openssl 2.2.1 → 3.2.0

data/ext/openssl/ossl_ssl.c

@@ -11,11 +11,15 @@
  */
 #include "ossl.h"
 
+#ifndef OPENSSL_NO_SOCK
 #define numberof(ary) (int)(sizeof(ary)/sizeof((ary)[0]))
 
+#if !defined(OPENSSL_NO_NEXTPROTONEG) && !OSSL_IS_LIBRESSL
+# define OSSL_USE_NEXTPROTONEG
+#endif
+
 #if !defined(TLS1_3_VERSION) && \
-    defined(LIBRESSL_VERSION_NUMBER) && \
-    LIBRESSL_VERSION_NUMBER >= 0x3020000fL
+    OSSL_LIBRESSL_PREREQ(3, 2, 0) && !OSSL_LIBRESSL_PREREQ(3, 4, 0)
 #  define TLS1_3_VERSION 0x0304
 #endif
 
@@ -30,7 +34,6 @@
 } while (0)
 
 VALUE mSSL;
-static VALUE mSSLExtConfig;
 static VALUE eSSLError;
 VALUE cSSLContext;
 VALUE cSSLSocket;
@@ -38,26 +41,23 @@ VALUE cSSLSocket;
 static VALUE eSSLErrorWaitReadable;
 static VALUE eSSLErrorWaitWritable;
 
-static ID id_call, ID_callback_state, id_tmp_dh_callback, id_tmp_ecdh_callback,
+static ID id_call, ID_callback_state, id_tmp_dh_callback,
 	  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,
 	  id_i_verify_depth, id_i_verify_callback, id_i_client_ca,
 	  id_i_renegotiation_cb, id_i_cert, id_i_key, id_i_extra_chain_cert,
-	  id_i_client_cert_cb, id_i_tmp_ecdh_callback, id_i_timeout,
+	  id_i_client_cert_cb, id_i_timeout,
 	  id_i_session_id_context, id_i_session_get_cb, id_i_session_new_cb,
 	  id_i_session_remove_cb, id_i_npn_select_cb, id_i_npn_protocols,
 	  id_i_alpn_select_cb, id_i_alpn_protocols, id_i_servername_cb,
-	  id_i_verify_hostname;
+	  id_i_verify_hostname, id_i_keylog_cb;
 static ID id_i_io, id_i_context, id_i_hostname;
 
 static int ossl_ssl_ex_vcb_idx;
 static int ossl_ssl_ex_ptr_idx;
 static int ossl_sslctx_ex_ptr_idx;
-#if !defined(HAVE_X509_STORE_UP_REF)
-static int ossl_sslctx_ex_store_p;
-#endif
 
 static void
 ossl_sslctx_mark(void *ptr)
@@ -69,12 +69,7 @@ ossl_sslctx_mark(void *ptr)
 static void
 ossl_sslctx_free(void *ptr)
 {
-    SSL_CTX *ctx = ptr;
-#if !defined(HAVE_X509_STORE_UP_REF)
-    if (ctx && SSL_CTX_get_ex_data(ctx, ossl_sslctx_ex_store_p))
-	ctx->cert_store = NULL;
-#endif
-    SSL_CTX_free(ctx);
+    SSL_CTX_free(ptr);
 }
 
 static const rb_data_type_t ossl_sslctx_type = {
@@ -82,7 +77,7 @@ static const rb_data_type_t ossl_sslctx_type = {
     {
         ossl_sslctx_mark, ossl_sslctx_free,
     },
-    0, 0, RUBY_TYPED_FREE_IMMEDIATELY,
+    0, 0, RUBY_TYPED_FREE_IMMEDIATELY | RUBY_TYPED_WB_PROTECTED,
 };
 
 static VALUE
@@ -96,7 +91,7 @@ ossl_sslctx_s_alloc(VALUE klass)
     VALUE obj;
 
     obj = TypedData_Wrap_Struct(klass, &ossl_sslctx_type, 0);
-#if OPENSSL_VERSION_NUMBER >= 0x10100000 && !defined(LIBRESSL_VERSION_NUMBER)
+#if OPENSSL_VERSION_NUMBER >= 0x10100000 || defined(LIBRESSL_VERSION_NUMBER)
     ctx = SSL_CTX_new(TLS_method());
 #else
     ctx = SSL_CTX_new(SSLv23_method());
@@ -108,14 +103,15 @@ ossl_sslctx_s_alloc(VALUE klass)
     RTYPEDDATA_DATA(obj) = ctx;
     SSL_CTX_set_ex_data(ctx, ossl_sslctx_ex_ptr_idx, (void *)obj);
 
-#if !defined(OPENSSL_NO_EC) && defined(HAVE_SSL_CTX_SET_ECDH_AUTO)
+#if !defined(OPENSSL_NO_EC) && OPENSSL_VERSION_NUMBER < 0x10100000 && \
+    !defined(LIBRESSL_VERSION_NUMBER)
     /* We use SSL_CTX_set1_curves_list() to specify the curve used in ECDH. It
      * allows to specify multiple curve names and OpenSSL will select
      * automatically from them. In OpenSSL 1.0.2, the automatic selection has to
-     * be enabled explicitly. But OpenSSL 1.1.0 removed the knob and it is
-     * always enabled. To uniform the behavior, we enable the automatic
-     * selection also in 1.0.2. Users can still disable ECDH by removing ECDH
-     * cipher suites by SSLContext#ciphers=. */
+     * be enabled explicitly. OpenSSL 1.1.0 and LibreSSL 2.6.1 removed the knob
+     * and it is always enabled. To uniform the behavior, we enable the
+     * automatic selection also in 1.0.2. Users can still disable ECDH by
+     * removing ECDH cipher suites by SSLContext#ciphers=. */
     if (!SSL_CTX_set_ecdh_auto(ctx, 1))
 	ossl_raise(eSSLError, "SSL_CTX_set_ecdh_auto");
 #endif
@@ -244,8 +240,7 @@ ossl_client_cert_cb(SSL *ssl, X509 **x509, EVP_PKEY **pkey)
     return 1;
 }
 
-#if !defined(OPENSSL_NO_DH) || \
-    !defined(OPENSSL_NO_EC) && defined(HAVE_SSL_CTX_SET_TMP_ECDH_CALLBACK)
+#if !defined(OPENSSL_NO_DH)
 struct tmp_dh_callback_args {
     VALUE ssl_obj;
     ID id;
@@ -254,22 +249,23 @@ struct tmp_dh_callback_args {
     int keylength;
 };
 
-static EVP_PKEY *
-ossl_call_tmp_dh_callback(struct tmp_dh_callback_args *args)
+static VALUE
+ossl_call_tmp_dh_callback(VALUE arg)
 {
+    struct tmp_dh_callback_args *args = (struct tmp_dh_callback_args *)arg;
     VALUE cb, dh;
     EVP_PKEY *pkey;
 
     cb = rb_funcall(args->ssl_obj, args->id, 0);
     if (NIL_P(cb))
-	return NULL;
+	return (VALUE)NULL;
     dh = rb_funcall(cb, id_call, 3, args->ssl_obj, INT2NUM(args->is_export),
 		    INT2NUM(args->keylength));
     pkey = GetPKeyPtr(dh);
     if (EVP_PKEY_base_id(pkey) != args->type)
-	return NULL;
+	return (VALUE)NULL;
 
-    return pkey;
+    return (VALUE)pkey;
 }
 #endif
 
@@ -289,7 +285,7 @@ ossl_tmp_dh_callback(SSL *ssl, int is_export, int keylength)
     args.keylength = keylength;
     args.type = EVP_PKEY_DH;
 
-    pkey = (EVP_PKEY *)rb_protect((VALUE (*)(VALUE))ossl_call_tmp_dh_callback,
+    pkey = (EVP_PKEY *)rb_protect(ossl_call_tmp_dh_callback,
 				  (VALUE)&args, &state);
     if (state) {
 	rb_ivar_set(rb_ssl, ID_callback_state, INT2NUM(state));
@@ -298,39 +294,10 @@ ossl_tmp_dh_callback(SSL *ssl, int is_export, int keylength)
     if (!pkey)
 	return NULL;
 
-    return EVP_PKEY_get0_DH(pkey);
+    return (DH *)EVP_PKEY_get0_DH(pkey);
 }
 #endif /* OPENSSL_NO_DH */
 
-#if !defined(OPENSSL_NO_EC) && defined(HAVE_SSL_CTX_SET_TMP_ECDH_CALLBACK)
-static EC_KEY *
-ossl_tmp_ecdh_callback(SSL *ssl, int is_export, int keylength)
-{
-    VALUE rb_ssl;
-    EVP_PKEY *pkey;
-    struct tmp_dh_callback_args args;
-    int state;
-
-    rb_ssl = (VALUE)SSL_get_ex_data(ssl, ossl_ssl_ex_ptr_idx);
-    args.ssl_obj = rb_ssl;
-    args.id = id_tmp_ecdh_callback;
-    args.is_export = is_export;
-    args.keylength = keylength;
-    args.type = EVP_PKEY_EC;
-
-    pkey = (EVP_PKEY *)rb_protect((VALUE (*)(VALUE))ossl_call_tmp_dh_callback,
-				  (VALUE)&args, &state);
-    if (state) {
-	rb_ivar_set(rb_ssl, ID_callback_state, INT2NUM(state));
-	return NULL;
-    }
-    if (!pkey)
-	return NULL;
-
-    return EVP_PKEY_get0_EC_KEY(pkey);
-}
-#endif
-
 static VALUE
 call_verify_certificate_identity(VALUE ctx_v)
 {
@@ -400,7 +367,7 @@ ossl_call_session_get_cb(VALUE ary)
 }
 
 static SSL_SESSION *
-#if (!defined(LIBRESSL_VERSION_NUMBER) ? OPENSSL_VERSION_NUMBER >= 0x10100000 : LIBRESSL_VERSION_NUMBER >= 0x2080000f)
+#if defined(LIBRESSL_VERSION_NUMBER) || OPENSSL_VERSION_NUMBER >= 0x10100000
 ossl_sslctx_session_get_cb(SSL *ssl, const unsigned char *buf, int len, int *copy)
 #else
 ossl_sslctx_session_get_cb(SSL *ssl, unsigned char *buf, int len, int *copy)
@@ -477,6 +444,54 @@ ossl_sslctx_session_new_cb(SSL *ssl, SSL_SESSION *sess)
     return 0;
 }
 
+#if OPENSSL_VERSION_NUMBER >= 0x10101000 && !defined(LIBRESSL_VERSION_NUMBER)
+/*
+ * It is only compatible with OpenSSL >= 1.1.1. Even if LibreSSL implements
+ * SSL_CTX_set_keylog_callback() from v3.4.2, it does nothing (see
+ * https://github.com/libressl-portable/openbsd/commit/648d39f0f035835d0653342d139883b9661e9cb6).
+ */
+
+struct ossl_call_keylog_cb_args {
+    VALUE ssl_obj;
+    const char * line;
+};
+
+static VALUE
+ossl_call_keylog_cb(VALUE args_v)
+{
+    VALUE sslctx_obj, cb, line_v;
+    struct ossl_call_keylog_cb_args *args = (struct ossl_call_keylog_cb_args *) args_v;
+
+    sslctx_obj = rb_attr_get(args->ssl_obj, id_i_context);
+
+    cb = rb_attr_get(sslctx_obj, id_i_keylog_cb);
+    if (NIL_P(cb)) return Qnil;
+
+    line_v = rb_str_new_cstr(args->line);
+
+    return rb_funcall(cb, id_call, 2, args->ssl_obj, line_v);
+}
+
+static void
+ossl_sslctx_keylog_cb(const SSL *ssl, const char *line)
+{
+    VALUE ssl_obj;
+    struct ossl_call_keylog_cb_args args;
+    int state = 0;
+
+    OSSL_Debug("SSL keylog callback entered");
+
+    ssl_obj = (VALUE)SSL_get_ex_data(ssl, ossl_ssl_ex_ptr_idx);
+    args.ssl_obj = ssl_obj;
+    args.line = line;
+
+    rb_protect(ossl_call_keylog_cb, (VALUE)&args, &state);
+    if (state) {
+        rb_ivar_set(ssl_obj, ID_callback_state, INT2NUM(state));
+    }
+}
+#endif
+
 static VALUE
 ossl_call_session_remove_cb(VALUE ary)
 {
@@ -609,8 +624,6 @@ ssl_renegotiation_cb(const SSL *ssl)
     rb_funcallv(cb, id_call, 1, &ssl_obj);
 }
 
-#if !defined(OPENSSL_NO_NEXTPROTONEG) || \
-    defined(HAVE_SSL_CTX_SET_ALPN_SELECT_CB)
 static VALUE
 ssl_npn_encode_protocol_i(RB_BLOCK_CALL_FUNC_ARGLIST(cur, encoded))
 {
@@ -692,9 +705,8 @@ ssl_npn_select_cb_common(SSL *ssl, VALUE cb, const unsigned char **out,
 
     return SSL_TLSEXT_ERR_OK;
 }
-#endif
 
-#ifndef OPENSSL_NO_NEXTPROTONEG
+#ifdef OSSL_USE_NEXTPROTONEG
 static int
 ssl_npn_advertise_cb(SSL *ssl, const unsigned char **out, unsigned int *outlen,
 		     void *arg)
@@ -721,7 +733,6 @@ ssl_npn_select_cb(SSL *ssl, unsigned char **out, unsigned char *outlen,
 }
 #endif
 
-#ifdef HAVE_SSL_CTX_SET_ALPN_SELECT_CB
 static int
 ssl_alpn_select_cb(SSL *ssl, const unsigned char **out, unsigned char *outlen,
 		   const unsigned char *in, unsigned int inlen, void *arg)
@@ -733,7 +744,6 @@ ssl_alpn_select_cb(SSL *ssl, const unsigned char **out, unsigned char *outlen,
 
     return ssl_npn_select_cb_common(ssl, cb, out, outlen, in, inlen);
 }
-#endif
 
 /* This function may serve as the entry point to support further callbacks. */
 static void
@@ -810,26 +820,6 @@ ossl_sslctx_setup(VALUE self)
     SSL_CTX_set_tmp_dh_callback(ctx, ossl_tmp_dh_callback);
 #endif
 
-#if !defined(OPENSSL_NO_EC)
-    /* We added SSLContext#tmp_ecdh_callback= in Ruby 2.3.0,
-     * but SSL_CTX_set_tmp_ecdh_callback() was removed in OpenSSL 1.1.0. */
-    if (RTEST(rb_attr_get(self, id_i_tmp_ecdh_callback))) {
-# if defined(HAVE_SSL_CTX_SET_TMP_ECDH_CALLBACK)
-	rb_warn("#tmp_ecdh_callback= is deprecated; use #ecdh_curves= instead");
-	SSL_CTX_set_tmp_ecdh_callback(ctx, ossl_tmp_ecdh_callback);
-#  if defined(HAVE_SSL_CTX_SET_ECDH_AUTO)
-	/* tmp_ecdh_callback and ecdh_auto conflict; OpenSSL ignores
-	 * tmp_ecdh_callback. So disable ecdh_auto. */
-	if (!SSL_CTX_set_ecdh_auto(ctx, 0))
-	    ossl_raise(eSSLError, "SSL_CTX_set_ecdh_auto");
-#  endif
-# else
-	ossl_raise(eSSLError, "OpenSSL does not support tmp_ecdh_callback; "
-		   "use #ecdh_curves= instead");
-# endif
-    }
-#endif /* OPENSSL_NO_EC */
-
 #ifdef HAVE_SSL_CTX_SET_POST_HANDSHAKE_AUTH
     SSL_CTX_set_post_handshake_auth(ctx, 1);
 #endif
@@ -838,17 +828,7 @@ ossl_sslctx_setup(VALUE self)
     if (!NIL_P(val)) {
 	X509_STORE *store = GetX509StorePtr(val); /* NO NEED TO DUP */
 	SSL_CTX_set_cert_store(ctx, store);
-#if !defined(HAVE_X509_STORE_UP_REF)
-	/*
-         * WORKAROUND:
-	 *   X509_STORE can count references, but
-	 *   X509_STORE_free() doesn't care it.
-	 *   So we won't increment it but mark it by ex_data.
-	 */
-        SSL_CTX_set_ex_data(ctx, ossl_sslctx_ex_store_p, ctx);
-#else /* Fixed in OpenSSL 1.0.2; bff9ce4db38b (master), 5b4b9ce976fc (1.0.2) */
 	X509_STORE_up_ref(store);
-#endif
     }
 
     val = rb_attr_get(self, id_i_extra_chain_cert);
@@ -899,10 +879,17 @@ ossl_sslctx_setup(VALUE self)
     ca_file = NIL_P(val) ? NULL : StringValueCStr(val);
     val = rb_attr_get(self, id_i_ca_path);
     ca_path = NIL_P(val) ? NULL : StringValueCStr(val);
-    if(ca_file || ca_path){
-	if (!SSL_CTX_load_verify_locations(ctx, ca_file, ca_path))
-	    rb_warning("can't set verify locations");
+#ifdef HAVE_SSL_CTX_LOAD_VERIFY_FILE
+    if (ca_file && !SSL_CTX_load_verify_file(ctx, ca_file))
+        ossl_raise(eSSLError, "SSL_CTX_load_verify_file");
+    if (ca_path && !SSL_CTX_load_verify_dir(ctx, ca_path))
+        ossl_raise(eSSLError, "SSL_CTX_load_verify_dir");
+#else
+    if (ca_file || ca_path) {
+        if (!SSL_CTX_load_verify_locations(ctx, ca_file, ca_path))
+            ossl_raise(eSSLError, "SSL_CTX_load_verify_locations");
     }
+#endif
 
     val = rb_attr_get(self, id_i_verify_mode);
     verify_mode = NIL_P(val) ? SSL_VERIFY_NONE : NUM2INT(val);
@@ -916,7 +903,7 @@ ossl_sslctx_setup(VALUE self)
     val = rb_attr_get(self, id_i_verify_depth);
     if(!NIL_P(val)) SSL_CTX_set_verify_depth(ctx, NUM2INT(val));
 
-#ifndef OPENSSL_NO_NEXTPROTONEG
+#ifdef OSSL_USE_NEXTPROTONEG
     val = rb_attr_get(self, id_i_npn_protocols);
     if (!NIL_P(val)) {
 	VALUE encoded = ssl_encode_npn_protocols(val);
@@ -930,7 +917,6 @@ ossl_sslctx_setup(VALUE self)
     }
 #endif
 
-#ifdef HAVE_SSL_CTX_SET_ALPN_SELECT_CB
     val = rb_attr_get(self, id_i_alpn_protocols);
     if (!NIL_P(val)) {
 	VALUE rprotos = ssl_encode_npn_protocols(val);
@@ -945,7 +931,6 @@ ossl_sslctx_setup(VALUE self)
 	SSL_CTX_set_alpn_select_cb(ctx, ssl_alpn_select_cb, (void *) self);
 	OSSL_Debug("SSL ALPN select callback added");
     }
-#endif
 
     rb_obj_freeze(self);
 
@@ -977,6 +962,18 @@ ossl_sslctx_setup(VALUE self)
 	OSSL_Debug("SSL TLSEXT servername callback added");
     }
 
+#if OPENSSL_VERSION_NUMBER >= 0x10101000 && !defined(LIBRESSL_VERSION_NUMBER)
+    /*
+     * It is only compatible with OpenSSL >= 1.1.1. Even if LibreSSL implements
+     * SSL_CTX_set_keylog_callback() from v3.4.2, it does nothing (see
+     * https://github.com/libressl-portable/openbsd/commit/648d39f0f035835d0653342d139883b9661e9cb6).
+     */
+    if (RTEST(rb_attr_get(self, id_i_keylog_cb))) {
+        SSL_CTX_set_keylog_callback(ctx, ossl_sslctx_keylog_cb);
+        OSSL_Debug("SSL keylog callback added");
+    }
+#endif
+
     return Qtrue;
 }
 
@@ -1025,27 +1022,13 @@ ossl_sslctx_get_ciphers(VALUE self)
     return ary;
 }
 
-/*
- * call-seq:
- *    ctx.ciphers = "cipher1:cipher2:..."
- *    ctx.ciphers = [name, ...]
- *    ctx.ciphers = [[name, version, bits, alg_bits], ...]
- *
- * Sets the list of available cipher suites for this context.  Note in a server
- * context some ciphers require the appropriate certificates.  For example, an
- * RSA cipher suite can only be chosen when an RSA certificate is available.
- */
 static VALUE
-ossl_sslctx_set_ciphers(VALUE self, VALUE v)
+build_cipher_string(VALUE v)
 {
-    SSL_CTX *ctx;
     VALUE str, elem;
     int i;
 
-    rb_check_frozen(self);
-    if (NIL_P(v))
-	return v;
-    else if (RB_TYPE_P(v, T_ARRAY)) {
+    if (RB_TYPE_P(v, T_ARRAY)) {
         str = rb_str_new(0, 0);
         for (i = 0; i < RARRAY_LEN(v); i++) {
             elem = rb_ary_entry(v, i);
@@ -1059,14 +1042,113 @@ ossl_sslctx_set_ciphers(VALUE self, VALUE v)
         StringValue(str);
     }
 
+    return str;
+}
+
+/*
+ * call-seq:
+ *    ctx.ciphers = "cipher1:cipher2:..."
+ *    ctx.ciphers = [name, ...]
+ *    ctx.ciphers = [[name, version, bits, alg_bits], ...]
+ *
+ * Sets the list of available cipher suites for this context.  Note in a server
+ * context some ciphers require the appropriate certificates.  For example, an
+ * RSA cipher suite can only be chosen when an RSA certificate is available.
+ */
+static VALUE
+ossl_sslctx_set_ciphers(VALUE self, VALUE v)
+{
+    SSL_CTX *ctx;
+    VALUE str;
+
+    rb_check_frozen(self);
+    if (NIL_P(v))
+        return v;
+
+    str = build_cipher_string(v);
+
     GetSSLCTX(self, ctx);
-    if (!SSL_CTX_set_cipher_list(ctx, StringValueCStr(str))) {
+    if (!SSL_CTX_set_cipher_list(ctx, StringValueCStr(str)))
         ossl_raise(eSSLError, "SSL_CTX_set_cipher_list");
-    }
 
     return v;
 }
 
+#ifdef HAVE_SSL_CTX_SET_CIPHERSUITES
+/*
+ * call-seq:
+ *    ctx.ciphersuites = "cipher1:cipher2:..."
+ *    ctx.ciphersuites = [name, ...]
+ *    ctx.ciphersuites = [[name, version, bits, alg_bits], ...]
+ *
+ * Sets the list of available TLSv1.3 cipher suites for this context.
+ */
+static VALUE
+ossl_sslctx_set_ciphersuites(VALUE self, VALUE v)
+{
+    SSL_CTX *ctx;
+    VALUE str;
+
+    rb_check_frozen(self);
+    if (NIL_P(v))
+        return v;
+
+    str = build_cipher_string(v);
+
+    GetSSLCTX(self, ctx);
+    if (!SSL_CTX_set_ciphersuites(ctx, StringValueCStr(str)))
+        ossl_raise(eSSLError, "SSL_CTX_set_ciphersuites");
+
+    return v;
+}
+#endif
+
+#ifndef OPENSSL_NO_DH
+/*
+ * call-seq:
+ *    ctx.tmp_dh = pkey
+ *
+ * Sets DH parameters used for ephemeral DH key exchange. This is relevant for
+ * servers only.
+ *
+ * +pkey+ is an instance of OpenSSL::PKey::DH. Note that key components
+ * contained in the key object, if any, are ignored. The server will always
+ * generate a new key pair for each handshake.
+ *
+ * Added in version 3.0. See also the man page SSL_set0_tmp_dh_pkey(3).
+ *
+ * Example:
+ *   ctx = OpenSSL::SSL::SSLContext.new
+ *   ctx.tmp_dh = OpenSSL::DH.generate(2048)
+ *   svr = OpenSSL::SSL::SSLServer.new(tcp_svr, ctx)
+ *   Thread.new { svr.accept }
+ */
+static VALUE
+ossl_sslctx_set_tmp_dh(VALUE self, VALUE arg)
+{
+    SSL_CTX *ctx;
+    EVP_PKEY *pkey;
+
+    rb_check_frozen(self);
+    GetSSLCTX(self, ctx);
+    pkey = GetPKeyPtr(arg);
+
+    if (EVP_PKEY_base_id(pkey) != EVP_PKEY_DH)
+        rb_raise(eSSLError, "invalid pkey type %s (expected DH)",
+                 OBJ_nid2sn(EVP_PKEY_base_id(pkey)));
+#ifdef HAVE_SSL_SET0_TMP_DH_PKEY
+    if (!SSL_CTX_set0_tmp_dh_pkey(ctx, pkey))
+        ossl_raise(eSSLError, "SSL_CTX_set0_tmp_dh_pkey");
+    EVP_PKEY_up_ref(pkey);
+#else
+    if (!SSL_CTX_set_tmp_dh(ctx, EVP_PKEY_get0_DH(pkey)))
+        ossl_raise(eSSLError, "SSL_CTX_set_tmp_dh");
+#endif
+
+    return arg;
+}
+#endif
+
 #if !defined(OPENSSL_NO_EC)
 /*
  * call-seq:
@@ -1078,9 +1160,6 @@ ossl_sslctx_set_ciphers(VALUE self, VALUE v)
  * Extension. For a server, the list is used by OpenSSL to determine the set of
  * shared curves. OpenSSL will pick the most appropriate one from it.
  *
- * Note that this works differently with old OpenSSL (<= 1.0.1). Only one curve
- * can be set, and this has no effect for TLS clients.
- *
  * === Example
  *   ctx1 = OpenSSL::SSL::SSLContext.new
  *   ctx1.ecdh_curves = "X25519:P-256:P-224"
@@ -1104,48 +1183,8 @@ ossl_sslctx_set_ecdh_curves(VALUE self, VALUE arg)
     GetSSLCTX(self, ctx);
     StringValueCStr(arg);
 
-#if defined(HAVE_SSL_CTX_SET1_CURVES_LIST)
     if (!SSL_CTX_set1_curves_list(ctx, RSTRING_PTR(arg)))
 	ossl_raise(eSSLError, NULL);
-#else
-    /* OpenSSL does not have SSL_CTX_set1_curves_list()... Fallback to
-     * SSL_CTX_set_tmp_ecdh(). So only the first curve is used. */
-    {
-	VALUE curve, splitted;
-	EC_KEY *ec;
-	int nid;
-
-	splitted = rb_str_split(arg, ":");
-	if (!RARRAY_LEN(splitted))
-	    ossl_raise(eSSLError, "invalid input format");
-	curve = RARRAY_AREF(splitted, 0);
-	StringValueCStr(curve);
-
-	/* SSL_CTX_set1_curves_list() accepts NIST names */
-	nid = EC_curve_nist2nid(RSTRING_PTR(curve));
-	if (nid == NID_undef)
-	    nid = OBJ_txt2nid(RSTRING_PTR(curve));
-	if (nid == NID_undef)
-	    ossl_raise(eSSLError, "unknown curve name");
-
-	ec = EC_KEY_new_by_curve_name(nid);
-	if (!ec)
-	    ossl_raise(eSSLError, NULL);
-	EC_KEY_set_asn1_flag(ec, OPENSSL_EC_NAMED_CURVE);
-	if (!SSL_CTX_set_tmp_ecdh(ctx, ec)) {
-	    EC_KEY_free(ec);
-	    ossl_raise(eSSLError, "SSL_CTX_set_tmp_ecdh");
-	}
-	EC_KEY_free(ec);
-# if defined(HAVE_SSL_CTX_SET_ECDH_AUTO)
-	/* tmp_ecdh and ecdh_auto conflict. tmp_ecdh is ignored when ecdh_auto
-	 * is enabled. So disable ecdh_auto. */
-	if (!SSL_CTX_set_ecdh_auto(ctx, 0))
-	    ossl_raise(eSSLError, "SSL_CTX_set_ecdh_auto");
-# endif
-    }
-#endif
-
     return arg;
 }
 #else
@@ -1236,7 +1275,7 @@ ossl_sslctx_enable_fallback_scsv(VALUE self)
 
 /*
  * call-seq:
- *    ctx.add_certificate(certiticate, pkey [, extra_certs]) -> self
+ *    ctx.add_certificate(certificate, pkey [, extra_certs]) -> self
  *
  * Adds a certificate to the context. _pkey_ must be a corresponding private
  * key with _certificate_.
@@ -1268,10 +1307,6 @@ ossl_sslctx_enable_fallback_scsv(VALUE self)
  *   ecdsa_pkey = ...
  *   another_ca_cert = ...
  *   ctx.add_certificate(ecdsa_cert, ecdsa_pkey, [another_ca_cert])
- *
- * === Note
- * OpenSSL before the version 1.0.2 could handle only one extra chain across
- * all key types. Calling this method discards the chain set previously.
  */
 static VALUE
 ossl_sslctx_add_certificate(int argc, VALUE *argv, VALUE self)
@@ -1296,7 +1331,7 @@ ossl_sslctx_add_certificate(int argc, VALUE *argv, VALUE self)
     EVP_PKEY_free(pub_pkey);
     if (!pub_pkey)
 	rb_raise(rb_eArgError, "certificate does not contain public key");
-    if (EVP_PKEY_cmp(pub_pkey, pkey) != 1)
+    if (EVP_PKEY_eq(pub_pkey, pkey) != 1)
 	rb_raise(rb_eArgError, "public key mismatch");
 
     if (argc >= 3)
@@ -1310,34 +1345,9 @@ ossl_sslctx_add_certificate(int argc, VALUE *argv, VALUE self)
 	sk_X509_pop_free(extra_chain, X509_free);
 	ossl_raise(eSSLError, "SSL_CTX_use_PrivateKey");
     }
-
-    if (extra_chain) {
-#if OPENSSL_VERSION_NUMBER >= 0x10002000 && !defined(LIBRESSL_VERSION_NUMBER)
-	if (!SSL_CTX_set0_chain(ctx, extra_chain)) {
-	    sk_X509_pop_free(extra_chain, X509_free);
-	    ossl_raise(eSSLError, "SSL_CTX_set0_chain");
-	}
-#else
-	STACK_OF(X509) *orig_extra_chain;
-	X509 *x509_tmp;
-
-	/* First, clear the existing chain */
-	SSL_CTX_get_extra_chain_certs(ctx, &orig_extra_chain);
-	if (orig_extra_chain && sk_X509_num(orig_extra_chain)) {
-	    rb_warning("SSL_CTX_set0_chain() is not available; " \
-		       "clearing previously set certificate chain");
-	    SSL_CTX_clear_extra_chain_certs(ctx);
-	}
-	while ((x509_tmp = sk_X509_shift(extra_chain))) {
-	    /* Transfers ownership */
-	    if (!SSL_CTX_add_extra_chain_cert(ctx, x509_tmp)) {
-		X509_free(x509_tmp);
-		sk_X509_pop_free(extra_chain, X509_free);
-		ossl_raise(eSSLError, "SSL_CTX_add_extra_chain_cert");
-	    }
-	}
-	sk_X509_free(extra_chain);
-#endif
+    if (extra_chain && !SSL_CTX_set0_chain(ctx, extra_chain)) {
+        sk_X509_pop_free(extra_chain, X509_free);
+        ossl_raise(eSSLError, "SSL_CTX_set0_chain");
     }
     return self;
 }
@@ -1531,12 +1541,11 @@ ossl_sslctx_flush_sessions(int argc, VALUE *argv, VALUE self)
 /*
  * SSLSocket class
  */
-#ifndef OPENSSL_NO_SOCK
 static inline int
 ssl_started(SSL *ssl)
 {
-    /* the FD is set in ossl_ssl_setup(), called by #connect or #accept */
-    return SSL_get_fd(ssl) >= 0;
+    /* BIO is created through ossl_ssl_setup(), called by #connect or #accept */
+    return SSL_get_rbio(ssl) != NULL;
 }
 
 static void
@@ -1544,6 +1553,10 @@ ossl_ssl_mark(void *ptr)
 {
     SSL *ssl = ptr;
     rb_gc_mark((VALUE)SSL_get_ex_data(ssl, ossl_ssl_ex_ptr_idx));
+
+    // Note: this reference is stored as @verify_callback so we don't need to mark it.
+    // However we do need to ensure GC compaction won't move it, hence why
+    // we call rb_gc_mark here.
     rb_gc_mark((VALUE)SSL_get_ex_data(ssl, ossl_ssl_ex_vcb_idx));
 }
 
@@ -1558,7 +1571,7 @@ const rb_data_type_t ossl_ssl_type = {
     {
         ossl_ssl_mark, ossl_ssl_free,
     },
-    0, 0, RUBY_TYPED_FREE_IMMEDIATELY,
+    0, 0, RUBY_TYPED_FREE_IMMEDIATELY | RUBY_TYPED_WB_PROTECTED,
 };
 
 static VALUE
@@ -1567,6 +1580,29 @@ ossl_ssl_s_alloc(VALUE klass)
     return TypedData_Wrap_Struct(klass, &ossl_ssl_type, NULL);
 }
 
+static VALUE
+peer_ip_address(VALUE self)
+{
+    VALUE remote_address = rb_funcall(rb_attr_get(self, id_i_io), rb_intern("remote_address"), 0);
+
+    return rb_funcall(remote_address, rb_intern("inspect_sockaddr"), 0);
+}
+
+static VALUE
+fallback_peer_ip_address(VALUE self, VALUE args)
+{
+    return rb_str_new_cstr("(null)");
+}
+
+static VALUE
+peeraddr_ip_str(VALUE self)
+{
+    VALUE rb_mErrno = rb_const_get(rb_cObject, rb_intern("Errno"));
+    VALUE rb_eSystemCallError = rb_const_get(rb_mErrno, rb_intern("SystemCallError"));
+
+    return rb_rescue2(peer_ip_address, self, fallback_peer_ip_address, (VALUE)0, rb_eSystemCallError, NULL);
+}
+
 /*
  * call-seq:
  *    SSLSocket.new(io) => aSSLSocket
@@ -1603,6 +1639,7 @@ ossl_ssl_initialize(int argc, VALUE *argv, VALUE self)
 
     if (rb_respond_to(io, rb_intern("nonblock=")))
 	rb_funcall(io, rb_intern("nonblock="), 1, Qtrue);
+    Check_Type(io, T_FILE);
     rb_ivar_set(self, id_i_io, io);
 
     ssl = SSL_new(ctx);
@@ -1613,6 +1650,8 @@ ossl_ssl_initialize(int argc, VALUE *argv, VALUE self)
     SSL_set_ex_data(ssl, ossl_ssl_ex_ptr_idx, (void *)self);
     SSL_set_info_callback(ssl, ssl_info_cb);
     verify_cb = rb_attr_get(v_ctx, id_i_verify_callback);
+    // We don't need to trigger a write barrier because it's already
+    // an instance variable of this object.
     SSL_set_ex_data(ssl, ossl_ssl_ex_vcb_idx, (void *)verify_cb);
 
     rb_call_super(0, NULL);
@@ -1620,6 +1659,17 @@ ossl_ssl_initialize(int argc, VALUE *argv, VALUE self)
     return self;
 }
 
+#ifndef HAVE_RB_IO_DESCRIPTOR
+static int
+io_descriptor_fallback(VALUE io)
+{
+    rb_io_t *fptr;
+    GetOpenFile(io, fptr);
+    return fptr->fd;
+}
+#define rb_io_descriptor io_descriptor_fallback
+#endif
+
 static VALUE
 ossl_ssl_setup(VALUE self)
 {
@@ -1635,8 +1685,8 @@ ossl_ssl_setup(VALUE self)
     GetOpenFile(io, fptr);
     rb_io_check_readable(fptr);
     rb_io_check_writable(fptr);
-    if (!SSL_set_fd(ssl, TO_SOCKET(fptr->fd)))
-	ossl_raise(eSSLError, "SSL_set_fd");
+    if (!SSL_set_fd(ssl, TO_SOCKET(rb_io_descriptor(io))))
+        ossl_raise(eSSLError, "SSL_set_fd");
 
     return Qtrue;
 }
@@ -1670,75 +1720,107 @@ no_exception_p(VALUE opts)
     return 0;
 }
 
+// Provided by Ruby 3.2.0 and later in order to support the default IO#timeout.
+#ifndef RUBY_IO_TIMEOUT_DEFAULT
+#define RUBY_IO_TIMEOUT_DEFAULT Qnil
+#endif
+
+static void
+io_wait_writable(VALUE io)
+{
+#ifdef HAVE_RB_IO_MAYBE_WAIT
+    rb_io_maybe_wait_writable(errno, io, RUBY_IO_TIMEOUT_DEFAULT);
+#else
+    rb_io_t *fptr;
+    GetOpenFile(io, fptr);
+    rb_io_wait_writable(fptr->fd);
+#endif
+}
+
+static void
+io_wait_readable(VALUE io)
+{
+#ifdef HAVE_RB_IO_MAYBE_WAIT
+    rb_io_maybe_wait_readable(errno, io, RUBY_IO_TIMEOUT_DEFAULT);
+#else
+    rb_io_t *fptr;
+    GetOpenFile(io, fptr);
+    rb_io_wait_readable(fptr->fd);
+#endif
+}
+
 static VALUE
-ossl_start_ssl(VALUE self, int (*func)(), const char *funcname, VALUE opts)
+ossl_start_ssl(VALUE self, int (*func)(SSL *), const char *funcname, VALUE opts)
 {
     SSL *ssl;
-    rb_io_t *fptr;
     int ret, ret2;
     VALUE cb_state;
     int nonblock = opts != Qfalse;
-#if defined(SSL_R_CERTIFICATE_VERIFY_FAILED)
-    unsigned long err;
-#endif
 
     rb_ivar_set(self, ID_callback_state, Qnil);
 
     GetSSL(self, ssl);
 
-    GetOpenFile(rb_attr_get(self, id_i_io), fptr);
-    for(;;){
-	ret = func(ssl);
+    VALUE io = rb_attr_get(self, id_i_io);
+    for (;;) {
+        ret = func(ssl);
 
-	cb_state = rb_attr_get(self, ID_callback_state);
+        cb_state = rb_attr_get(self, ID_callback_state);
         if (!NIL_P(cb_state)) {
-	    /* must cleanup OpenSSL error stack before re-raising */
-	    ossl_clear_error();
-	    rb_jump_tag(NUM2INT(cb_state));
-	}
+            /* must cleanup OpenSSL error stack before re-raising */
+            ossl_clear_error();
+            rb_jump_tag(NUM2INT(cb_state));
+        }
 
-	if (ret > 0)
-	    break;
+        if (ret > 0)
+            break;
 
-	switch((ret2 = ssl_get_error(ssl, ret))){
-	case SSL_ERROR_WANT_WRITE:
+        switch ((ret2 = ssl_get_error(ssl, ret))) {
+          case SSL_ERROR_WANT_WRITE:
             if (no_exception_p(opts)) { return sym_wait_writable; }
             write_would_block(nonblock);
-            rb_io_wait_writable(fptr->fd);
+            io_wait_writable(io);
             continue;
-	case SSL_ERROR_WANT_READ:
+          case SSL_ERROR_WANT_READ:
             if (no_exception_p(opts)) { return sym_wait_readable; }
             read_would_block(nonblock);
-            rb_io_wait_readable(fptr->fd);
+            io_wait_readable(io);
             continue;
-	case SSL_ERROR_SYSCALL:
+          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 (errno) rb_sys_fail(funcname);
+            /* fallthrough */
+          default: {
+              VALUE error_append = Qnil;
 #if defined(SSL_R_CERTIFICATE_VERIFY_FAILED)
-	case SSL_ERROR_SSL:
-	    err = ERR_peek_last_error();
-	    if (ERR_GET_LIB(err) == ERR_LIB_SSL &&
-		ERR_GET_REASON(err) == SSL_R_CERTIFICATE_VERIFY_FAILED) {
-		const char *err_msg = ERR_reason_error_string(err),
-		      *verify_msg = X509_verify_cert_error_string(SSL_get_verify_result(ssl));
-		if (!err_msg)
-		    err_msg = "(null)";
-		if (!verify_msg)
-		    verify_msg = "(null)";
-		ossl_clear_error(); /* let ossl_raise() not append message */
-		ossl_raise(eSSLError, "%s returned=%d errno=%d state=%s: %s (%s)",
-			   funcname, ret2, errno, SSL_state_string_long(ssl),
-			   err_msg, verify_msg);
-	    }
+              unsigned long err = ERR_peek_last_error();
+              if (ERR_GET_LIB(err) == ERR_LIB_SSL &&
+                  ERR_GET_REASON(err) == SSL_R_CERTIFICATE_VERIFY_FAILED) {
+                  const char *err_msg = ERR_reason_error_string(err),
+                        *verify_msg = X509_verify_cert_error_string(SSL_get_verify_result(ssl));
+                  if (!err_msg)
+                      err_msg = "(null)";
+                  if (!verify_msg)
+                      verify_msg = "(null)";
+                  ossl_clear_error(); /* let ossl_raise() not append message */
+                  error_append = rb_sprintf(": %s (%s)", err_msg, verify_msg);
+              }
 #endif
-	default:
-	    ossl_raise(eSSLError, "%s returned=%d errno=%d state=%s", funcname, ret2, errno, SSL_state_string_long(ssl));
-	}
+              ossl_raise(eSSLError,
+                         "%s%s returned=%d errno=%d peeraddr=%"PRIsVALUE" state=%s%"PRIsVALUE,
+                         funcname,
+                         ret2 == SSL_ERROR_SYSCALL ? " SYSCALL" : "",
+                         ret2,
+                         errno,
+                         peeraddr_ip_str(self),
+                         SSL_state_string_long(ssl),
+                         error_append);
+          }
+        }
     }
 
     return self;
@@ -1748,8 +1830,7 @@ ossl_start_ssl(VALUE self, int (*func)(), const char *funcname, VALUE opts)
  * call-seq:
  *    ssl.connect => self
  *
- * Initiates an SSL/TLS handshake with a server.  The handshake may be started
- * after unencrypted data has been sent over the socket.
+ * Initiates an SSL/TLS handshake with a server.
  */
 static VALUE
 ossl_ssl_connect(VALUE self)
@@ -1796,8 +1877,7 @@ ossl_ssl_connect_nonblock(int argc, VALUE *argv, VALUE self)
  * call-seq:
  *    ssl.accept => self
  *
- * Waits for a SSL/TLS client to initiate a handshake.  The handshake may be
- * started after unencrypted data has been sent over the socket.
+ * Waits for a SSL/TLS client to initiate a handshake.
  */
 static VALUE
 ossl_ssl_accept(VALUE self)
@@ -1844,16 +1924,18 @@ static VALUE
 ossl_ssl_read_internal(int argc, VALUE *argv, VALUE self, int nonblock)
 {
     SSL *ssl;
-    int ilen, nread = 0;
+    int ilen;
     VALUE len, str;
-    rb_io_t *fptr;
-    VALUE io, opts = Qnil;
+    VALUE opts = Qnil;
 
     if (nonblock) {
 	rb_scan_args(argc, argv, "11:", &len, &str, &opts);
     } else {
 	rb_scan_args(argc, argv, "11", &len, &str);
     }
+    GetSSL(self, ssl);
+    if (!ssl_started(ssl))
+        rb_raise(eSSLError, "SSL session is not started yet");
 
     ilen = NUM2INT(len);
     if (NIL_P(str))
@@ -1869,85 +1951,59 @@ ossl_ssl_read_internal(int argc, VALUE *argv, VALUE self, int nonblock)
     if (ilen == 0)
 	return str;
 
-    GetSSL(self, ssl);
-    io = rb_attr_get(self, id_i_io);
-    GetOpenFile(io, fptr);
-    if (ssl_started(ssl)) {
-        rb_str_locktmp(str);
-        for (;;) {
-	    nread = SSL_read(ssl, RSTRING_PTR(str), ilen);
-	    switch(ssl_get_error(ssl, nread)){
-	    case SSL_ERROR_NONE:
+    VALUE io = rb_attr_get(self, id_i_io);
+
+    rb_str_locktmp(str);
+    for (;;) {
+        int nread = SSL_read(ssl, RSTRING_PTR(str), ilen);
+        switch (ssl_get_error(ssl, nread)) {
+          case SSL_ERROR_NONE:
+            rb_str_unlocktmp(str);
+            rb_str_set_len(str, nread);
+            return str;
+          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 (nonblock) {
                 rb_str_unlocktmp(str);
-		goto end;
-	    case SSL_ERROR_ZERO_RETURN:
+                if (no_exception_p(opts)) { return sym_wait_writable; }
+                write_would_block(nonblock);
+            }
+            io_wait_writable(io);
+            continue;
+          case SSL_ERROR_WANT_READ:
+            if (nonblock) {
                 rb_str_unlocktmp(str);
-		if (no_exception_p(opts)) { return Qnil; }
-		rb_eof_error();
-	    case SSL_ERROR_WANT_WRITE:
-                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 (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 {
-			/*
-			 * The underlying BIO returned 0. This is actually a
-			 * protocol error. But unfortunately, not all
-			 * implementations cleanly shutdown the TLS connection
-			 * but just shutdown/close the TCP connection. So report
-			 * EOF for now...
-			 */
-			if (no_exception_p(opts)) { return Qnil; }
-			rb_eof_error();
-		    }
-		}
-                /* fall through */
-	    default:
+                if (no_exception_p(opts)) { return sym_wait_readable; }
+                read_would_block(nonblock);
+            }
+            io_wait_readable(io);
+            continue;
+          case SSL_ERROR_SYSCALL:
+            if (!ERR_peek_error()) {
                 rb_str_unlocktmp(str);
-		ossl_raise(eSSLError, "SSL_read");
-	    }
-        }
-    }
-    else {
-        ID meth = nonblock ? rb_intern("read_nonblock") : rb_intern("sysread");
-
-        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
-        if (nonblock) {
-            return rb_funcall(io, meth, 3, len, str, opts);
+                if (errno)
+                    rb_sys_fail(0);
+                else {
+                    /*
+                     * The underlying BIO returned 0. This is actually a
+                     * protocol error. But unfortunately, not all
+                     * implementations cleanly shutdown the TLS connection
+                     * but just shutdown/close the TCP connection. So report
+                     * EOF for now...
+                     */
+                    if (no_exception_p(opts)) { return Qnil; }
+                    rb_eof_error();
+                }
+            }
+            /* fall through */
+          default:
+            rb_str_unlocktmp(str);
+            ossl_raise(eSSLError, "SSL_read");
         }
-#endif
-        else
-            return rb_funcall(io, meth, 2, len, str);
     }
-
-  end:
-    rb_str_set_len(str, nread);
-    return str;
 }
 
 /*
@@ -1987,77 +2043,55 @@ static VALUE
 ossl_ssl_write_internal(VALUE self, VALUE str, VALUE opts)
 {
     SSL *ssl;
-    int nwrite = 0;
     rb_io_t *fptr;
-    int nonblock = opts != Qfalse;
-    VALUE tmp, io;
+    int num, nonblock = opts != Qfalse;
+    VALUE tmp;
 
-    tmp = rb_str_new_frozen(StringValue(str));
     GetSSL(self, ssl);
-    io = rb_attr_get(self, id_i_io);
+    if (!ssl_started(ssl))
+        rb_raise(eSSLError, "SSL session is not started yet");
+
+    tmp = rb_str_new_frozen(StringValue(str));
+    VALUE io = rb_attr_get(self, id_i_io);
     GetOpenFile(io, fptr);
-    if (ssl_started(ssl)) {
-	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(tmp), num);
-	    switch(ssl_get_error(ssl, nwrite)){
-	    case SSL_ERROR_NONE:
-		goto end;
-	    case SSL_ERROR_WANT_WRITE:
-		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);
-                rb_io_wait_readable(fptr->fd);
-                continue;
-	    case SSL_ERROR_SYSCALL:
+
+    /* SSL_write(3ssl) manpage states num == 0 is undefined */
+    num = RSTRING_LENINT(tmp);
+    if (num == 0)
+        return INT2FIX(0);
+
+    for (;;) {
+        int nwritten = SSL_write(ssl, RSTRING_PTR(tmp), num);
+        switch (ssl_get_error(ssl, nwritten)) {
+          case SSL_ERROR_NONE:
+            return INT2NUM(nwritten);
+          case SSL_ERROR_WANT_WRITE:
+            if (no_exception_p(opts)) { return sym_wait_writable; }
+            write_would_block(nonblock);
+            io_wait_writable(io);
+            continue;
+          case SSL_ERROR_WANT_READ:
+            if (no_exception_p(opts)) { return sym_wait_readable; }
+            read_would_block(nonblock);
+            io_wait_readable(io);
+            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;
+            /*
+             * 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");
-	    }
+            if (errno) rb_sys_fail(0);
+            /* fallthrough */
+          default:
+            ossl_raise(eSSLError, "SSL_write");
         }
     }
-    else {
-	ID meth = nonblock ?
-	    rb_intern("write_nonblock") : rb_intern("syswrite");
-
-        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
-        if (nonblock) {
-            return rb_funcall(io, meth, 2, str, opts);
-        }
-#endif
-        else
-            return rb_funcall(io, meth, 1, str);
-    }
-
-  end:
-    return INT2NUM(nwrite);
 }
 
 /*
@@ -2432,7 +2466,7 @@ ossl_ssl_get_client_ca_list(VALUE self)
     return ossl_x509name_sk2ary(ca);
 }
 
-# ifndef OPENSSL_NO_NEXTPROTONEG
+# ifdef OSSL_USE_NEXTPROTONEG
 /*
  * call-seq:
  *    ssl.npn_protocol => String | nil
@@ -2457,7 +2491,6 @@ ossl_ssl_npn_protocol(VALUE self)
 }
 # endif
 
-# ifdef HAVE_SSL_CTX_SET_ALPN_SELECT_CB
 /*
  * call-seq:
  *    ssl.alpn_protocol => String | nil
@@ -2480,9 +2513,50 @@ ossl_ssl_alpn_protocol(VALUE self)
     else
 	return rb_str_new((const char *) out, outlen);
 }
-# endif
 
-# ifdef HAVE_SSL_GET_SERVER_TMP_KEY
+/*
+ * call-seq:
+ *    session.export_keying_material(label, length) -> String
+ *
+ * Enables use of shared session key material in accordance with RFC 5705.
+ */
+static VALUE
+ossl_ssl_export_keying_material(int argc, VALUE *argv, VALUE self)
+{
+    SSL *ssl;
+    VALUE str;
+    VALUE label;
+    VALUE length;
+    VALUE context;
+    unsigned char *p;
+    size_t len;
+    int use_ctx = 0;
+    unsigned char *ctx = NULL;
+    size_t ctx_len = 0;
+    int ret;
+
+    rb_scan_args(argc, argv, "21", &label, &length, &context);
+    StringValue(label);
+
+    GetSSL(self, ssl);
+
+    len = (size_t)NUM2LONG(length);
+    str = rb_str_new(0, len);
+    p = (unsigned char *)RSTRING_PTR(str);
+    if (!NIL_P(context)) {
+	use_ctx = 1;
+	StringValue(context);
+	ctx = (unsigned char *)RSTRING_PTR(context);
+	ctx_len = RSTRING_LEN(context);
+    }
+    ret = SSL_export_keying_material(ssl, p, len, (char *)RSTRING_PTR(label),
+				     RSTRING_LENINT(label), ctx, ctx_len, use_ctx);
+    if (ret == 0 || ret == -1) {
+	ossl_raise(eSSLError, "SSL_export_keying_material");
+    }
+    return str;
+}
+
 /*
  * call-seq:
  *    ssl.tmp_key => PKey or nil
@@ -2500,7 +2574,6 @@ ossl_ssl_tmp_key(VALUE self)
 	return Qnil;
     return ossl_pkey_new(key);
 }
-# endif /* defined(HAVE_SSL_GET_SERVER_TMP_KEY) */
 #endif /* !defined(OPENSSL_NO_SOCK) */
 
 void
@@ -2513,6 +2586,7 @@ Init_ossl_ssl(void)
     rb_mWaitWritable = rb_define_module_under(rb_cIO, "WaitWritable");
 #endif
 
+#ifndef OPENSSL_NO_SOCK
     id_call = rb_intern_const("call");
     ID_callback_state = rb_intern_const("callback_state");
 
@@ -2525,11 +2599,6 @@ Init_ossl_ssl(void)
     ossl_sslctx_ex_ptr_idx = SSL_CTX_get_ex_new_index(0, (void *)"ossl_sslctx_ex_ptr_idx", 0, 0, 0);
     if (ossl_sslctx_ex_ptr_idx < 0)
 	ossl_raise(rb_eRuntimeError, "SSL_CTX_get_ex_new_index");
-#if !defined(HAVE_X509_STORE_UP_REF)
-    ossl_sslctx_ex_store_p = SSL_CTX_get_ex_new_index(0, (void *)"ossl_sslctx_ex_store_p", 0, 0, 0);
-    if (ossl_sslctx_ex_store_p < 0)
-	ossl_raise(rb_eRuntimeError, "SSL_CTX_get_ex_new_index");
-#endif
 
     /* Document-module: OpenSSL::SSL
      *
@@ -2540,16 +2609,6 @@ Init_ossl_ssl(void)
      */
     mSSL = rb_define_module_under(mOSSL, "SSL");
 
-    /* Document-module: OpenSSL::ExtConfig
-     *
-     * This module contains configuration information about the SSL extension,
-     * for example if socket support is enabled, or the host name TLS extension
-     * is enabled.  Constants in this module will always be defined, but contain
-     * +true+ or +false+ values depending on the configuration of your OpenSSL
-     * installation.
-     */
-    mSSLExtConfig = rb_define_module_under(mOSSL, "ExtConfig");
-
     /* Document-class: OpenSSL::SSL::SSLError
      *
      * Generic error class raised by SSLSocket and SSLContext.
@@ -2677,20 +2736,6 @@ Init_ossl_ssl(void)
      */
     rb_attr(cSSLContext, rb_intern_const("client_cert_cb"), 1, 1, Qfalse);
 
-#if !defined(OPENSSL_NO_EC) && defined(HAVE_SSL_CTX_SET_TMP_ECDH_CALLBACK)
-    /*
-     * A callback invoked when ECDH parameters are required.
-     *
-     * The callback is invoked with the Session for the key exchange, an
-     * flag indicating the use of an export cipher and the keylength
-     * required.
-     *
-     * The callback is deprecated. This does not work with recent versions of
-     * OpenSSL. Use OpenSSL::SSL::SSLContext#ecdh_curves= instead.
-     */
-    rb_attr(cSSLContext, rb_intern_const("tmp_ecdh_callback"), 1, 1, Qfalse);
-#endif
-
     /*
      * Sets the context in which a session can be reused.  This allows
      * sessions for multiple applications to be distinguished, for example, by
@@ -2726,8 +2771,6 @@ Init_ossl_ssl(void)
      */
     rb_attr(cSSLContext, rb_intern_const("session_remove_cb"), 1, 1, Qfalse);
 
-    rb_define_const(mSSLExtConfig, "HAVE_TLSEXT_HOST_NAME", Qtrue);
-
     /*
      * A callback invoked whenever a new handshake is initiated on an
      * established connection. May be used to disable renegotiation entirely.
@@ -2748,7 +2791,7 @@ Init_ossl_ssl(void)
      *   end
      */
     rb_attr(cSSLContext, rb_intern_const("renegotiation_cb"), 1, 1, Qfalse);
-#ifndef OPENSSL_NO_NEXTPROTONEG
+#ifdef OSSL_USE_NEXTPROTONEG
     /*
      * An Enumerable of Strings. Each String represents a protocol to be
      * advertised as the list of supported protocols for Next Protocol
@@ -2780,7 +2823,6 @@ Init_ossl_ssl(void)
     rb_attr(cSSLContext, rb_intern_const("npn_select_cb"), 1, 1, Qfalse);
 #endif
 
-#ifdef HAVE_SSL_CTX_SET_ALPN_SELECT_CB
     /*
      * An Enumerable of Strings. Each String represents a protocol to be
      * advertised as the list of supported protocols for Application-Layer
@@ -2810,7 +2852,29 @@ Init_ossl_ssl(void)
      *   end
      */
     rb_attr(cSSLContext, rb_intern_const("alpn_select_cb"), 1, 1, Qfalse);
-#endif
+
+    /*
+     * A callback invoked when TLS key material is generated or received, in
+     * order to allow applications to store this keying material for debugging
+     * purposes.
+     *
+     * The callback is invoked with an SSLSocket and a string containing the
+     * key material in the format used by NSS for its SSLKEYLOGFILE debugging
+     * output.
+     *
+     * It is only compatible with OpenSSL >= 1.1.1. Even if LibreSSL implements
+     * SSL_CTX_set_keylog_callback() from v3.4.2, it does nothing (see
+     * https://github.com/libressl-portable/openbsd/commit/648d39f0f035835d0653342d139883b9661e9cb6).
+     *
+     * === Example
+     *
+     *   context.keylog_cb = proc do |_sock, line|
+     *     File.open('ssl_keylog_file', "a") do |f|
+     *       f.write("#{line}\n")
+     *     end
+     *   end
+     */
+    rb_attr(cSSLContext, rb_intern_const("keylog_cb"), 1, 1, Qfalse);
 
     rb_define_alias(cSSLContext, "ssl_timeout", "timeout");
     rb_define_alias(cSSLContext, "ssl_timeout=", "timeout=");
@@ -2818,6 +2882,12 @@ Init_ossl_ssl(void)
 			     ossl_sslctx_set_minmax_proto_version, 2);
     rb_define_method(cSSLContext, "ciphers",     ossl_sslctx_get_ciphers, 0);
     rb_define_method(cSSLContext, "ciphers=",    ossl_sslctx_set_ciphers, 1);
+#ifdef HAVE_SSL_CTX_SET_CIPHERSUITES
+    rb_define_method(cSSLContext, "ciphersuites=", ossl_sslctx_set_ciphersuites, 1);
+#endif
+#ifndef OPENSSL_NO_DH
+    rb_define_method(cSSLContext, "tmp_dh=", ossl_sslctx_set_tmp_dh, 1);
+#endif
     rb_define_method(cSSLContext, "ecdh_curves=", ossl_sslctx_set_ecdh_curves, 1);
     rb_define_method(cSSLContext, "security_level", ossl_sslctx_get_security_level, 0);
     rb_define_method(cSSLContext, "security_level=", ossl_sslctx_set_security_level, 1);
@@ -2891,11 +2961,6 @@ Init_ossl_ssl(void)
      * Document-class: OpenSSL::SSL::SSLSocket
      */
     cSSLSocket = rb_define_class_under(mSSL, "SSLSocket", rb_cObject);
-#ifdef OPENSSL_NO_SOCK
-    rb_define_const(mSSLExtConfig, "OPENSSL_NO_SOCK", Qtrue);
-    rb_define_method(cSSLSocket, "initialize", rb_f_notimplement, -1);
-#else
-    rb_define_const(mSSLExtConfig, "OPENSSL_NO_SOCK", Qfalse);
     rb_define_alloc_func(cSSLSocket, ossl_ssl_s_alloc);
     rb_define_method(cSSLSocket, "initialize", ossl_ssl_initialize, -1);
     rb_undef_method(cSSLSocket, "initialize_copy");
@@ -2924,16 +2989,12 @@ Init_ossl_ssl(void)
     rb_define_method(cSSLSocket, "hostname=", ossl_ssl_set_hostname, 1);
     rb_define_method(cSSLSocket, "finished_message", ossl_ssl_get_finished, 0);
     rb_define_method(cSSLSocket, "peer_finished_message", ossl_ssl_get_peer_finished, 0);
-# ifdef HAVE_SSL_GET_SERVER_TMP_KEY
     rb_define_method(cSSLSocket, "tmp_key", ossl_ssl_tmp_key, 0);
-# endif
-# ifdef HAVE_SSL_CTX_SET_ALPN_SELECT_CB
     rb_define_method(cSSLSocket, "alpn_protocol", ossl_ssl_alpn_protocol, 0);
-# endif
-# ifndef OPENSSL_NO_NEXTPROTONEG
+    rb_define_method(cSSLSocket, "export_keying_material", ossl_ssl_export_keying_material, -1);
+# ifdef OSSL_USE_NEXTPROTONEG
     rb_define_method(cSSLSocket, "npn_protocol", ossl_ssl_npn_protocol, 0);
 # endif
-#endif
 
     rb_define_const(mSSL, "VERIFY_NONE", INT2NUM(SSL_VERIFY_NONE));
     rb_define_const(mSSL, "VERIFY_PEER", INT2NUM(SSL_VERIFY_PEER));
@@ -2941,12 +3002,23 @@ Init_ossl_ssl(void)
     rb_define_const(mSSL, "VERIFY_CLIENT_ONCE", INT2NUM(SSL_VERIFY_CLIENT_ONCE));
 
     rb_define_const(mSSL, "OP_ALL", ULONG2NUM(SSL_OP_ALL));
+#ifdef SSL_OP_CLEANSE_PLAINTEXT /* OpenSSL 3.0 */
+    rb_define_const(mSSL, "OP_CLEANSE_PLAINTEXT", ULONG2NUM(SSL_OP_CLEANSE_PLAINTEXT));
+#endif
     rb_define_const(mSSL, "OP_LEGACY_SERVER_CONNECT", ULONG2NUM(SSL_OP_LEGACY_SERVER_CONNECT));
-#ifdef SSL_OP_TLSEXT_PADDING /* OpenSSL 1.0.1h and OpenSSL 1.0.2 */
-    rb_define_const(mSSL, "OP_TLSEXT_PADDING", ULONG2NUM(SSL_OP_TLSEXT_PADDING));
+#ifdef SSL_OP_ENABLE_KTLS /* OpenSSL 3.0 */
+    rb_define_const(mSSL, "OP_ENABLE_KTLS", ULONG2NUM(SSL_OP_ENABLE_KTLS));
 #endif
-#ifdef SSL_OP_SAFARI_ECDHE_ECDSA_BUG /* OpenSSL 1.0.1f and OpenSSL 1.0.2 */
+    rb_define_const(mSSL, "OP_TLSEXT_PADDING", ULONG2NUM(SSL_OP_TLSEXT_PADDING));
     rb_define_const(mSSL, "OP_SAFARI_ECDHE_ECDSA_BUG", ULONG2NUM(SSL_OP_SAFARI_ECDHE_ECDSA_BUG));
+#ifdef SSL_OP_IGNORE_UNEXPECTED_EOF /* OpenSSL 3.0 */
+    rb_define_const(mSSL, "OP_IGNORE_UNEXPECTED_EOF", ULONG2NUM(SSL_OP_IGNORE_UNEXPECTED_EOF));
+#endif
+#ifdef SSL_OP_ALLOW_CLIENT_RENEGOTIATION /* OpenSSL 3.0 */
+    rb_define_const(mSSL, "OP_ALLOW_CLIENT_RENEGOTIATION", ULONG2NUM(SSL_OP_ALLOW_CLIENT_RENEGOTIATION));
+#endif
+#ifdef SSL_OP_DISABLE_TLSEXT_CA_NAMES /* OpenSSL 3.0 */
+    rb_define_const(mSSL, "OP_DISABLE_TLSEXT_CA_NAMES", ULONG2NUM(SSL_OP_DISABLE_TLSEXT_CA_NAMES));
 #endif
 #ifdef SSL_OP_ALLOW_NO_DHE_KEX /* OpenSSL 1.1.1 */
     rb_define_const(mSSL, "OP_ALLOW_NO_DHE_KEX", ULONG2NUM(SSL_OP_ALLOW_NO_DHE_KEX));
@@ -2959,13 +3031,15 @@ Init_ossl_ssl(void)
 #ifdef SSL_OP_NO_ENCRYPT_THEN_MAC /* OpenSSL 1.1.1 */
     rb_define_const(mSSL, "OP_NO_ENCRYPT_THEN_MAC", ULONG2NUM(SSL_OP_NO_ENCRYPT_THEN_MAC));
 #endif
-    rb_define_const(mSSL, "OP_CIPHER_SERVER_PREFERENCE", ULONG2NUM(SSL_OP_CIPHER_SERVER_PREFERENCE));
-    rb_define_const(mSSL, "OP_TLS_ROLLBACK_BUG", ULONG2NUM(SSL_OP_TLS_ROLLBACK_BUG));
-#ifdef SSL_OP_NO_RENEGOTIATION /* OpenSSL 1.1.1 */
-    rb_define_const(mSSL, "OP_NO_RENEGOTIATION", ULONG2NUM(SSL_OP_NO_RENEGOTIATION));
+#ifdef SSL_OP_ENABLE_MIDDLEBOX_COMPAT /* OpenSSL 1.1.1 */
+    rb_define_const(mSSL, "OP_ENABLE_MIDDLEBOX_COMPAT", ULONG2NUM(SSL_OP_ENABLE_MIDDLEBOX_COMPAT));
+#endif
+#ifdef SSL_OP_PRIORITIZE_CHACHA /* OpenSSL 1.1.1 */
+    rb_define_const(mSSL, "OP_PRIORITIZE_CHACHA", ULONG2NUM(SSL_OP_PRIORITIZE_CHACHA));
+#endif
+#ifdef SSL_OP_NO_ANTI_REPLAY /* OpenSSL 1.1.1 */
+    rb_define_const(mSSL, "OP_NO_ANTI_REPLAY", ULONG2NUM(SSL_OP_NO_ANTI_REPLAY));
 #endif
-    rb_define_const(mSSL, "OP_CRYPTOPRO_TLSEXT_BUG", ULONG2NUM(SSL_OP_CRYPTOPRO_TLSEXT_BUG));
-
     rb_define_const(mSSL, "OP_NO_SSLv3", ULONG2NUM(SSL_OP_NO_SSLv3));
     rb_define_const(mSSL, "OP_NO_TLSv1", ULONG2NUM(SSL_OP_NO_TLSv1));
     rb_define_const(mSSL, "OP_NO_TLSv1_1", ULONG2NUM(SSL_OP_NO_TLSv1_1));
@@ -2973,6 +3047,12 @@ Init_ossl_ssl(void)
 #ifdef SSL_OP_NO_TLSv1_3 /* OpenSSL 1.1.1 */
     rb_define_const(mSSL, "OP_NO_TLSv1_3", ULONG2NUM(SSL_OP_NO_TLSv1_3));
 #endif
+    rb_define_const(mSSL, "OP_CIPHER_SERVER_PREFERENCE", ULONG2NUM(SSL_OP_CIPHER_SERVER_PREFERENCE));
+    rb_define_const(mSSL, "OP_TLS_ROLLBACK_BUG", ULONG2NUM(SSL_OP_TLS_ROLLBACK_BUG));
+#ifdef SSL_OP_NO_RENEGOTIATION /* OpenSSL 1.1.1 */
+    rb_define_const(mSSL, "OP_NO_RENEGOTIATION", ULONG2NUM(SSL_OP_NO_RENEGOTIATION));
+#endif
+    rb_define_const(mSSL, "OP_CRYPTOPRO_TLSEXT_BUG", ULONG2NUM(SSL_OP_CRYPTOPRO_TLSEXT_BUG));
 
     /* SSL_OP_* flags for DTLS */
 #if 0
@@ -3042,7 +3122,6 @@ Init_ossl_ssl(void)
     sym_wait_writable = ID2SYM(rb_intern_const("wait_writable"));
 
     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");
 
@@ -3061,7 +3140,6 @@ Init_ossl_ssl(void)
     DefIVarID(key);
     DefIVarID(extra_chain_cert);
     DefIVarID(client_cert_cb);
-    DefIVarID(tmp_ecdh_callback);
     DefIVarID(timeout);
     DefIVarID(session_id_context);
     DefIVarID(session_get_cb);
@@ -3073,8 +3151,10 @@ Init_ossl_ssl(void)
     DefIVarID(alpn_select_cb);
     DefIVarID(servername_cb);
     DefIVarID(verify_hostname);
+    DefIVarID(keylog_cb);
 
     DefIVarID(io);
     DefIVarID(context);
     DefIVarID(hostname);
+#endif /* !defined(OPENSSL_NO_SOCK) */
 }