openssl: import v2.2.1

Bring the local copy of ruby/openssl in sync with the upstream gem
release v2.2.1. The commits happened in the upstream repository can be
found at:

	https://github.com/ruby/openssl/compare/v2.2.0...v2.2.1

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

18 files changed, 375 insertions, 102 deletions

diff --git a/ext/openssl/History.md b/ext/openssl/History.md
index a4a82a146c..46435f9be6 100644
--- a/ext/openssl/History.md
+++ b/ext/openssl/History.md
@@ -1,3 +1,20 @@
+Version 2.2.1
+=============
+
+Merged changes in 2.1.3. Additionally, the following issues are fixed by this
+release.
+
+Bug fixes
+---------
+
+* Fix crash in `OpenSSL::Timestamp::{Request,Response,TokenInfo}.new` when
+  invalid arguments are given.
+  [[GitHub #407]](https://github.com/ruby/openssl/pull/407)
+* Fix `OpenSSL::Timestamp::Factory#create_timestamp` with LibreSSL on platforms
+  where `time_t` has a different size from `long`.
+  [[GitHub #454]](https://github.com/ruby/openssl/pull/454)
+
+
 Version 2.2.0
 =============
 
@@ -75,6 +92,42 @@ Notable changes
   [[GitHub #297]](https://github.com/ruby/openssl/pull/297)
 
 
+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 693e55cd97..e13595c7c7 100644
--- a/ext/openssl/extconf.rb
+++ b/ext/openssl/extconf.rb
@@ -33,9 +33,6 @@ if $mswin || $mingw
   have_library("ws2_32")
 end
 
-Logging::message "=== Checking for required stuff... ===\n"
-result = pkg_config("openssl") && have_header("openssl/ssl.h")
-
 if $mingw
   append_cflags '-D_FORTIFY_SOURCE=2'
   append_ldflags '-fstack-protector'
@@ -92,19 +89,33 @@ 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"
@@ -116,10 +127,6 @@ engines.each { |name|
   have_func("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/lib/openssl/version.rb b/ext/openssl/lib/openssl/version.rb
index 9c7515ba0f..d541cbf162 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"
+  VERSION = "2.2.1"
 end
diff --git a/ext/openssl/openssl.gemspec b/ext/openssl/openssl.gemspec
index 471a3c4265..ebbd0923dd 100644
--- a/ext/openssl/openssl.gemspec
+++ b/ext/openssl/openssl.gemspec
@@ -1,6 +1,6 @@
 Gem::Specification.new do |spec|
   spec.name          = "openssl"
-  spec.version       = "2.2.0"
+  spec.version       = "2.2.1"
   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.}
@@ -17,6 +17,7 @@ Gem::Specification.new do |spec|
 
   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"
diff --git a/ext/openssl/ossl_bn.c b/ext/openssl/ossl_bn.c
index d94b8e375c..bec37299f7 100644
--- a/ext/openssl/ossl_bn.c
+++ b/ext/openssl/ossl_bn.c
@@ -453,7 +453,7 @@ 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);			\
 	}						\
@@ -479,7 +479,7 @@ 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);			\
 	}						\
@@ -512,7 +512,7 @@ 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);				\
 	}							\
@@ -556,11 +556,21 @@ 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:
@@ -609,7 +619,7 @@ 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);				\
 	}							\
@@ -651,7 +661,7 @@ 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;					\
@@ -711,7 +721,7 @@ 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);		\
 	}						\
@@ -741,7 +751,7 @@ 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;					\
     }
@@ -780,7 +790,7 @@ 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);				\
 	}							\
@@ -809,7 +819,7 @@ 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_cipher.c b/ext/openssl/ossl_cipher.c
index 0b78f40b72..5b92fc39f0 100644
--- a/ext/openssl/ossl_cipher.c
+++ b/ext/openssl/ossl_cipher.c
@@ -814,6 +814,31 @@ ossl_cipher_block_size(VALUE self)
 }
 
 /*
+ *  call-seq:
+ *     cipher.ccm_data_len = integer -> integer
+ *
+ *  Sets the length of the plaintext / ciphertext message that will be
+ *  processed in CCM mode. Make sure to call this method after #key= and
+ *  #iv= have been set, and before #auth_data=.
+ *
+ *  Only call this method after calling Cipher#encrypt or Cipher#decrypt.
+ */
+static VALUE
+ossl_cipher_set_ccm_data_len(VALUE self, VALUE data_len)
+{
+    int in_len, out_len;
+    EVP_CIPHER_CTX *ctx;
+
+    in_len = NUM2INT(data_len);
+
+    GetCipher(self, ctx);
+    if (EVP_CipherUpdate(ctx, NULL, &out_len, NULL, in_len) != 1)
+        ossl_raise(eCipherError, NULL);
+
+    return data_len;
+}
+
+/*
  * INIT
  */
 void
@@ -1043,6 +1068,7 @@ Init_ossl_cipher(void)
     rb_define_method(cCipher, "iv_len", ossl_cipher_iv_length, 0);
     rb_define_method(cCipher, "block_size", ossl_cipher_block_size, 0);
     rb_define_method(cCipher, "padding=", ossl_cipher_set_padding, 1);
+    rb_define_method(cCipher, "ccm_data_len=", ossl_cipher_set_ccm_data_len, 1);
 
     id_auth_tag_len = rb_intern_const("auth_tag_len");
     id_key_set = rb_intern_const("key_set");
diff --git a/ext/openssl/ossl_digest.c b/ext/openssl/ossl_digest.c
index e2157cb02f..6294fa2acf 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);
@@ -398,6 +396,12 @@ 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_pkey_ec.c b/ext/openssl/ossl_pkey_ec.c
index fc2bc6c815..1d105abd35 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 4b7efa39f5..7654be12ee 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,
 };
@@ -616,7 +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;
 }
 
@@ -686,7 +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);
@@ -908,7 +921,7 @@ 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))) {
@@ -1527,6 +1540,14 @@ 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);
@@ -1535,7 +1556,7 @@ 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,
 };
@@ -1691,6 +1712,11 @@ 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)
@@ -1847,26 +1873,36 @@ 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 {
@@ -1883,6 +1919,7 @@ ossl_ssl_read_internal(int argc, VALUE *argv, VALUE self, int nonblock)
 		}
                 /* fall through */
 	    default:
+                rb_str_unlocktmp(str);
 		ossl_raise(eSSLError, "SSL_read");
 	    }
         }
@@ -1953,21 +1990,21 @@ 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;
@@ -1982,6 +2019,16 @@ 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");
@@ -2997,6 +3044,7 @@ Init_ossl_ssl(void)
     id_tmp_dh_callback = rb_intern_const("tmp_dh_callback");
     id_tmp_ecdh_callback = rb_intern_const("tmp_ecdh_callback");
     id_npn_protocols_encoded = rb_intern_const("npn_protocols_encoded");
+    id_each = rb_intern_const("each");
 
 #define DefIVarID(name) do \
     id_i_##name = rb_intern_const("@"#name); while (0)
diff --git a/ext/openssl/ossl_ts.c b/ext/openssl/ossl_ts.c
index 692c0d620f..cff9b7bfff 100644
--- a/ext/openssl/ossl_ts.c
+++ b/ext/openssl/ossl_ts.c
@@ -205,8 +205,10 @@ ossl_ts_req_initialize(int argc, VALUE *argv, VALUE self)
     in = ossl_obj2bio(&arg);
     ts_req = d2i_TS_REQ_bio(in, &ts_req);
     BIO_free(in);
-    if (!ts_req)
+    if (!ts_req) {
+        DATA_PTR(self) = NULL;
         ossl_raise(eTimestampError, "Error when decoding the timestamp request");
+    }
     DATA_PTR(self) = ts_req;
 
     return self;
@@ -529,8 +531,10 @@ ossl_ts_resp_initialize(VALUE self, VALUE der)
     in  = ossl_obj2bio(&der);
     ts_resp = d2i_TS_RESP_bio(in, &ts_resp);
     BIO_free(in);
-    if (!ts_resp)
+    if (!ts_resp) {
+        DATA_PTR(self) = NULL;
         ossl_raise(eTimestampError, "Error when decoding the timestamp response");
+    }
     DATA_PTR(self) = ts_resp;
 
     return self;
@@ -871,8 +875,10 @@ ossl_ts_token_info_initialize(VALUE self, VALUE der)
     in  = ossl_obj2bio(&der);
     info = d2i_TS_TST_INFO_bio(in, &info);
     BIO_free(in);
-    if (!info)
+    if (!info) {
+        DATA_PTR(self) = NULL;
         ossl_raise(eTimestampError, "Error when decoding the timestamp token info");
+    }
     DATA_PTR(self) = info;
 
     return self;
@@ -1074,7 +1080,11 @@ ossl_tsfac_serial_cb(struct TS_resp_ctx *ctx, void *data)
 }
 
 static int
+#if !defined(LIBRESSL_VERSION_NUMBER)
 ossl_tsfac_time_cb(struct TS_resp_ctx *ctx, void *data, long *sec, long *usec)
+#else
+ossl_tsfac_time_cb(struct TS_resp_ctx *ctx, void *data, time_t *sec, long *usec)
+#endif
 {
     *sec = *((long *)data);
     *usec = 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_cipher.rb b/test/openssl/test_cipher.rb
index 178f5aba0e..65b36dd180 100644
--- a/test/openssl/test_cipher.rb
+++ b/test/openssl/test_cipher.rb
@@ -174,6 +174,48 @@ class OpenSSL::TestCipher < OpenSSL::TestCase
     assert_not_predicate(cipher, :authenticated?)
   end
 
+  def test_aes_ccm
+    # RFC 3610 Section 8, Test Case 1
+    key = ["c0c1c2c3c4c5c6c7c8c9cacbcccdcecf"].pack("H*")
+    iv =  ["00000003020100a0a1a2a3a4a5"].pack("H*")
+    aad = ["0001020304050607"].pack("H*")
+    pt =  ["08090a0b0c0d0e0f101112131415161718191a1b1c1d1e"].pack("H*")
+    ct =  ["588c979a61c663d2f066d0c2c0f989806d5f6b61dac384"].pack("H*")
+    tag = ["17e8d12cfdf926e0"].pack("H*")
+
+    kwargs = {auth_tag_len: 8, iv_len: 13, key: key, iv: iv}
+    cipher = new_encryptor("aes-128-ccm", **kwargs, ccm_data_len: pt.length, auth_data: aad)
+    assert_equal ct, cipher.update(pt) << cipher.final
+    assert_equal tag, cipher.auth_tag
+    cipher = new_decryptor("aes-128-ccm", **kwargs, ccm_data_len: ct.length, auth_tag: tag, auth_data: aad)
+    assert_equal pt, cipher.update(ct) << cipher.final
+
+    # truncated tag is accepted
+    cipher = new_encryptor("aes-128-ccm", **kwargs, ccm_data_len: pt.length, auth_data: aad)
+    assert_equal ct, cipher.update(pt) << cipher.final
+    assert_equal tag[0, 8], cipher.auth_tag(8)
+    cipher = new_decryptor("aes-128-ccm", **kwargs, ccm_data_len: ct.length, auth_tag: tag[0, 8], auth_data: aad)
+    assert_equal pt, cipher.update(ct) << cipher.final
+
+    # wrong tag is rejected
+    tag2 = tag.dup
+    tag2.setbyte(-1, (tag2.getbyte(-1) + 1) & 0xff)
+    cipher = new_decryptor("aes-128-ccm", **kwargs, ccm_data_len: ct.length, auth_tag: tag2, auth_data: aad)
+    assert_raise(OpenSSL::Cipher::CipherError) { cipher.update(ct) }
+
+    # wrong aad is rejected
+    aad2 = aad[0..-2] << aad[-1].succ
+    cipher = new_decryptor("aes-128-ccm", **kwargs, ccm_data_len: ct.length, auth_tag: tag, auth_data: aad2)
+    assert_raise(OpenSSL::Cipher::CipherError) { cipher.update(ct) }
+
+    # wrong ciphertext is rejected
+    ct2 = ct[0..-2] << ct[-1].succ
+    cipher = new_decryptor("aes-128-ccm", **kwargs, ccm_data_len: ct2.length, auth_tag: tag, auth_data: aad)
+    assert_raise(OpenSSL::Cipher::CipherError) { cipher.update(ct2) }
+  end if has_cipher?("aes-128-ccm") &&
+         OpenSSL::Cipher.new("aes-128-ccm").authenticated? &&
+         OpenSSL::OPENSSL_VERSION_NUMBER >= 0x10101000  # version >= v1.1.1
+
   def test_aes_gcm
     # GCM spec Appendix B Test Case 4
     key = ["feffe9928665731c6d6a8f9467308308"].pack("H*")
diff --git a/test/openssl/test_config.rb b/test/openssl/test_config.rb
index f65392c18d..e041c1a3ba 100644
--- a/test/openssl/test_config.rb
+++ b/test/openssl/test_config.rb
@@ -61,14 +61,14 @@ foo\\bar::foo\\bar = baz
 [default1  default2]\t\t  # space is allowed in section name
           fo =b  ar       # space allowed in value
 [emptysection]
- [doller ]
+ [dollar ]
 foo=bar
 bar = $(foo)
 baz = 123$(default::bar)456${foo}798
 qux = ${baz}
 quxx = $qux.$qux
 __EOC__
-    assert_equal(['default', 'default1  default2', 'doller', 'emptysection', 'foo', 'foo\\bar'], c.sections.sort)
+    assert_equal(['default', 'default1  default2', 'dollar', 'emptysection', 'foo', 'foo\\bar'], c.sections.sort)
     assert_equal(['', 'a', 'bar', 'baz', 'd', 'dq', 'dq2', 'esc', 'foo\\bar', 'sq'], c['default'].keys.sort)
     assert_equal('c', c['default'][''])
     assert_equal('', c['default']['a'])
@@ -84,12 +84,12 @@ __EOC__
     assert_equal('baz', c['foo\\bar']['foo\\bar'])
     assert_equal('b  ar', c['default1  default2']['fo'])
 
-    # dolloer
-    assert_equal('bar', c['doller']['foo'])
-    assert_equal('bar', c['doller']['bar'])
-    assert_equal('123baz456bar798', c['doller']['baz'])
-    assert_equal('123baz456bar798', c['doller']['qux'])
-    assert_equal('123baz456bar798.123baz456bar798', c['doller']['quxx'])
+    # dollar
+    assert_equal('bar', c['dollar']['foo'])
+    assert_equal('bar', c['dollar']['bar'])
+    assert_equal('123baz456bar798', c['dollar']['baz'])
+    assert_equal('123baz456bar798', c['dollar']['qux'])
+    assert_equal('123baz456bar798.123baz456bar798', c['dollar']['quxx'])
 
     excn = assert_raise(OpenSSL::ConfigError) do
       OpenSSL::Config.parse("foo = $bar")
diff --git a/test/openssl/test_ssl.rb b/test/openssl/test_ssl.rb
index 6095d545b5..2d9ee7bc70 100644
--- a/test/openssl/test_ssl.rb
+++ b/test/openssl/test_ssl.rb
@@ -257,7 +257,10 @@ 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
@@ -303,6 +306,8 @@ 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
@@ -481,6 +486,7 @@ class OpenSSL::TestSSL < OpenSSL::SSLTestCase
     }) { |port|
       ctx = OpenSSL::SSL::SSLContext.new
       ctx.verify_mode = OpenSSL::SSL::VERIFY_NONE
+      ctx.max_version = :TLS1_2 if libressl?(3, 2, 0) && !libressl?(3, 3, 0)
       server_connect(port, ctx) { |ssl|
         ssl.puts "abc"; ssl.gets
 
@@ -868,11 +874,13 @@ 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
     }
@@ -893,6 +901,7 @@ 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)
@@ -1581,12 +1590,13 @@ 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|
@@ -1595,13 +1605,9 @@ 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
       }
@@ -1625,6 +1631,26 @@ 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 89726d4463..a98efdae2a 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_ts.rb b/test/openssl/test_ts.rb
index 8e31a7d28d..7cb1a1fe8e 100644
--- a/test/openssl/test_ts.rb
+++ b/test/openssl/test_ts.rb
@@ -181,6 +181,12 @@ _end_of_pem_
     assert_equal(42, qer2.nonce)
   end
 
+  def test_request_invalid_asn1
+    assert_raise(OpenSSL::Timestamp::TimestampError) do
+      OpenSSL::Timestamp::Request.new("*" * 44)
+    end
+  end
+
   def test_response_constants
     assert_equal(0, OpenSSL::Timestamp::Response::GRANTED)
     assert_equal(1, OpenSSL::Timestamp::Response::GRANTED_WITH_MODS)
@@ -338,6 +344,12 @@ _end_of_pem_
     end
   end
 
+  def test_response_invalid_asn1
+    assert_raise(OpenSSL::Timestamp::TimestampError) do
+      OpenSSL::Timestamp::Response.new("*" * 44)
+    end
+  end
+
   def test_no_cert_requested
     req = OpenSSL::Timestamp::Request.new
     req.algorithm = "SHA1"
@@ -590,6 +602,12 @@ _end_of_pem_
     assert_equal(123, info.nonce)
   end
 
+  def test_token_info_invalid_asn1
+    assert_raise(OpenSSL::Timestamp::TimestampError) do
+      OpenSSL::Timestamp::TokenInfo.new("*" * 44)
+    end
+  end
+
   private
 
   def assert_cert expected, actual
diff --git a/test/openssl/test_x509store.rb b/test/openssl/test_x509store.rb
index 1cbc73d539..e9602e3434 100644
--- a/test/openssl/test_x509store.rb
+++ b/test/openssl/test_x509store.rb
@@ -66,7 +66,7 @@ class OpenSSL::TestX509Store < OpenSSL::TestCase
     ee1_cert = issue_cert(@ee1, @dsa256, 10, ee_exts, ca2_cert, @rsa1024)
     ee2_cert = issue_cert(@ee2, @dsa512, 20, ee_exts, ca2_cert, @rsa1024)
     ee3_cert = issue_cert(@ee2, @dsa512, 30,  ee_exts, ca2_cert, @rsa1024,
-                          not_before: now-100, not_after: now-50)
+                          not_before: now-100, not_after: now-1)
     ee4_cert = issue_cert(@ee2, @dsa512, 40, ee_exts, ca2_cert, @rsa1024,
                           not_before: now+1000, not_after: now+2000,)
 
@@ -128,7 +128,7 @@ class OpenSSL::TestX509Store < OpenSSL::TestCase
     assert_equal(@ee2.to_der, chain[0].subject.to_der)
     assert_equal(@ca2.to_der, chain[1].subject.to_der)
     assert_equal(@ca1.to_der, chain[2].subject.to_der)
-    assert_equal(false, store.verify(ee3_cert), "now=#{now.inspect} Time.now=#{Time.now.inspect} store=#{store.inspect} ee3_cert=#{ee3_cert.inspect}")
+    assert_equal(false, store.verify(ee3_cert))
     assert_equal(OpenSSL::X509::V_ERR_CERT_HAS_EXPIRED, store.error)
     assert_match(/expire/i, store.error_string)
     assert_equal(false, store.verify(ee4_cert))
diff --git a/test/openssl/utils.rb b/test/openssl/utils.rb
index 3776fbac4e..ee734d98a4 100644
--- a/test/openssl/utils.rb
+++ b/test/openssl/utils.rb
@@ -199,6 +199,14 @@ 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)