 +1869,36 @@ ossl_ssl_read_internal(int argc, VALUE *argv, VALUE self, int nonblock)
     io = rb_attr_get(self, id_i_io);
     GetOpenFile(io, fptr);
     if (ssl_started(ssl)) {
-	for (;;){
+        rb_str_locktmp(str);
+        for (;;) {
 	    nread = SSL_read(ssl, RSTRING_PTR(str), ilen);
 	    switch(ssl_get_error(ssl, nread)){
 	    case SSL_ERROR_NONE:
+                rb_str_unlocktmp(str);
 		goto end;
 	    case SSL_ERROR_ZERO_RETURN:
+                rb_str_unlocktmp(str);
 		if (no_exception_p(opts)) { return Qnil; }
 		rb_eof_error();
 	    case SSL_ERROR_WANT_WRITE:
-		if (no_exception_p(opts)) { return sym_wait_writable; }
-                write_would_block(nonblock);
+                if (nonblock) {
+                    rb_str_unlocktmp(str);
+                    if (no_exception_p(opts)) { return sym_wait_writable; }
+                    write_would_block(nonblock);
+                }
                 rb_io_wait_writable(fptr->fd);
                 continue;
 	    case SSL_ERROR_WANT_READ:
-		if (no_exception_p(opts)) { return sym_wait_readable; }
-                read_would_block(nonblock);
+                if (nonblock) {
+                    rb_str_unlocktmp(str);
+                    if (no_exception_p(opts)) { return sym_wait_readable; }
+                    read_would_block(nonblock);
+                }
                 rb_io_wait_readable(fptr->fd);
 		continue;
 	    case SSL_ERROR_SYSCALL:
 		if (!ERR_peek_error()) {
+                    rb_str_unlocktmp(str);
 		    if (errno)
 			rb_sys_fail(0);
 		    else {
@@ -1872,23 +1915,30 @@ ossl_ssl_read_internal(int argc, VALUE *argv, VALUE self, int nonblock)
 		}
                 /* fall through */
 	    default:
+                rb_str_unlocktmp(str);
 		ossl_raise(eSSLError, "SSL_read");
 	    }
         }
     }
     else {
-	ID meth = nonblock ? rb_intern("read_nonblock") : rb_intern("sysread");
+        ID meth = nonblock ? rb_intern("read_nonblock") : rb_intern("sysread");
 
-	rb_warning("SSL session is not started yet.");
-	if (nonblock) {
+        rb_warning("SSL session is not started yet.");
+#if defined(RB_PASS_KEYWORDS)
+        if (nonblock) {
             VALUE argv[3];
             argv[0] = len;
             argv[1] = str;
             argv[2] = opts;
             return rb_funcallv_kw(io, meth, 3, argv, RB_PASS_KEYWORDS);
         }
-	else
-	    return rb_funcall(io, meth, 2, len, str);
+#else
+        if (nonblock) {
+            return rb_funcall(io, meth, 3, len, str, opts);
+        }
+#endif
+        else
+            return rb_funcall(io, meth, 2, len, str);
     }
 
   end:
@@ -1936,21 +1986,21 @@ ossl_ssl_write_internal(VALUE self, VALUE str, VALUE opts)
     int nwrite = 0;
     rb_io_t *fptr;
     int nonblock = opts != Qfalse;
-    VALUE io;
+    VALUE tmp, io;
 
-    StringValue(str);
+    tmp = rb_str_new_frozen(StringValue(str));
     GetSSL(self, ssl);
     io = rb_attr_get(self, id_i_io);
     GetOpenFile(io, fptr);
     if (ssl_started(ssl)) {
-	for (;;){
-	    int num = RSTRING_LENINT(str);
+	for (;;) {
+	    int num = RSTRING_LENINT(tmp);
 
 	    /* SSL_write(3ssl) manpage states num == 0 is undefined */
 	    if (num == 0)
 		goto end;
 
-	    nwrite = SSL_write(ssl, RSTRING_PTR(str), num);
+	    nwrite = SSL_write(ssl, RSTRING_PTR(tmp), num);
 	    switch(ssl_get_error(ssl, nwrite)){
 	    case SSL_ERROR_NONE:
 		goto end;
@@ -1965,6 +2015,16 @@ ossl_ssl_write_internal(VALUE self, VALUE str, VALUE opts)
                 rb_io_wait_readable(fptr->fd);
                 continue;
 	    case SSL_ERROR_SYSCALL:
+#ifdef __APPLE__
+                /*
+                 * It appears that send syscall can return EPROTOTYPE if the
+                 * socket is being torn down. Retry to get a proper errno to
+                 * make the error handling in line with the socket library.
+                 * [Bug #14713] https://bugs.ruby-lang.org/issues/14713
+                 */
+                if (errno == EPROTOTYPE)
+                    continue;
+#endif
 		if (errno) rb_sys_fail(0);
 	    default:
 		ossl_raise(eSSLError, "SSL_write");
@@ -1975,15 +2035,21 @@ ossl_ssl_write_internal(VALUE self, VALUE str, VALUE opts)
 	ID meth = nonblock ?
 	    rb_intern("write_nonblock") : rb_intern("syswrite");
 
-	rb_warning("SSL session is not started yet.");
-	if (nonblock) {
+        rb_warning("SSL session is not started yet.");
+#if defined(RB_PASS_KEYWORDS)
+        if (nonblock) {
             VALUE argv[2];
             argv[0] = str;
             argv[1] = opts;
             return rb_funcallv_kw(io, meth, 2, argv, RB_PASS_KEYWORDS);
         }
-	else
-	    return rb_funcall(io, meth, 1, str);
+#else
+        if (nonblock) {
+            return rb_funcall(io, meth, 2, str, opts);
+        }
+#endif
+        else
+            return rb_funcall(io, meth, 1, str);
     }
 
   end:
@@ -2926,6 +2992,7 @@ Init_ossl_ssl(void)
     id_tmp_dh_callback = rb_intern("tmp_dh_callback");
     id_tmp_ecdh_callback = rb_intern("tmp_ecdh_callback");
     id_npn_protocols_encoded = rb_intern("npn_protocols_encoded");
+    id_each = rb_intern_const("each");
 
 #define DefIVarID(name) do \
     id_i_##name = rb_intern("@"#name); while (0)
diff --git a/ext/openssl/ossl_version.h b/ext/openssl/ossl_version.h
index c162f8c2a8..edbd8ce3fa 100644
--- a/ext/openssl/ossl_version.h
+++ b/ext/openssl/ossl_version.h
@@ -10,6 +10,6 @@
 #if !defined(_OSSL_VERSION_H_)
 #define _OSSL_VERSION_H_
 
-#define OSSL_VERSION "2.1.2"
+#define OSSL_VERSION "2.1.3"
 
 #endif /* _OSSL_VERSION_H_ */
diff --git a/ext/openssl/ossl_x509.c b/ext/openssl/ossl_x509.c
index 8a061b0687..4fc0648614 100644
--- a/ext/openssl/ossl_x509.c
+++ b/ext/openssl/ossl_x509.c
@@ -44,7 +44,13 @@ Init_ossl_x509(void)
     Init_ossl_x509revoked();
     Init_ossl_x509store();
 
+    /* Constants are up-to-date with 1.1.1. */
+
+    /* Certificate verification error code */
     DefX509Const(V_OK);
+#if defined(X509_V_ERR_UNSPECIFIED) /* 1.0.1r, 1.0.2f, 1.1.0 */
+    DefX509Const(V_ERR_UNSPECIFIED);
+#endif
     DefX509Const(V_ERR_UNABLE_TO_GET_ISSUER_CERT);
     DefX509Const(V_ERR_UNABLE_TO_GET_CRL);
     DefX509Const(V_ERR_UNABLE_TO_DECRYPT_CERT_SIGNATURE);
@@ -76,8 +82,73 @@ Init_ossl_x509(void)
     DefX509Const(V_ERR_AKID_SKID_MISMATCH);
     DefX509Const(V_ERR_AKID_ISSUER_SERIAL_MISMATCH);
     DefX509Const(V_ERR_KEYUSAGE_NO_CERTSIGN);
+    DefX509Const(V_ERR_UNABLE_TO_GET_CRL_ISSUER);
+    DefX509Const(V_ERR_UNHANDLED_CRITICAL_EXTENSION);
+    DefX509Const(V_ERR_KEYUSAGE_NO_CRL_SIGN);
+    DefX509Const(V_ERR_UNHANDLED_CRITICAL_CRL_EXTENSION);
+    DefX509Const(V_ERR_INVALID_NON_CA);
+    DefX509Const(V_ERR_PROXY_PATH_LENGTH_EXCEEDED);
+    DefX509Const(V_ERR_KEYUSAGE_NO_DIGITAL_SIGNATURE);
+    DefX509Const(V_ERR_PROXY_CERTIFICATES_NOT_ALLOWED);
+    DefX509Const(V_ERR_INVALID_EXTENSION);
+    DefX509Const(V_ERR_INVALID_POLICY_EXTENSION);
+    DefX509Const(V_ERR_NO_EXPLICIT_POLICY);
+    DefX509Const(V_ERR_DIFFERENT_CRL_SCOPE);
+    DefX509Const(V_ERR_UNSUPPORTED_EXTENSION_FEATURE);
+    DefX509Const(V_ERR_UNNESTED_RESOURCE);
+    DefX509Const(V_ERR_PERMITTED_VIOLATION);
+    DefX509Const(V_ERR_EXCLUDED_VIOLATION);
+    DefX509Const(V_ERR_SUBTREE_MINMAX);
     DefX509Const(V_ERR_APPLICATION_VERIFICATION);
+    DefX509Const(V_ERR_UNSUPPORTED_CONSTRAINT_TYPE);
+    DefX509Const(V_ERR_UNSUPPORTED_CONSTRAINT_SYNTAX);
+    DefX509Const(V_ERR_UNSUPPORTED_NAME_SYNTAX);
+    DefX509Const(V_ERR_CRL_PATH_VALIDATION_ERROR);
+#if defined(X509_V_ERR_PATH_LOOP)
+    DefX509Const(V_ERR_PATH_LOOP);
+#endif
+#if defined(X509_V_ERR_SUITE_B_INVALID_VERSION)
+    DefX509Const(V_ERR_SUITE_B_INVALID_VERSION);
+    DefX509Const(V_ERR_SUITE_B_INVALID_ALGORITHM);
+    DefX509Const(V_ERR_SUITE_B_INVALID_CURVE);
+    DefX509Const(V_ERR_SUITE_B_INVALID_SIGNATURE_ALGORITHM);
+    DefX509Const(V_ERR_SUITE_B_LOS_NOT_ALLOWED);
+    DefX509Const(V_ERR_SUITE_B_CANNOT_SIGN_P_384_WITH_P_256);
+#endif
+#if defined(X509_V_ERR_HOSTNAME_MISMATCH)
+    DefX509Const(V_ERR_HOSTNAME_MISMATCH);
+    DefX509Const(V_ERR_EMAIL_MISMATCH);
+    DefX509Const(V_ERR_IP_ADDRESS_MISMATCH);
+#endif
+#if defined(X509_V_ERR_DANE_NO_MATCH)
+    DefX509Const(V_ERR_DANE_NO_MATCH);
+#endif
+#if defined(X509_V_ERR_EE_KEY_TOO_SMALL)
+    DefX509Const(V_ERR_EE_KEY_TOO_SMALL);
+    DefX509Const(V_ERR_CA_KEY_TOO_SMALL);
+    DefX509Const(V_ERR_CA_MD_TOO_WEAK);
+#endif
+#if defined(X509_V_ERR_INVALID_CALL)
+    DefX509Const(V_ERR_INVALID_CALL);
+#endif
+#if defined(X509_V_ERR_STORE_LOOKUP)
+    DefX509Const(V_ERR_STORE_LOOKUP);
+#endif
+#if defined(X509_V_ERR_NO_VALID_SCTS)
+    DefX509Const(V_ERR_NO_VALID_SCTS);
+#endif
+#if defined(X509_V_ERR_PROXY_SUBJECT_NAME_VIOLATION)
+    DefX509Const(V_ERR_PROXY_SUBJECT_NAME_VIOLATION);
+#endif
+#if defined(X509_V_ERR_OCSP_VERIFY_NEEDED)
+    DefX509Const(V_ERR_OCSP_VERIFY_NEEDED);
+    DefX509Const(V_ERR_OCSP_VERIFY_FAILED);
+    DefX509Const(V_ERR_OCSP_CERT_UNKNOWN);
+#endif
 
+    /* Certificate verify flags */
+    /* Set by Store#flags= and StoreContext#flags=. */
+    DefX509Const(V_FLAG_USE_CHECK_TIME);
     /* Set by Store#flags= and StoreContext#flags=. Enables CRL checking for the
      * certificate chain leaf. */
     DefX509Const(V_FLAG_CRL_CHECK);
@@ -122,6 +193,26 @@ Init_ossl_x509(void)
      * Enabled by default in OpenSSL >= 1.1.0. */
     DefX509Const(V_FLAG_TRUSTED_FIRST);
 #endif
+#if defined(X509_V_FLAG_SUITEB_128_LOS_ONLY)
+    /* Set by Store#flags= and StoreContext#flags=.
+     * Enables Suite B 128 bit only mode. */
+    DefX509Const(V_FLAG_SUITEB_128_LOS_ONLY);
+#endif
+#if defined(X509_V_FLAG_SUITEB_192_LOS)
+    /* Set by Store#flags= and StoreContext#flags=.
+     * Enables Suite B 192 bit only mode. */
+    DefX509Const(V_FLAG_SUITEB_192_LOS);
+#endif
+#if defined(X509_V_FLAG_SUITEB_128_LOS)
+    /* Set by Store#flags= and StoreContext#flags=.
+     * Enables Suite B 128 bit mode allowing 192 bit algorithms. */
+    DefX509Const(V_FLAG_SUITEB_128_LOS);
+#endif
+#if defined(X509_V_FLAG_PARTIAL_CHAIN)
+    /* Set by Store#flags= and StoreContext#flags=.
+     * Allows partial chains if at least one certificate is in trusted store. */
+    DefX509Const(V_FLAG_PARTIAL_CHAIN);
+#endif
 #if defined(X509_V_FLAG_NO_ALT_CHAINS)
     /* Set by Store#flags= and StoreContext#flags=. Suppresses searching for
      * a alternative chain. No effect in OpenSSL >= 1.1.0. */
diff --git a/ext/openssl/ossl_x509store.c b/ext/openssl/ossl_x509store.c
index 61543d44f6..9035a70aa9 100644
--- a/ext/openssl/ossl_x509store.c
+++ b/ext/openssl/ossl_x509store.c
@@ -106,6 +106,13 @@ VALUE cX509StoreContext;
 VALUE eX509StoreError;
 
 static void
+ossl_x509store_mark(void *ptr)
+{
+    X509_STORE *store = ptr;
+    rb_gc_mark((VALUE)X509_STORE_get_ex_data(store, store_ex_verify_cb_idx));
+}
+
+static void
 ossl_x509store_free(void *ptr)
 {
     X509_STORE_free(ptr);
@@ -114,7 +121,7 @@ ossl_x509store_free(void *ptr)
 static const rb_data_type_t ossl_x509store_type = {
     "OpenSSL/X509/STORE",
     {
-	0, ossl_x509store_free,
+        ossl_x509store_mark, ossl_x509store_free,
     },
     0, 0, RUBY_TYPED_FREE_IMMEDIATELY,
 };
@@ -457,23 +464,16 @@ ossl_x509store_verify(int argc, VALUE *argv, VALUE self)
 }
 
 /*
- * Public Functions
- */
-static void ossl_x509stctx_free(void*);
-
-
-static const rb_data_type_t ossl_x509stctx_type = {
-    "OpenSSL/X509/STORE_CTX",
-    {
-	0, ossl_x509stctx_free,
-    },
-    0, 0, RUBY_TYPED_FREE_IMMEDIATELY,
-};
-
-/*
  * Private functions
  */
 static void
+ossl_x509stctx_mark(void *ptr)
+{
+    X509_STORE_CTX *ctx = ptr;
+    rb_gc_mark((VALUE)X509_STORE_CTX_get_ex_data(ctx, stctx_ex_verify_cb_idx));
+}
+
+static void
 ossl_x509stctx_free(void *ptr)
 {
     X509_STORE_CTX *ctx = ptr;
@@ -484,6 +484,14 @@ ossl_x509stctx_free(void *ptr)
     X509_STORE_CTX_free(ctx);
 }
 
+static const rb_data_type_t ossl_x509stctx_type = {
+    "OpenSSL/X509/STORE_CTX",
+    {
+        ossl_x509stctx_mark, ossl_x509stctx_free,
+    },
+    0, 0, RUBY_TYPED_FREE_IMMEDIATELY,
+};
+
 static VALUE
 ossl_x509stctx_alloc(VALUE klass)
 {
@@ -517,7 +525,9 @@ static VALUE ossl_x509stctx_set_time(VALUE, VALUE);
 
 /*
  * call-seq:
- *   StoreContext.new(store, cert = nil, chain = nil)
+ *   StoreContext.new(store, cert = nil, untrusted = nil)
+ *
+ * Sets up a StoreContext for a verification of the X.509 certificate _cert_.
  */
 static VALUE
 ossl_x509stctx_initialize(int argc, VALUE *argv, VALUE self)
@@ -527,15 +537,24 @@ ossl_x509stctx_initialize(int argc, VALUE *argv, VALUE self)
     X509_STORE *x509st;
     X509 *x509 = NULL;
     STACK_OF(X509) *x509s = NULL;
+    int state;
 
     rb_scan_args(argc, argv, "12", &store, &cert, &chain);
     GetX509StCtx(self, ctx);
     GetX509Store(store, x509st);
-    if(!NIL_P(cert)) x509 = DupX509CertPtr(cert); /* NEED TO DUP */
-    if(!NIL_P(chain)) x509s = ossl_x509_ary2sk(chain);
-    if(X509_STORE_CTX_init(ctx, x509st, x509, x509s) != 1){
+    if (!NIL_P(cert))
+        x509 = DupX509CertPtr(cert); /* NEED TO DUP */
+    if (!NIL_P(chain)) {
+        x509s = ossl_protect_x509_ary2sk(chain, &state);
+        if (state) {
+            X509_free(x509);
+            rb_jump_tag(state);
+        }
+    }
+    if (X509_STORE_CTX_init(ctx, x509st, x509, x509s) != 1){
+        X509_free(x509);
         sk_X509_pop_free(x509s, X509_free);
-        ossl_raise(eX509StoreError, NULL);
+        ossl_raise(eX509StoreError, "X509_STORE_CTX_init");
     }
     if (!NIL_P(t = rb_iv_get(store, "@time")))
 	ossl_x509stctx_set_time(self, t);
diff --git a/test/openssl/test_asn1.rb b/test/openssl/test_asn1.rb
index cc11301804..1170703775 100644
--- a/test/openssl/test_asn1.rb
+++ b/test/openssl/test_asn1.rb
@@ -635,11 +635,6 @@ 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
-
   private
 
   def B(ary)
diff --git a/test/openssl/test_bn.rb b/test/openssl/test_bn.rb
index 0b5cd84241..274afba3bb 100644
--- a/test/openssl/test_bn.rb
+++ b/test/openssl/test_bn.rb
@@ -272,11 +272,6 @@ class OpenSSL::TestBN < OpenSSL::TestCase
     assert_equal(0, @e1.ucmp(-999))
     assert_instance_of(String, @e1.hash.to_s)
   end
-
-  def test_type_error
-    bug15760 = '[ruby-core:92231] [Bug #15760]'
-    assert_raise(TypeError, bug15760) { OpenSSL::BN.new(nil, 2) }
-  end
 end
 
 end
diff --git a/test/openssl/test_pkcs7.rb b/test/openssl/test_pkcs7.rb
index 6437112b74..149d3b9b5d 100644
--- a/test/openssl/test_pkcs7.rb
+++ b/test/openssl/test_pkcs7.rb
@@ -133,8 +133,6 @@ class OpenSSL::TestPKCS7 < OpenSSL::TestCase
     assert_equal(@ca_cert.subject.to_s, recip[1].issuer.to_s)
     assert_equal(3, recip[1].serial)
     assert_equal(data, p7.decrypt(@rsa1024, @ee2_cert))
-
-    assert_equal(data, p7.decrypt(@rsa1024))
   end
 
   def test_graceful_parsing_failure #[ruby-core:43250]
diff --git a/test/openssl/test_ssl.rb b/test/openssl/test_ssl.rb
index 13c3bde34d..53457e21d3 100644
--- a/test/openssl/test_ssl.rb
+++ b/test/openssl/test_ssl.rb
@@ -155,21 +155,6 @@ 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
-
   def test_sync_close
     start_server { |port|
       begin
@@ -222,7 +207,10 @@ class OpenSSL::TestSSL < OpenSSL::SSLTestCase
 
   def test_client_auth_success
     vflag = OpenSSL::SSL::VERIFY_PEER|OpenSSL::SSL::VERIFY_FAIL_IF_NO_PEER_CERT
-    start_server(verify_mode: vflag) { |port|
+    start_server(verify_mode: vflag,
+      ctx_proc: proc { |ctx|
+        ctx.max_version = OpenSSL::SSL::TLS1_2_VERSION if libressl?(3, 2, 0)
+    }) { |port|
       ctx = OpenSSL::SSL::SSLContext.new
       ctx.key = @cli_key
       ctx.cert = @cli_cert
@@ -268,6 +256,8 @@ class OpenSSL::TestSSL < OpenSSL::SSLTestCase
   end
 
   def test_client_ca
+    pend "LibreSSL 3.2 has broken client CA support" if libressl?(3, 2, 0)
+
     ctx_proc = Proc.new do |ctx|
       ctx.client_ca = [@ca_cert]
     end
@@ -808,11 +798,13 @@ class OpenSSL::TestSSL < OpenSSL::SSLTestCase
 
   def test_verify_hostname_on_connect
     ctx_proc = proc { |ctx|
+      san = "DNS:a.example.com,DNS:*.b.example.com"
+      san += ",DNS:c*.example.com,DNS:d.*.example.com" unless libressl?(3, 2, 2)
       exts = [
         ["keyUsage", "keyEncipherment,digitalSignature", true],
-        ["subjectAltName", "DNS:a.example.com,DNS:*.b.example.com," \
-                           "DNS:c*.example.com,DNS:d.*.example.com"],
+        ["subjectAltName", san],
       ]
+
       ctx.cert = issue_cert(@svr, @svr_key, 4, exts, @ca_cert, @ca_key)
       ctx.key = @svr_key
     }
@@ -833,6 +825,7 @@ class OpenSSL::TestSSL < OpenSSL::SSLTestCase
         ["cx.example.com", true],
         ["d.x.example.com", false],
       ].each do |name, expected_ok|
+        next if name.start_with?('cx') if libressl?(3, 2, 2)
         begin
           sock = TCPSocket.new("127.0.0.1", port)
           ssl = OpenSSL::SSL::SSLSocket.new(sock, ctx)
@@ -851,6 +844,46 @@ class OpenSSL::TestSSL < OpenSSL::SSLTestCase
     end
   end
 
+  def test_verify_hostname_failure_error_code
+    ctx_proc = proc { |ctx|
+      exts = [
+        ["keyUsage", "keyEncipherment,digitalSignature", true],
+        ["subjectAltName", "DNS:a.example.com"],
+      ]
+      ctx.cert = issue_cert(@svr, @svr_key, 4, exts, @ca_cert, @ca_key)
+      ctx.key = @svr_key
+    }
+
+    start_server(ctx_proc: ctx_proc, ignore_listener_error: true) do |port|
+      verify_callback_ok = verify_callback_err = nil
+
+      ctx = OpenSSL::SSL::SSLContext.new
+      ctx.verify_hostname = true
+      ctx.cert_store = OpenSSL::X509::Store.new
+      ctx.cert_store.add_cert(@ca_cert)
+      ctx.verify_mode = OpenSSL::SSL::VERIFY_PEER
+      ctx.verify_callback = -> (preverify_ok, store_ctx) {
+        verify_callback_ok = preverify_ok
+        verify_callback_err = store_ctx.error
+        preverify_ok
+      }
+
+      begin
+        sock = TCPSocket.new("127.0.0.1", port)
+        ssl = OpenSSL::SSL::SSLSocket.new(sock, ctx)
+        ssl.hostname = "b.example.com"
+        assert_handshake_error { ssl.connect }
+        assert_equal false, verify_callback_ok
+        code_expected = openssl?(1, 0, 2) || defined?(OpenSSL::X509::V_ERR_HOSTNAME_MISMATCH) ?
+          OpenSSL::X509::V_ERR_HOSTNAME_MISMATCH :
+          OpenSSL::X509::V_ERR_CERT_REJECTED
+        assert_equal code_expected, verify_callback_err
+      ensure
+        sock&.close
+      end
+    end
+  end
+
   def test_connect_certificate_verify_failed_exception_message
     start_server(ignore_listener_error: true) { |port|
       ctx = OpenSSL::SSL::SSLContext.new
@@ -1476,12 +1509,13 @@ end
     end
   end
 
-  def test_ecdh_curves
+  def test_ecdh_curves_tls12
     pend "EC is disabled" unless defined?(OpenSSL::PKey::EC)
 
     ctx_proc = -> ctx {
       # Enable both ECDHE (~ TLS 1.2) cipher suites and TLS 1.3
-      ctx.ciphers = "DEFAULT:!kRSA:!kEDH"
+      ctx.max_version = OpenSSL::SSL::TLS1_2_VERSION
+      ctx.ciphers = "kEECDH"
       ctx.ecdh_curves = "P-384:P-521"
     }
     start_server(ctx_proc: ctx_proc, ignore_listener_error: true) do |port|
@@ -1490,13 +1524,9 @@ end
 
       server_connect(port, ctx) { |ssl|
         cs = ssl.cipher[0]
-        if /\ATLS/ =~ cs # Is TLS 1.3 is used?
+        assert_match (/\AECDH/), cs
+        if ssl.respond_to?(:tmp_key)
           assert_equal "secp384r1", ssl.tmp_key.group.curve_name
-        else
-          assert_match (/\AECDH/), cs
-          if ssl.respond_to?(:tmp_key)
-            assert_equal "secp384r1", ssl.tmp_key.group.curve_name
-          end
         end
         ssl.puts "abc"; assert_equal "abc\n", ssl.gets
       }
@@ -1520,6 +1550,26 @@ end
     end
   end
 
+  def test_ecdh_curves_tls13
+    pend "EC is disabled" unless defined?(OpenSSL::PKey::EC)
+    pend "TLS 1.3 not supported" unless tls13_supported?
+
+    ctx_proc = -> ctx {
+      # Assume TLS 1.3 is enabled and chosen by default
+      ctx.ecdh_curves = "P-384:P-521"
+    }
+    start_server(ctx_proc: ctx_proc, ignore_listener_error: true) do |port|
+      ctx = OpenSSL::SSL::SSLContext.new
+      ctx.ecdh_curves = "P-256:P-384" # disable P-521
+
+      server_connect(port, ctx) { |ssl|
+        assert_equal "TLSv1.3", ssl.ssl_version
+        assert_equal "secp384r1", ssl.tmp_key.group.curve_name
+        ssl.puts "abc"; assert_equal "abc\n", ssl.gets
+      }
+    end
+  end
+
   def test_security_level
     ctx = OpenSSL::SSL::SSLContext.new
     begin
diff --git a/test/openssl/test_ssl_session.rb b/test/openssl/test_ssl_session.rb
index e199f86d2b..1d82aebfd5 100644
--- a/test/openssl/test_ssl_session.rb
+++ b/test/openssl/test_ssl_session.rb
@@ -122,6 +122,7 @@ __EOS__
       ctx.options &= ~OpenSSL::SSL::OP_NO_TICKET
       # Disable server-side session cache which is enabled by default
       ctx.session_cache_mode = OpenSSL::SSL::SSLContext::SESSION_CACHE_OFF
+      ctx.max_version = OpenSSL::SSL::TLS1_2_VERSION if libressl?(3, 2, 0)
     }
     start_server(ctx_proc: ctx_proc) do |port|
       sess1 = server_connect_with_session(port, nil, nil) { |ssl|
diff --git a/test/openssl/test_x509name.rb b/test/openssl/test_x509name.rb
index 8a4596ea6e..f0146595d6 100644
--- a/test/openssl/test_x509name.rb
+++ b/test/openssl/test_x509name.rb
@@ -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)
diff --git a/test/openssl/utils.rb b/test/openssl/utils.rb
index bf19163052..34c89a2e04 100644
--- a/test/openssl/utils.rb
+++ b/test/openssl/utils.rb
@@ -181,6 +181,14 @@ class OpenSSL::SSLTestCase < OpenSSL::TestCase
   rescue
   end
 
+  def tls13_supported?
+    return false unless defined?(OpenSSL::SSL::TLS1_3_VERSION)
+    ctx = OpenSSL::SSL::SSLContext.new
+    ctx.min_version = ctx.max_version = OpenSSL::SSL::TLS1_3_VERSION
+    true
+  rescue
+  end
+
   def readwrite_loop(ctx, ssl)
     while line = ssl.gets
       ssl.write(line)