From 67f523ce13a3d6c8adf02530173679cf1dc0ddd6 Mon Sep 17 00:00:00 2001
From: Alexander Polcyn <apolcyn@google.com>
Date: Fri, 28 Dec 2018 07:55:36 -0800
Subject: Add support for ruby 2.6.0 binary package builds, drop 2.1 and 2.0
 binary package builds; pin bundler to 1.17.3 where necessary

---
 Rakefile                                           |  6 ++--
 templates/tools/dockerfile/ruby_deps.include       | 14 ++++----
 third_party/rake-compiler-dock/Dockerfile          |  3 +-
 tools/distrib/build_ruby_environment_macos.sh      |  2 +-
 .../distribtest/ruby_centos6_x64/Dockerfile        | 15 ++++++--
 .../distribtest/ruby_centos7_x64/Dockerfile        | 18 ++++++++--
 .../distribtest/ruby_fedora20_x64/Dockerfile       | 21 +++++++++--
 .../distribtest/ruby_fedora21_x64/Dockerfile       | 19 ++++++++--
 .../ruby_jessie_x64_ruby_2_0_0/Dockerfile          | 40 ---------------------
 .../ruby_jessie_x64_ruby_2_2/Dockerfile            | 40 +++++++++++++++++++++
 .../ruby_jessie_x64_ruby_2_3/Dockerfile            | 41 ++++++++++++++++++++++
 .../ruby_jessie_x64_ruby_2_4/Dockerfile            | 40 +++++++++++++++++++++
 .../ruby_jessie_x64_ruby_2_5/Dockerfile            | 40 +++++++++++++++++++++
 .../ruby_jessie_x64_ruby_2_6/Dockerfile            | 40 +++++++++++++++++++++
 .../dockerfile/grpc_artifact_linux_x64/Dockerfile  |  2 +-
 .../dockerfile/grpc_artifact_linux_x86/Dockerfile  |  2 +-
 .../interoptest/grpc_interop_ruby/Dockerfile       | 14 ++++----
 .../interoptest/grpc_interop_ruby/build_interop.sh |  2 +-
 tools/dockerfile/test/ruby_jessie_x64/Dockerfile   | 14 ++++----
 .../helper_scripts/prepare_build_macos_rc          |  2 +-
 tools/run_tests/artifacts/distribtest_targets.py   |  8 +++--
 21 files changed, 300 insertions(+), 83 deletions(-)
 delete mode 100644 tools/dockerfile/distribtest/ruby_jessie_x64_ruby_2_0_0/Dockerfile
 create mode 100644 tools/dockerfile/distribtest/ruby_jessie_x64_ruby_2_2/Dockerfile
 create mode 100644 tools/dockerfile/distribtest/ruby_jessie_x64_ruby_2_3/Dockerfile
 create mode 100644 tools/dockerfile/distribtest/ruby_jessie_x64_ruby_2_4/Dockerfile
 create mode 100644 tools/dockerfile/distribtest/ruby_jessie_x64_ruby_2_5/Dockerfile
 create mode 100644 tools/dockerfile/distribtest/ruby_jessie_x64_ruby_2_6/Dockerfile

diff --git a/Rakefile b/Rakefile
index 0068a3b8e4..d604f7935b 100755
--- a/Rakefile
+++ b/Rakefile
@@ -105,7 +105,7 @@ task 'dlls' do
     env_comp = "CC=#{opt[:cross]}-gcc "
     env_comp += "CXX=#{opt[:cross]}-g++ "
     env_comp += "LD=#{opt[:cross]}-gcc "
-    docker_for_windows "gem update --system --no-ri --no-doc && #{env} #{env_comp} make -j #{out} && #{opt[:cross]}-strip -x -S #{out} && cp #{out} #{opt[:out]}"
+    docker_for_windows "gem update --system --no-document && #{env} #{env_comp} make -j #{out} && #{opt[:cross]}-strip -x -S #{out} && cp #{out} #{opt[:out]}"
   end
 
 end
@@ -124,10 +124,10 @@ task 'gem:native' do
         "invoked on macos with ruby #{RUBY_VERSION}. The ruby macos artifact " \
         "build should be running on ruby 2.5."
     end
-    system "rake cross native gem RUBY_CC_VERSION=2.5.0:2.4.0:2.3.0:2.2.2:2.1.6:2.0.0 V=#{verbose} GRPC_CONFIG=#{grpc_config}"
+    system "rake cross native gem RUBY_CC_VERSION=2.6.0:2.5.0:2.4.0:2.3.0:2.2.2 V=#{verbose} GRPC_CONFIG=#{grpc_config}"
   else
     Rake::Task['dlls'].execute
-    docker_for_windows "gem update --system --no-ri --no-doc && bundle && rake cross native gem RUBY_CC_VERSION=2.5.0:2.4.0:2.3.0:2.2.2:2.1.6:2.0.0 V=#{verbose} GRPC_CONFIG=#{grpc_config}"
+    docker_for_windows "gem update --system --no-document && bundle && rake cross native gem RUBY_CC_VERSION=2.6.0:2.5.0:2.4.0:2.3.0:2.2.2 V=#{verbose} GRPC_CONFIG=#{grpc_config}"
   end
 end
 
diff --git a/templates/tools/dockerfile/ruby_deps.include b/templates/tools/dockerfile/ruby_deps.include
index a8ee3ec7dc..c2d330988c 100644
--- a/templates/tools/dockerfile/ruby_deps.include
+++ b/templates/tools/dockerfile/ruby_deps.include
@@ -2,13 +2,13 @@
 # Ruby dependencies
 
 # Install rvm
-RUN gpg --keyserver hkp://keys.gnupg.net --recv-keys 409B6B1796C275462A1703113804BB82D39DC0E3
+RUN gpg --keyserver hkp://keys.gnupg.net --recv-keys 409B6B1796C275462A1703113804BB82D39DC0E3 7D2BAF1CF37B13E2069D6956105BD0E739499BDB
 RUN \curl -sSL https://get.rvm.io | bash -s stable
 
-# Install Ruby 2.1
-RUN /bin/bash -l -c "rvm install ruby-2.1"
-RUN /bin/bash -l -c "rvm use --default ruby-2.1"
-RUN /bin/bash -l -c "echo 'gem: --no-ri --no-rdoc' > ~/.gemrc"
+# Install Ruby 2.5
+RUN /bin/bash -l -c "rvm install ruby-2.5"
+RUN /bin/bash -l -c "rvm use --default ruby-2.5"
+RUN /bin/bash -l -c "echo 'gem: --no-document' > ~/.gemrc"
 RUN /bin/bash -l -c "echo 'export PATH=/usr/local/rvm/bin:$PATH' >> ~/.bashrc"
-RUN /bin/bash -l -c "echo 'rvm --default use ruby-2.1' >> ~/.bashrc"
-RUN /bin/bash -l -c "gem install bundler --no-ri --no-rdoc"
+RUN /bin/bash -l -c "echo 'rvm --default use ruby-2.5' >> ~/.bashrc"
+RUN /bin/bash -l -c "gem install bundler --no-document"
diff --git a/third_party/rake-compiler-dock/Dockerfile b/third_party/rake-compiler-dock/Dockerfile
index 06c721c39b..44eddc82e8 100644
--- a/third_party/rake-compiler-dock/Dockerfile
+++ b/third_party/rake-compiler-dock/Dockerfile
@@ -1,8 +1,7 @@
-FROM larskanis/rake-compiler-dock:0.6.2
+FROM larskanis/rake-compiler-dock-mri:0.7.0
 
 RUN find / -name rbconfig.rb | while read f ; do sed -i 's/0x0501/0x0600/' $f ; done
 RUN find / -name win32.h | while read f ; do sed -i 's/gettimeofday/rb_gettimeofday/' $f ; done
-RUN sed -i 's/defined.__MINGW64__.$/1/' /usr/local/rake-compiler/ruby/i686-w64-mingw32/ruby-2.0.0-p645/include/ruby-2.0.0/ruby/win32.h
 RUN find / -name libwinpthread.dll.a | xargs rm
 RUN find / -name libwinpthread-1.dll | xargs rm
 RUN find / -name *msvcrt-ruby*.dll.a | while read f ; do n=`echo $f | sed s/.dll//` ; mv $f $n ; done
diff --git a/tools/distrib/build_ruby_environment_macos.sh b/tools/distrib/build_ruby_environment_macos.sh
index 9e3e3b46f8..c2c0dcde6b 100644
--- a/tools/distrib/build_ruby_environment_macos.sh
+++ b/tools/distrib/build_ruby_environment_macos.sh
@@ -49,7 +49,7 @@ EOF
 
 MAKE="make -j8"
 
-for v in 2.5.0 2.4.0 2.3.0 2.2.2 2.1.6 2.0.0-p645 ; do
+for v in 2.6.0 2.5.0 2.4.0 2.3.0 2.2.2 ; do
   ccache -c
   rake -f "$CROSS_RUBY" cross-ruby VERSION="$v" HOST=x86_64-darwin11 MAKE="$MAKE"
 done
diff --git a/tools/dockerfile/distribtest/ruby_centos6_x64/Dockerfile b/tools/dockerfile/distribtest/ruby_centos6_x64/Dockerfile
index c3d6e03f6a..b53ffc22d4 100644
--- a/tools/dockerfile/distribtest/ruby_centos6_x64/Dockerfile
+++ b/tools/dockerfile/distribtest/ruby_centos6_x64/Dockerfile
@@ -19,10 +19,19 @@ RUN yum install -y curl
 RUN yum install -y tar which
 
 # Install rvm
-RUN gpg --keyserver hkp://keys.gnupg.net --recv-keys 409B6B1796C275462A1703113804BB82D39DC0E3
+RUN gpg --keyserver hkp://keys.gnupg.net --recv-keys 409B6B1796C275462A1703113804BB82D39DC0E3 7D2BAF1CF37B13E2069D6956105BD0E739499BDB
+RUN curl -sSL https://get.rvm.io | bash -s stable
+
+# Install Ruby 2.2
 # Running the installation twice to work around docker issue when using overlay.
 # https://github.com/docker/docker/issues/10180
-RUN (curl -sSL https://get.rvm.io | bash -s stable --ruby) || (curl -sSL https://get.rvm.io | bash -s stable --ruby)
+RUN (/bin/bash -l -c "rvm install ruby-2.2.10") || (/bin/bash -l -c "rvm install ruby-2.2.10")
+RUN /bin/bash -l -c "rvm use --default ruby-2.2.10"
+RUN /bin/bash -l -c "echo 'gem: --no-document' > ~/.gemrc"
+RUN /bin/bash -l -c "echo 'export PATH=/usr/local/rvm/bin:$PATH' >> ~/.bashrc"
+RUN /bin/bash -l -c "echo 'rvm --default use ruby-2.2.10' >> ~/.bashrc"
+RUN /bin/bash -l -c "gem install bundler -v 1.17.3 --no-document"
+
+RUN mkdir /var/local/jenkins
 
 RUN /bin/bash -l -c "echo '. /etc/profile.d/rvm.sh' >> ~/.bashrc"
-RUN /bin/bash -l -c "gem install --update bundler"
diff --git a/tools/dockerfile/distribtest/ruby_centos7_x64/Dockerfile b/tools/dockerfile/distribtest/ruby_centos7_x64/Dockerfile
index 73207e4210..72235bfba7 100644
--- a/tools/dockerfile/distribtest/ruby_centos7_x64/Dockerfile
+++ b/tools/dockerfile/distribtest/ruby_centos7_x64/Dockerfile
@@ -14,6 +14,20 @@
 
 FROM centos:7
 
-RUN yum install -y ruby
+RUN yum update && yum install -y curl tar which
 
-RUN gem install bundler
+# Install rvm
+RUN gpg --keyserver hkp://keys.gnupg.net --recv-keys 409B6B1796C275462A1703113804BB82D39DC0E3 7D2BAF1CF37B13E2069D6956105BD0E739499BDB
+RUN curl -sSL https://get.rvm.io | bash -s stable
+
+# Install Ruby 2.2
+RUN /bin/bash -l -c "rvm install ruby-2.2.10"
+RUN /bin/bash -l -c "rvm use --default ruby-2.2.10"
+RUN /bin/bash -l -c "echo 'gem: --no-document' > ~/.gemrc"
+RUN /bin/bash -l -c "echo 'export PATH=/usr/local/rvm/bin:$PATH' >> ~/.bashrc"
+RUN /bin/bash -l -c "echo 'rvm --default use ruby-2.2.10' >> ~/.bashrc"
+RUN /bin/bash -l -c "gem install bundler -v 1.17.3 --no-document"
+
+RUN mkdir /var/local/jenkins
+
+RUN /bin/bash -l -c "echo '. /etc/profile.d/rvm.sh' >> ~/.bashrc"
diff --git a/tools/dockerfile/distribtest/ruby_fedora20_x64/Dockerfile b/tools/dockerfile/distribtest/ruby_fedora20_x64/Dockerfile
index 200c5c2803..3d688a889f 100644
--- a/tools/dockerfile/distribtest/ruby_fedora20_x64/Dockerfile
+++ b/tools/dockerfile/distribtest/ruby_fedora20_x64/Dockerfile
@@ -14,6 +14,23 @@
 
 FROM fedora:20
 
-RUN yum clean all && yum update -y && yum install -y ruby findutils
+# distro-sync and install openssl, per https://github.com/fedora-cloud/docker-brew-fedora/issues/19
+RUN yum clean all && yum update -y && yum distro-sync -y && yum install -y openssl gnupg which findutils
 
-RUN gem install bundler
+# Install rvm
+RUN gpg --keyserver hkp://keys.gnupg.net --recv-keys 409B6B1796C275462A1703113804BB82D39DC0E3 7D2BAF1CF37B13E2069D6956105BD0E739499BDB
+RUN curl -sSL https://get.rvm.io | bash -s stable
+
+# Install Ruby 2.2
+# Running the installation twice to work around docker issue when using overlay.
+# https://github.com/docker/docker/issues/10180
+RUN (/bin/bash -l -c "rvm install ruby-2.2.10") || (/bin/bash -l -c "rvm install ruby-2.2.10")
+RUN /bin/bash -l -c "rvm use --default ruby-2.2.10"
+RUN /bin/bash -l -c "echo 'gem: --no-document' > ~/.gemrc"
+RUN /bin/bash -l -c "echo 'export PATH=/usr/local/rvm/bin:$PATH' >> ~/.bashrc"
+RUN /bin/bash -l -c "echo 'rvm --default use ruby-2.2.10' >> ~/.bashrc"
+RUN /bin/bash -l -c "gem install bundler -v 1.17.3 --no-document"
+
+RUN mkdir /var/local/jenkins
+
+RUN /bin/bash -l -c "echo '. /etc/profile.d/rvm.sh' >> ~/.bashrc"
diff --git a/tools/dockerfile/distribtest/ruby_fedora21_x64/Dockerfile b/tools/dockerfile/distribtest/ruby_fedora21_x64/Dockerfile
index e1177fd99a..8044adf15d 100644
--- a/tools/dockerfile/distribtest/ruby_fedora21_x64/Dockerfile
+++ b/tools/dockerfile/distribtest/ruby_fedora21_x64/Dockerfile
@@ -19,6 +19,21 @@ FROM fedora:21
 # https://github.com/docker/docker/issues/10180
 RUN yum install -y yum-plugin-ovl
 
-RUN yum clean all && yum update -y && yum install -y ruby findutils
+# distro-sync and install openssl, per https://github.com/fedora-cloud/docker-brew-fedora/issues/19
+RUN yum clean all && yum update -y && yum distro-sync -y && yum install -y openssl gnupg which findutils tar
 
-RUN gem install bundler
+# Install rvm
+RUN gpg --keyserver hkp://keys.gnupg.net --recv-keys 409B6B1796C275462A1703113804BB82D39DC0E3 7D2BAF1CF37B13E2069D6956105BD0E739499BDB
+RUN curl -sSL https://get.rvm.io | bash -s stable
+
+# Install Ruby 2.2
+RUN /bin/bash -l -c "rvm install ruby-2.2.10"
+RUN /bin/bash -l -c "rvm use --default ruby-2.2.10"
+RUN /bin/bash -l -c "echo 'gem: --no-document' > ~/.gemrc"
+RUN /bin/bash -l -c "echo 'export PATH=/usr/local/rvm/bin:$PATH' >> ~/.bashrc"
+RUN /bin/bash -l -c "echo 'rvm --default use ruby-2.2.10' >> ~/.bashrc"
+RUN /bin/bash -l -c "gem install bundler -v 1.17.3 --no-document"
+
+RUN mkdir /var/local/jenkins
+
+RUN /bin/bash -l -c "echo '. /etc/profile.d/rvm.sh' >> ~/.bashrc"
diff --git a/tools/dockerfile/distribtest/ruby_jessie_x64_ruby_2_0_0/Dockerfile b/tools/dockerfile/distribtest/ruby_jessie_x64_ruby_2_0_0/Dockerfile
deleted file mode 100644
index ff43c92c9e..0000000000
--- a/tools/dockerfile/distribtest/ruby_jessie_x64_ruby_2_0_0/Dockerfile
+++ /dev/null
@@ -1,40 +0,0 @@
-# Copyright 2015 gRPC authors.
-#
-# Licensed under the Apache License, Version 2.0 (the "License");
-# you may not use this file except in compliance with the License.
-# You may obtain a copy of the License at
-#
-#     http://www.apache.org/licenses/LICENSE-2.0
-#
-# Unless required by applicable law or agreed to in writing, software
-# distributed under the License is distributed on an "AS IS" BASIS,
-# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
-# See the License for the specific language governing permissions and
-# limitations under the License.
-
-FROM debian:jessie
-
-# Install Git and basic packages.
-RUN apt-get update && apt-get install -y \
-  curl \
-  gcc && apt-get clean
-
-#==================
-# Ruby dependencies
-
-# Install rvm
-RUN gpg --keyserver hkp://keys.gnupg.net --recv-keys 409B6B1796C275462A1703113804BB82D39DC0E3
-RUN \curl -sSL https://get.rvm.io | bash -s stable
-
-# Install Ruby 2.1
-RUN /bin/bash -l -c "rvm install ruby-2.0"
-RUN /bin/bash -l -c "rvm use --default ruby-2.0"
-RUN /bin/bash -l -c "echo 'gem: --no-ri --no-rdoc' > ~/.gemrc"
-RUN /bin/bash -l -c "echo 'export PATH=/usr/local/rvm/bin:$PATH' >> ~/.bashrc"
-RUN /bin/bash -l -c "echo 'rvm --default use ruby-2.0' >> ~/.bashrc"
-RUN /bin/bash -l -c "gem install bundler --no-ri --no-rdoc"
-
-RUN mkdir /var/local/jenkins
-
-# Define the default command.
-CMD ["bash"]
diff --git a/tools/dockerfile/distribtest/ruby_jessie_x64_ruby_2_2/Dockerfile b/tools/dockerfile/distribtest/ruby_jessie_x64_ruby_2_2/Dockerfile
new file mode 100644
index 0000000000..337fc3b5d8
--- /dev/null
+++ b/tools/dockerfile/distribtest/ruby_jessie_x64_ruby_2_2/Dockerfile
@@ -0,0 +1,40 @@
+# Copyright 2015 gRPC authors.
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#     http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+FROM debian:jessie
+
+# Install Git and basic packages.
+RUN apt-get update && apt-get install -y \
+  curl \
+  gcc && apt-get clean
+
+#==================
+# Ruby dependencies
+
+# Install rvm
+RUN gpg --keyserver hkp://keys.gnupg.net --recv-keys 409B6B1796C275462A1703113804BB82D39DC0E3 7D2BAF1CF37B13E2069D6956105BD0E739499BDB
+RUN \curl -sSL https://get.rvm.io | bash -s stable
+
+# Install Ruby 2.2
+RUN /bin/bash -l -c "rvm install ruby-2.2.10"
+RUN /bin/bash -l -c "rvm use --default ruby-2.2.10"
+RUN /bin/bash -l -c "echo 'gem: --no-document' > ~/.gemrc"
+RUN /bin/bash -l -c "echo 'export PATH=/usr/local/rvm/bin:$PATH' >> ~/.bashrc"
+RUN /bin/bash -l -c "echo 'rvm --default use ruby-2.2.10' >> ~/.bashrc"
+RUN /bin/bash -l -c "gem install bundler -v 1.17.3 --no-document"
+
+RUN mkdir /var/local/jenkins
+
+# Define the default command.
+CMD ["bash"]
diff --git a/tools/dockerfile/distribtest/ruby_jessie_x64_ruby_2_3/Dockerfile b/tools/dockerfile/distribtest/ruby_jessie_x64_ruby_2_3/Dockerfile
new file mode 100644
index 0000000000..9deff0661b
--- /dev/null
+++ b/tools/dockerfile/distribtest/ruby_jessie_x64_ruby_2_3/Dockerfile
@@ -0,0 +1,41 @@
+# Copyright 2015 gRPC authors.
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#     http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+FROM debian:jessie
+
+# Install Git and basic packages.
+RUN apt-get update && apt-get install -y \
+  curl \
+  gcc && apt-get clean
+
+#==================
+# Ruby dependencies
+
+# Install rvm
+RUN gpg --keyserver hkp://keys.gnupg.net --recv-keys 409B6B1796C275462A1703113804BB82D39DC0E3 7D2BAF1CF37B13E2069D6956105BD0E739499BDB
+RUN \curl -sSL https://get.rvm.io | bash -s stable
+
+# Install Ruby 2.3
+RUN /bin/bash -l -c "rvm install ruby-2.3.8"
+RUN /bin/bash -l -c "rvm use --default ruby-2.3.8"
+RUN /bin/bash -l -c "echo 'gem: --no-document' > ~/.gemrc"
+RUN /bin/bash -l -c "echo 'export PATH=/usr/local/rvm/bin:$PATH' >> ~/.bashrc"
+RUN /bin/bash -l -c "echo 'rvm --default use ruby-2.3.8' >> ~/.bashrc"
+RUN /bin/bash -l -c "gem update --system"
+RUN /bin/bash -l -c "gem install bundler -v 1.17.3 --no-document"
+
+RUN mkdir /var/local/jenkins
+
+# Define the default command.
+CMD ["bash"]
diff --git a/tools/dockerfile/distribtest/ruby_jessie_x64_ruby_2_4/Dockerfile b/tools/dockerfile/distribtest/ruby_jessie_x64_ruby_2_4/Dockerfile
new file mode 100644
index 0000000000..55b1b1e731
--- /dev/null
+++ b/tools/dockerfile/distribtest/ruby_jessie_x64_ruby_2_4/Dockerfile
@@ -0,0 +1,40 @@
+# Copyright 2015 gRPC authors.
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#     http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+FROM debian:jessie
+
+# Install Git and basic packages.
+RUN apt-get update && apt-get install -y \
+  curl \
+  gcc && apt-get clean
+
+#==================
+# Ruby dependencies
+
+# Install rvm
+RUN gpg --keyserver hkp://keys.gnupg.net --recv-keys 409B6B1796C275462A1703113804BB82D39DC0E3 7D2BAF1CF37B13E2069D6956105BD0E739499BDB
+RUN \curl -sSL https://get.rvm.io | bash -s stable
+
+# Install Ruby 2.4
+RUN /bin/bash -l -c "rvm install ruby-2.4.5"
+RUN /bin/bash -l -c "rvm use --default ruby-2.4.5"
+RUN /bin/bash -l -c "echo 'gem: --no-document' > ~/.gemrc"
+RUN /bin/bash -l -c "echo 'export PATH=/usr/local/rvm/bin:$PATH' >> ~/.bashrc"
+RUN /bin/bash -l -c "echo 'rvm --default use ruby-2.4.5' >> ~/.bashrc"
+RUN /bin/bash -l -c "gem install bundler -v 1.17.3 --no-document"
+
+RUN mkdir /var/local/jenkins
+
+# Define the default command.
+CMD ["bash"]
diff --git a/tools/dockerfile/distribtest/ruby_jessie_x64_ruby_2_5/Dockerfile b/tools/dockerfile/distribtest/ruby_jessie_x64_ruby_2_5/Dockerfile
new file mode 100644
index 0000000000..bed4b3a93e
--- /dev/null
+++ b/tools/dockerfile/distribtest/ruby_jessie_x64_ruby_2_5/Dockerfile
@@ -0,0 +1,40 @@
+# Copyright 2015 gRPC authors.
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#     http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+FROM debian:jessie
+
+# Install Git and basic packages.
+RUN apt-get update && apt-get install -y \
+  curl \
+  gcc && apt-get clean
+
+#==================
+# Ruby dependencies
+
+# Install rvm
+RUN gpg --keyserver hkp://keys.gnupg.net --recv-keys 409B6B1796C275462A1703113804BB82D39DC0E3 7D2BAF1CF37B13E2069D6956105BD0E739499BDB
+RUN \curl -sSL https://get.rvm.io | bash -s stable
+
+# Install Ruby 2.5
+RUN /bin/bash -l -c "rvm install ruby-2.5.3"
+RUN /bin/bash -l -c "rvm use --default ruby-2.5.3"
+RUN /bin/bash -l -c "echo 'gem: --no-document' > ~/.gemrc"
+RUN /bin/bash -l -c "echo 'export PATH=/usr/local/rvm/bin:$PATH' >> ~/.bashrc"
+RUN /bin/bash -l -c "echo 'rvm --default use ruby-2.5.3' >> ~/.bashrc"
+RUN /bin/bash -l -c "gem install bundler -v 1.17.3 --no-document"
+
+RUN mkdir /var/local/jenkins
+
+# Define the default command.
+CMD ["bash"]
diff --git a/tools/dockerfile/distribtest/ruby_jessie_x64_ruby_2_6/Dockerfile b/tools/dockerfile/distribtest/ruby_jessie_x64_ruby_2_6/Dockerfile
new file mode 100644
index 0000000000..af1839eba9
--- /dev/null
+++ b/tools/dockerfile/distribtest/ruby_jessie_x64_ruby_2_6/Dockerfile
@@ -0,0 +1,40 @@
+# Copyright 2015 gRPC authors.
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#     http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+FROM debian:jessie
+
+# Install Git and basic packages.
+RUN apt-get update && apt-get install -y \
+  curl \
+  gcc && apt-get clean
+
+#==================
+# Ruby dependencies
+
+# Install rvm
+RUN gpg --keyserver hkp://keys.gnupg.net --recv-keys 409B6B1796C275462A1703113804BB82D39DC0E3 7D2BAF1CF37B13E2069D6956105BD0E739499BDB
+RUN \curl -sSL https://get.rvm.io | bash -s stable
+
+# Install Ruby 2.6
+RUN /bin/bash -l -c "rvm install ruby-2.6.0"
+RUN /bin/bash -l -c "rvm use --default ruby-2.6.0"
+RUN /bin/bash -l -c "echo 'gem: --no-document' > ~/.gemrc"
+RUN /bin/bash -l -c "echo 'export PATH=/usr/local/rvm/bin:$PATH' >> ~/.bashrc"
+RUN /bin/bash -l -c "echo 'rvm --default use ruby-2.6.0' >> ~/.bashrc"
+RUN /bin/bash -l -c "gem install bundler --no-document"
+
+RUN mkdir /var/local/jenkins
+
+# Define the default command.
+CMD ["bash"]
diff --git a/tools/dockerfile/grpc_artifact_linux_x64/Dockerfile b/tools/dockerfile/grpc_artifact_linux_x64/Dockerfile
index 7ec061ebe5..e3e549f987 100644
--- a/tools/dockerfile/grpc_artifact_linux_x64/Dockerfile
+++ b/tools/dockerfile/grpc_artifact_linux_x64/Dockerfile
@@ -58,7 +58,7 @@ RUN /bin/bash -l -c "rvm use --default ruby-2.1"
 RUN /bin/bash -l -c "echo 'gem: --no-ri --no-rdoc' > ~/.gemrc"
 RUN /bin/bash -l -c "echo 'export PATH=/usr/local/rvm/bin:$PATH' >> ~/.bashrc"
 RUN /bin/bash -l -c "echo 'rvm --default use ruby-2.1' >> ~/.bashrc"
-RUN /bin/bash -l -c "gem install bundler --no-ri --no-rdoc"
+RUN /bin/bash -l -c "gem install bundler -v 1.17.3 --no-ri --no-rdoc"
 
 
 ##################
diff --git a/tools/dockerfile/grpc_artifact_linux_x86/Dockerfile b/tools/dockerfile/grpc_artifact_linux_x86/Dockerfile
index f81d8e5ba0..ec4fcbae36 100644
--- a/tools/dockerfile/grpc_artifact_linux_x86/Dockerfile
+++ b/tools/dockerfile/grpc_artifact_linux_x86/Dockerfile
@@ -58,7 +58,7 @@ RUN /bin/bash -l -c "rvm use --default ruby-2.1"
 RUN /bin/bash -l -c "echo 'gem: --no-ri --no-rdoc' > ~/.gemrc"
 RUN /bin/bash -l -c "echo 'export PATH=/usr/local/rvm/bin:$PATH' >> ~/.bashrc"
 RUN /bin/bash -l -c "echo 'rvm --default use ruby-2.1' >> ~/.bashrc"
-RUN /bin/bash -l -c "gem install bundler --no-ri --no-rdoc"
+RUN /bin/bash -l -c "gem install bundler -v 1.17.3 --no-ri --no-rdoc"
 
 ##################
 # C# dependencies (needed to build grpc_csharp_ext)
diff --git a/tools/dockerfile/interoptest/grpc_interop_ruby/Dockerfile b/tools/dockerfile/interoptest/grpc_interop_ruby/Dockerfile
index 97c146bb53..1f6f03edd8 100644
--- a/tools/dockerfile/interoptest/grpc_interop_ruby/Dockerfile
+++ b/tools/dockerfile/interoptest/grpc_interop_ruby/Dockerfile
@@ -68,16 +68,16 @@ RUN pip install futures==2.2.0 enum34==1.0.4 protobuf==3.5.2.post1 six==1.10.0 t
 # Ruby dependencies
 
 # Install rvm
-RUN gpg --keyserver hkp://keys.gnupg.net --recv-keys 409B6B1796C275462A1703113804BB82D39DC0E3
+RUN gpg --keyserver hkp://keys.gnupg.net --recv-keys 409B6B1796C275462A1703113804BB82D39DC0E3 7D2BAF1CF37B13E2069D6956105BD0E739499BDB
 RUN \curl -sSL https://get.rvm.io | bash -s stable
 
-# Install Ruby 2.1
-RUN /bin/bash -l -c "rvm install ruby-2.1"
-RUN /bin/bash -l -c "rvm use --default ruby-2.1"
-RUN /bin/bash -l -c "echo 'gem: --no-ri --no-rdoc' > ~/.gemrc"
+# Install Ruby 2.5
+RUN /bin/bash -l -c "rvm install ruby-2.5"
+RUN /bin/bash -l -c "rvm use --default ruby-2.5"
+RUN /bin/bash -l -c "echo 'gem: --no-document' > ~/.gemrc"
 RUN /bin/bash -l -c "echo 'export PATH=/usr/local/rvm/bin:$PATH' >> ~/.bashrc"
-RUN /bin/bash -l -c "echo 'rvm --default use ruby-2.1' >> ~/.bashrc"
-RUN /bin/bash -l -c "gem install bundler --no-ri --no-rdoc"
+RUN /bin/bash -l -c "echo 'rvm --default use ruby-2.5' >> ~/.bashrc"
+RUN /bin/bash -l -c "gem install bundler --no-document"
 
 
 RUN mkdir /var/local/jenkins
diff --git a/tools/dockerfile/interoptest/grpc_interop_ruby/build_interop.sh b/tools/dockerfile/interoptest/grpc_interop_ruby/build_interop.sh
index b6b122ef0f..67f66090ae 100755
--- a/tools/dockerfile/interoptest/grpc_interop_ruby/build_interop.sh
+++ b/tools/dockerfile/interoptest/grpc_interop_ruby/build_interop.sh
@@ -27,7 +27,7 @@ ${name}')
 cp -r /var/local/jenkins/service_account $HOME || true
 
 cd /var/local/git/grpc
-rvm --default use ruby-2.1
+rvm --default use ruby-2.5
 
 # build Ruby interop client and server
 (cd src/ruby && gem update bundler && bundle && rake compile)
diff --git a/tools/dockerfile/test/ruby_jessie_x64/Dockerfile b/tools/dockerfile/test/ruby_jessie_x64/Dockerfile
index 321b501de2..cf6a5b254f 100644
--- a/tools/dockerfile/test/ruby_jessie_x64/Dockerfile
+++ b/tools/dockerfile/test/ruby_jessie_x64/Dockerfile
@@ -72,16 +72,16 @@ RUN pip install futures==2.2.0 enum34==1.0.4 protobuf==3.5.2.post1 six==1.10.0 t
 # Ruby dependencies
 
 # Install rvm
-RUN gpg --keyserver hkp://keys.gnupg.net --recv-keys 409B6B1796C275462A1703113804BB82D39DC0E3
+RUN gpg --keyserver hkp://keys.gnupg.net --recv-keys 409B6B1796C275462A1703113804BB82D39DC0E3 7D2BAF1CF37B13E2069D6956105BD0E739499BDB
 RUN \curl -sSL https://get.rvm.io | bash -s stable
 
-# Install Ruby 2.1
-RUN /bin/bash -l -c "rvm install ruby-2.1"
-RUN /bin/bash -l -c "rvm use --default ruby-2.1"
-RUN /bin/bash -l -c "echo 'gem: --no-ri --no-rdoc' > ~/.gemrc"
+# Install Ruby 2.5
+RUN /bin/bash -l -c "rvm install ruby-2.5"
+RUN /bin/bash -l -c "rvm use --default ruby-2.5"
+RUN /bin/bash -l -c "echo 'gem: --no-document' > ~/.gemrc"
 RUN /bin/bash -l -c "echo 'export PATH=/usr/local/rvm/bin:$PATH' >> ~/.bashrc"
-RUN /bin/bash -l -c "echo 'rvm --default use ruby-2.1' >> ~/.bashrc"
-RUN /bin/bash -l -c "gem install bundler --no-ri --no-rdoc"
+RUN /bin/bash -l -c "echo 'rvm --default use ruby-2.5' >> ~/.bashrc"
+RUN /bin/bash -l -c "gem install bundler --no-document"
 
 
 RUN mkdir /var/local/jenkins
diff --git a/tools/internal_ci/helper_scripts/prepare_build_macos_rc b/tools/internal_ci/helper_scripts/prepare_build_macos_rc
index ce054ac259..632db5ae14 100644
--- a/tools/internal_ci/helper_scripts/prepare_build_macos_rc
+++ b/tools/internal_ci/helper_scripts/prepare_build_macos_rc
@@ -42,7 +42,7 @@ source $HOME/.rvm/scripts/rvm
 set -e  # rvm commands are very verbose
 time rvm install 2.5.0
 rvm use 2.5.0 --default
-time gem install bundler --no-ri --no-doc
+time gem install bundler -v 1.17.3 --no-ri --no-doc
 time gem install cocoapods --version 1.3.1 --no-ri --no-doc
 time gem install rake-compiler --no-ri --no-doc
 rvm osx-ssl-certs status all
diff --git a/tools/run_tests/artifacts/distribtest_targets.py b/tools/run_tests/artifacts/distribtest_targets.py
index e02f4bffcd..fd68a4dc74 100644
--- a/tools/run_tests/artifacts/distribtest_targets.py
+++ b/tools/run_tests/artifacts/distribtest_targets.py
@@ -336,9 +336,11 @@ def targets():
         PythonDistribTest('linux', 'x64', 'ubuntu1404', source=True),
         PythonDistribTest('linux', 'x64', 'ubuntu1604', source=True),
         RubyDistribTest('linux', 'x64', 'wheezy'),
-        RubyDistribTest('linux', 'x64', 'jessie'),
-        RubyDistribTest('linux', 'x86', 'jessie'),
-        RubyDistribTest('linux', 'x64', 'jessie', ruby_version='ruby_2_0_0'),
+        RubyDistribTest('linux', 'x64', 'jessie', ruby_version='ruby_2_2'),
+        RubyDistribTest('linux', 'x64', 'jessie', ruby_version='ruby_2_3'),
+        RubyDistribTest('linux', 'x64', 'jessie', ruby_version='ruby_2_4'),
+        RubyDistribTest('linux', 'x64', 'jessie', ruby_version='ruby_2_5'),
+        RubyDistribTest('linux', 'x64', 'jessie', ruby_version='ruby_2_6'),
         RubyDistribTest('linux', 'x64', 'centos6'),
         RubyDistribTest('linux', 'x64', 'centos7'),
         RubyDistribTest('linux', 'x64', 'fedora20'),
-- 
cgit v1.2.3