From 13dc364810e28edc1268cfbadd873fb6eed66209 Mon Sep 17 00:00:00 2001 From: Kazuki Yamaguchi Date: Mon, 6 Aug 2018 20:29:10 +0900 Subject: [PATCH 1/2] tool/ruby-openssl-docker: update to latest versions --- .travis.yml | 18 +++++++----- Dockerfile | 2 +- tool/ruby-openssl-docker/Dockerfile | 44 +++++++++++++++++++++-------- tool/ruby-openssl-docker/init.sh | 2 +- 4 files changed, 46 insertions(+), 20 deletions(-) diff --git a/.travis.yml b/.travis.yml index 1342da6d7..e6b18af38 100644 --- a/.travis.yml +++ b/.travis.yml @@ -18,14 +18,17 @@ matrix: fast_finish: true include: - env: RUBY_VERSION=ruby-2.3 OPENSSL_VERSION=openssl-1.0.2 - - env: RUBY_VERSION=ruby-2.4 OPENSSL_VERSION=openssl-1.0.0 - - env: RUBY_VERSION=ruby-2.4 OPENSSL_VERSION=openssl-1.0.1 - env: RUBY_VERSION=ruby-2.4 OPENSSL_VERSION=openssl-1.0.2 - - env: RUBY_VERSION=ruby-2.4 OPENSSL_VERSION=openssl-1.1.0 - - env: RUBY_VERSION=ruby-2.4 OPENSSL_VERSION=libressl-2.3 - - env: RUBY_VERSION=ruby-2.4 OPENSSL_VERSION=libressl-2.4 - - env: RUBY_VERSION=ruby-2.4 OPENSSL_VERSION=libressl-2.5 - - env: RUBY_VERSION=ruby-2.4 OPENSSL_VERSION=libressl-2.6 + - env: RUBY_VERSION=ruby-2.5 OPENSSL_VERSION=openssl-1.0.0 + - env: RUBY_VERSION=ruby-2.5 OPENSSL_VERSION=openssl-1.0.1 + - env: RUBY_VERSION=ruby-2.5 OPENSSL_VERSION=openssl-1.0.2 + - env: RUBY_VERSION=ruby-2.5 OPENSSL_VERSION=openssl-1.1.0 + - env: RUBY_VERSION=ruby-2.5 OPENSSL_VERSION=openssl-1.1.1 + - env: RUBY_VERSION=ruby-2.5 OPENSSL_VERSION=libressl-2.3 + - env: RUBY_VERSION=ruby-2.5 OPENSSL_VERSION=libressl-2.4 + - env: RUBY_VERSION=ruby-2.5 OPENSSL_VERSION=libressl-2.5 + - env: RUBY_VERSION=ruby-2.5 OPENSSL_VERSION=libressl-2.6 + - env: RUBY_VERSION=ruby-2.5 OPENSSL_VERSION=libressl-2.7 - language: ruby rvm: ruby-head before_install: @@ -36,3 +39,4 @@ matrix: allow_failures: - language: ruby rvm: ruby-head + - env: RUBY_VERSION=ruby-2.5 OPENSSL_VERSION=openssl-1.1.1 diff --git a/Dockerfile b/Dockerfile index ab7f09e25..fbf4acec5 100644 --- a/Dockerfile +++ b/Dockerfile @@ -1 +1 @@ -FROM zzak/ruby-openssl-docker:2.0 +FROM zzak/ruby-openssl-docker:testing diff --git a/tool/ruby-openssl-docker/Dockerfile b/tool/ruby-openssl-docker/Dockerfile index b8ed4bca1..4e28493ad 100644 --- a/tool/ruby-openssl-docker/Dockerfile +++ b/tool/ruby-openssl-docker/Dockerfile @@ -1,4 +1,4 @@ -FROM ubuntu:16.04 +FROM ubuntu:18.04 RUN apt-get update && apt-get install -y --no-install-recommends \ autoconf \ @@ -29,21 +29,29 @@ RUN curl -s https://www.openssl.org/source/openssl-1.0.1u.tar.gz | tar -C /build shared linux-x86_64 && \ make && make install_sw -RUN curl -s https://www.openssl.org/source/openssl-1.0.2l.tar.gz | tar -C /build/openssl -xzf - && \ - cd /build/openssl/openssl-1.0.2l && \ +RUN curl -s https://www.openssl.org/source/openssl-1.0.2o.tar.gz | tar -C /build/openssl -xzf - && \ + cd /build/openssl/openssl-1.0.2o && \ ./Configure \ --openssldir=/opt/openssl/openssl-1.0.2 \ shared linux-x86_64 && \ make && make install_sw -RUN curl -s https://www.openssl.org/source/openssl-1.1.0f.tar.gz | tar -C /build/openssl -xzf - && \ - cd /build/openssl/openssl-1.1.0f && \ +RUN curl -s https://www.openssl.org/source/openssl-1.1.0h.tar.gz | tar -C /build/openssl -xzf - && \ + cd /build/openssl/openssl-1.1.0h && \ ./Configure \ --prefix=/opt/openssl/openssl-1.1.0 \ enable-crypto-mdebug enable-crypto-mdebug-backtrace \ linux-x86_64 && \ make && make install_sw +RUN curl -s https://www.openssl.org/source/openssl-1.1.1-pre8.tar.gz | tar -C /build/openssl -xzf - && \ + cd /build/openssl/openssl-1.1.1-pre8 && \ + ./Configure \ + --prefix=/opt/openssl/openssl-1.1.1 \ + enable-crypto-mdebug enable-crypto-mdebug-backtrace \ + linux-x86_64 && \ + make && make install_sw + # Supported libressl versions: 2.3- RUN curl -s http://ftp.openbsd.org/pub/OpenBSD/LibreSSL/libressl-2.3.10.tar.gz | tar -C /build/openssl -xzf - && \ cd /build/openssl/libressl-2.3.10 && \ @@ -63,30 +71,44 @@ RUN curl -s http://ftp.openbsd.org/pub/OpenBSD/LibreSSL/libressl-2.5.5.tar.gz | --prefix=/opt/openssl/libressl-2.5 && \ make && make install -RUN curl -s http://ftp.openbsd.org/pub/OpenBSD/LibreSSL/libressl-2.6.1.tar.gz | tar -C /build/openssl -xzf - && \ - cd /build/openssl/libressl-2.6.1 && \ +RUN curl -s http://ftp.openbsd.org/pub/OpenBSD/LibreSSL/libressl-2.6.5.tar.gz | tar -C /build/openssl -xzf - && \ + cd /build/openssl/libressl-2.6.5 && \ ./configure \ --prefix=/opt/openssl/libressl-2.6 && \ make && make install +RUN curl -s http://ftp.openbsd.org/pub/OpenBSD/LibreSSL/libressl-2.7.4.tar.gz | tar -C /build/openssl -xzf - && \ + cd /build/openssl/libressl-2.7.4 && \ + ./configure \ + --prefix=/opt/openssl/libressl-2.7 && \ + make && make install + # Supported Ruby versions: 2.3- RUN mkdir -p /build/ruby -RUN curl -s https://cache.ruby-lang.org/pub/ruby/2.3/ruby-2.3.5.tar.gz | tar -C /build/ruby -xzf - && \ - cd /build/ruby/ruby-2.3.5 && \ +RUN curl -s https://cache.ruby-lang.org/pub/ruby/2.3/ruby-2.3.7.tar.gz | tar -C /build/ruby -xzf - && \ + cd /build/ruby/ruby-2.3.7 && \ autoconf && ./configure \ --without-openssl \ --prefix=/opt/ruby/ruby-2.3 \ --disable-install-doc && \ make && make install -RUN curl -s https://cache.ruby-lang.org/pub/ruby/2.4/ruby-2.4.2.tar.gz | tar -C /build/ruby -xzf - && \ - cd /build/ruby/ruby-2.4.2 && \ +RUN curl -s https://cache.ruby-lang.org/pub/ruby/2.4/ruby-2.4.4.tar.gz | tar -C /build/ruby -xzf - && \ + cd /build/ruby/ruby-2.4.4 && \ autoconf && ./configure \ --without-openssl \ --prefix=/opt/ruby/ruby-2.4 \ --disable-install-doc && \ make && make install +RUN curl -s https://cache.ruby-lang.org/pub/ruby/2.5/ruby-2.5.1.tar.gz | tar -C /build/ruby -xzf - && \ + cd /build/ruby/ruby-2.5.1 && \ + autoconf && ./configure \ + --without-openssl \ + --prefix=/opt/ruby/ruby-2.5 \ + --disable-install-doc && \ + make && make install + ONBUILD ADD . /home/openssl/code ONBUILD WORKDIR /home/openssl/code diff --git a/tool/ruby-openssl-docker/init.sh b/tool/ruby-openssl-docker/init.sh index 4d97e28c7..a6bc66070 100755 --- a/tool/ruby-openssl-docker/init.sh +++ b/tool/ruby-openssl-docker/init.sh @@ -2,7 +2,7 @@ if [[ "$RUBY_VERSION" = "" ]] then - RUBY_VERSION=ruby-2.4 + RUBY_VERSION=ruby-2.5 fi if [[ "$OPENSSL_VERSION" = "" ]] From 6fcc6c0efc42d1c6325cf4bb0ca16e2a448cdbed Mon Sep 17 00:00:00 2001 From: Kazuki Yamaguchi Date: Mon, 6 Aug 2018 20:51:42 +0900 Subject: [PATCH 2/2] test/test_ssl: fix test failure with TLS 1.3 SSL_connect() on the client side may return before SSL_accept() on server side returns. This will fix test failures with OpenSSL's current master. --- test/test_ssl.rb | 45 ++++++++++++++++++++++++++-------------- test/test_ssl_session.rb | 1 + 2 files changed, 31 insertions(+), 15 deletions(-) diff --git a/test/test_ssl.rb b/test/test_ssl.rb index 7bb32adf9..408c7d820 100644 --- a/test/test_ssl.rb +++ b/test/test_ssl.rb @@ -48,6 +48,8 @@ def test_ssl_with_server_cert 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 @@ -77,6 +79,7 @@ def test_sync_close 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 @@ -88,6 +91,7 @@ def test_sync_close 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 @@ -179,7 +183,10 @@ def test_client_ca client_ca_from_server = sslconn.client_ca [@cli_cert, @cli_key] end - server_connect(port, ctx) { |ssl| assert_equal([@ca], client_ca_from_server) } + server_connect(port, ctx) { |ssl| + assert_equal([@ca], client_ca_from_server) + ssl.puts "abc"; assert_equal "abc\n", ssl.gets + } } end @@ -276,21 +283,16 @@ def test_verify_result } start_server { |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 true end - ssl = OpenSSL::SSL::SSLSocket.new(sock, ctx) - ssl.sync_close = true - begin - ssl.connect + server_connect(port, ctx) { |ssl| assert_equal(OpenSSL::X509::V_OK, ssl.verify_result) - ensure - ssl.close - end + ssl.puts "abc"; assert_equal "abc\n", ssl.gets + } } start_server(ignore_listener_error: true) { |port| @@ -377,6 +379,8 @@ def test_post_connection_check 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")) @@ -398,6 +402,8 @@ def test_post_connection_check @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")} @@ -418,6 +424,8 @@ def test_post_connection_check @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")} @@ -644,6 +652,8 @@ def test_tlsext_hostname 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 @@ -655,6 +665,8 @@ def test_tlsext_hostname 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 @@ -727,7 +739,8 @@ def test_verify_hostname_on_connect ssl = OpenSSL::SSL::SSLSocket.new(sock, ctx) ssl.hostname = name if expected_ok - assert_nothing_raised { ssl.connect } + ssl.connect + ssl.puts "abc"; assert_equal "abc\n", ssl.gets else assert_handshake_error { ssl.connect } end @@ -856,6 +869,7 @@ def test_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 @@ -874,6 +888,7 @@ def test_alpn_protocol_selection_ary 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 @@ -996,14 +1011,11 @@ def test_npn_selected_protocol_too_long end def test_close_after_socket_close - server_proc = proc { |ctx, ssl| - # Do nothing - } - start_server(server_proc: server_proc) { |port| + start_server { |port| 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 sock.close assert_nothing_raised do ssl.close @@ -1068,6 +1080,7 @@ def test_get_ephemeral_key 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 @@ -1158,6 +1171,7 @@ def test_ecdh_curves assert_equal "secp384r1", ssl.tmp_key.group.curve_name end end + ssl.puts "abc"; assert_equal "abc\n", ssl.gets } if openssl?(1, 0, 2) || libressl?(2, 5, 1) @@ -1173,6 +1187,7 @@ def test_ecdh_curves 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 diff --git a/test/test_ssl_session.rb b/test/test_ssl_session.rb index 6db0c2d19..78b160eda 100644 --- a/test/test_ssl_session.rb +++ b/test/test_ssl_session.rb @@ -113,6 +113,7 @@ def test_resumption non_resumable = nil start_server { |port| server_connect_with_session(port, nil, nil) { |ssl| + ssl.puts "abc"; assert_equal "abc\n", ssl.gets non_resumable = ssl.session } }