openssl: sync with upstream repository

Import current master (2c43241dc0ed) of ruby/openssl.git.

Below are the commits that were made since the last batch at commit
b99775b163ce (ruby/openssl.git commit f49e7110ca1e). Note that some of
them have been applied already.

----------------------------------------------------------------
Benoit Daloze (1):
      Remove redundant and ignored workflow file

DBL-Lee (1):
      add support for SHA512_256/SHA512_224

Hiroshi SHIBATA (2):
      Guard for OpenSSL::PKey::EC::Group::Error with unsupported platforms
      Fixed inconsistency directory structure with ruby/ruby repo

Jeremy Evans (2):
      Fix keyword argument separation issues in OpenSSL::SSL::SSLSocket#sys{read,write}_nonblock
      Remove taint support

Kazuki Yamaguchi (26):
      config: support .include directive
      random: make OpenSSL::Random.pseudo_bytes alias of .random_bytes
      extconf.rb: get rid of -Werror=deprecated-declarations
      test/openssl/test_ssl: skip test_fallback_scsv if necessary
      ts: simplify OpenSSL::Timestamp::Request#algorithm
      History.md: add missing references to GitHub issues
      config: deprecate OpenSSL::Config#add_value and #[]=
      test/openssl/test_ssl: remove sleep from test_finished_messages
      test/openssl/test_ssl: fix random failure in SSLSocket.open test
      test/openssl/test_ssl: avoid explicitly-sized private keys
      test/openssl/test_ssl: remove commented-out test case
      test/openssl/test_ssl: allow kRSA tests to fail
      ssl: avoid declarations after statements
      engine: revert OpenSSL::Engine.load changes for cloudhsm
      engine: remove really outdated static engines
      engine: do not check for ENGINE_load_builtin_engines()
      engine: fix guards for 'dynamic' and 'cryptodev' engines
      lib/openssl.rb: require openssl/version.rb
      x509: add error code and verify flags constants
      ssl: set verify error code in the case of verify_hostname failure
      .github/workflows: merge CI jobs into a single workflow
      .github/workflows: test against different OpenSSL versions
      .travis.yml: fully migrate to GitHub Actions
      ssl: suppress test failure with SSLContext#add_certificate_chain_file
      ssl: remove test case test_puts_meta from test_pair
      Revert "Use version.rb in gemspec"

MSP-Greg (2):
      .travis.yml - remove 2.3/1.0.2, 2.5/1.1.1, head/1.0.2
      Use version.rb in gemspec

Samuel Williams (1):
      Restore compatibility with older versions of Ruby.

Yusuke Endoh (1):
      Make OpenSSL::OSSL#test_memcmp_timing robust

19 files changed, 426 insertions, 264 deletions

diff --git a/ext/openssl/History.md b/ext/openssl/History.md
index cdb44b1293..929d91961d 100644
--- a/ext/openssl/History.md
+++ b/ext/openssl/History.md
@@ -1,34 +1,55 @@
 Version 2.2.0 (not yet released)
 =============
 
+Compatibility notes
+-------------------
+
+* Remove unsupported MDC2, DSS, DSS1, and SHA algorithms.
+* Remove `OpenSSL::PKCS7::SignerInfo#name` alias for `#issuer`.
+  [[GitHub #266]](https://github.com/ruby/openssl/pull/266)
+* Deprecate `OpenSSL::Config#add_value` and `#[]=` for future removal.
+  [[GitHub #322]](https://github.com/ruby/openssl/pull/322)
+
+
+Notable changes
+---------------
+
 * Change default `OpenSSL::SSL::SSLServer#listen` backlog argument from
   5 to `Socket::SOMAXCONN`.
+  [[GitHub #286]](https://github.com/ruby/openssl/issues/286)
 * Make `OpenSSL::HMAC#==` use a timing safe string comparison.
-* Remove unsupported MDC2, DSS, DSS1, and SHA algorithms.
+  [[GitHub #284]](https://github.com/ruby/openssl/pull/284)
 * Add support for SHA3 and BLAKE digests.
+  [[GitHub #282]](https://github.com/ruby/openssl/pull/282)
 * Add `OpenSSL::SSL::SSLSocket.open` for opening a `TCPSocket` and
   returning an `OpenSSL::SSL::SSLSocket` for it.
+  [[GitHub #225]](https://github.com/ruby/openssl/issues/225)
 * Support marshalling of `OpenSSL::X509` objects.
+  [[GitHub #281]](https://github.com/ruby/openssl/pull/281)
 * Add `OpenSSL.secure_compare` for timing safe string comparison for
   strings of possibly unequal length.
+  [[GitHub #280]](https://github.com/ruby/openssl/pull/280)
 * Add `OpenSSL.fixed_length_secure_compare` for timing safe string
   comparison for strings of equal length.
+  [[GitHub #269]](https://github.com/ruby/openssl/pull/269)
 * Add `OpenSSL::SSL::SSLSocket#{finished_message,peer_finished_message}`
   for last finished message sent and received.
+  [[GitHub #250]](https://github.com/ruby/openssl/pull/250)
 * Add `OpenSSL::Timestamp` module for handing timestamp requests and
   responses.
+  [[GitHub #204]](https://github.com/ruby/openssl/pull/204)
 * Add helper methods for `OpenSSL::X509::Certificate`:
   `find_extension`, `subject_key_identifier`,
   `authority_key_identifier`, `crl_uris`, `ca_issuer_uris` and
-  `ocsp_uris`.
-* Add helper methods for `OpenSSL::X509::CRL`:
+  `ocsp_uris`, and for `OpenSSL::X509::CRL`:
   `find_extension` and `subject_key_identifier`.
-* Remove `OpenSSL::PKCS7::SignerInfo#name` alias for `#issuer`.
-* Add `OpenSSL::ECPoint#add` for adding points to an elliptic curve
-  group.
+  [[GitHub #260]](https://github.com/ruby/openssl/pull/260)
+  [[GitHub #275]](https://github.com/ruby/openssl/pull/275)
+  [[GitHub #293]](https://github.com/ruby/openssl/pull/293)
+* Add `OpenSSL::ECPoint#add` for performing elliptic curve point addition.
   [[GitHub #261]](https://github.com/ruby/openssl/pull/261)
-* Make `OpenSSL::PKey::RSA#{export,to_der}` correctly check `key`,
-  `factors`, and `crt_params`.
+* Make `OpenSSL::PKey::RSA#{export,to_der}` check `key`, `factors`, and
+  `crt_params` to do proper private key serialization.
   [[GitHub #258]](https://github.com/ruby/openssl/pull/258)
 * Add `OpenSSL::SSL::{SSLSocket,SSLServer}#fileno`, returning the
   underlying socket file descriptor number.
@@ -40,16 +61,18 @@ Version 2.2.0 (not yet released)
 * Add `OpenSSL::X509::Extension#value_der` for the raw value of
   the extension.
   [[GitHub #234]](https://github.com/ruby/openssl/pull/234)
-* Signficantly reduce allocated memory in `OpenSSL::Buffering#do_write`.
+* Significantly reduce allocated memory in `OpenSSL::Buffering#do_write`.
   [[GitHub #212]](https://github.com/ruby/openssl/pull/212)
 * Ensure all valid IPv6 addresses are considered valid as elements
   of subjectAlternativeName in certificates.
   [[GitHub #185]](https://github.com/ruby/openssl/pull/185)
 * Allow recipient's certificate to be omitted in PCKS7#decrypt.
   [[GitHub #183]](https://github.com/ruby/openssl/pull/183)
-* Add support for reading keys in PKCS8 format and export via instance methods
+* Add support for reading keys in PKCS #8 format and export via instance methods
   added to `OpenSSL::PKey` classes: `private_to_der`, `private_to_pem`,
   `public_to_der` and `public_to_pem`.
+  [[GitHub #297]](https://github.com/ruby/openssl/pull/297)
+
 
 Version 2.1.2
 =============
diff --git a/ext/openssl/deprecation.rb b/ext/openssl/deprecation.rb
deleted file mode 100644
index fdf2d30ed0..0000000000
--- a/ext/openssl/deprecation.rb
+++ /dev/null
@@ -1,27 +0,0 @@
-# frozen_string_literal: true
-module OpenSSL
-  def self.deprecated_warning_flag
-    unless flag = (@deprecated_warning_flag ||= nil)
-      if try_compile("", flag = "-Werror=deprecated-declarations")
-        $warnflags << " #{flag}"
-      else
-        flag = ""
-      end
-      @deprecated_warning_flag = flag
-    end
-    flag
-  end
-
-  def self.restore_warning_flag
-    $warnflags = @warnflags
-  end
-
-  def self.check_func(func, header)
-    have_func(func, header, deprecated_warning_flag)
-  end
-
-  def self.check_func_or_macro(func, header)
-    check_func(func, header) or
-      have_macro(func, header) && $defs.push("-DHAVE_#{func.upcase}")
-  end
-end
diff --git a/ext/openssl/extconf.rb b/ext/openssl/extconf.rb
index 87a682b4ab..693e55cd97 100644
--- a/ext/openssl/extconf.rb
+++ b/ext/openssl/extconf.rb
@@ -12,16 +12,12 @@
 =end
 
 require "mkmf"
-require File.expand_path('../deprecation', __FILE__)
 
 dir_config("openssl")
 dir_config("kerberos")
 
 Logging::message "=== OpenSSL for Ruby configurator ===\n"
 
-# Check with -Werror=deprecated-declarations if available
-OpenSSL.deprecated_warning_flag
-
 ##
 # Adds -DOSSL_DEBUG for compilation and some more targets when GCC is used
 # To turn it on, use: --with-debug or --enable-debug
@@ -114,11 +110,10 @@ end
 Logging::message "=== Checking for OpenSSL features... ===\n"
 # compile options
 have_func("RAND_egd")
-engines = %w{builtin_engines openbsd_dev_crypto dynamic 4758cca aep atalla chil
-             cswift nuron sureware ubsec padlock capi gmp gost cryptodev aesni
-             cloudhsm}
+engines = %w{dynamic 4758cca aep atalla chil
+             cswift nuron sureware ubsec padlock capi gmp gost cryptodev}
 engines.each { |name|
-  OpenSSL.check_func_or_macro("ENGINE_load_#{name}", "openssl/engine.h")
+  have_func("ENGINE_load_#{name}()", "openssl/engine.h")
 }
 
 if ($mswin || $mingw) && have_macro("LIBRESSL_VERSION_NUMBER", "openssl/opensslv.h")
@@ -130,9 +125,9 @@ have_func("EC_curve_nist2nid")
 have_func("X509_REVOKED_dup")
 have_func("X509_STORE_CTX_get0_store")
 have_func("SSL_CTX_set_alpn_select_cb")
-OpenSSL.check_func_or_macro("SSL_CTX_set1_curves_list", "openssl/ssl.h")
-OpenSSL.check_func_or_macro("SSL_CTX_set_ecdh_auto", "openssl/ssl.h")
-OpenSSL.check_func_or_macro("SSL_get_server_tmp_key", "openssl/ssl.h")
+have_func("SSL_CTX_set1_curves_list(NULL, NULL)", "openssl/ssl.h")
+have_func("SSL_CTX_set_ecdh_auto(NULL, 0)", "openssl/ssl.h")
+have_func("SSL_get_server_tmp_key(NULL, NULL)", "openssl/ssl.h")
 have_func("SSL_is_server")
 
 # added in 1.1.0
@@ -148,7 +143,6 @@ have_func("EVP_MD_CTX_new")
 have_func("EVP_MD_CTX_free")
 have_func("HMAC_CTX_new")
 have_func("HMAC_CTX_free")
-OpenSSL.check_func("RAND_pseudo_bytes", "openssl/rand.h") # deprecated
 have_func("X509_STORE_get_ex_data")
 have_func("X509_STORE_set_ex_data")
 have_func("X509_STORE_get_ex_new_index")
@@ -167,8 +161,8 @@ have_func("X509_CRL_up_ref")
 have_func("X509_STORE_up_ref")
 have_func("SSL_SESSION_up_ref")
 have_func("EVP_PKEY_up_ref")
-OpenSSL.check_func_or_macro("SSL_CTX_set_tmp_ecdh_callback", "openssl/ssl.h") # removed
-OpenSSL.check_func_or_macro("SSL_CTX_set_min_proto_version", "openssl/ssl.h")
+have_func("SSL_CTX_set_tmp_ecdh_callback(NULL, NULL)", "openssl/ssl.h") # removed
+have_func("SSL_CTX_set_min_proto_version(NULL, 0)", "openssl/ssl.h")
 have_func("SSL_CTX_get_security_level")
 have_func("X509_get0_notBefore")
 have_func("SSL_SESSION_get_protocol_version")
@@ -185,6 +179,5 @@ have_func("SSL_CTX_set_post_handshake_auth")
 Logging::message "=== Checking done. ===\n"
 
 create_header
-OpenSSL.restore_warning_flag
 create_makefile("openssl")
 Logging::message "Done.\n"
diff --git a/ext/openssl/lib/openssl.rb b/ext/openssl/lib/openssl.rb
index 7ba2229a1b..00e2db1f40 100644
--- a/ext/openssl/lib/openssl.rb
+++ b/ext/openssl/lib/openssl.rb
@@ -21,6 +21,7 @@ require_relative 'openssl/hmac'
 require_relative 'openssl/x509'
 require_relative 'openssl/ssl'
 require_relative 'openssl/pkcs5'
+require_relative 'openssl/version'
 
 module OpenSSL
   # call-seq:
diff --git a/ext/openssl/lib/openssl/config.rb b/ext/openssl/lib/openssl/config.rb
index ef83c57b20..9a0b787420 100644
--- a/ext/openssl/lib/openssl/config.rb
+++ b/ext/openssl/lib/openssl/config.rb
@@ -37,7 +37,7 @@ module OpenSSL
       def parse(string)
         c = new()
         parse_config(StringIO.new(string)).each do |section, hash|
-          c[section] = hash
+          c.set_section(section, hash)
         end
         c
       end
@@ -76,29 +76,44 @@ module OpenSSL
       def parse_config_lines(io)
         section = 'default'
         data = {section => {}}
-        while definition = get_definition(io)
+        io_stack = [io]
+        while definition = get_definition(io_stack)
           definition = clear_comments(definition)
           next if definition.empty?
-          if definition[0] == ?[
+          case definition
+          when /\A\[/
             if /\[([^\]]*)\]/ =~ definition
               section = $1.strip
               data[section] ||= {}
             else
               raise ConfigError, "missing close square bracket"
             end
-          else
-            if /\A([^:\s]*)(?:::([^:\s]*))?\s*=(.*)\z/ =~ definition
-              if $2
-                section = $1
-                key = $2
-              else
-                key = $1
+          when /\A\.include (\s*=\s*)?(.+)\z/
+            path = $2
+            if File.directory?(path)
+              files = Dir.glob(File.join(path, "*.{cnf,conf}"), File::FNM_EXTGLOB)
+            else
+              files = [path]
+            end
+
+            files.each do |filename|
+              begin
+                io_stack << StringIO.new(File.read(filename))
+              rescue
+                raise ConfigError, "could not include file '%s'" % filename
               end
-              value = unescape_value(data, section, $3)
-              (data[section] ||= {})[key] = value.strip
+            end
+          when /\A([^:\s]*)(?:::([^:\s]*))?\s*=(.*)\z/
+            if $2
+              section = $1
+              key = $2
             else
-              raise ConfigError, "missing equal sign"
+              key = $1
             end
+            value = unescape_value(data, section, $3)
+            (data[section] ||= {})[key] = value.strip
+          else
+            raise ConfigError, "missing equal sign"
           end
         end
         data
@@ -211,10 +226,10 @@ module OpenSSL
         scanned.join
       end
 
-      def get_definition(io)
-        if line = get_line(io)
+      def get_definition(io_stack)
+        if line = get_line(io_stack)
           while /[^\\]\\\z/ =~ line
-            if extra = get_line(io)
+            if extra = get_line(io_stack)
               line += extra
             else
               break
@@ -224,9 +239,12 @@ module OpenSSL
         end
       end
 
-      def get_line(io)
-        if line = io.gets
-          line.gsub(/[\r\n]*/, '')
+      def get_line(io_stack)
+        while io = io_stack.last
+          if line = io.gets
+            return line.gsub(/[\r\n]*/, '')
+          end
+          io_stack.pop
         end
       end
     end
@@ -248,7 +266,7 @@ module OpenSSL
       if filename
         File.open(filename.to_s) do |file|
           Config.parse_config(file).each do |section, hash|
-            self[section] = hash
+            set_section(section, hash)
           end
         end
       end
@@ -297,6 +315,8 @@ module OpenSSL
     end
 
     ##
+    # *Deprecated in v2.2.0*. This method will be removed in a future release.
+    #
     # Set the target _key_ with a given _value_ under a specific _section_.
     #
     # Given the following configurating file being loaded:
@@ -351,6 +371,8 @@ module OpenSSL
     end
 
     ##
+    # *Deprecated in v2.2.0*. This method will be removed in a future release.
+    #
     # Sets a specific _section_ name with a Hash _pairs_.
     #
     # Given the following configuration being created:
@@ -376,9 +398,13 @@ module OpenSSL
     #
     def []=(section, pairs)
       check_modify
-      @data[section] ||= {}
+      set_section(section, pairs)
+    end
+
+    def set_section(section, pairs) # :nodoc:
+      hash = @data[section] ||= {}
       pairs.each do |key, value|
-        self.add_value(section, key, value)
+        hash[key] = value
       end
     end
 
@@ -463,6 +489,8 @@ module OpenSSL
     end
 
     def check_modify
+      warn "#{caller(2, 1)[0]}: warning: do not modify OpenSSL::Config; this " \
+        "method is deprecated and will be removed in a future release."
       raise TypeError.new("Insecure: can't modify OpenSSL config") if frozen?
     end
 
diff --git a/ext/openssl/lib/openssl/digest.rb b/ext/openssl/lib/openssl/digest.rb
index c953911954..92d358d241 100644
--- a/ext/openssl/lib/openssl/digest.rb
+++ b/ext/openssl/lib/openssl/digest.rb
@@ -21,7 +21,7 @@ module OpenSSL
     ALGORITHMS = %w(MD4 MD5 RIPEMD160 SHA1 SHA224 SHA256 SHA384 SHA512)
 
     if !OPENSSL_VERSION.include?("LibreSSL") && OPENSSL_VERSION_NUMBER > 0x10101000
-      ALGORITHMS.concat %w(BLAKE2b512 BLAKE2s256 SHA3-224 SHA3-256 SHA3-384 SHA3-512)
+      ALGORITHMS.concat %w(BLAKE2b512 BLAKE2s256 SHA3-224 SHA3-256 SHA3-384 SHA3-512 SHA512-224 SHA512-256)
     end
 
     ALGORITHMS.freeze
diff --git a/ext/openssl/lib/openssl/version.rb b/ext/openssl/lib/openssl/version.rb
index b07bb33009..9c7515ba0f 100644
--- a/ext/openssl/lib/openssl/version.rb
+++ b/ext/openssl/lib/openssl/version.rb
@@ -1,5 +1,5 @@
 # frozen_string_literal: true
 
 module OpenSSL
-  VERSION = "2.2.0" unless defined?(VERSION)
+  VERSION = "2.2.0"
 end
diff --git a/ext/openssl/ossl_engine.c b/ext/openssl/ossl_engine.c
index f90bf061df..90546934d1 100644
--- a/ext/openssl/ossl_engine.c
+++ b/ext/openssl/ossl_engine.c
@@ -93,9 +93,6 @@ static const rb_data_type_t ossl_engine_type = {
 static VALUE
 ossl_engine_s_load(int argc, VALUE *argv, VALUE klass)
 {
-#if !defined(HAVE_ENGINE_LOAD_BUILTIN_ENGINES)
-    return Qnil;
-#else
     VALUE name;
 
     rb_scan_args(argc, argv, "01", &name);
@@ -104,10 +101,10 @@ ossl_engine_s_load(int argc, VALUE *argv, VALUE klass)
         return Qtrue;
     }
     StringValueCStr(name);
-#ifndef OPENSSL_NO_STATIC_ENGINE
 #if HAVE_ENGINE_LOAD_DYNAMIC
     OSSL_ENGINE_LOAD_IF_MATCH(dynamic, DYNAMIC);
 #endif
+#ifndef OPENSSL_NO_STATIC_ENGINE
 #if HAVE_ENGINE_LOAD_4758CCA
     OSSL_ENGINE_LOAD_IF_MATCH(4758cca, 4758CCA);
 #endif
@@ -144,23 +141,13 @@ ossl_engine_s_load(int argc, VALUE *argv, VALUE klass)
 #if HAVE_ENGINE_LOAD_GOST
     OSSL_ENGINE_LOAD_IF_MATCH(gost, GOST);
 #endif
+#endif
 #if HAVE_ENGINE_LOAD_CRYPTODEV
     OSSL_ENGINE_LOAD_IF_MATCH(cryptodev, CRYPTODEV);
 #endif
-#if HAVE_ENGINE_LOAD_AESNI
-    OSSL_ENGINE_LOAD_IF_MATCH(aesni, AESNI);
-#endif
-#if HAVE_ENGINE_LOAD_CLOUDHSM
-    OSSL_ENGINE_LOAD_IF_MATCH(cloudhsm, CLOUDHSM);
-#endif
-#endif
-#ifdef HAVE_ENGINE_LOAD_OPENBSD_DEV_CRYPTO
-    OSSL_ENGINE_LOAD_IF_MATCH(openbsd_dev_crypto, OPENBSD_DEV_CRYPTO);
-#endif
     OSSL_ENGINE_LOAD_IF_MATCH(openssl, OPENSSL);
     rb_warning("no such builtin loader for `%"PRIsVALUE"'", name);
     return Qnil;
-#endif /* HAVE_ENGINE_LOAD_BUILTIN_ENGINES */
 }
 
 /*
diff --git a/ext/openssl/ossl_rand.c b/ext/openssl/ossl_rand.c
index 4a4f9dd5bf..659dc818b6 100644
--- a/ext/openssl/ossl_rand.c
+++ b/ext/openssl/ossl_rand.c
@@ -120,36 +120,6 @@ ossl_rand_bytes(VALUE self, VALUE len)
     return str;
 }
 
-#if defined(HAVE_RAND_PSEUDO_BYTES)
-/*
- *  call-seq:
- *	pseudo_bytes(length) -> string
- *
- * Generates a String with _length_ number of pseudo-random bytes.
- *
- * Pseudo-random byte sequences generated by ::pseudo_bytes will be unique if
- * they are of sufficient length, but are not necessarily unpredictable.
- *
- * === Example
- *
- *    OpenSSL::Random.pseudo_bytes(12)
- *    #=> "..."
- */
-static VALUE
-ossl_rand_pseudo_bytes(VALUE self, VALUE len)
-{
-    VALUE str;
-    int n = NUM2INT(len);
-
-    str = rb_str_new(0, n);
-    if (RAND_pseudo_bytes((unsigned char *)RSTRING_PTR(str), n) < 1) {
-	ossl_raise(eRandomError, NULL);
-    }
-
-    return str;
-}
-#endif
-
 #ifdef HAVE_RAND_EGD
 /*
  *  call-seq:
@@ -219,8 +189,8 @@ Init_ossl_rand(void)
     rb_define_module_function(mRandom, "load_random_file", ossl_rand_load_file, 1);
     rb_define_module_function(mRandom, "write_random_file", ossl_rand_write_file, 1);
     rb_define_module_function(mRandom, "random_bytes", ossl_rand_bytes, 1);
-#if defined(HAVE_RAND_PSEUDO_BYTES)
-    rb_define_module_function(mRandom, "pseudo_bytes", ossl_rand_pseudo_bytes, 1);
+#if OPENSSL_VERSION_NUMBER < 0x10101000 || defined(LIBRESSL_VERSION_NUMBER)
+    rb_define_alias(rb_singleton_class(mRandom), "pseudo_bytes", "random_bytes");
 #endif
 #ifdef HAVE_RAND_EGD
     rb_define_module_function(mRandom, "egd", ossl_rand_egd, 1);
diff --git a/ext/openssl/ossl_ssl.c b/ext/openssl/ossl_ssl.c
index dfbfbb22ee..34bb636ead 100644
--- a/ext/openssl/ossl_ssl.c
+++ b/ext/openssl/ossl_ssl.c
@@ -359,7 +359,14 @@ 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);
@@ -1325,12 +1332,16 @@ ossl_sslctx_add_certificate(int argc, VALUE *argv, VALUE self)
 static VALUE
 ossl_sslctx_add_certificate_chain_file(VALUE self, VALUE path)
 {
-    StringValue(path);
-    SSL_CTX *ctx = NULL;
+    SSL_CTX *ctx;
+    int ret;
 
     GetSSLCTX(self, ctx);
+    StringValueCStr(path);
+    ret = SSL_CTX_use_certificate_chain_file(ctx, RSTRING_PTR(path));
+    if (ret != 1)
+        ossl_raise(eSSLError, "SSL_CTX_use_certificate_chain_file");
 
-    return SSL_CTX_use_certificate_chain_file(ctx, RSTRING_PTR(path)) == 1 ? Qtrue : Qfalse;
+    return Qtrue;
 }
 
 /*
@@ -2327,16 +2338,16 @@ static VALUE
 ossl_ssl_get_finished(VALUE self)
 {
     SSL *ssl;
+    char sizer[1], *buf;
+    size_t len;
 
     GetSSL(self, ssl);
 
-    char sizer[1];
-    size_t len = SSL_get_finished(ssl, sizer, 0);
-
-    if(len == 0)
-      return Qnil;
+    len = SSL_get_finished(ssl, sizer, 0);
+    if (len == 0)
+        return Qnil;
 
-    char* buf = ALLOCA_N(char, len);
+    buf = ALLOCA_N(char, len);
     SSL_get_finished(ssl, buf, len);
     return rb_str_new(buf, len);
 }
@@ -2352,16 +2363,16 @@ static VALUE
 ossl_ssl_get_peer_finished(VALUE self)
 {
     SSL *ssl;
+    char sizer[1], *buf;
+    size_t len;
 
     GetSSL(self, ssl);
 
-    char sizer[1];
-    size_t len = SSL_get_peer_finished(ssl, sizer, 0);
-
-    if(len == 0)
-      return Qnil;
+    len = SSL_get_peer_finished(ssl, sizer, 0);
+    if (len == 0)
+        return Qnil;
 
-    char* buf = ALLOCA_N(char, len);
+    buf = ALLOCA_N(char, len);
     SSL_get_peer_finished(ssl, buf, len);
     return rb_str_new(buf, len);
 }
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/test/openssl/fixtures/chain/dh512.pem b/test/openssl/fixtures/chain/dh512.pem
deleted file mode 100644
index fec138c7a9..0000000000
--- a/test/openssl/fixtures/chain/dh512.pem
+++ /dev/null
@@ -1,4 +0,0 @@
------BEGIN DH PARAMETERS-----
-MEYCQQCjDVzTg9C4u43MV0TKDGsBuYdChrPMczr4IYjy+jHQvXm2DDadNNWBIDau
-4zNtwfLCg2gMwOc7t18m4Ten/NOLAgEC
------END DH PARAMETERS-----
diff --git a/test/openssl/fixtures/chain/server.crt b/test/openssl/fixtures/chain/server.crt
deleted file mode 100644
index d6b814f450..0000000000
--- a/test/openssl/fixtures/chain/server.crt
+++ /dev/null
@@ -1,13 +0,0 @@
------BEGIN CERTIFICATE-----
-MIICATCCAWoCCQDbxIRGgXeWaDANBgkqhkiG9w0BAQsFADBFMQswCQYDVQQGEwJO
-WjETMBEGA1UECAwKU29tZS1TdGF0ZTEhMB8GA1UECgwYSW50ZXJuZXQgV2lkZ2l0
-cyBQdHkgTHRkMB4XDTE5MDYxMzA1MDU0MloXDTI5MDYxMDA1MDU0MlowRTELMAkG
-A1UEBhMCTloxEzARBgNVBAgMClNvbWUtU3RhdGUxITAfBgNVBAoMGEludGVybmV0
-IFdpZGdpdHMgUHR5IEx0ZDCBnzANBgkqhkiG9w0BAQEFAAOBjQAwgYkCgYEA29Vu
-Y6m8pRrsXxUhlK2BX48CDChr8D53SqZozcQI26BCm+05TBnQxKAHOknR3y/ige2U
-2zftSwbSoK/zKUC8o5pKVL+l36anDEnZ6RWc9Z9CvmaCFjlcP4nXZO+yD1Is/jCy
-KqGGC8lQ920VXOCFflJj6AWg88+4C3GLjxJe6bMCAwEAATANBgkqhkiG9w0BAQsF
-AAOBgQCDaqKGBkYxNxnv37vEKp7zi/cov8LvEsZaAD1pcSU+ysBiBes/B7a/Qjcj
-PTZsH/hedn9mVynLkjc7LrztUWngTeW9gk5EB9YSwJdPhwLntV1TdaBlf/tu0n/c
-s7QxaZhFMUyo1Eof28zXVHhs1OEhlSjwJ8lxuC3vBE4F1BjSNQ==
------END CERTIFICATE-----
diff --git a/test/openssl/fixtures/chain/server.csr b/test/openssl/fixtures/chain/server.csr
deleted file mode 100644
index 51b38e33f2..0000000000
--- a/test/openssl/fixtures/chain/server.csr
+++ /dev/null
@@ -1,11 +0,0 @@
------BEGIN CERTIFICATE REQUEST-----
-MIIBhDCB7gIBADBFMQswCQYDVQQGEwJOWjETMBEGA1UECAwKU29tZS1TdGF0ZTEh
-MB8GA1UECgwYSW50ZXJuZXQgV2lkZ2l0cyBQdHkgTHRkMIGfMA0GCSqGSIb3DQEB
-AQUAA4GNADCBiQKBgQDb1W5jqbylGuxfFSGUrYFfjwIMKGvwPndKpmjNxAjboEKb
-7TlMGdDEoAc6SdHfL+KB7ZTbN+1LBtKgr/MpQLyjmkpUv6XfpqcMSdnpFZz1n0K+
-ZoIWOVw/iddk77IPUiz+MLIqoYYLyVD3bRVc4IV+UmPoBaDzz7gLcYuPEl7pswID
-AQABoAAwDQYJKoZIhvcNAQELBQADgYEAONaTWYVfyMmd8irCtognRoM4tFF4xvDg
-PTcnHjVb/6oPPMU+mtQVD9qNf8SOdhNuYVTZ61mDLQGeq45CLM5qWjZkqFPHnngf
-ajfZRE7Y3vA8ZaWFvsTJYcU+R3/FRS0XnFYj99+q9Yi3JExSY+arElyAW3tFYlcs
-RWOCk1pT2Yc=
------END CERTIFICATE REQUEST-----
diff --git a/test/openssl/fixtures/chain/server.key b/test/openssl/fixtures/chain/server.key
deleted file mode 100644
index 9590235db8..0000000000
--- a/test/openssl/fixtures/chain/server.key
+++ /dev/null
@@ -1,15 +0,0 @@
------BEGIN RSA PRIVATE KEY-----
-MIICXAIBAAKBgQDb1W5jqbylGuxfFSGUrYFfjwIMKGvwPndKpmjNxAjboEKb7TlM
-GdDEoAc6SdHfL+KB7ZTbN+1LBtKgr/MpQLyjmkpUv6XfpqcMSdnpFZz1n0K+ZoIW
-OVw/iddk77IPUiz+MLIqoYYLyVD3bRVc4IV+UmPoBaDzz7gLcYuPEl7pswIDAQAB
-AoGAGO+q5+83ENtu+JIjDwRnanmEV/C13biYO4WI2d5kytTw+VL9bt52yfcFGt2I
-yvJZlTdn7T340svhVIzg3ksTmp1xQk3zh6zR00zQy45kYwY8uyd8Xfh2IsnpByoc
-h2jWVX6LSqi1Iy3RxanHmMYPSMy15otsjwlwnnTAHLnnvzECQQDvw3TL90DucQSD
-S0h6DWAGakaiOMhY/PpFbTsjzw+uG+Up65tpz4QqPbsXfoReeK0CQIuyE/LlYoJl
-VOlIsL6HAkEA6rh4zsWi6KVTGa7qd5x70TEgxeMMAW1qUbak1THxeZTFYnyvucBz
-i+VQvHEVnCadhVpHIwbBNUeOyS5DXjj6dQJAA0Caf/3Noq5jykgmJomx6MReSusM
-RLDB0FlH+Rdg9hKozCXHCOtoto350LrFnuZyKlqnynWc0OHCNQ+uzm6fVwJAbtyW
-YsNCQLPlXhoZsEj+yj10B0NH5lyxfMrRa8jdDtnPqMbPkOJvMMIssfSPimNKvzN2
-qfqEww97R1ZMh3JOCQJBAIIwGHBN5rDGIb4CgR+PLsh8bve1X+gO8UnOYJXa/Uzx
-gAXE0uzHNH6rNSG0V/IQnFYlSHpNJGgcdSl+MZNLldQ=
------END RSA PRIVATE KEY-----
diff --git a/test/openssl/test_config.rb b/test/openssl/test_config.rb
index dba66b0802..f65392c18d 100644
--- a/test/openssl/test_config.rb
+++ b/test/openssl/test_config.rb
@@ -120,6 +120,49 @@ __EOC__
     assert_equal("error in line 7: missing close square bracket", excn.message)
   end
 
+  def test_s_parse_include
+    in_tmpdir("ossl-config-include-test") do |dir|
+      Dir.mkdir("child")
+      File.write("child/a.conf", <<~__EOC__)
+        [default]
+        file-a = a.conf
+        [sec-a]
+        a = 123
+      __EOC__
+      File.write("child/b.cnf", <<~__EOC__)
+        [default]
+        file-b = b.cnf
+        [sec-b]
+        b = 123
+      __EOC__
+      File.write("include-child.conf", <<~__EOC__)
+        key_outside_section = value_a
+        .include child
+      __EOC__
+
+      include_file = <<~__EOC__
+        [default]
+        file-main = unnamed
+        [sec-main]
+        main = 123
+        .include = include-child.conf
+      __EOC__
+
+      # Include a file by relative path
+      c1 = OpenSSL::Config.parse(include_file)
+      assert_equal(["default", "sec-a", "sec-b", "sec-main"], c1.sections.sort)
+      assert_equal(["file-main", "file-a", "file-b"], c1["default"].keys)
+      assert_equal({"a" => "123"}, c1["sec-a"])
+      assert_equal({"b" => "123"}, c1["sec-b"])
+      assert_equal({"main" => "123", "key_outside_section" => "value_a"}, c1["sec-main"])
+
+      # Relative paths are from the working directory
+      assert_raise(OpenSSL::ConfigError) do
+        Dir.chdir("child") { OpenSSL::Config.parse(include_file) }
+      end
+    end
+  end
+
   def test_s_load
     # alias of new
     c = OpenSSL::Config.load
@@ -211,45 +254,54 @@ __EOC__
 
   def test_sections
     assert_equal(['CA_default', 'ca', 'default'], @it.sections.sort)
-    @it['new_section'] = {'foo' => 'bar'}
-    assert_equal(['CA_default', 'ca', 'default', 'new_section'], @it.sections.sort)
-    @it['new_section'] = {}
-    assert_equal(['CA_default', 'ca', 'default', 'new_section'], @it.sections.sort)
+    # OpenSSL::Config#[]= is deprecated
+    EnvUtil.suppress_warning do
+      @it['new_section'] = {'foo' => 'bar'}
+      assert_equal(['CA_default', 'ca', 'default', 'new_section'], @it.sections.sort)
+      @it['new_section'] = {}
+      assert_equal(['CA_default', 'ca', 'default', 'new_section'], @it.sections.sort)
+    end
   end
 
   def test_add_value
-    c = OpenSSL::Config.new
-    assert_equal("", c.to_s)
-    # add key
-    c.add_value('default', 'foo', 'bar')
-    assert_equal("[ default ]\nfoo=bar\n\n", c.to_s)
-    # add another key
-    c.add_value('default', 'baz', 'qux')
-    assert_equal('bar', c['default']['foo'])
-    assert_equal('qux', c['default']['baz'])
-    # update the value
-    c.add_value('default', 'baz', 'quxxx')
-    assert_equal('bar', c['default']['foo'])
-    assert_equal('quxxx', c['default']['baz'])
-    # add section and key
-    c.add_value('section', 'foo', 'bar')
-    assert_equal('bar', c['default']['foo'])
-    assert_equal('quxxx', c['default']['baz'])
-    assert_equal('bar', c['section']['foo'])
+    # OpenSSL::Config#add_value is deprecated
+    EnvUtil.suppress_warning do
+      c = OpenSSL::Config.new
+      assert_equal("", c.to_s)
+      # add key
+      c.add_value('default', 'foo', 'bar')
+      assert_equal("[ default ]\nfoo=bar\n\n", c.to_s)
+      # add another key
+      c.add_value('default', 'baz', 'qux')
+      assert_equal('bar', c['default']['foo'])
+      assert_equal('qux', c['default']['baz'])
+      # update the value
+      c.add_value('default', 'baz', 'quxxx')
+      assert_equal('bar', c['default']['foo'])
+      assert_equal('quxxx', c['default']['baz'])
+      # add section and key
+      c.add_value('section', 'foo', 'bar')
+      assert_equal('bar', c['default']['foo'])
+      assert_equal('quxxx', c['default']['baz'])
+      assert_equal('bar', c['section']['foo'])
+    end
   end
 
   def test_aset
-    @it['foo'] = {'bar' => 'baz'}
-    assert_equal({'bar' => 'baz'}, @it['foo'])
-    @it['foo'] = {'bar' => 'qux', 'baz' => 'quxx'}
-    assert_equal({'bar' => 'qux', 'baz' => 'quxx'}, @it['foo'])
-
-    # OpenSSL::Config is add only for now.
-    @it['foo'] = {'foo' => 'foo'}
-    assert_equal({'foo' => 'foo', 'bar' => 'qux', 'baz' => 'quxx'}, @it['foo'])
-    # you cannot override or remove any section and key.
-    @it['foo'] = {}
-    assert_equal({'foo' => 'foo', 'bar' => 'qux', 'baz' => 'quxx'}, @it['foo'])
+    # OpenSSL::Config#[]= is deprecated
+    EnvUtil.suppress_warning do
+      @it['foo'] = {'bar' => 'baz'}
+      assert_equal({'bar' => 'baz'}, @it['foo'])
+      @it['foo'] = {'bar' => 'qux', 'baz' => 'quxx'}
+      assert_equal({'bar' => 'qux', 'baz' => 'quxx'}, @it['foo'])
+
+      # OpenSSL::Config is add only for now.
+      @it['foo'] = {'foo' => 'foo'}
+      assert_equal({'foo' => 'foo', 'bar' => 'qux', 'baz' => 'quxx'}, @it['foo'])
+      # you cannot override or remove any section and key.
+      @it['foo'] = {}
+      assert_equal({'foo' => 'foo', 'bar' => 'qux', 'baz' => 'quxx'}, @it['foo'])
+    end
   end
 
   def test_each
@@ -272,32 +324,50 @@ __EOC__
   end
 
   def test_freeze
-    c = OpenSSL::Config.new
-    c['foo'] = [['key', 'value']]
-    c.freeze
+    @it.freeze
 
-    bug = '[ruby-core:18377]'
-    # RuntimeError for 1.9, TypeError for 1.8
-    e = assert_raise(TypeError, bug) do
-      c['foo'] = [['key', 'wrong']]
+    # Modifying OpenSSL::Config produces a warning
+    EnvUtil.suppress_warning do
+      bug = '[ruby-core:18377]'
+      # RuntimeError for 1.9, TypeError for 1.8
+      e = assert_raise(TypeError, bug) do
+        @it['foo'] = [['key', 'wrong']]
+      end
+      assert_match(/can't modify/, e.message, bug)
     end
-    assert_match(/can't modify/, e.message, bug)
   end
 
   def test_dup
     assert(!@it.sections.empty?)
     c = @it.dup
     assert_equal(@it.sections.sort, c.sections.sort)
-    @it['newsection'] = {'a' => 'b'}
-    assert_not_equal(@it.sections.sort, c.sections.sort)
+    # OpenSSL::Config#[]= is deprecated
+    EnvUtil.suppress_warning do
+      @it['newsection'] = {'a' => 'b'}
+      assert_not_equal(@it.sections.sort, c.sections.sort)
+    end
   end
 
   def test_clone
     assert(!@it.sections.empty?)
     c = @it.clone
     assert_equal(@it.sections.sort, c.sections.sort)
-    @it['newsection'] = {'a' => 'b'}
-    assert_not_equal(@it.sections.sort, c.sections.sort)
+    # OpenSSL::Config#[]= is deprecated
+    EnvUtil.suppress_warning do
+      @it['newsection'] = {'a' => 'b'}
+      assert_not_equal(@it.sections.sort, c.sections.sort)
+    end
+  end
+
+  private
+
+  def in_tmpdir(*args)
+    Dir.mktmpdir(*args) do |dir|
+      dir = File.realpath(dir)
+      Dir.chdir(dir) do
+        yield dir
+      end
+    end
   end
 end
 
diff --git a/test/openssl/test_digest.rb b/test/openssl/test_digest.rb
index e47fc0a356..0bf66b826a 100644
--- a/test/openssl/test_digest.rb
+++ b/test/openssl/test_digest.rb
@@ -98,6 +98,18 @@ class OpenSSL::TestDigest < OpenSSL::TestCase
     assert_equal(sha512_a, encode16(OpenSSL::Digest::SHA512.digest("a")))
   end
 
+  def test_sha512_truncate
+    pend "SHA512_224 is not implemented" unless OpenSSL::Digest.const_defined?(:SHA512_224)
+    sha512_224_a = "d5cdb9ccc769a5121d4175f2bfdd13d6310e0d3d361ea75d82108327"
+    sha512_256_a = "455e518824bc0601f9fb858ff5c37d417d67c2f8e0df2babe4808858aea830f8"
+
+    assert_equal(sha512_224_a, OpenSSL::Digest::SHA512_224.hexdigest("a"))
+    assert_equal(sha512_256_a, OpenSSL::Digest::SHA512_256.hexdigest("a"))
+
+    assert_equal(sha512_224_a, encode16(OpenSSL::Digest::SHA512_224.digest("a")))
+    assert_equal(sha512_256_a, encode16(OpenSSL::Digest::SHA512_256.digest("a")))
+  end
+
   def test_sha3
     pend "SHA3 is not implemented" unless OpenSSL::Digest.const_defined?(:SHA3_224)
     s224 = '6b4e03423667dbb73b6e15454f0eb1abd4597f9a1b078e3f5b5a6bc7'
diff --git a/test/openssl/test_pair.rb b/test/openssl/test_pair.rb
index a77abfd923..8316ec2a9c 100644
--- a/test/openssl/test_pair.rb
+++ b/test/openssl/test_pair.rb
@@ -156,20 +156,6 @@ module OpenSSL::TestPairM
     }
   end
 
-  def test_puts_meta
-    ssl_pair {|s1, s2|
-      begin
-        old = $/
-        EnvUtil.suppress_warning {$/ = '*'}
-        s1.puts 'a'
-      ensure
-        EnvUtil.suppress_warning {$/ = old}
-      end
-      s1.close
-      assert_equal("a\n", s2.read)
-    }
-  end
-
   def test_puts_empty
     ssl_pair {|s1, s2|
       s1.puts
diff --git a/test/openssl/test_ssl.rb b/test/openssl/test_ssl.rb
index cce1a4472e..ce899ba085 100644
--- a/test/openssl/test_ssl.rb
+++ b/test/openssl/test_ssl.rb
@@ -89,13 +89,17 @@ class OpenSSL::TestSSL < OpenSSL::SSLTestCase
   def test_socket_open_with_local_address_port_context
     start_server { |port|
       begin
+        # Guess a free port number
+        random_port = rand(49152..65535)
         ctx = OpenSSL::SSL::SSLContext.new
-        ssl = OpenSSL::SSL::SSLSocket.open("127.0.0.1", port, "127.0.0.1", 8000, context: ctx)
+        ssl = OpenSSL::SSL::SSLSocket.open("127.0.0.1", port, "127.0.0.1", random_port, context: ctx)
         ssl.sync_close = true
         ssl.connect
 
-        assert_equal ssl.context, ctx
+        assert_equal ctx, ssl.context
+        assert_equal random_port, ssl.io.local_address.ip_port
         ssl.puts "abc"; assert_equal "abc\n", ssl.gets
+      rescue Errno::EADDRINUSE
       ensure
         ssl&.close
       end
@@ -127,7 +131,7 @@ class OpenSSL::TestSSL < OpenSSL::SSLTestCase
     add0_chain_supported = openssl?(1, 0, 2)
 
     if add0_chain_supported
-      ca2_key = Fixtures.pkey("rsa2048")
+      ca2_key = Fixtures.pkey("rsa-3")
       ca2_exts = [
         ["basicConstraints", "CA:TRUE", true],
         ["keyUsage", "cRLSign, keyCertSign", true],
@@ -186,9 +190,31 @@ class OpenSSL::TestSSL < OpenSSL::SSLTestCase
   end
 
   def test_add_certificate_chain_file
-    pend "The current server.crt seems too short for OpenSSL 1.1.1d or later" if OpenSSL::OPENSSL_VERSION_NUMBER >= 0x10101040
-    ctx = OpenSSL::SSL::SSLContext.new
-    assert ctx.add_certificate_chain_file(Fixtures.file_path("chain", "server.crt"))
+    # Create chain certificates file
+    certs = Tempfile.open { |f| f << @svr_cert.to_pem << @ca_cert.to_pem; f }
+    pkey = Tempfile.open { |f| f << @svr_key.to_pem; f }
+
+    ctx_proc = -> ctx {
+      # FIXME: This is a temporary test case written just to match the current
+      # state. ctx.add_certificate_chain_file should take two arguments.
+      ctx.add_certificate_chain_file(certs.path)
+      # # Unset values set by start_server
+      # ctx.cert = ctx.key = ctx.extra_chain_cert = nil
+      # assert_nothing_raised { ctx.add_certificate_chain_file(certs.path, pkey.path) }
+    }
+
+    start_server(ctx_proc: ctx_proc) { |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)
+
+        ssl.puts "abc"; assert_equal "abc\n", ssl.gets
+      }
+    }
+  ensure
+    certs&.unlink
+    pkey&.unlink
   end
 
   def test_sysread_and_syswrite
@@ -207,19 +233,6 @@ class OpenSSL::TestSSL < OpenSSL::SSLTestCase
     }
   end
 
-  # TODO fix this test
-  # def test_sysread_nonblock_and_syswrite_nonblock_keywords
-  #   start_server do |port|
-  #     server_connect(port) do |ssl|
-  #       assert_warning("") do
-  #         ssl.send(:syswrite_nonblock, "12", exception: false)
-  #         ssl.send(:sysread_nonblock, 1, exception: false) rescue nil
-  #         ssl.send(:sysread_nonblock, 1, String.new, exception: false) rescue nil
-  #       end
-  #     end
-  #   end
-  # end
-
   def test_sync_close
     start_server do |port|
       begin
@@ -497,12 +510,14 @@ class OpenSSL::TestSSL < OpenSSL::SSLTestCase
       ctx = OpenSSL::SSL::SSLContext.new
       ctx.verify_mode = OpenSSL::SSL::VERIFY_NONE
       server_connect(port, ctx) { |ssl|
+        ssl.puts "abc"; ssl.gets
+
         client_finished = ssl.finished_message
         client_peer_finished = ssl.peer_finished_message
-        sleep 0.05
-        ssl.send :stop
       }
     }
+    assert_not_nil(server_finished)
+    assert_not_nil(client_finished)
     assert_equal(server_finished, client_peer_finished)
     assert_equal(server_peer_finished, client_finished)
   end
@@ -924,6 +939,46 @@ 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
@@ -1377,11 +1432,16 @@ end
         ctx.ssl_version = :TLSv1_2
         ctx.ciphers = "kRSA"
       }
-      start_server(ctx_proc: ctx_proc1) do |port|
+      start_server(ctx_proc: ctx_proc1, ignore_listener_error: true) do |port|
         ctx = OpenSSL::SSL::SSLContext.new
         ctx.ssl_version = :TLSv1_2
         ctx.ciphers = "kRSA"
-        server_connect(port, ctx) { |ssl| assert_nil ssl.tmp_key }
+        begin
+          server_connect(port, ctx) { |ssl| assert_nil ssl.tmp_key }
+        rescue OpenSSL::SSL::SSLError
+          # kRSA seems disabled
+          raise unless $!.message =~ /no cipher/
+        end
       end
     end