diff --git a/py3_ruby/Dockerfile b/py3_ruby/Dockerfile
index 3a65c96..ea06a09 100644
--- a/py3_ruby/Dockerfile
+++ b/py3_ruby/Dockerfile
@@ -18,12 +18,11 @@ RUN DEBIAN_FRONTEND=noninteractive apt-get -y update && \
 # Ruby installation
 ##################################################
 
-# update the rubygems system version to latest
-# RUN gem update --system 3.0.2
-
 # skip installing gem documentation
 RUN echo 'gem: --no-rdoc --no-ri --no-document' >> "/etc/gemrc" && \
-  gem install bundler -v 1.17
+  gem update --system && \
+  gem install bundler --no-document -v 1.17.3 && \
+  gem install bundler --no-document -v 2.0.1
 
 ##################################################
 # Python installation
diff --git a/ruby/2.1/Dockerfile b/ruby/2.1/Dockerfile
index c1bda7f..b4d7ec3 100644
--- a/ruby/2.1/Dockerfile
+++ b/ruby/2.1/Dockerfile
@@ -11,7 +11,7 @@ RUN DEBIAN_FRONTEND=noninteractive apt-get -y update && \
 
 # skip installing gem documentation
 RUN echo 'gem: --no-rdoc --no-ri --no-document' >> "/etc/gemrc" && \
-  gem install bundler -v 1.17 --no-document
+  gem install bundler --no-document -v 1.17.3
 
 # LABEL must be last for proper base image discoverability
 LABEL repository.socrata/ruby:2.1=""
diff --git a/ruby/2.2/Dockerfile b/ruby/2.2/Dockerfile
index af366d9..358b483 100644
--- a/ruby/2.2/Dockerfile
+++ b/ruby/2.2/Dockerfile
@@ -11,7 +11,7 @@ RUN DEBIAN_FRONTEND=noninteractive apt-get -y update && \
 
 # skip installing gem documentation
 RUN echo 'gem: --no-rdoc --no-ri --no-document' >> "/etc/gemrc" && \
-  gem install bundler -v 1.17 --no-document
+  gem install bundler --no-document -v 1.17.3
 
 # LABEL must be last for proper base image discoverability
 LABEL repository.socrata/ruby:2.2=""
diff --git a/ruby/2.3.5/Dockerfile b/ruby/2.3.5/Dockerfile
index 8664761..102725a 100644
--- a/ruby/2.3.5/Dockerfile
+++ b/ruby/2.3.5/Dockerfile
@@ -11,9 +11,9 @@ RUN mkdir -p /usr/local/etc \
 ENV RUBY_MAJOR 2.3
 ENV RUBY_VERSION 2.3.5
 ENV RUBY_DOWNLOAD_SHA256 7d3a7dabb190c2da06c963063342ca9a214bcd26f2158e904f0ec059b065ffda
-ENV RUBYGEMS_VERSION 2.7.4
-ENV BUNDLER_VERSION 1.17
-
+ENV RUBYGEMS_VERSION 3.0.3
+ENV BUNDLER_VERSION_1 1.17.3
+ENV BUNDLER_VERSION_2 2.0.1
 # some of ruby's build scripts are written in ruby
 #   we purge system ruby later to make sure our final image uses what we just built
 RUN set -ex \
@@ -96,7 +96,8 @@ RUN set -ex \
 	&& rm -r /usr/src/ruby \
 	\
 	&& gem update --system "$RUBYGEMS_VERSION" \
-	&& gem install bundler --version "$BUNDLER_VERSION" --force \
+	&& gem install bundler --version "$BUNDLER_VERSION_1" --force \
+	&& gem install bundler --version "$BUNDLER_VERSION_2" --force \
 	&& rm -r /root/.gem/
 
 # LABEL must be last for proper base image discoverability
diff --git a/ruby/2.3.6/Dockerfile b/ruby/2.3.6/Dockerfile
index 2662261..4737d0c 100644
--- a/ruby/2.3.6/Dockerfile
+++ b/ruby/2.3.6/Dockerfile
@@ -11,9 +11,9 @@ RUN mkdir -p /usr/local/etc \
 ENV RUBY_MAJOR 2.3
 ENV RUBY_VERSION 2.3.6
 ENV RUBY_DOWNLOAD_SHA256 e0d969ac22d4a403c1204868bb9c0d068aa35045bb3934cf50b17b7f66059f56
-ENV RUBYGEMS_VERSION 2.7.4
-ENV BUNDLER_VERSION 1.17
-
+ENV RUBYGEMS_VERSION 3.0.3
+ENV BUNDLER_VERSION_1 1.17.3
+ENV BUNDLER_VERSION_2 2.0.1
 # some of ruby's build scripts are written in ruby
 #   we purge system ruby later to make sure our final image uses what we just built
 RUN set -ex \
@@ -96,7 +96,8 @@ RUN set -ex \
 	&& rm -r /usr/src/ruby \
 	\
 	&& gem update --system "$RUBYGEMS_VERSION" \
-	&& gem install bundler --version "$BUNDLER_VERSION" --force \
+	&& gem install bundler --version "$BUNDLER_VERSION_1" --force \
+	&& gem install bundler --version "$BUNDLER_VERSION_2" --force \
 	&& rm -r /root/.gem/
 
 # LABEL must be last for proper base image discoverability
diff --git a/ruby/2.3/Dockerfile b/ruby/2.3/Dockerfile
index 94375b2..c0132d8 100644
--- a/ruby/2.3/Dockerfile
+++ b/ruby/2.3/Dockerfile
@@ -9,11 +9,11 @@ RUN DEBIAN_FRONTEND=noninteractive apt-get -y update && \
   DEBIAN_FRONTEND=noninteractive apt-get purge -y --auto-remove software-properties-common && \
   rm -rf /var/lib/apt/lists/*
 
-# RUN gem update --system 3.0.2
-
 # skip installing gem documentation
 RUN echo 'gem: --no-rdoc --no-ri --no-document' >> "/etc/gemrc" && \
-  gem install bundler -v 1.17 --no-document
+  gem update --system && \
+  gem install bundler --no-document -v 2.0.1 && \
+  gem install bundler --no-document -v 1.17.3
 
 # LABEL must be last for proper base image discoverability
 LABEL repository.socrata/ruby2.3=""
diff --git a/ruby/2.5.0/Dockerfile b/ruby/2.5.0/Dockerfile
index 2f310cb..4ee3a9d 100644
--- a/ruby/2.5.0/Dockerfile
+++ b/ruby/2.5.0/Dockerfile
@@ -11,9 +11,9 @@ RUN mkdir -p /usr/local/etc \
 ENV RUBY_MAJOR 2.5
 ENV RUBY_VERSION 2.5.0
 ENV RUBY_DOWNLOAD_SHA256 1da0afed833a0dab94075221a615c14487b05d0c407f991c8080d576d985b49b
-ENV RUBYGEMS_VERSION 2.7.4
-ENV BUNDLER_VERSION 1.17
-
+ENV RUBYGEMS_VERSION 3.0.3
+ENV BUNDLER_VERSION_1 1.17.3
+ENV BUNDLER_VERSION_2 2.0.1
 # some of ruby's build scripts are written in ruby
 #   we purge system ruby later to make sure our final image uses what we just built
 RUN set -ex \
@@ -96,7 +96,8 @@ RUN set -ex \
 	&& rm -r /usr/src/ruby \
 	\
 	&& gem update --system "$RUBYGEMS_VERSION" \
-	&& gem install bundler --version "$BUNDLER_VERSION" --force \
+	&& gem install bundler --version "$BUNDLER_VERSION_1" --force \
+	&& gem install bundler --version "$BUNDLER_VERSION_2" --force \
 	&& rm -r /root/.gem/
 
 # LABEL must be last for proper base image discoverability
diff --git a/ruby/2.5.3/Dockerfile b/ruby/2.5.3/Dockerfile
index 896f01a..6e4f905 100644
--- a/ruby/2.5.3/Dockerfile
+++ b/ruby/2.5.3/Dockerfile
@@ -11,9 +11,9 @@ RUN mkdir -p /usr/local/etc \
 ENV RUBY_MAJOR 2.5
 ENV RUBY_VERSION 2.5.3
 ENV RUBY_DOWNLOAD_SHA256 1cc9d0359a8ea35fc6111ec830d12e60168f3b9b305a3c2578357d360fcf306f
-ENV RUBYGEMS_VERSION 2.7.4
-ENV BUNDLER_VERSION 1.17
-
+ENV RUBYGEMS_VERSION 3.0.3
+ENV BUNDLER_VERSION_1 1.17.3
+ENV BUNLDER_VERSION_2 2.0.1
 # some of ruby's build scripts are written in ruby
 #   we purge system ruby later to make sure our final image uses what we just built
 RUN set -ex \
@@ -96,7 +96,8 @@ RUN set -ex \
 	&& rm -r /usr/src/ruby \
 	\
 	&& gem update --system "$RUBYGEMS_VERSION" \
-	&& gem install bundler --version "$BUNDLER_VERSION" --force \
+	&& gem install bundler --version "$BUNDLER_VERSION_1" --force \
+	&& gem install bundler --version "$BUNDLER_VERSION_22" --force \
 	&& rm -r /root/.gem/
 
 # LABEL must be last for proper base image discoverability
diff --git a/runit-ruby/2.2/Dockerfile b/runit-ruby/2.2/Dockerfile
index 9d12641..95206f5 100644
--- a/runit-ruby/2.2/Dockerfile
+++ b/runit-ruby/2.2/Dockerfile
@@ -11,7 +11,7 @@ RUN DEBIAN_FRONTEND=noninteractive apt-get -y update && \
 
 # skip installing gem documentation
 RUN echo 'gem: --no-rdoc --no-ri --no-document' >> "/etc/gemrc" && \
-  gem install bundler -v 1.17 --no-document
+  gem install bundler --no-document -v 1.17.3
 
 # LABEL must be last for proper base image discoverability
 LABEL repository.socrata/runit-ruby2.2=""
diff --git a/runit-ruby/2.3.5/Dockerfile b/runit-ruby/2.3.5/Dockerfile
index 9ff6553..a2b5277 100644
--- a/runit-ruby/2.3.5/Dockerfile
+++ b/runit-ruby/2.3.5/Dockerfile
@@ -11,9 +11,9 @@ RUN mkdir -p /usr/local/etc \
 ENV RUBY_MAJOR 2.3
 ENV RUBY_VERSION 2.3.5
 ENV RUBY_DOWNLOAD_SHA256 7d3a7dabb190c2da06c963063342ca9a214bcd26f2158e904f0ec059b065ffda
-ENV RUBYGEMS_VERSION 2.7.4
-ENV BUNDLER_VERSION 1.17
-
+ENV RUBYGEMS_VERSION 3.0.3
+ENV BUNDLER_VERSION_1 1.17.3
+ENV BUNLDER_VERSION_2 2.0.1
 # some of ruby's build scripts are written in ruby
 #   we purge system ruby later to make sure our final image uses what we just built
 RUN set -ex \
@@ -96,7 +96,8 @@ RUN set -ex \
 	&& rm -r /usr/src/ruby \
 	\
 	&& gem update --system "$RUBYGEMS_VERSION" \
-	&& gem install bundler --version "$BUNDLER_VERSION" --force \
+	&& gem install bundler --version "$BUNDLER_VERSION_1" --force \
+	&& gem install bundler --version "$BUNDLER_VERSION_2" --force \
 	&& rm -r /root/.gem/
 
 # LABEL must be last for proper base image discoverability
diff --git a/runit-ruby/2.3.6/Dockerfile b/runit-ruby/2.3.6/Dockerfile
index cde3131..9b28db2 100644
--- a/runit-ruby/2.3.6/Dockerfile
+++ b/runit-ruby/2.3.6/Dockerfile
@@ -11,9 +11,9 @@ RUN mkdir -p /usr/local/etc \
 ENV RUBY_MAJOR 2.3
 ENV RUBY_VERSION 2.3.6
 ENV RUBY_DOWNLOAD_SHA256 e0d969ac22d4a403c1204868bb9c0d068aa35045bb3934cf50b17b7f66059f56
-ENV RUBYGEMS_VERSION 2.7.4
-ENV BUNDLER_VERSION 1.16.1
-
+ENV RUBYGEMS_VERSION 3.0.3
+ENV BUNDLER_VERSION_1 1.17.3
+ENV BUNDLER_VERSION_2 2.0.1
 # some of ruby's build scripts are written in ruby
 #   we purge system ruby later to make sure our final image uses what we just built
 RUN set -ex \
@@ -96,7 +96,8 @@ RUN set -ex \
 	&& rm -r /usr/src/ruby \
 	\
 	&& gem update --system "$RUBYGEMS_VERSION" \
-	&& gem install bundler --version "$BUNDLER_VERSION" --force \
+	&& gem install bundler --version "$BUNDLER_VERSION_1" --force \
+	&& gem install bundler --version "$BUNDLER_VERSION_2" --force \
 	&& rm -r /root/.gem/
 
 # LABEL must be last for proper base image discoverability
diff --git a/runit-ruby/2.3/Dockerfile b/runit-ruby/2.3/Dockerfile
index bd6cfda..2e7d461 100644
--- a/runit-ruby/2.3/Dockerfile
+++ b/runit-ruby/2.3/Dockerfile
@@ -9,11 +9,11 @@ RUN DEBIAN_FRONTEND=noninteractive apt-get -y update && \
   DEBIAN_FRONTEND=noninteractive apt-get purge -y --auto-remove software-properties-common && \
   rm -rf /var/lib/apt/lists/*
 
-# RUN gem update --system 3.0.2
-
 # skip installing gem documentation
 RUN echo 'gem: --no-rdoc --no-ri --no-document' >> "/etc/gemrc" && \
-  gem install bundler --no-document -v 1.17
+  gem update --system && \
+  gem install bundler --no-document -v 2.0.1 && \
+  gem install bundler --no-document -v 1.17.3
 
 # LABEL must be last for proper base image discoverability
 LABEL repository.socrata/runit-ruby2.3=""
diff --git a/runit-ruby/2.5.0/Dockerfile b/runit-ruby/2.5.0/Dockerfile
index be3c6d3..33acbcb 100644
--- a/runit-ruby/2.5.0/Dockerfile
+++ b/runit-ruby/2.5.0/Dockerfile
@@ -11,9 +11,9 @@ RUN mkdir -p /usr/local/etc \
 ENV RUBY_MAJOR 2.5
 ENV RUBY_VERSION 2.5.0
 ENV RUBY_DOWNLOAD_SHA256 1da0afed833a0dab94075221a615c14487b05d0c407f991c8080d576d985b49b
-ENV RUBYGEMS_VERSION 2.7.4
-ENV BUNDLER_VERSION 1.17
-
+ENV RUBYGEMS_VERSION 3.0.3
+ENV BUNDLER_VERSION_1 1.17.3
+ENV BUNDLER_VERSION_2 2.0.1
 # some of ruby's build scripts are written in ruby
 #   we purge system ruby later to make sure our final image uses what we just built
 RUN set -ex \
@@ -96,7 +96,8 @@ RUN set -ex \
 	&& rm -r /usr/src/ruby \
 	\
 	&& gem update --system "$RUBYGEMS_VERSION" \
-	&& gem install bundler --version "$BUNDLER_VERSION" --force \
+	&& gem install bundler --version "$BUNDLER_VERSION_1" --force \
+	&& gem install bundler --version "$BUNDLER_VERSION_2" --force \
 	&& rm -r /root/.gem/
 
 # LABEL must be last for proper base image discoverability
diff --git a/runit-ruby/2.5.3/Dockerfile b/runit-ruby/2.5.3/Dockerfile
index d346ce8..da8a9e1 100644
--- a/runit-ruby/2.5.3/Dockerfile
+++ b/runit-ruby/2.5.3/Dockerfile
@@ -11,9 +11,9 @@ RUN mkdir -p /usr/local/etc \
 ENV RUBY_MAJOR 2.5
 ENV RUBY_VERSION 2.5.3
 ENV RUBY_DOWNLOAD_SHA256 1cc9d0359a8ea35fc6111ec830d12e60168f3b9b305a3c2578357d360fcf306f
-ENV RUBYGEMS_VERSION 2.7.6
-ENV BUNDLER_VERSION 1.17
-
+ENV RUBYGEMS_VERSION 3.0.3
+ENV BUNDLER_VERSION_1 1.17.3
+ENV BUNDLER_VERSION_2 2.0.1
 # some of ruby's build scripts are written in ruby
 #   we purge system ruby later to make sure our final image uses what we just built
 RUN set -ex \
@@ -96,7 +96,8 @@ RUN set -ex \
 	&& rm -r /usr/src/ruby \
 	\
 	&& gem update --system "$RUBYGEMS_VERSION" \
-	&& gem install bundler --version "$BUNDLER_VERSION" --force \
+	&& gem install bundler --version "$BUNDLER_VERSION_1" --force \
+	&& gem install bundler --version "$BUNDLER_VERSION_2" --force \
 	&& rm -r /root/.gem/
 
 # LABEL must be last for proper base image discoverability