# frozen_string_literal: true require_relative "utils" if defined?(OpenSSL) class OpenSSL::TestSSL < OpenSSL::SSLTestCase def test_bad_socket bad_socket = Struct.new(:sync).new assert_raise TypeError do socket = OpenSSL::SSL::SSLSocket.new bad_socket # if the socket is not a T_FILE, `connect` will segv because it tries # to get the underlying file descriptor but the API it calls assumes # the object type is T_FILE socket.connect end end def test_ctx_options ctx = OpenSSL::SSL::SSLContext.new assert (OpenSSL::SSL::OP_ALL & ctx.options) == OpenSSL::SSL::OP_ALL, "OP_ALL is set by default" ctx.options = 4 assert_equal 4, ctx.options & 4 if ctx.options != 4 pend "SSL_CTX_set_options() seems to be modified by distributor" end ctx.options = nil assert_equal OpenSSL::SSL::OP_ALL, ctx.options assert_equal true, ctx.setup assert_predicate ctx, :frozen? assert_equal nil, ctx.setup end def test_ssl_with_server_cert ctx_proc = -> ctx { ctx.cert = @svr_cert ctx.key = @svr_key ctx.extra_chain_cert = [@ca_cert] } server_proc = -> (ctx, ssl) { assert_equal @svr_cert.to_der, ssl.cert.to_der assert_equal nil, ssl.peer_cert readwrite_loop(ctx, ssl) } start_server(ctx_proc: ctx_proc, server_proc: server_proc) { |port| begin sock = TCPSocket.new("127.0.0.1", port) ctx = OpenSSL::SSL::SSLContext.new ssl = OpenSSL::SSL::SSLSocket.new(sock, ctx) ssl.connect assert_equal sock, ssl.io assert_equal nil, ssl.cert assert_equal @svr_cert.to_der, ssl.peer_cert.to_der assert_equal 2, ssl.peer_cert_chain.size assert_equal @svr_cert.to_der, ssl.peer_cert_chain[0].to_der assert_equal @ca_cert.to_der, ssl.peer_cert_chain[1].to_der ssl.puts "abc"; assert_equal "abc\n", ssl.gets ensure ssl&.close sock&.close end } end def test_socket_open start_server { |port| begin ssl = OpenSSL::SSL::SSLSocket.open("127.0.0.1", port) ssl.sync_close = true ssl.connect ssl.puts "abc"; assert_equal "abc\n", ssl.gets ensure ssl&.close end } end def test_socket_open_with_context start_server { |port| begin ctx = OpenSSL::SSL::SSLContext.new ssl = OpenSSL::SSL::SSLSocket.open("127.0.0.1", port, context: ctx) ssl.sync_close = true ssl.connect assert_equal ssl.context, ctx ssl.puts "abc"; assert_equal "abc\n", ssl.gets ensure ssl&.close end } end def test_socket_open_with_local_address_port_context start_server { |port| begin # Guess a free port number random_port = rand(49152..65535) ctx = OpenSSL::SSL::SSLContext.new ssl = OpenSSL::SSL::SSLSocket.open("127.0.0.1", port, "127.0.0.1", random_port, context: ctx) ssl.sync_close = true ssl.connect assert_equal ctx, ssl.context assert_equal random_port, ssl.io.local_address.ip_port ssl.puts "abc"; assert_equal "abc\n", ssl.gets rescue Errno::EADDRINUSE, Errno::EACCES ensure ssl&.close end } end def test_add_certificate ctx_proc = -> ctx { # Unset values set by start_server ctx.cert = ctx.key = ctx.extra_chain_cert = nil ctx.add_certificate(@svr_cert, @svr_key, [@ca_cert]) # RSA } start_server(ctx_proc: ctx_proc) do |port| server_connect(port) { |ssl| assert_equal @svr_cert.subject, ssl.peer_cert.subject assert_equal [@svr_cert.subject, @ca_cert.subject], ssl.peer_cert_chain.map(&:subject) ssl.puts "abc"; assert_equal "abc\n", ssl.gets } end end def test_add_certificate_multiple_certs ca2_key = Fixtures.pkey("rsa-3") ca2_exts = [ ["basicConstraints", "CA:TRUE", true], ["keyUsage", "cRLSign, keyCertSign", true], ] ca2_dn = OpenSSL::X509::Name.parse_rfc2253("CN=CA2") ca2_cert = issue_cert(ca2_dn, ca2_key, 123, ca2_exts, nil, nil) ecdsa_key = Fixtures.pkey("p256") exts = [ ["keyUsage", "digitalSignature", false], ] ecdsa_dn = OpenSSL::X509::Name.parse_rfc2253("CN=localhost2") ecdsa_cert = issue_cert(ecdsa_dn, ecdsa_key, 456, exts, ca2_cert, ca2_key) ctx_proc = -> ctx { # Unset values set by start_server ctx.cert = ctx.key = ctx.extra_chain_cert = nil ctx.add_certificate(@svr_cert, @svr_key, [@ca_cert]) # RSA ctx.add_certificate(ecdsa_cert, ecdsa_key, [ca2_cert]) } start_server(ctx_proc: ctx_proc) do |port| ctx = OpenSSL::SSL::SSLContext.new ctx.max_version = :TLS1_2 # TODO: We need this to force certificate type ctx.ciphers = "aECDSA" server_connect(port, ctx) { |ssl| assert_equal ecdsa_cert.subject, ssl.peer_cert.subject assert_equal [ecdsa_cert.subject, ca2_cert.subject], ssl.peer_cert_chain.map(&:subject) } ctx = OpenSSL::SSL::SSLContext.new ctx.max_version = :TLS1_2 ctx.ciphers = "aRSA" server_connect(port, ctx) { |ssl| assert_equal @svr_cert.subject, ssl.peer_cert.subject assert_equal [@svr_cert.subject, @ca_cert.subject], ssl.peer_cert_chain.map(&:subject) } end end def test_sysread_and_syswrite start_server { |port| server_connect(port) { |ssl| str = +("x" * 100 + "\n") ssl.syswrite(str) newstr = ssl.sysread(str.bytesize) assert_equal(str, newstr) buf = String.new ssl.syswrite(str) assert_same buf, ssl.sysread(str.size, buf) assert_equal(str, buf) } } end def test_getbyte start_server { |port| server_connect(port) { |ssl| str = +("x" * 100 + "\n") ssl.syswrite(str) newstr = str.bytesize.times.map { |i| ssl.getbyte }.pack("C*") assert_equal(str, newstr) } } end def test_sync_close start_server do |port| begin sock = TCPSocket.new("127.0.0.1", port) ssl = OpenSSL::SSL::SSLSocket.new(sock) ssl.connect ssl.puts "abc"; assert_equal "abc\n", ssl.gets ssl.close assert_not_predicate sock, :closed? ensure sock&.close end begin sock = TCPSocket.new("127.0.0.1", port) ssl = OpenSSL::SSL::SSLSocket.new(sock) ssl.sync_close = true # !! ssl.connect ssl.puts "abc"; assert_equal "abc\n", ssl.gets ssl.close assert_predicate sock, :closed? ensure sock&.close end end end def test_copy_stream start_server do |port| server_connect(port) do |ssl| IO.pipe do |r, w| str = "hello world\n" w.write(str) IO.copy_stream(r, ssl, str.bytesize) IO.copy_stream(ssl, w, str.bytesize) assert_equal str, r.read(str.bytesize) end end end end def test_verify_mode_default ctx = OpenSSL::SSL::SSLContext.new assert_equal OpenSSL::SSL::VERIFY_NONE, ctx.verify_mode end def test_verify_mode_server_cert start_server(ignore_listener_error: true) { |port| populated_store = OpenSSL::X509::Store.new populated_store.add_cert(@ca_cert) empty_store = OpenSSL::X509::Store.new # Valid certificate, SSL_VERIFY_PEER assert_nothing_raised { ctx = OpenSSL::SSL::SSLContext.new ctx.verify_mode = OpenSSL::SSL::VERIFY_PEER ctx.cert_store = populated_store server_connect(port, ctx) { |ssl| ssl.puts("abc"); ssl.gets } } # Invalid certificate, SSL_VERIFY_NONE assert_nothing_raised { ctx = OpenSSL::SSL::SSLContext.new ctx.verify_mode = OpenSSL::SSL::VERIFY_NONE ctx.cert_store = empty_store server_connect(port, ctx) { |ssl| ssl.puts("abc"); ssl.gets } } # Invalid certificate, SSL_VERIFY_PEER assert_handshake_error { ctx = OpenSSL::SSL::SSLContext.new ctx.verify_mode = OpenSSL::SSL::VERIFY_PEER ctx.cert_store = empty_store server_connect(port, ctx) { |ssl| ssl.puts("abc"); ssl.gets } } } end def test_verify_mode_client_cert_required # Optional, client certificate not supplied vflag = OpenSSL::SSL::VERIFY_PEER accept_proc = -> ssl { assert_equal nil, ssl.peer_cert } start_server(verify_mode: vflag, accept_proc: accept_proc) { |port| assert_nothing_raised { server_connect(port) { |ssl| ssl.puts("abc"); ssl.gets } } } # Required, client certificate not supplied vflag = OpenSSL::SSL::VERIFY_PEER|OpenSSL::SSL::VERIFY_FAIL_IF_NO_PEER_CERT start_server(verify_mode: vflag, ignore_listener_error: true) { |port| assert_handshake_error { server_connect(port) { |ssl| ssl.puts("abc"); ssl.gets } } } end def test_client_auth_success vflag = OpenSSL::SSL::VERIFY_PEER|OpenSSL::SSL::VERIFY_FAIL_IF_NO_PEER_CERT 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 server_connect(port, ctx) { |ssl| ssl.puts("foo") assert_equal("foo\n", ssl.gets) } called = nil ctx = OpenSSL::SSL::SSLContext.new ctx.client_cert_cb = Proc.new{ |sslconn| called = true [@cli_cert, @cli_key] } server_connect(port, ctx) { |ssl| assert(called) ssl.puts("foo") assert_equal("foo\n", ssl.gets) } } end def test_client_cert_cb_ignore_error vflag = OpenSSL::SSL::VERIFY_PEER|OpenSSL::SSL::VERIFY_FAIL_IF_NO_PEER_CERT start_server(verify_mode: vflag, ignore_listener_error: true) do |port| ctx = OpenSSL::SSL::SSLContext.new ctx.client_cert_cb = -> ssl { raise "exception in client_cert_cb must be suppressed" } # 1. Exception in client_cert_cb is suppressed # 2. No client certificate will be sent to the server # 3. SSL_VERIFY_FAIL_IF_NO_PEER_CERT causes the handshake to fail assert_handshake_error { server_connect(port, ctx) { |ssl| ssl.puts("abc"); ssl.gets } } end 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 vflag = OpenSSL::SSL::VERIFY_PEER|OpenSSL::SSL::VERIFY_FAIL_IF_NO_PEER_CERT start_server(verify_mode: vflag, ctx_proc: ctx_proc) { |port| ctx = OpenSSL::SSL::SSLContext.new client_ca_from_server = nil ctx.client_cert_cb = Proc.new do |sslconn| client_ca_from_server = sslconn.client_ca [@cli_cert, @cli_key] end server_connect(port, ctx) { |ssl| assert_equal([@ca], client_ca_from_server) ssl.puts "abc"; assert_equal "abc\n", ssl.gets } } end def test_unstarted_session start_server do |port| sock = TCPSocket.new("127.0.0.1", port) ssl = OpenSSL::SSL::SSLSocket.new(sock) assert_raise(OpenSSL::SSL::SSLError) { ssl.syswrite("data") } assert_raise(OpenSSL::SSL::SSLError) { ssl.sysread(1) } ssl.connect ssl.puts "abc" assert_equal "abc\n", ssl.gets ensure ssl&.close sock&.close end end def test_parallel start_server { |port| ssls = [] 10.times{ sock = TCPSocket.new("127.0.0.1", port) ssl = OpenSSL::SSL::SSLSocket.new(sock) ssl.connect ssl.sync_close = true ssls << ssl } str = "x" * 1000 + "\n" ITERATIONS.times{ ssls.each{|ssl| ssl.puts(str) assert_equal(str, ssl.gets) } } ssls.each{|ssl| ssl.close } } end def test_verify_result start_server(ignore_listener_error: true) { |port| sock = TCPSocket.new("127.0.0.1", port) ctx = OpenSSL::SSL::SSLContext.new ctx.verify_mode = OpenSSL::SSL::VERIFY_PEER ssl = OpenSSL::SSL::SSLSocket.new(sock, ctx) ssl.sync_close = true begin assert_raise(OpenSSL::SSL::SSLError){ ssl.connect } assert_equal(OpenSSL::X509::V_ERR_SELF_SIGNED_CERT_IN_CHAIN, ssl.verify_result) ensure ssl.close end } start_server { |port| ctx = OpenSSL::SSL::SSLContext.new ctx.verify_mode = OpenSSL::SSL::VERIFY_PEER ctx.verify_callback = Proc.new do |preverify_ok, store_ctx| store_ctx.error = OpenSSL::X509::V_OK true end server_connect(port, ctx) { |ssl| assert_equal(OpenSSL::X509::V_OK, ssl.verify_result) ssl.puts "abc"; assert_equal "abc\n", ssl.gets } } start_server(ignore_listener_error: true) { |port| sock = TCPSocket.new("127.0.0.1", port) ctx = OpenSSL::SSL::SSLContext.new ctx.verify_mode = OpenSSL::SSL::VERIFY_PEER ctx.verify_callback = Proc.new do |preverify_ok, store_ctx| store_ctx.error = OpenSSL::X509::V_ERR_APPLICATION_VERIFICATION false end ssl = OpenSSL::SSL::SSLSocket.new(sock, ctx) ssl.sync_close = true begin assert_raise(OpenSSL::SSL::SSLError){ ssl.connect } assert_equal(OpenSSL::X509::V_ERR_APPLICATION_VERIFICATION, ssl.verify_result) ensure ssl.close end } end def test_exception_in_verify_callback_is_ignored start_server(ignore_listener_error: true) { |port| sock = TCPSocket.new("127.0.0.1", port) ctx = OpenSSL::SSL::SSLContext.new ctx.verify_mode = OpenSSL::SSL::VERIFY_PEER ctx.verify_callback = Proc.new do |preverify_ok, store_ctx| store_ctx.error = OpenSSL::X509::V_OK raise RuntimeError end ssl = OpenSSL::SSL::SSLSocket.new(sock, ctx) ssl.sync_close = true begin EnvUtil.suppress_warning do # SSLError, not RuntimeError assert_raise(OpenSSL::SSL::SSLError) { ssl.connect } end assert_equal(OpenSSL::X509::V_ERR_CERT_REJECTED, ssl.verify_result) ensure ssl.close end } end def test_finished_messages server_finished = nil server_peer_finished = nil client_finished = nil client_peer_finished = nil start_server(accept_proc: proc { |server| server_finished = server.finished_message server_peer_finished = server.peer_finished_message }, ctx_proc: proc { |ctx| ctx.max_version = OpenSSL::SSL::TLS1_2_VERSION if libressl?(3, 2, 0) }) { |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 client_finished = ssl.finished_message client_peer_finished = ssl.peer_finished_message } } assert_not_nil(server_finished) assert_not_nil(client_finished) assert_equal(server_finished, client_peer_finished) assert_equal(server_peer_finished, client_finished) end def test_sslctx_set_params ctx = OpenSSL::SSL::SSLContext.new ctx.set_params assert_equal OpenSSL::SSL::VERIFY_PEER, ctx.verify_mode ciphers_names = ctx.ciphers.collect{|v, _, _, _| v } assert ciphers_names.all?{|v| /A(EC)?DH/ !~ v }, "anon ciphers are disabled" assert ciphers_names.all?{|v| /(RC4|MD5|EXP|DES(?!-EDE|-CBC3))/ !~ v }, "weak ciphers are disabled" assert_equal 0, ctx.options & OpenSSL::SSL::OP_DONT_INSERT_EMPTY_FRAGMENTS assert_equal OpenSSL::SSL::OP_NO_COMPRESSION, ctx.options & OpenSSL::SSL::OP_NO_COMPRESSION end def test_post_connect_check_with_anon_ciphers ctx_proc = -> ctx { ctx.ssl_version = :TLSv1_2 ctx.ciphers = "aNULL" ctx.tmp_dh = Fixtures.pkey("dh-1") ctx.security_level = 0 } start_server(ctx_proc: ctx_proc) { |port| ctx = OpenSSL::SSL::SSLContext.new ctx.ssl_version = :TLSv1_2 ctx.ciphers = "aNULL" ctx.security_level = 0 server_connect(port, ctx) { |ssl| assert_raise_with_message(OpenSSL::SSL::SSLError, /anonymous cipher suite/i) { ssl.post_connection_check("localhost.localdomain") } } } end def test_post_connection_check sslerr = OpenSSL::SSL::SSLError start_server { |port| server_connect(port) { |ssl| ssl.puts "abc"; assert_equal "abc\n", ssl.gets assert_raise(sslerr){ssl.post_connection_check("localhost.localdomain")} assert_raise(sslerr){ssl.post_connection_check("127.0.0.1")} assert(ssl.post_connection_check("localhost")) assert_raise(sslerr){ssl.post_connection_check("foo.example.com")} cert = ssl.peer_cert assert(!OpenSSL::SSL.verify_certificate_identity(cert, "localhost.localdomain")) assert(!OpenSSL::SSL.verify_certificate_identity(cert, "127.0.0.1")) assert(OpenSSL::SSL.verify_certificate_identity(cert, "localhost")) assert(!OpenSSL::SSL.verify_certificate_identity(cert, "foo.example.com")) } } exts = [ ["keyUsage","keyEncipherment,digitalSignature",true], ["subjectAltName","DNS:localhost.localdomain,IP:127.0.0.1",false], ] @svr_cert = issue_cert(@svr, @svr_key, 4, exts, @ca_cert, @ca_key) start_server { |port| server_connect(port) { |ssl| ssl.puts "abc"; assert_equal "abc\n", ssl.gets assert(ssl.post_connection_check("localhost.localdomain")) assert(ssl.post_connection_check("127.0.0.1")) assert_raise(sslerr){ssl.post_connection_check("localhost")} assert_raise(sslerr){ssl.post_connection_check("foo.example.com")} cert = ssl.peer_cert assert(OpenSSL::SSL.verify_certificate_identity(cert, "localhost.localdomain")) assert(OpenSSL::SSL.verify_certificate_identity(cert, "127.0.0.1")) assert(!OpenSSL::SSL.verify_certificate_identity(cert, "localhost")) assert(!OpenSSL::SSL.verify_certificate_identity(cert, "foo.example.com")) } } exts = [ ["keyUsage","keyEncipherment,digitalSignature",true], ["subjectAltName","DNS:*.localdomain",false], ] @svr_cert = issue_cert(@svr, @svr_key, 5, exts, @ca_cert, @ca_key) start_server { |port| server_connect(port) { |ssl| ssl.puts "abc"; assert_equal "abc\n", ssl.gets assert(ssl.post_connection_check("localhost.localdomain")) assert_raise(sslerr){ssl.post_connection_check("127.0.0.1")} assert_raise(sslerr){ssl.post_connection_check("localhost")} assert_raise(sslerr){ssl.post_connection_check("foo.example.com")} cert = ssl.peer_cert assert(OpenSSL::SSL.verify_certificate_identity(cert, "localhost.localdomain")) assert(!OpenSSL::SSL.verify_certificate_identity(cert, "127.0.0.1")) assert(!OpenSSL::SSL.verify_certificate_identity(cert, "localhost")) assert(!OpenSSL::SSL.verify_certificate_identity(cert, "foo.example.com")) } } end def test_verify_certificate_identity [true, false].each do |criticality| cert = create_null_byte_SAN_certificate(criticality) assert_equal(false, OpenSSL::SSL.verify_certificate_identity(cert, 'www.example.com')) assert_equal(true, OpenSSL::SSL.verify_certificate_identity(cert, "www.example.com\0.evil.com")) assert_equal(false, OpenSSL::SSL.verify_certificate_identity(cert, '192.168.7.255')) assert_equal(true, OpenSSL::SSL.verify_certificate_identity(cert, '192.168.7.1')) assert_equal(true, OpenSSL::SSL.verify_certificate_identity(cert, '13::17')) assert_equal(false, OpenSSL::SSL.verify_certificate_identity(cert, '13::18')) assert_equal(true, OpenSSL::SSL.verify_certificate_identity(cert, '13:0:0:0:0:0:0:17')) assert_equal(false, OpenSSL::SSL.verify_certificate_identity(cert, '44:0:0:0:0:0:0:17')) assert_equal(true, OpenSSL::SSL.verify_certificate_identity(cert, '0013:0000:0000:0000:0000:0000:0000:0017')) assert_equal(false, OpenSSL::SSL.verify_certificate_identity(cert, '1313:0000:0000:0000:0000:0000:0000:0017')) end end def test_verify_hostname assert_equal(true, OpenSSL::SSL.verify_hostname("www.example.com", "*.example.com")) assert_equal(false, OpenSSL::SSL.verify_hostname("www.subdomain.example.com", "*.example.com")) end def test_verify_wildcard assert_equal(false, OpenSSL::SSL.verify_wildcard("foo", "x*")) assert_equal(true, OpenSSL::SSL.verify_wildcard("foo", "foo")) assert_equal(true, OpenSSL::SSL.verify_wildcard("foo", "f*")) assert_equal(true, OpenSSL::SSL.verify_wildcard("foo", "*")) assert_equal(false, OpenSSL::SSL.verify_wildcard("abc*bcd", "abcd")) assert_equal(false, OpenSSL::SSL.verify_wildcard("xn--qdk4b9b", "x*")) assert_equal(false, OpenSSL::SSL.verify_wildcard("xn--qdk4b9b", "*--qdk4b9b")) assert_equal(true, OpenSSL::SSL.verify_wildcard("xn--qdk4b9b", "xn--qdk4b9b")) end # Comments in this test is excerpted from http://tools.ietf.org/html/rfc6125#page-27 def test_post_connection_check_wildcard_san # case-insensitive ASCII comparison # RFC 6125, section 6.4.1 # # "..matching of the reference identifier against the presented identifier # is performed by comparing the set of domain name labels using a # case-insensitive ASCII comparison, as clarified by [DNS-CASE] (e.g., # "WWW.Example.Com" would be lower-cased to "www.example.com" for # comparison purposes) assert_equal(true, OpenSSL::SSL.verify_certificate_identity( create_cert_with_san('DNS:*.example.com'), 'www.example.com')) assert_equal(true, OpenSSL::SSL.verify_certificate_identity( create_cert_with_san('DNS:*.Example.COM'), 'www.example.com')) assert_equal(true, OpenSSL::SSL.verify_certificate_identity( create_cert_with_san('DNS:*.example.com'), 'WWW.Example.COM')) # 1. The client SHOULD NOT attempt to match a presented identifier in # which the wildcard character comprises a label other than the # left-most label (e.g., do not match bar.*.example.net). assert_equal(false, OpenSSL::SSL.verify_certificate_identity( create_cert_with_san('DNS:www.*.com'), 'www.example.com')) # 2. If the wildcard character is the only character of the left-most # label in the presented identifier, the client SHOULD NOT compare # against anything but the left-most label of the reference # identifier (e.g., *.example.com would match foo.example.com but # not bar.foo.example.com or example.com). assert_equal(true, OpenSSL::SSL.verify_certificate_identity( create_cert_with_san('DNS:*.example.com'), 'foo.example.com')) assert_equal(false, OpenSSL::SSL.verify_certificate_identity( create_cert_with_san('DNS:*.example.com'), 'bar.foo.example.com')) # 3. The client MAY match a presented identifier in which the wildcard # character is not the only character of the label (e.g., # baz*.example.net and *baz.example.net and b*z.example.net would # be taken to match baz1.example.net and foobaz.example.net and # buzz.example.net, respectively). ... assert_equal(true, OpenSSL::SSL.verify_certificate_identity( create_cert_with_san('DNS:baz*.example.com'), 'baz1.example.com')) # LibreSSL 3.5.0+ doesn't support other wildcard certificates # (it isn't required to, as RFC states MAY, not MUST) return if libressl?(3, 5, 0) assert_equal(true, OpenSSL::SSL.verify_certificate_identity( create_cert_with_san('DNS:*baz.example.com'), 'foobaz.example.com')) assert_equal(true, OpenSSL::SSL.verify_certificate_identity( create_cert_with_san('DNS:b*z.example.com'), 'buzz.example.com')) # Section 6.4.3 of RFC6125 states that client should NOT match identifier # where wildcard is other than left-most label. # # Also implicitly mentions the wildcard character only in singular form, # and discourages matching against more than one wildcard. # # See RFC 6125, section 7.2, subitem 2. assert_equal(false, OpenSSL::SSL.verify_certificate_identity( create_cert_with_san('DNS:*b*.example.com'), 'abc.example.com')) assert_equal(false, OpenSSL::SSL.verify_certificate_identity( create_cert_with_san('DNS:*b*.example.com'), 'ab.example.com')) assert_equal(false, OpenSSL::SSL.verify_certificate_identity( create_cert_with_san('DNS:*b*.example.com'), 'bc.example.com')) # ... However, the client SHOULD NOT # attempt to match a presented identifier where the wildcard # character is embedded within an A-label or U-label [IDNA-DEFS] of # an internationalized domain name [IDNA-PROTO]. assert_equal(true, OpenSSL::SSL.verify_certificate_identity( create_cert_with_san('DNS:xn*.example.com'), 'xn1ca.example.com')) # part of A-label assert_equal(false, OpenSSL::SSL.verify_certificate_identity( create_cert_with_san('DNS:xn--*.example.com'), 'xn--1ca.example.com')) # part of U-label # dNSName in RFC5280 is an IA5String so U-label should NOT be allowed # regardless of wildcard. # # See Section 7.2 of RFC 5280: # IA5String is limited to the set of ASCII characters. assert_equal(false, OpenSSL::SSL.verify_certificate_identity( create_cert_with_san('DNS:á*.example.com'), 'á1.example.com')) end def test_post_connection_check_wildcard_cn assert_equal(true, OpenSSL::SSL.verify_certificate_identity( create_cert_with_name('*.example.com'), 'www.example.com')) assert_equal(true, OpenSSL::SSL.verify_certificate_identity( create_cert_with_name('*.Example.COM'), 'www.example.com')) assert_equal(true, OpenSSL::SSL.verify_certificate_identity( create_cert_with_name('*.example.com'), 'WWW.Example.COM')) assert_equal(false, OpenSSL::SSL.verify_certificate_identity( create_cert_with_name('www.*.com'), 'www.example.com')) assert_equal(true, OpenSSL::SSL.verify_certificate_identity( create_cert_with_name('*.example.com'), 'foo.example.com')) assert_equal(false, OpenSSL::SSL.verify_certificate_identity( create_cert_with_name('*.example.com'), 'bar.foo.example.com')) assert_equal(true, OpenSSL::SSL.verify_certificate_identity( create_cert_with_name('baz*.example.com'), 'baz1.example.com')) assert_equal(true, OpenSSL::SSL.verify_certificate_identity( create_cert_with_name('*baz.example.com'), 'foobaz.example.com')) assert_equal(true, OpenSSL::SSL.verify_certificate_identity( create_cert_with_name('b*z.example.com'), 'buzz.example.com')) # Section 6.4.3 of RFC6125 states that client should NOT match identifier # where wildcard is other than left-most label. # # Also implicitly mentions the wildcard character only in singular form, # and discourages matching against more than one wildcard. # # See RFC 6125, section 7.2, subitem 2. assert_equal(false, OpenSSL::SSL.verify_certificate_identity( create_cert_with_name('*b*.example.com'), 'abc.example.com')) assert_equal(false, OpenSSL::SSL.verify_certificate_identity( create_cert_with_name('*b*.example.com'), 'ab.example.com')) assert_equal(false, OpenSSL::SSL.verify_certificate_identity( create_cert_with_name('*b*.example.com'), 'bc.example.com')) assert_equal(true, OpenSSL::SSL.verify_certificate_identity( create_cert_with_name('xn*.example.com'), 'xn1ca.example.com')) assert_equal(false, OpenSSL::SSL.verify_certificate_identity( create_cert_with_name('xn--*.example.com'), 'xn--1ca.example.com')) # part of U-label # Subject in RFC5280 states case-insensitive ASCII comparison. # # See Section 7.2 of RFC 5280: # IA5String is limited to the set of ASCII characters. assert_equal(false, OpenSSL::SSL.verify_certificate_identity( create_cert_with_name('á*.example.com'), 'á1.example.com')) end def create_cert_with_san(san) ef = OpenSSL::X509::ExtensionFactory.new cert = OpenSSL::X509::Certificate.new cert.subject = OpenSSL::X509::Name.parse("/DC=some/DC=site/CN=Some Site") ext = ef.create_ext('subjectAltName', san) cert.add_extension(ext) cert end def create_cert_with_name(name) cert = OpenSSL::X509::Certificate.new cert.subject = OpenSSL::X509::Name.new([['DC', 'some'], ['DC', 'site'], ['CN', name]]) cert end # Create NULL byte SAN certificate def create_null_byte_SAN_certificate(critical = false) ef = OpenSSL::X509::ExtensionFactory.new cert = OpenSSL::X509::Certificate.new cert.subject = OpenSSL::X509::Name.parse "/DC=some/DC=site/CN=Some Site" ext = ef.create_ext('subjectAltName', 'DNS:placeholder,IP:192.168.7.1,IP:13::17', critical) ext_asn1 = OpenSSL::ASN1.decode(ext.to_der) san_list_der = ext_asn1.value.reduce(nil) { |memo,val| val.tag == 4 ? val.value : memo } san_list_asn1 = OpenSSL::ASN1.decode(san_list_der) san_list_asn1.value[0].value = "www.example.com\0.evil.com" pos = critical ? 2 : 1 ext_asn1.value[pos].value = san_list_asn1.to_der real_ext = OpenSSL::X509::Extension.new ext_asn1 cert.add_extension(real_ext) cert end def socketpair if defined? UNIXSocket UNIXSocket.pair else Socket.pair(Socket::AF_INET, Socket::SOCK_STREAM, 0) end end def test_keylog_cb pend "Keylog callback is not supported" if !openssl?(1, 1, 1) || libressl? prefix = 'CLIENT_RANDOM' context = OpenSSL::SSL::SSLContext.new context.min_version = context.max_version = OpenSSL::SSL::TLS1_2_VERSION cb_called = false context.keylog_cb = proc do |_sock, line| cb_called = true assert_equal(prefix, line.split.first) end start_server do |port| server_connect(port, context) do |ssl| ssl.puts "abc" assert_equal("abc\n", ssl.gets) assert_equal(true, cb_called) end end if tls13_supported? prefixes = [ 'SERVER_HANDSHAKE_TRAFFIC_SECRET', 'EXPORTER_SECRET', 'SERVER_TRAFFIC_SECRET_0', 'CLIENT_HANDSHAKE_TRAFFIC_SECRET', 'CLIENT_TRAFFIC_SECRET_0', ] context = OpenSSL::SSL::SSLContext.new context.min_version = context.max_version = OpenSSL::SSL::TLS1_3_VERSION cb_called = false context.keylog_cb = proc do |_sock, line| cb_called = true assert_not_nil(prefixes.delete(line.split.first)) end start_server do |port| server_connect(port, context) do |ssl| ssl.puts "abc" assert_equal("abc\n", ssl.gets) assert_equal(true, cb_called) end assert_equal(0, prefixes.size) end end end def test_tlsext_hostname fooctx = OpenSSL::SSL::SSLContext.new fooctx.cert = @cli_cert fooctx.key = @cli_key ctx_proc = proc { |ctx| ctx.servername_cb = proc { |ssl, servername| case servername when "foo.example.com" fooctx when "bar.example.com" nil else raise "unreachable" end } } start_server(ctx_proc: ctx_proc) do |port| sock = TCPSocket.new("127.0.0.1", port) begin ssl = OpenSSL::SSL::SSLSocket.new(sock) ssl.hostname = "foo.example.com" ssl.connect assert_equal @cli_cert.serial, ssl.peer_cert.serial assert_predicate fooctx, :frozen? ssl.puts "abc"; assert_equal "abc\n", ssl.gets ensure ssl&.close sock.close end sock = TCPSocket.new("127.0.0.1", port) begin ssl = OpenSSL::SSL::SSLSocket.new(sock) ssl.hostname = "bar.example.com" ssl.connect assert_equal @svr_cert.serial, ssl.peer_cert.serial ssl.puts "abc"; assert_equal "abc\n", ssl.gets ensure ssl&.close sock.close end end end def test_servername_cb_raises_an_exception_on_unknown_objects hostname = 'example.org' ctx2 = OpenSSL::SSL::SSLContext.new ctx2.cert = @svr_cert ctx2.key = @svr_key ctx2.servername_cb = lambda { |args| Object.new } sock1, sock2 = socketpair s2 = OpenSSL::SSL::SSLSocket.new(sock2, ctx2) ctx1 = OpenSSL::SSL::SSLContext.new s1 = OpenSSL::SSL::SSLSocket.new(sock1, ctx1) s1.hostname = hostname t = Thread.new { assert_raise(OpenSSL::SSL::SSLError) do s1.connect end } assert_raise(ArgumentError) do s2.accept end assert t.join ensure sock1.close if sock1 sock2.close if sock2 end def test_accept_errors_include_peeraddr context = OpenSSL::SSL::SSLContext.new context.cert = @svr_cert context.key = @svr_key server = TCPServer.new("127.0.0.1", 0) port = server.connect_address.ip_port ssl_server = OpenSSL::SSL::SSLServer.new(server, context) t = Thread.new do assert_raise_with_message(OpenSSL::SSL::SSLError, /peeraddr=127\.0\.0\.1/) do ssl_server.accept end end sock = TCPSocket.new("127.0.0.1", port) sock << "\x00" * 1024 assert t.join ensure sock&.close server.close end 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", san], ] ctx.cert = issue_cert(@svr, @svr_key, 4, exts, @ca_cert, @ca_key) ctx.key = @svr_key } start_server(ctx_proc: ctx_proc, ignore_listener_error: true) do |port| ctx = OpenSSL::SSL::SSLContext.new assert_equal false, ctx.verify_hostname ctx.verify_hostname = true ctx.cert_store = OpenSSL::X509::Store.new ctx.cert_store.add_cert(@ca_cert) ctx.verify_mode = OpenSSL::SSL::VERIFY_PEER [ ["a.example.com", true], ["A.Example.Com", true], ["x.example.com", false], ["b.example.com", false], ["x.b.example.com", true], ["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) ssl.hostname = name if expected_ok ssl.connect ssl.puts "abc"; assert_equal "abc\n", ssl.gets else assert_handshake_error { ssl.connect } end ensure ssl.close if ssl sock.close if sock end end end end def test_verify_hostname_failure_error_code ctx_proc = proc { |ctx| exts = [ ["keyUsage", "keyEncipherment,digitalSignature", true], ["subjectAltName", "DNS:a.example.com"], ] ctx.cert = issue_cert(@svr, @svr_key, 4, exts, @ca_cert, @ca_key) ctx.key = @svr_key } start_server(ctx_proc: ctx_proc, ignore_listener_error: true) do |port| verify_callback_ok = verify_callback_err = nil ctx = OpenSSL::SSL::SSLContext.new ctx.verify_hostname = true ctx.cert_store = OpenSSL::X509::Store.new ctx.cert_store.add_cert(@ca_cert) ctx.verify_mode = OpenSSL::SSL::VERIFY_PEER ctx.verify_callback = -> (preverify_ok, store_ctx) { verify_callback_ok = preverify_ok verify_callback_err = store_ctx.error preverify_ok } begin sock = TCPSocket.new("127.0.0.1", port) ssl = OpenSSL::SSL::SSLSocket.new(sock, ctx) ssl.hostname = "b.example.com" assert_handshake_error { ssl.connect } assert_equal false, verify_callback_ok assert_equal OpenSSL::X509::V_ERR_HOSTNAME_MISMATCH, verify_callback_err ensure sock&.close end end end def test_connect_certificate_verify_failed_exception_message start_server(ignore_listener_error: true) { |port| ctx = OpenSSL::SSL::SSLContext.new ctx.set_params # OpenSSL <= 1.1.0: "self signed certificate in certificate chain" # OpenSSL >= 3.0.0: "self-signed certificate in certificate chain" assert_raise_with_message(OpenSSL::SSL::SSLError, /self.signed/) { server_connect(port, ctx) } } ctx_proc = proc { |ctx| now = Time.now ctx.cert = issue_cert(@svr, @svr_key, 30, [], @ca_cert, @ca_key, not_before: now - 7200, not_after: now - 3600) } start_server(ignore_listener_error: true, ctx_proc: ctx_proc) { |port| store = OpenSSL::X509::Store.new store.add_cert(@ca_cert) ctx = OpenSSL::SSL::SSLContext.new ctx.set_params(cert_store: store) assert_raise_with_message(OpenSSL::SSL::SSLError, /expired/) { server_connect(port, ctx) } } end def test_unset_OP_ALL ctx_proc = Proc.new { |ctx| # If OP_DONT_INSERT_EMPTY_FRAGMENTS is not defined, this test is # redundant because the default options already are equal to OP_ALL. # But it also degrades gracefully, so keep it ctx.options = OpenSSL::SSL::OP_ALL } start_server(ctx_proc: ctx_proc) { |port| server_connect(port) { |ssl| ssl.puts('hello') assert_equal("hello\n", ssl.gets) } } end 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) { |ssl| ssl.puts "abc"; assert_equal "abc\n", ssl.gets } rescue OpenSSL::SSL::SSLError, Errno::ECONNRESET else supported << ver end end } end assert_not_empty supported supported end def test_set_params_min_version supported = check_supported_protocol_versions store = OpenSSL::X509::Store.new store.add_cert(@ca_cert) if supported.include?(OpenSSL::SSL::SSL3_VERSION) # SSLContext#set_params properly disables SSL 3.0 by default ctx_proc = proc { |ctx| ctx.min_version = ctx.max_version = OpenSSL::SSL::SSL3_VERSION } start_server(ctx_proc: ctx_proc, ignore_listener_error: true) { |port| ctx = OpenSSL::SSL::SSLContext.new ctx.set_params(cert_store: store, verify_hostname: false) assert_handshake_error { server_connect(port, ctx) { } } } end end 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 }, } # 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 ssl.puts "abc"; assert_equal "abc\n", ssl.gets } else assert_handshake_error { server_connect(port, ctx1) { } } end # 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 ssl.puts "abc"; assert_equal "abc\n", ssl.gets } else assert_handshake_error { server_connect(port, ctx2) { } } end end 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 ssl.puts "abc"; assert_equal "abc\n", ssl.gets } } end if supported.size == 1 pend "More than one protocol version must be supported" 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 ssl.puts "abc"; assert_equal "abc\n", ssl.gets } # 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 ssl.puts "abc"; assert_equal "abc\n", ssl.gets } else assert_handshake_error { server_connect(port, ctx2) { } } end end } # 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 ssl.puts "abc"; assert_equal "abc\n", ssl.gets } else assert_handshake_error { server_connect(port, ctx1) { } } end # 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 ssl.puts "abc"; assert_equal "abc\n", ssl.gets } end } end def test_options_disable_versions # It's recommended to use SSLContext#{min,max}_version= instead in real # applications. The purpose of this test case is to check that SSL options # are properly propagated to OpenSSL library. supported = check_supported_protocol_versions if !defined?(OpenSSL::SSL::TLS1_3_VERSION) || !supported.include?(OpenSSL::SSL::TLS1_2_VERSION) || !supported.include?(OpenSSL::SSL::TLS1_3_VERSION) || !defined?(OpenSSL::SSL::OP_NO_TLSv1_3) # LibreSSL < 3.4 pend "this test case requires both TLS 1.2 and TLS 1.3 to be supported " \ "and enabled by default" end # Server disables TLS 1.2 and earlier 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 | OpenSSL::SSL::OP_NO_TLSv1_2 } start_server(ctx_proc: ctx_proc, ignore_listener_error: true) { |port| # Client only supports TLS 1.2 ctx1 = OpenSSL::SSL::SSLContext.new ctx1.min_version = ctx1.max_version = OpenSSL::SSL::TLS1_2_VERSION assert_handshake_error { server_connect(port, ctx1) { } } # Client only supports TLS 1.3 ctx2 = OpenSSL::SSL::SSLContext.new ctx2.min_version = ctx2.max_version = OpenSSL::SSL::TLS1_3_VERSION assert_nothing_raised { server_connect(port, ctx2) { } } } # Server only supports TLS 1.2 ctx_proc = proc { |ctx| ctx.min_version = ctx.max_version = OpenSSL::SSL::TLS1_2_VERSION } start_server(ctx_proc: ctx_proc, ignore_listener_error: true) { |port| # Client doesn't support TLS 1.2 ctx1 = OpenSSL::SSL::SSLContext.new ctx1.options |= OpenSSL::SSL::OP_NO_TLSv1_2 assert_handshake_error { server_connect(port, ctx1) { } } # Client supports TLS 1.2 by default ctx2 = OpenSSL::SSL::SSLContext.new ctx2.options |= OpenSSL::SSL::OP_NO_TLSv1_3 assert_nothing_raised { server_connect(port, ctx2) { } } } end 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 def test_renegotiation_cb num_handshakes = 0 renegotiation_cb = Proc.new { |ssl| num_handshakes += 1 } ctx_proc = Proc.new { |ctx| ctx.renegotiation_cb = renegotiation_cb } start_server_version(:SSLv23, ctx_proc) { |port| server_connect(port) { |ssl| assert_equal(1, num_handshakes) ssl.puts "abc"; assert_equal "abc\n", ssl.gets } } end def test_alpn_protocol_selection_ary advertised = ["http/1.1", "spdy/2"] ctx_proc = Proc.new { |ctx| ctx.alpn_select_cb = -> (protocols) { protocols.first } ctx.alpn_protocols = advertised } start_server_version(:SSLv23, ctx_proc) { |port| ctx = OpenSSL::SSL::SSLContext.new ctx.alpn_protocols = advertised server_connect(port, ctx) { |ssl| assert_equal(advertised.first, ssl.alpn_protocol) ssl.puts "abc"; assert_equal "abc\n", ssl.gets } } end def test_alpn_protocol_selection_cancel sock1, sock2 = socketpair ctx1 = OpenSSL::SSL::SSLContext.new ctx1.cert = @svr_cert ctx1.key = @svr_key ctx1.alpn_select_cb = -> (protocols) { nil } ssl1 = OpenSSL::SSL::SSLSocket.new(sock1, ctx1) ctx2 = OpenSSL::SSL::SSLContext.new ctx2.alpn_protocols = ["http/1.1"] ssl2 = OpenSSL::SSL::SSLSocket.new(sock2, ctx2) t = Thread.new { ssl2.connect_nonblock(exception: false) } assert_raise_with_message(TypeError, /nil/) { ssl1.accept } t.join ensure sock1&.close sock2&.close ssl1&.close ssl2&.close t&.kill t&.join end def test_npn_protocol_selection_ary pend "NPN is not supported" unless \ OpenSSL::SSL::SSLContext.method_defined?(:npn_select_cb) pend "LibreSSL 2.6 has broken NPN functions" if libressl?(2, 6, 1) advertised = ["http/1.1", "spdy/2"] ctx_proc = proc { |ctx| ctx.npn_protocols = advertised } start_server_version(:TLSv1_2, ctx_proc) { |port| selector = lambda { |which| ctx = OpenSSL::SSL::SSLContext.new ctx.npn_select_cb = -> (protocols) { protocols.send(which) } server_connect(port, ctx) { |ssl| assert_equal(advertised.send(which), ssl.npn_protocol) } } selector.call(:first) selector.call(:last) } end def test_npn_protocol_selection_enum pend "NPN is not supported" unless \ OpenSSL::SSL::SSLContext.method_defined?(:npn_select_cb) pend "LibreSSL 2.6 has broken NPN functions" if libressl?(2, 6, 1) advertised = Object.new def advertised.each yield "http/1.1" yield "spdy/2" end ctx_proc = Proc.new { |ctx| ctx.npn_protocols = advertised } start_server_version(:TLSv1_2, ctx_proc) { |port| selector = lambda { |selected, which| ctx = OpenSSL::SSL::SSLContext.new ctx.npn_select_cb = -> (protocols) { protocols.to_a.send(which) } server_connect(port, ctx) { |ssl| assert_equal(selected, ssl.npn_protocol) } } selector.call("http/1.1", :first) selector.call("spdy/2", :last) } end def test_npn_protocol_selection_cancel pend "NPN is not supported" unless \ OpenSSL::SSL::SSLContext.method_defined?(:npn_select_cb) pend "LibreSSL 2.6 has broken NPN functions" if libressl?(2, 6, 1) ctx_proc = Proc.new { |ctx| ctx.npn_protocols = ["http/1.1"] } start_server_version(:TLSv1_2, ctx_proc) { |port| ctx = OpenSSL::SSL::SSLContext.new ctx.npn_select_cb = -> (protocols) { raise RuntimeError.new } assert_raise(RuntimeError) { server_connect(port, ctx) } } end def test_npn_advertised_protocol_too_long pend "NPN is not supported" unless \ OpenSSL::SSL::SSLContext.method_defined?(:npn_select_cb) pend "LibreSSL 2.6 has broken NPN functions" if libressl?(2, 6, 1) ctx_proc = Proc.new { |ctx| ctx.npn_protocols = ["a" * 256] } start_server_version(:TLSv1_2, ctx_proc) { |port| ctx = OpenSSL::SSL::SSLContext.new ctx.npn_select_cb = -> (protocols) { protocols.first } assert_handshake_error { server_connect(port, ctx) } } end def test_npn_selected_protocol_too_long pend "NPN is not supported" unless \ OpenSSL::SSL::SSLContext.method_defined?(:npn_select_cb) pend "LibreSSL 2.6 has broken NPN functions" if libressl?(2, 6, 1) ctx_proc = Proc.new { |ctx| ctx.npn_protocols = ["http/1.1"] } start_server_version(:TLSv1_2, ctx_proc) { |port| ctx = OpenSSL::SSL::SSLContext.new ctx.npn_select_cb = -> (protocols) { "a" * 256 } assert_handshake_error { server_connect(port, ctx) } } end def readwrite_loop_safe(ctx, ssl) readwrite_loop(ctx, ssl) rescue OpenSSL::SSL::SSLError end def test_close_after_socket_close start_server(server_proc: method(:readwrite_loop_safe)) { |port| sock = TCPSocket.new("127.0.0.1", port) ssl = OpenSSL::SSL::SSLSocket.new(sock) ssl.connect ssl.puts "abc"; assert_equal "abc\n", ssl.gets sock.close assert_nothing_raised do ssl.close end } end def test_sync_close_without_connect Socket.open(:INET, :STREAM) {|s| ssl = OpenSSL::SSL::SSLSocket.new(s) ssl.sync_close = true ssl.close assert(s.closed?) } end def test_get_ephemeral_key # kRSA ctx_proc1 = proc { |ctx| ctx.ssl_version = :TLSv1_2 ctx.ciphers = "kRSA" } start_server(ctx_proc: ctx_proc1, ignore_listener_error: true) do |port| ctx = OpenSSL::SSL::SSLContext.new ctx.ssl_version = :TLSv1_2 ctx.ciphers = "kRSA" begin server_connect(port, ctx) { |ssl| assert_nil ssl.tmp_key } rescue OpenSSL::SSL::SSLError # kRSA seems disabled raise unless $!.message =~ /no cipher/ end end # DHE # TODO: How to test this with TLS 1.3? ctx_proc2 = proc { |ctx| ctx.ssl_version = :TLSv1_2 ctx.ciphers = "EDH" ctx.tmp_dh = Fixtures.pkey("dh-1") } start_server(ctx_proc: ctx_proc2) do |port| ctx = OpenSSL::SSL::SSLContext.new ctx.ssl_version = :TLSv1_2 ctx.ciphers = "EDH" server_connect(port, ctx) { |ssl| assert_instance_of OpenSSL::PKey::DH, ssl.tmp_key } end # ECDHE ctx_proc3 = proc { |ctx| ctx.ciphers = "DEFAULT:!kRSA:!kEDH" ctx.ecdh_curves = "P-256" } start_server(ctx_proc: ctx_proc3) do |port| ctx = OpenSSL::SSL::SSLContext.new ctx.ciphers = "DEFAULT:!kRSA:!kEDH" server_connect(port, ctx) { |ssl| assert_instance_of OpenSSL::PKey::EC, ssl.tmp_key ssl.puts "abc"; assert_equal "abc\n", ssl.gets } end end def test_fallback_scsv supported = check_supported_protocol_versions return unless supported.include?(OpenSSL::SSL::TLS1_1_VERSION) && supported.include?(OpenSSL::SSL::TLS1_2_VERSION) pend "Fallback SCSV is not supported" unless \ OpenSSL::SSL::SSLContext.method_defined?(:enable_fallback_scsv) start_server do |port| ctx = OpenSSL::SSL::SSLContext.new ctx.max_version = OpenSSL::SSL::TLS1_2_VERSION # Here is OK # TLS1.2 supported and this is what we ask the first time server_connect(port, ctx) end ctx_proc = proc { |ctx| ctx.max_version = OpenSSL::SSL::TLS1_1_VERSION } start_server(ctx_proc: ctx_proc) do |port| ctx = OpenSSL::SSL::SSLContext.new ctx.enable_fallback_scsv ctx.max_version = OpenSSL::SSL::TLS1_1_VERSION # Here is OK too # TLS1.2 not supported, fallback to TLS1.1 and signaling the fallback # Server doesn't support better, so connection OK server_connect(port, ctx) end # Here is not OK # TLS1.2 is supported, fallback to TLS1.1 (downgrade attack) and signaling the fallback # Server support better, so refuse the connection sock1, sock2 = socketpair begin # This test is for the downgrade protection mechanism of TLS1.2. # This is why ctx1 bounds max_version == TLS1.2. # Otherwise, this test fails when using openssl 1.1.1 (or later) that supports TLS1.3. # TODO: We may need another test for TLS1.3 because it seems to have a different mechanism. ctx1 = OpenSSL::SSL::SSLContext.new ctx1.max_version = OpenSSL::SSL::TLS1_2_VERSION s1 = OpenSSL::SSL::SSLSocket.new(sock1, ctx1) ctx2 = OpenSSL::SSL::SSLContext.new ctx2.enable_fallback_scsv ctx2.max_version = OpenSSL::SSL::TLS1_1_VERSION s2 = OpenSSL::SSL::SSLSocket.new(sock2, ctx2) t = Thread.new { assert_raise_with_message(OpenSSL::SSL::SSLError, /inappropriate fallback/) { s2.connect } } assert_raise_with_message(OpenSSL::SSL::SSLError, /inappropriate fallback/) { s1.accept } t.join ensure sock1.close sock2.close end end def test_tmp_dh_callback dh = Fixtures.pkey("dh-1") called = false ctx_proc = -> ctx { ctx.max_version = :TLS1_2 ctx.ciphers = "DH:!NULL" ctx.tmp_dh_callback = ->(*args) { called = true dh } } start_server(ctx_proc: ctx_proc) do |port| server_connect(port) { |ssl| assert called, "dh callback should be called" assert_equal dh.to_der, ssl.tmp_key.to_der } end end def test_ciphersuites_method_tls_connection ssl_ctx = OpenSSL::SSL::SSLContext.new if !tls13_supported? || !ssl_ctx.respond_to?(:ciphersuites=) pend 'TLS 1.3 not supported' end csuite = ['TLS_AES_128_GCM_SHA256', 'TLSv1.3', 128, 128] inputs = [csuite[0], [csuite[0]], [csuite]] start_server do |port| inputs.each do |input| cli_ctx = OpenSSL::SSL::SSLContext.new cli_ctx.min_version = cli_ctx.max_version = OpenSSL::SSL::TLS1_3_VERSION cli_ctx.ciphersuites = input server_connect(port, cli_ctx) do |ssl| assert_equal('TLSv1.3', ssl.ssl_version) if libressl?(3, 4, 0) && !libressl?(3, 5, 0) assert_equal("AEAD-AES128-GCM-SHA256", ssl.cipher[0]) else assert_equal(csuite[0], ssl.cipher[0]) end ssl.puts('abc'); assert_equal("abc\n", ssl.gets) end end end end def test_ciphersuites_method_nil_argument ssl_ctx = OpenSSL::SSL::SSLContext.new pend 'ciphersuites= method is missing' unless ssl_ctx.respond_to?(:ciphersuites=) assert_nothing_raised { ssl_ctx.ciphersuites = nil } end def test_ciphersuites_method_frozen_object ssl_ctx = OpenSSL::SSL::SSLContext.new pend 'ciphersuites= method is missing' unless ssl_ctx.respond_to?(:ciphersuites=) ssl_ctx.freeze assert_raise(FrozenError) { ssl_ctx.ciphersuites = 'TLS_AES_256_GCM_SHA384' } end def test_ciphersuites_method_bogus_csuite ssl_ctx = OpenSSL::SSL::SSLContext.new pend 'ciphersuites= method is missing' unless ssl_ctx.respond_to?(:ciphersuites=) assert_raise_with_message( OpenSSL::SSL::SSLError, /SSL_CTX_set_ciphersuites: no cipher match/i ) { ssl_ctx.ciphersuites = 'BOGUS' } end def test_ciphers_method_tls_connection csuite = ['ECDHE-RSA-AES256-GCM-SHA384', 'TLSv1.2', 256, 256] inputs = [csuite[0], [csuite[0]], [csuite]] start_server do |port| inputs.each do |input| cli_ctx = OpenSSL::SSL::SSLContext.new cli_ctx.min_version = cli_ctx.max_version = OpenSSL::SSL::TLS1_2_VERSION cli_ctx.ciphers = input server_connect(port, cli_ctx) do |ssl| assert_equal('TLSv1.2', ssl.ssl_version) assert_equal(csuite[0], ssl.cipher[0]) ssl.puts('abc'); assert_equal("abc\n", ssl.gets) end end end end def test_ciphers_method_nil_argument ssl_ctx = OpenSSL::SSL::SSLContext.new assert_nothing_raised { ssl_ctx.ciphers = nil } end def test_ciphers_method_frozen_object ssl_ctx = OpenSSL::SSL::SSLContext.new ssl_ctx.freeze assert_raise(FrozenError) { ssl_ctx.ciphers = 'ECDHE-RSA-AES128-SHA' } end def test_ciphers_method_bogus_csuite omit "Old #{OpenSSL::OPENSSL_LIBRARY_VERSION}" if year = OpenSSL::OPENSSL_LIBRARY_VERSION[/\A OpenSSL\s+[01]\..*\s\K\d+\z/x] and year.to_i <= 2018 ssl_ctx = OpenSSL::SSL::SSLContext.new assert_raise_with_message( OpenSSL::SSL::SSLError, /SSL_CTX_set_cipher_list: no cipher match/i ) { ssl_ctx.ciphers = 'BOGUS' } end def test_connect_works_when_setting_dh_callback_to_nil ctx_proc = -> ctx { ctx.max_version = :TLS1_2 ctx.ciphers = "DH:!NULL" # use DH ctx.tmp_dh_callback = nil } start_server(ctx_proc: ctx_proc) do |port| EnvUtil.suppress_warning { # uses default callback assert_nothing_raised { server_connect(port) { } } } end end def test_tmp_dh dh = Fixtures.pkey("dh-1") ctx_proc = -> ctx { ctx.max_version = :TLS1_2 ctx.ciphers = "DH:!NULL" # use DH ctx.tmp_dh = dh } start_server(ctx_proc: ctx_proc) do |port| server_connect(port) { |ssl| assert_equal dh.to_der, ssl.tmp_key.to_der } end end def test_ecdh_curves_tls12 ctx_proc = -> ctx { # Enable both ECDHE (~ TLS 1.2) cipher suites and TLS 1.3 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| # Test 1: Client=P-256:P-384, Server=P-384:P-521 --> P-384 ctx = OpenSSL::SSL::SSLContext.new ctx.ecdh_curves = "P-256:P-384" server_connect(port, ctx) { |ssl| cs = ssl.cipher[0] assert_match (/\AECDH/), cs assert_equal "secp384r1", ssl.tmp_key.group.curve_name ssl.puts "abc"; assert_equal "abc\n", ssl.gets } # Test 2: Client=P-256, Server=P-521:P-384 --> Fail ctx = OpenSSL::SSL::SSLContext.new ctx.ecdh_curves = "P-256" assert_raise(OpenSSL::SSL::SSLError) { server_connect(port, ctx) { } } # Test 3: Client=P-521:P-384, Server=P-521:P-384 --> P-521 ctx = OpenSSL::SSL::SSLContext.new ctx.ecdh_curves = "P-521:P-384" server_connect(port, ctx) { |ssl| assert_equal "secp521r1", ssl.tmp_key.group.curve_name ssl.puts "abc"; assert_equal "abc\n", ssl.gets } end end def test_ecdh_curves_tls13 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 ctx.security_level = 1 rescue NotImplementedError assert_equal(0, ctx.security_level) return end assert_equal(1, ctx.security_level) dsa512 = Fixtures.pkey("dsa512") dsa512_cert = issue_cert(@svr, dsa512, 50, [], @ca_cert, @ca_key) rsa1024 = Fixtures.pkey("rsa1024") rsa1024_cert = issue_cert(@svr, rsa1024, 51, [], @ca_cert, @ca_key) assert_raise(OpenSSL::SSL::SSLError) { # 512 bit DSA key is rejected because it offers < 80 bits of security ctx.add_certificate(dsa512_cert, dsa512) } assert_nothing_raised { ctx.add_certificate(rsa1024_cert, rsa1024) } ctx.security_level = 2 assert_raise(OpenSSL::SSL::SSLError) { # < 112 bits of security ctx.add_certificate(rsa1024_cert, rsa1024) } end def test_dup ctx = OpenSSL::SSL::SSLContext.new sock1, sock2 = socketpair ssl = OpenSSL::SSL::SSLSocket.new(sock1, ctx) assert_raise(NoMethodError) { ctx.dup } assert_raise(NoMethodError) { ssl.dup } ensure ssl.close if ssl sock1.close sock2.close end def test_freeze_calls_setup bug = "[ruby/openssl#85]" start_server(ignore_listener_error: true) { |port| ctx = OpenSSL::SSL::SSLContext.new ctx.verify_mode = OpenSSL::SSL::VERIFY_PEER ctx.freeze assert_raise(OpenSSL::SSL::SSLError, bug) { server_connect(port, ctx) } } end def test_fileno ctx = OpenSSL::SSL::SSLContext.new sock1, sock2 = socketpair socket = OpenSSL::SSL::SSLSocket.new(sock1) server = OpenSSL::SSL::SSLServer.new(sock2, ctx) assert_equal socket.fileno, socket.to_io.fileno assert_equal server.fileno, server.to_io.fileno ensure sock1.close sock2.close end def test_export_keying_material start_server do |port| cli_ctx = OpenSSL::SSL::SSLContext.new server_connect(port, cli_ctx) do |ssl| assert_instance_of(String, ssl.export_keying_material('ttls keying material', 64)) assert_operator(64, :==, ssl.export_keying_material('ttls keying material', 64).b.length) assert_operator(8, :==, ssl.export_keying_material('ttls keying material', 8).b.length) assert_operator(5, :==, ssl.export_keying_material('test', 5, 'context').b.length) ssl.puts "abc"; ssl.gets # workaround to make tests work on windows end end end private def start_server_version(version, ctx_proc = nil, server_proc = method(:readwrite_loop), &blk) ctx_wrap = Proc.new { |ctx| ctx.ssl_version = version ctx_proc.call(ctx) if ctx_proc } start_server( ctx_proc: ctx_wrap, server_proc: server_proc, ignore_listener_error: true, &blk ) end def server_connect(port, ctx = nil) sock = TCPSocket.new("127.0.0.1", port) ssl = ctx ? OpenSSL::SSL::SSLSocket.new(sock, ctx) : OpenSSL::SSL::SSLSocket.new(sock) ssl.sync_close = true ssl.connect yield ssl if block_given? ensure if ssl ssl.close elsif sock sock.close end end def assert_handshake_error # different OpenSSL versions react differently when facing a SSL/TLS version # that has been marked as forbidden, therefore any of these may be raised assert_raise(OpenSSL::SSL::SSLError, Errno::ECONNRESET, Errno::EPIPE) { yield } end end end