diff --git a/ext/openssl/extconf.rb b/ext/openssl/extconf.rb
index 0f099fc3b7a95..5212903b9aae8 100644
--- a/ext/openssl/extconf.rb
+++ b/ext/openssl/extconf.rb
@@ -104,11 +104,6 @@ def find_openssl_library
 
 Logging::message "=== Checking for OpenSSL features... ===\n"
 # compile options
-
-# SSLv2 and SSLv3 may be removed in future versions of OpenSSL, and even macros
-# like OPENSSL_NO_SSL2 may not be defined.
-have_func("SSLv2_method")
-have_func("SSLv3_method")
 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}
diff --git a/ext/openssl/ossl_ssl.c b/ext/openssl/ossl_ssl.c
index 828e934d6c0c0..18d5f5e9ec9ea 100644
--- a/ext/openssl/ossl_ssl.c
+++ b/ext/openssl/ossl_ssl.c
@@ -46,44 +46,6 @@ static ID id_i_cert_store, id_i_ca_file, id_i_ca_path, id_i_verify_mode,
 	  id_i_verify_hostname;
 static ID id_i_io, id_i_context, id_i_hostname;
 
-/*
- * SSLContext class
- */
-static const struct {
-    const char *name;
-    const SSL_METHOD *(*func)(void);
-    int version;
-} ossl_ssl_method_tab[] = {
-#if defined(HAVE_SSL_CTX_SET_MIN_PROTO_VERSION)
-#define OSSL_SSL_METHOD_ENTRY(name, version) \
-    { #name,          TLS_method, version }, \
-    { #name"_server", TLS_server_method, version }, \
-    { #name"_client", TLS_client_method, version }
-#else
-#define OSSL_SSL_METHOD_ENTRY(name, version) \
-    { #name,          name##_method, version }, \
-    { #name"_server", name##_server_method, version }, \
-    { #name"_client", name##_client_method, version }
-#endif
-#if !defined(OPENSSL_NO_SSL2) && !defined(OPENSSL_NO_SSL2_METHOD) && defined(HAVE_SSLV2_METHOD)
-    OSSL_SSL_METHOD_ENTRY(SSLv2, SSL2_VERSION),
-#endif
-#if !defined(OPENSSL_NO_SSL3) && !defined(OPENSSL_NO_SSL3_METHOD) && defined(HAVE_SSLV3_METHOD)
-    OSSL_SSL_METHOD_ENTRY(SSLv3, SSL3_VERSION),
-#endif
-#if !defined(OPENSSL_NO_TLS1) && !defined(OPENSSL_NO_TLS1_METHOD)
-    OSSL_SSL_METHOD_ENTRY(TLSv1, TLS1_VERSION),
-#endif
-#if !defined(OPENSSL_NO_TLS1_1) && !defined(OPENSSL_NO_TLS1_1_METHOD)
-    OSSL_SSL_METHOD_ENTRY(TLSv1_1, TLS1_1_VERSION),
-#endif
-#if !defined(OPENSSL_NO_TLS1_2) && !defined(OPENSSL_NO_TLS1_2_METHOD)
-    OSSL_SSL_METHOD_ENTRY(TLSv1_2, TLS1_2_VERSION),
-#endif
-    OSSL_SSL_METHOD_ENTRY(SSLv23, 0),
-#undef OSSL_SSL_METHOD_ENTRY
-};
-
 static int ossl_ssl_ex_vcb_idx;
 static int ossl_ssl_ex_ptr_idx;
 static int ossl_sslctx_ex_ptr_idx;
@@ -121,7 +83,11 @@ 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)
+    ctx = SSL_CTX_new(TLS_method());
+#else
     ctx = SSL_CTX_new(SSLv23_method());
+#endif
     if (!ctx) {
         ossl_raise(eSSLError, "SSL_CTX_new");
     }
@@ -144,49 +110,89 @@ ossl_sslctx_s_alloc(VALUE klass)
     return obj;
 }
 
+static int
+parse_proto_version(VALUE str)
+{
+    int i;
+    static const struct {
+	const char *name;
+	int version;
+    } map[] = {
+	{ "SSL2", SSL2_VERSION },
+	{ "SSL3", SSL3_VERSION },
+	{ "TLS1", TLS1_VERSION },
+	{ "TLS1_1", TLS1_1_VERSION },
+	{ "TLS1_2", TLS1_2_VERSION },
+#ifdef TLS1_3_VERSION
+	{ "TLS1_3", TLS1_3_VERSION },
+#endif
+    };
+
+    if (NIL_P(str))
+	return 0;
+    if (RB_INTEGER_TYPE_P(str))
+	return NUM2INT(str);
+
+    if (SYMBOL_P(str))
+	str = rb_sym2str(str);
+    StringValue(str);
+    for (i = 0; i < numberof(map); i++)
+	if (!strncmp(map[i].name, RSTRING_PTR(str), RSTRING_LEN(str)))
+	    return map[i].version;
+    rb_raise(rb_eArgError, "unrecognized version %+"PRIsVALUE, str);
+}
+
 /*
  * call-seq:
- *    ctx.ssl_version = :TLSv1
- *    ctx.ssl_version = "SSLv23_client"
- *
- * Sets the SSL/TLS protocol version for the context. This forces connections to
- * use only the specified protocol version.
+ *    ctx.set_minmax_proto_version(min, max) -> nil
  *
- * You can get a list of valid versions with OpenSSL::SSL::SSLContext::METHODS
+ * Sets the minimum and maximum supported protocol versions. See #min_version=
+ * and #max_version=.
  */
 static VALUE
-ossl_sslctx_set_ssl_version(VALUE self, VALUE ssl_method)
+ossl_sslctx_set_minmax_proto_version(VALUE self, VALUE min_v, VALUE max_v)
 {
     SSL_CTX *ctx;
-    const char *s;
-    VALUE m = ssl_method;
-    int i;
+    int min, max;
 
     GetSSLCTX(self, ctx);
-    if (RB_TYPE_P(ssl_method, T_SYMBOL))
-	m = rb_sym2str(ssl_method);
-    s = StringValueCStr(m);
-    for (i = 0; i < numberof(ossl_ssl_method_tab); i++) {
-        if (strcmp(ossl_ssl_method_tab[i].name, s) == 0) {
-#if defined(HAVE_SSL_CTX_SET_MIN_PROTO_VERSION)
-	    int version = ossl_ssl_method_tab[i].version;
-#endif
-	    const SSL_METHOD *method = ossl_ssl_method_tab[i].func();
-
-	    if (SSL_CTX_set_ssl_version(ctx, method) != 1)
-		ossl_raise(eSSLError, "SSL_CTX_set_ssl_version");
+    min = parse_proto_version(min_v);
+    max = parse_proto_version(max_v);
+
+#ifdef HAVE_SSL_CTX_SET_MIN_PROTO_VERSION
+    if (!SSL_CTX_set_min_proto_version(ctx, min))
+	ossl_raise(eSSLError, "SSL_CTX_set_min_proto_version");
+    if (!SSL_CTX_set_max_proto_version(ctx, max))
+	ossl_raise(eSSLError, "SSL_CTX_set_max_proto_version");
+#else
+    {
+	unsigned long sum = 0, opts = 0;
+	int i;
+	static const struct {
+	    int ver;
+	    unsigned long opts;
+	} options_map[] = {
+	    { SSL2_VERSION, SSL_OP_NO_SSLv2 },
+	    { SSL3_VERSION, SSL_OP_NO_SSLv3 },
+	    { TLS1_VERSION, SSL_OP_NO_TLSv1 },
+	    { TLS1_1_VERSION, SSL_OP_NO_TLSv1_1 },
+	    { TLS1_2_VERSION, SSL_OP_NO_TLSv1_2 },
+# if defined(TLS1_3_VERSION)
+	    { TLS1_3_VERSION, SSL_OP_NO_TLSv1_3 },
+# endif
+	};
 
-#if defined(HAVE_SSL_CTX_SET_MIN_PROTO_VERSION)
-	    if (!SSL_CTX_set_min_proto_version(ctx, version))
-		ossl_raise(eSSLError, "SSL_CTX_set_min_proto_version");
-	    if (!SSL_CTX_set_max_proto_version(ctx, version))
-		ossl_raise(eSSLError, "SSL_CTX_set_max_proto_version");
-#endif
-	    return ssl_method;
-        }
+	for (i = 0; i < numberof(options_map); i++) {
+	    sum |= options_map[i].opts;
+	    if (min && min > options_map[i].ver || max && max < options_map[i].ver)
+		opts |= options_map[i].opts;
+	}
+	SSL_CTX_clear_options(ctx, sum);
+	SSL_CTX_set_options(ctx, opts);
     }
+#endif
 
-    ossl_raise(rb_eArgError, "unknown SSL method `%"PRIsVALUE"'.", m);
+    return Qnil;
 }
 
 static VALUE
@@ -727,7 +733,11 @@ ossl_sslctx_get_options(VALUE self)
 {
     SSL_CTX *ctx;
     GetSSLCTX(self, ctx);
-    return LONG2NUM(SSL_CTX_get_options(ctx));
+    /*
+     * Do explicit cast because SSL_CTX_get_options() returned (signed) long in
+     * OpenSSL before 1.1.0.
+     */
+    return ULONG2NUM((unsigned long)SSL_CTX_get_options(ctx));
 }
 
 /*
@@ -746,7 +756,7 @@ ossl_sslctx_set_options(VALUE self, VALUE options)
     if (NIL_P(options)) {
 	SSL_CTX_set_options(ctx, SSL_OP_ALL);
     } else {
-	SSL_CTX_set_options(ctx, NUM2LONG(options));
+	SSL_CTX_set_options(ctx, NUM2ULONG(options));
     }
 
     return self;
@@ -2240,9 +2250,6 @@ ossl_ssl_tmp_key(VALUE self)
 void
 Init_ossl_ssl(void)
 {
-    int i;
-    VALUE ary;
-
 #if 0
     mOSSL = rb_define_module("OpenSSL");
     eOSSLError = rb_define_class_under(mOSSL, "OpenSSLError", rb_eStandardError);
@@ -2539,7 +2546,8 @@ Init_ossl_ssl(void)
 
     rb_define_alias(cSSLContext, "ssl_timeout", "timeout");
     rb_define_alias(cSSLContext, "ssl_timeout=", "timeout=");
-    rb_define_method(cSSLContext, "ssl_version=", ossl_sslctx_set_ssl_version, 1);
+    rb_define_private_method(cSSLContext, "set_minmax_proto_version",
+			     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);
     rb_define_method(cSSLContext, "ecdh_curves=", ossl_sslctx_set_ecdh_curves, 1);
@@ -2607,14 +2615,6 @@ Init_ossl_ssl(void)
     rb_define_method(cSSLContext, "options",     ossl_sslctx_get_options, 0);
     rb_define_method(cSSLContext, "options=",     ossl_sslctx_set_options, 1);
 
-    ary = rb_ary_new2(numberof(ossl_ssl_method_tab));
-    for (i = 0; i < numberof(ossl_ssl_method_tab); i++) {
-        rb_ary_push(ary, ID2SYM(rb_intern(ossl_ssl_method_tab[i].name)));
-    }
-    rb_obj_freeze(ary);
-    /* The list of available SSL/TLS methods */
-    rb_define_const(cSSLContext, "METHODS", ary);
-
     /*
      * Document-class: OpenSSL::SSL::SSLSocket
      */
@@ -2661,44 +2661,107 @@ Init_ossl_ssl(void)
 # endif
 #endif
 
-#define ossl_ssl_def_const(x) rb_define_const(mSSL, #x, LONG2NUM(SSL_##x))
+    rb_define_const(mSSL, "VERIFY_NONE", INT2NUM(SSL_VERIFY_NONE));
+    rb_define_const(mSSL, "VERIFY_PEER", INT2NUM(SSL_VERIFY_PEER));
+    rb_define_const(mSSL, "VERIFY_FAIL_IF_NO_PEER_CERT", INT2NUM(SSL_VERIFY_FAIL_IF_NO_PEER_CERT));
+    rb_define_const(mSSL, "VERIFY_CLIENT_ONCE", INT2NUM(SSL_VERIFY_CLIENT_ONCE));
+
+    rb_define_const(mSSL, "OP_ALL", ULONG2NUM(SSL_OP_ALL));
+    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));
+#endif
+#ifdef SSL_OP_SAFARI_ECDHE_ECDSA_BUG /* OpenSSL 1.0.1f and OpenSSL 1.0.2 */
+    rb_define_const(mSSL, "OP_SAFARI_ECDHE_ECDSA_BUG", ULONG2NUM(SSL_OP_SAFARI_ECDHE_ECDSA_BUG));
+#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));
+#endif
+    rb_define_const(mSSL, "OP_DONT_INSERT_EMPTY_FRAGMENTS", ULONG2NUM(SSL_OP_DONT_INSERT_EMPTY_FRAGMENTS));
+    rb_define_const(mSSL, "OP_NO_TICKET", ULONG2NUM(SSL_OP_NO_TICKET));
+    rb_define_const(mSSL, "OP_NO_SESSION_RESUMPTION_ON_RENEGOTIATION", ULONG2NUM(SSL_OP_NO_SESSION_RESUMPTION_ON_RENEGOTIATION));
+    rb_define_const(mSSL, "OP_NO_COMPRESSION", ULONG2NUM(SSL_OP_NO_COMPRESSION));
+    rb_define_const(mSSL, "OP_ALLOW_UNSAFE_LEGACY_RENEGOTIATION", ULONG2NUM(SSL_OP_ALLOW_UNSAFE_LEGACY_RENEGOTIATION));
+#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));
+#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));
+    rb_define_const(mSSL, "OP_NO_TLSv1_2", ULONG2NUM(SSL_OP_NO_TLSv1_2));
+#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
+
+    /* SSL_OP_* flags for DTLS */
+#if 0
+    rb_define_const(mSSL, "OP_NO_QUERY_MTU", ULONG2NUM(SSL_OP_NO_QUERY_MTU));
+    rb_define_const(mSSL, "OP_COOKIE_EXCHANGE", ULONG2NUM(SSL_OP_COOKIE_EXCHANGE));
+    rb_define_const(mSSL, "OP_CISCO_ANYCONNECT", ULONG2NUM(SSL_OP_CISCO_ANYCONNECT));
+#endif
+
+    /* Deprecated in OpenSSL 1.1.0. */
+    rb_define_const(mSSL, "OP_MICROSOFT_SESS_ID_BUG", ULONG2NUM(SSL_OP_MICROSOFT_SESS_ID_BUG));
+    /* Deprecated in OpenSSL 1.1.0. */
+    rb_define_const(mSSL, "OP_NETSCAPE_CHALLENGE_BUG", ULONG2NUM(SSL_OP_NETSCAPE_CHALLENGE_BUG));
+    /* Deprecated in OpenSSL 0.9.8q and 1.0.0c. */
+    rb_define_const(mSSL, "OP_NETSCAPE_REUSE_CIPHER_CHANGE_BUG", ULONG2NUM(SSL_OP_NETSCAPE_REUSE_CIPHER_CHANGE_BUG));
+    /* Deprecated in OpenSSL 1.0.1h and 1.0.2. */
+    rb_define_const(mSSL, "OP_SSLREF2_REUSE_CERT_TYPE_BUG", ULONG2NUM(SSL_OP_SSLREF2_REUSE_CERT_TYPE_BUG));
+    /* Deprecated in OpenSSL 1.1.0. */
+    rb_define_const(mSSL, "OP_MICROSOFT_BIG_SSLV3_BUFFER", ULONG2NUM(SSL_OP_MICROSOFT_BIG_SSLV3_BUFFER));
+    /* Deprecated in OpenSSL 0.9.7h and 0.9.8b. */
+    rb_define_const(mSSL, "OP_MSIE_SSLV2_RSA_PADDING", ULONG2NUM(SSL_OP_MSIE_SSLV2_RSA_PADDING));
+    /* Deprecated in OpenSSL 1.1.0. */
+    rb_define_const(mSSL, "OP_SSLEAY_080_CLIENT_DH_BUG", ULONG2NUM(SSL_OP_SSLEAY_080_CLIENT_DH_BUG));
+    /* Deprecated in OpenSSL 1.1.0. */
+    rb_define_const(mSSL, "OP_TLS_D5_BUG", ULONG2NUM(SSL_OP_TLS_D5_BUG));
+    /* Deprecated in OpenSSL 1.1.0. */
+    rb_define_const(mSSL, "OP_TLS_BLOCK_PADDING_BUG", ULONG2NUM(SSL_OP_TLS_BLOCK_PADDING_BUG));
+    /* Deprecated in OpenSSL 1.1.0. */
+    rb_define_const(mSSL, "OP_SINGLE_ECDH_USE", ULONG2NUM(SSL_OP_SINGLE_ECDH_USE));
+    /* Deprecated in OpenSSL 1.1.0. */
+    rb_define_const(mSSL, "OP_SINGLE_DH_USE", ULONG2NUM(SSL_OP_SINGLE_DH_USE));
+    /* Deprecated in OpenSSL 1.0.1k and 1.0.2. */
+    rb_define_const(mSSL, "OP_EPHEMERAL_RSA", ULONG2NUM(SSL_OP_EPHEMERAL_RSA));
+    /* Deprecated in OpenSSL 1.1.0. */
+    rb_define_const(mSSL, "OP_NO_SSLv2", ULONG2NUM(SSL_OP_NO_SSLv2));
+    /* Deprecated in OpenSSL 1.0.1. */
+    rb_define_const(mSSL, "OP_PKCS1_CHECK_1", ULONG2NUM(SSL_OP_PKCS1_CHECK_1));
+    /* Deprecated in OpenSSL 1.0.1. */
+    rb_define_const(mSSL, "OP_PKCS1_CHECK_2", ULONG2NUM(SSL_OP_PKCS1_CHECK_2));
+    /* Deprecated in OpenSSL 1.1.0. */
+    rb_define_const(mSSL, "OP_NETSCAPE_CA_DN_BUG", ULONG2NUM(SSL_OP_NETSCAPE_CA_DN_BUG));
+    /* Deprecated in OpenSSL 1.1.0. */
+    rb_define_const(mSSL, "OP_NETSCAPE_DEMO_CIPHER_CHANGE_BUG", ULONG2NUM(SSL_OP_NETSCAPE_DEMO_CIPHER_CHANGE_BUG));
+
 
-    ossl_ssl_def_const(VERIFY_NONE);
-    ossl_ssl_def_const(VERIFY_PEER);
-    ossl_ssl_def_const(VERIFY_FAIL_IF_NO_PEER_CERT);
-    ossl_ssl_def_const(VERIFY_CLIENT_ONCE);
-    /* Introduce constants included in OP_ALL.  These constants are mostly for
-     * unset some bits in OP_ALL such as;
-     *   ctx.options = OP_ALL & ~OP_DONT_INSERT_EMPTY_FRAGMENTS
+    /*
+     * SSL/TLS version constants. Used by SSLContext#min_version= and
+     * #max_version=
      */
-    ossl_ssl_def_const(OP_MICROSOFT_SESS_ID_BUG);
-    ossl_ssl_def_const(OP_NETSCAPE_CHALLENGE_BUG);
-    ossl_ssl_def_const(OP_NETSCAPE_REUSE_CIPHER_CHANGE_BUG);
-    ossl_ssl_def_const(OP_SSLREF2_REUSE_CERT_TYPE_BUG);
-    ossl_ssl_def_const(OP_MICROSOFT_BIG_SSLV3_BUFFER);
-    ossl_ssl_def_const(OP_MSIE_SSLV2_RSA_PADDING);
-    ossl_ssl_def_const(OP_SSLEAY_080_CLIENT_DH_BUG);
-    ossl_ssl_def_const(OP_TLS_D5_BUG);
-    ossl_ssl_def_const(OP_TLS_BLOCK_PADDING_BUG);
-    ossl_ssl_def_const(OP_DONT_INSERT_EMPTY_FRAGMENTS);
-    ossl_ssl_def_const(OP_ALL);
-    ossl_ssl_def_const(OP_NO_SESSION_RESUMPTION_ON_RENEGOTIATION);
-    ossl_ssl_def_const(OP_SINGLE_ECDH_USE);
-    ossl_ssl_def_const(OP_SINGLE_DH_USE);
-    ossl_ssl_def_const(OP_EPHEMERAL_RSA);
-    ossl_ssl_def_const(OP_CIPHER_SERVER_PREFERENCE);
-    ossl_ssl_def_const(OP_TLS_ROLLBACK_BUG);
-    ossl_ssl_def_const(OP_NO_SSLv2);
-    ossl_ssl_def_const(OP_NO_SSLv3);
-    ossl_ssl_def_const(OP_NO_TLSv1);
-    ossl_ssl_def_const(OP_NO_TLSv1_1);
-    ossl_ssl_def_const(OP_NO_TLSv1_2);
-    ossl_ssl_def_const(OP_NO_TICKET);
-    ossl_ssl_def_const(OP_NO_COMPRESSION);
-    ossl_ssl_def_const(OP_PKCS1_CHECK_1);
-    ossl_ssl_def_const(OP_PKCS1_CHECK_2);
-    ossl_ssl_def_const(OP_NETSCAPE_CA_DN_BUG);
-    ossl_ssl_def_const(OP_NETSCAPE_DEMO_CIPHER_CHANGE_BUG);
+    /* SSL 2.0 */
+    rb_define_const(mSSL, "SSL2_VERSION", INT2NUM(SSL2_VERSION));
+    /* SSL 3.0 */
+    rb_define_const(mSSL, "SSL3_VERSION", INT2NUM(SSL3_VERSION));
+    /* TLS 1.0 */
+    rb_define_const(mSSL, "TLS1_VERSION", INT2NUM(TLS1_VERSION));
+    /* TLS 1.1 */
+    rb_define_const(mSSL, "TLS1_1_VERSION", INT2NUM(TLS1_1_VERSION));
+    /* TLS 1.2 */
+    rb_define_const(mSSL, "TLS1_2_VERSION", INT2NUM(TLS1_2_VERSION));
+#ifdef TLS1_3_VERSION /* OpenSSL 1.1.1 */
+    /* TLS 1.3 */
+    rb_define_const(mSSL, "TLS1_3_VERSION", INT2NUM(TLS1_3_VERSION));
+#endif
+
 
     sym_exception = ID2SYM(rb_intern("exception"));
     sym_wait_readable = ID2SYM(rb_intern("wait_readable"));
diff --git a/lib/openssl/ssl.rb b/lib/openssl/ssl.rb
index d74b7d5436db6..a628648e71db5 100644
--- a/lib/openssl/ssl.rb
+++ b/lib/openssl/ssl.rb
@@ -17,14 +17,13 @@ module OpenSSL
   module SSL
     class SSLContext
       DEFAULT_PARAMS = { # :nodoc:
-        :ssl_version => "SSLv23",
+        :min_version => OpenSSL::SSL::TLS1_VERSION,
         :verify_mode => OpenSSL::SSL::VERIFY_PEER,
         :verify_hostname => true,
         :options => -> {
           opts = OpenSSL::SSL::OP_ALL
           opts &= ~OpenSSL::SSL::OP_DONT_INSERT_EMPTY_FRAGMENTS
           opts |= OpenSSL::SSL::OP_NO_COMPRESSION
-          opts |= OpenSSL::SSL::OP_NO_SSLv2 | OpenSSL::SSL::OP_NO_SSLv3
           opts
         }.call
       }
@@ -109,11 +108,15 @@ class SSLContext
       attr_accessor :servername_cb
 
       # call-seq:
-      #    SSLContext.new => ctx
-      #    SSLContext.new(:TLSv1) => ctx
-      #    SSLContext.new("SSLv23_client") => ctx
+      #    SSLContext.new           -> ctx
+      #    SSLContext.new(:TLSv1)   -> ctx
+      #    SSLContext.new("SSLv23") -> ctx
       #
-      # You can get a list of valid methods with OpenSSL::SSL::SSLContext::METHODS
+      # Creates a new SSL context.
+      #
+      # If an argument is given, #ssl_version= is called with the value. Note
+      # that this form is deprecated. New applications should use #min_version=
+      # and #max_version= as necessary.
       def initialize(version = nil)
         self.options |= OpenSSL::SSL::OP_ALL
         self.ssl_version = version if version
@@ -141,6 +144,88 @@ def set_params(params={})
         end
         return params
       end
+
+      # call-seq:
+      #    ctx.min_version = OpenSSL::SSL::TLS1_2_VERSION
+      #    ctx.min_version = :TLS1_2
+      #    ctx.min_version = nil
+      #
+      # Sets the lower bound on the supported SSL/TLS protocol version. The
+      # version may be specified by an integer constant named
+      # OpenSSL::SSL::*_VERSION, a Symbol, or +nil+ which means "any version".
+      #
+      # Be careful that you don't overwrite OpenSSL::SSL::OP_NO_{SSL,TLS}v*
+      # options by #options= once you have called #min_version= or
+      # #max_version=.
+      #
+      # === Example
+      #   ctx = OpenSSL::SSL::SSLContext.new
+      #   ctx.min_version = OpenSSL::SSL::TLS1_1_VERSION
+      #   ctx.max_version = OpenSSL::SSL::TLS1_2_VERSION
+      #
+      #   sock = OpenSSL::SSL::SSLSocket.new(tcp_sock, ctx)
+      #   sock.connect # Initiates a connection using either TLS 1.1 or TLS 1.2
+      def min_version=(version)
+        set_minmax_proto_version(version, @max_proto_version ||= nil)
+        @min_proto_version = version
+      end
+
+      # call-seq:
+      #    ctx.max_version = OpenSSL::SSL::TLS1_2_VERSION
+      #    ctx.max_version = :TLS1_2
+      #    ctx.max_version = nil
+      #
+      # Sets the upper bound of the supported SSL/TLS protocol version. See
+      # #min_version= for the possible values.
+      def max_version=(version)
+        set_minmax_proto_version(@min_proto_version ||= nil, version)
+        @max_proto_version = version
+      end
+
+      # call-seq:
+      #    ctx.ssl_version = :TLSv1
+      #    ctx.ssl_version = "SSLv23"
+      #
+      # Sets the SSL/TLS protocol version for the context. This forces
+      # connections to use only the specified protocol version. This is
+      # deprecated and only provided for backwards compatibility. Use
+      # #min_version= and #max_version= instead.
+      #
+      # === History
+      # As the name hints, this used to call the SSL_CTX_set_ssl_version()
+      # function which sets the SSL method used for connections created from
+      # the context. As of Ruby/OpenSSL 2.1, this accessor method is
+      # implemented to call #min_version= and #max_version= instead.
+      def ssl_version=(meth)
+        meth = meth.to_s if meth.is_a?(Symbol)
+        if /(?<type>_client|_server)\z/ =~ meth
+          meth = $`
+          if $VERBOSE
+            warn "#{caller(1)[0]}: method type #{type.inspect} is ignored"
+          end
+        end
+        version = METHODS_MAP[meth.intern] or
+          raise ArgumentError, "unknown SSL method `%s'" % meth
+        set_minmax_proto_version(version, version)
+        @min_proto_version = @max_proto_version = version
+      end
+
+      METHODS_MAP = {
+        SSLv23: 0,
+        SSLv2: OpenSSL::SSL::SSL2_VERSION,
+        SSLv3: OpenSSL::SSL::SSL3_VERSION,
+        TLSv1: OpenSSL::SSL::TLS1_VERSION,
+        TLSv1_1: OpenSSL::SSL::TLS1_1_VERSION,
+        TLSv1_2: OpenSSL::SSL::TLS1_2_VERSION,
+      }.freeze
+      private_constant :METHODS_MAP
+
+      # The list of available SSL/TLS methods. This constant is only provided
+      # for backwards compatibility.
+      METHODS = METHODS_MAP.flat_map { |name,|
+        [name, :"#{name}_client", :"#{name}_server"]
+      }.freeze
+      deprecate_constant :METHODS
     end
 
     module SocketForwarder
diff --git a/test/test_ssl.rb b/test/test_ssl.rb
index fd4afa69bdde7..3f17ab0d3851a 100644
--- a/test/test_ssl.rb
+++ b/test/test_ssl.rb
@@ -775,101 +775,211 @@ def test_unset_OP_ALL
     }
   end
 
-if OpenSSL::SSL::SSLContext::METHODS.include?(:TLSv1) && OpenSSL::SSL::SSLContext::METHODS.include?(:SSLv3)
+  def check_supported_protocol_versions
+    possible_versions = [
+      OpenSSL::SSL::SSL3_VERSION,
+      OpenSSL::SSL::TLS1_VERSION,
+      OpenSSL::SSL::TLS1_1_VERSION,
+      OpenSSL::SSL::TLS1_2_VERSION,
+      # OpenSSL 1.1.1
+      defined?(OpenSSL::SSL::TLS1_3_VERSION) && OpenSSL::SSL::TLS1_3_VERSION,
+    ].compact
+
+    # Prepare for testing & do sanity check
+    supported = []
+    possible_versions.each do |ver|
+      catch(:unsupported) {
+        ctx_proc = proc { |ctx|
+          begin
+            ctx.min_version = ctx.max_version = ver
+          rescue ArgumentError, OpenSSL::SSL::SSLError
+            throw :unsupported
+          end
+        }
+        start_server(ctx_proc: ctx_proc, ignore_listener_error: true) do |port|
+          begin
+            server_connect(port) { }
+          rescue OpenSSL::SSL::SSLError, Errno::ECONNRESET
+          else
+            supported << ver
+          end
+        end
+      }
+    end
+    assert_not_empty supported
 
-  def test_forbid_ssl_v3_for_client
-    ctx_proc = Proc.new { |ctx| ctx.options = OpenSSL::SSL::OP_ALL | OpenSSL::SSL::OP_NO_SSLv3 }
-    start_server_version(:SSLv23, ctx_proc) { |port|
-      ctx = OpenSSL::SSL::SSLContext.new
-      ctx.ssl_version = :SSLv3
-      assert_handshake_error { server_connect(port, ctx) }
-    }
+    supported
   end
 
-  def test_forbid_ssl_v3_from_server
-    start_server_version(:SSLv3) { |port|
-      ctx = OpenSSL::SSL::SSLContext.new
-      ctx.options = OpenSSL::SSL::OP_ALL | OpenSSL::SSL::OP_NO_SSLv3
-      assert_handshake_error { server_connect(port, ctx) }
+  def test_minmax_version
+    supported = check_supported_protocol_versions
+
+    # name: The string that would be returned by SSL_get_version()
+    # method: The version-specific method name (if any)
+    vmap = {
+      OpenSSL::SSL::SSL3_VERSION => { name: "SSLv3", method: "SSLv3" },
+      OpenSSL::SSL::SSL3_VERSION => { name: "SSLv3", method: "SSLv3" },
+      OpenSSL::SSL::TLS1_VERSION => { name: "TLSv1", method: "TLSv1" },
+      OpenSSL::SSL::TLS1_1_VERSION => { name: "TLSv1.1", method: "TLSv1_1" },
+      OpenSSL::SSL::TLS1_2_VERSION => { name: "TLSv1.2", method: "TLSv1_2" },
+      # OpenSSL 1.1.1
+      defined?(OpenSSL::SSL::TLS1_3_VERSION) && OpenSSL::SSL::TLS1_3_VERSION =>
+      { name: "TLSv1.3", method: nil },
     }
-  end
 
-end
+    # Server enables a single version
+    supported.each do |ver|
+      ctx_proc = proc { |ctx| ctx.min_version = ctx.max_version = ver }
+      start_server(ctx_proc: ctx_proc, ignore_listener_error: true) { |port|
+        supported.each do |cver|
+          # Client enables a single version
+          ctx1 = OpenSSL::SSL::SSLContext.new
+          ctx1.min_version = ctx1.max_version = cver
+          if ver == cver
+            server_connect(port, ctx1) { |ssl|
+              assert_equal vmap[cver][:name], ssl.ssl_version
+            }
+          else
+            assert_handshake_error { server_connect(port, ctx1) { } }
+          end
 
-if OpenSSL::SSL::SSLContext::METHODS.include?(:TLSv1_1) && OpenSSL::SSL::SSLContext::METHODS.include?(:TLSv1)
+          # There is no version-specific SSL methods for TLS 1.3
+          if cver <= OpenSSL::SSL::TLS1_2_VERSION
+            # Client enables a single version using #ssl_version=
+            ctx2 = OpenSSL::SSL::SSLContext.new
+            ctx2.ssl_version = vmap[cver][:method]
+            if ver == cver
+              server_connect(port, ctx2) { |ssl|
+                assert_equal vmap[cver][:name], ssl.ssl_version
+              }
+            else
+              assert_handshake_error { server_connect(port, ctx2) { } }
+            end
+          end
+        end
 
-  def test_tls_v1_1
-    start_server_version(:TLSv1_1) { |port|
-      ctx = OpenSSL::SSL::SSLContext.new(:TLSv1_1)
-      server_connect(port, ctx) { |ssl| assert_equal("TLSv1.1", ssl.ssl_version) }
-    }
-  end
+        # Client enables all supported versions
+        ctx3 = OpenSSL::SSL::SSLContext.new
+        ctx3.min_version = ctx3.max_version = nil
+        server_connect(port, ctx3) { |ssl|
+          assert_equal vmap[ver][:name], ssl.ssl_version
+        }
+      }
+    end
 
-  def test_forbid_tls_v1_for_client
-    ctx_proc = Proc.new { |ctx| ctx.options = OpenSSL::SSL::OP_ALL | OpenSSL::SSL::OP_NO_TLSv1 }
-    start_server_version(:SSLv23, ctx_proc) { |port|
-      ctx = OpenSSL::SSL::SSLContext.new
-      ctx.ssl_version = :TLSv1
-      assert_handshake_error { server_connect(port, ctx) }
-    }
-  end
+    if supported.size == 1
+      pend "More than one protocol version must be supported"
+    end
 
-  def test_forbid_tls_v1_from_server
-    start_server_version(:TLSv1) { |port|
-      ctx = OpenSSL::SSL::SSLContext.new
-      ctx.options = OpenSSL::SSL::OP_ALL | OpenSSL::SSL::OP_NO_TLSv1
-      assert_handshake_error { server_connect(port, ctx) }
-    }
-  end
+    # Server sets min_version (earliest is disabled)
+    sver = supported[1]
+    ctx_proc = proc { |ctx| ctx.min_version = sver }
+    start_server(ctx_proc: ctx_proc, ignore_listener_error: true) { |port|
+      supported.each do |cver|
+        # Client sets min_version
+        ctx1 = OpenSSL::SSL::SSLContext.new
+        ctx1.min_version = cver
+        server_connect(port, ctx1) { |ssl|
+          assert_equal vmap[supported.last][:name], ssl.ssl_version
+        }
 
-end
+        # Client sets max_version
+        ctx2 = OpenSSL::SSL::SSLContext.new
+        ctx2.max_version = cver
+        if cver >= sver
+          server_connect(port, ctx2) { |ssl|
+            assert_equal vmap[cver][:name], ssl.ssl_version
+          }
+        else
+          assert_handshake_error { server_connect(port, ctx2) { } }
+        end
+      end
+    }
 
-if OpenSSL::SSL::SSLContext::METHODS.include?(:TLSv1_2) && OpenSSL::SSL::SSLContext::METHODS.include?(:TLSv1_1)
+    # Server sets max_version (latest is disabled)
+    sver = supported[-2]
+    ctx_proc = proc { |ctx| ctx.max_version = sver }
+    start_server(ctx_proc: ctx_proc, ignore_listener_error: true) { |port|
+      supported.each do |cver|
+        # Client sets min_version
+        ctx1 = OpenSSL::SSL::SSLContext.new
+        ctx1.min_version = cver
+        if cver <= sver
+          server_connect(port, ctx1) { |ssl|
+            assert_equal vmap[sver][:name], ssl.ssl_version
+          }
+        else
+          assert_handshake_error { server_connect(port, ctx1) { } }
+        end
 
-  def test_tls_v1_2
-    start_server_version(:TLSv1_2) { |port|
-      ctx = OpenSSL::SSL::SSLContext.new
-      ctx.ssl_version = :TLSv1_2_client
-      server_connect(port, ctx) { |ssl| assert_equal("TLSv1.2", ssl.ssl_version) }
+        # Client sets max_version
+        ctx2 = OpenSSL::SSL::SSLContext.new
+        ctx2.max_version = cver
+        server_connect(port, ctx2) { |ssl|
+          if cver >= sver
+            assert_equal vmap[sver][:name], ssl.ssl_version
+          else
+            assert_equal vmap[cver][:name], ssl.ssl_version
+          end
+        }
+      end
     }
   end
 
-  def test_forbid_tls_v1_1_for_client
-    ctx_proc = Proc.new { |ctx| ctx.options = OpenSSL::SSL::OP_ALL | OpenSSL::SSL::OP_NO_TLSv1_1 }
-    start_server_version(:SSLv23, ctx_proc) { |port|
-      ctx = OpenSSL::SSL::SSLContext.new
-      ctx.ssl_version = :TLSv1_1
-      assert_handshake_error { server_connect(port, ctx) }
-    }
-  end
+  def test_options_disable_versions
+    # Note: Use of these OP_* flags has been deprecated since OpenSSL 1.1.0.
+    supported = check_supported_protocol_versions
 
-  def test_forbid_tls_v1_1_from_server
-    start_server_version(:TLSv1_1) { |port|
-      ctx = OpenSSL::SSL::SSLContext.new
-      ctx.options = OpenSSL::SSL::OP_ALL | OpenSSL::SSL::OP_NO_TLSv1_1
-      assert_handshake_error { server_connect(port, ctx) }
-    }
-  end
+    if supported.include?(OpenSSL::SSL::TLS1_1_VERSION) &&
+        supported.include?(OpenSSL::SSL::TLS1_2_VERSION)
+      # Server disables ~ TLS 1.1
+      ctx_proc = proc { |ctx|
+        ctx.options |= OpenSSL::SSL::OP_NO_SSLv2 | OpenSSL::SSL::OP_NO_SSLv3 |
+          OpenSSL::SSL::OP_NO_TLSv1 | OpenSSL::SSL::OP_NO_TLSv1_1
+      }
+      start_server(ctx_proc: ctx_proc, ignore_listener_error: true) { |port|
+        # Client only supports TLS 1.1
+        ctx1 = OpenSSL::SSL::SSLContext.new
+        ctx1.min_version = ctx1.max_version = OpenSSL::SSL::TLS1_1_VERSION
+        assert_handshake_error { server_connect(port, ctx1) { } }
+
+        # Client only supports TLS 1.2
+        ctx2 = OpenSSL::SSL::SSLContext.new
+        ctx2.min_version = ctx2.max_version = OpenSSL::SSL::TLS1_2_VERSION
+        assert_nothing_raised { server_connect(port, ctx2) { } }
+      }
 
-  def test_forbid_tls_v1_2_for_client
-    ctx_proc = Proc.new { |ctx| ctx.options = OpenSSL::SSL::OP_ALL | OpenSSL::SSL::OP_NO_TLSv1_2 }
-    start_server_version(:SSLv23, ctx_proc) { |port|
-      ctx = OpenSSL::SSL::SSLContext.new
-      ctx.ssl_version = :TLSv1_2
-      assert_handshake_error { server_connect(port, ctx) }
-    }
+      # Server only supports TLS 1.1
+      ctx_proc = proc { |ctx|
+        ctx.min_version = ctx.max_version = OpenSSL::SSL::TLS1_1_VERSION
+      }
+      start_server(ctx_proc: ctx_proc, ignore_listener_error: true) { |port|
+        # Client disables TLS 1.1
+        ctx1 = OpenSSL::SSL::SSLContext.new
+        ctx1.options |= OpenSSL::SSL::OP_NO_TLSv1_1
+        assert_handshake_error { server_connect(port, ctx1) { } }
+
+        # Client disables TLS 1.2
+        ctx2 = OpenSSL::SSL::SSLContext.new
+        ctx2.options |= OpenSSL::SSL::OP_NO_TLSv1_2
+        assert_nothing_raised { server_connect(port, ctx2) { } }
+      }
+    else
+      pend "TLS 1.1 and TLS 1.2 must be supported; skipping"
+    end
   end
 
-  def test_forbid_tls_v1_2_from_server
-    start_server_version(:TLSv1_2) { |port|
-      ctx = OpenSSL::SSL::SSLContext.new
-      ctx.options = OpenSSL::SSL::OP_ALL | OpenSSL::SSL::OP_NO_TLSv1_2
-      assert_handshake_error { server_connect(port, ctx) }
+  def test_ssl_methods_constant
+    EnvUtil.suppress_warning { # Deprecated in v2.1.0
+      base = [:TLSv1_2, :TLSv1_1, :TLSv1, :SSLv3, :SSLv2, :SSLv23]
+      base.each do |name|
+        assert_include OpenSSL::SSL::SSLContext::METHODS, name
+        assert_include OpenSSL::SSL::SSLContext::METHODS, :"#{name}_client"
+        assert_include OpenSSL::SSL::SSLContext::METHODS, :"#{name}_server"
+      end
     }
   end
 
-end
-
   def test_renegotiation_cb
     num_handshakes = 0
     renegotiation_cb = Proc.new { |ssl| num_handshakes += 1 }
diff --git a/test/utils.rb b/test/utils.rb
index a5dd38c267a3e..f59d53b0d19c7 100644
--- a/test/utils.rb
+++ b/test/utils.rb
@@ -177,7 +177,10 @@ def setup
   end
 
   def tls12_supported?
-    OpenSSL::SSL::SSLContext::METHODS.include?(:TLSv1_2)
+    ctx = OpenSSL::SSL::SSLContext.new
+    ctx.min_version = ctx.max_version = OpenSSL::SSL::TLS1_2_VERSION
+    true
+  rescue
   end
 
   def readwrite_loop(ctx, ssl)