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

17 files changed, 256 insertions, 38 deletions

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:$PATH' >> ~/.bashrc"
+RUN /bin/bash -l -c "echo 'rvm --default use ruby-2.2.10' >> ~/.bashrc"
+RUN /bin/bash -l -c "gem install bundler -v 1.17.3 --no-document"
+
+RUN mkdir /var/local/jenkins
+
+RUN /bin/bash -l -c "echo '. /etc/profile.d/rvm.sh' >> ~/.bashrc"
diff --git a/tools/dockerfile/distribtest/ruby_jessie_x64_ruby_2_2/Dockerfile b/tools/dockerfile/distribtest/ruby_jessie_x64_ruby_2_2/Dockerfile
new file mode 100644
index 0000000000..337fc3b5d8
--- /dev/null
+++ b/tools/dockerfile/distribtest/ruby_jessie_x64_ruby_2_2/Dockerfile
@@ -0,0 +1,40 @@
+# Copyright 2015 gRPC authors.
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#     http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+FROM debian:jessie
+
+# Install Git and basic packages.
+RUN apt-get update && apt-get install -y \
+  curl \
+  gcc && apt-get clean
+
+#==================
+# Ruby dependencies
+
+# Install rvm
+RUN gpg --keyserver hkp://keys.gnupg.net --recv-keys 409B6B1796C275462A1703113804BB82D39DC0E3 7D2BAF1CF37B13E2069D6956105BD0E739499BDB
+RUN \curl -sSL https://get.rvm.io | bash -s stable
+
+# Install Ruby 2.2
+RUN /bin/bash -l -c "rvm install ruby-2.2.10"
+RUN /bin/bash -l -c "rvm use --default ruby-2.2.10"
+RUN /bin/bash -l -c "echo 'gem: --no-document' > ~/.gemrc"
+RUN /bin/bash -l -c "echo 'export PATH=/usr/local/rvm/bin:$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_0_0/Dockerfile b/tools/dockerfile/distribtest/ruby_jessie_x64_ruby_2_6/Dockerfile
index ff43c92c9e..af1839eba9 100644
--- a/tools/dockerfile/distribtest/ruby_jessie_x64_ruby_2_0_0/Dockerfile
+++ b/tools/dockerfile/distribtest/ruby_jessie_x64_ruby_2_6/Dockerfile
@@ -23,16 +23,16 @@ RUN apt-get update && apt-get install -y \
 # 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-2.0"
-RUN /bin/bash -l -c "rvm use --default ruby-2.0"
-RUN /bin/bash -l -c "echo 'gem: --no-ri --no-rdoc' > ~/.gemrc"
+# 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-2.0' >> ~/.bashrc"
-RUN /bin/bash -l -c "gem install bundler --no-ri --no-rdoc"
+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
 
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'),