diff --git a/src/engines/jruby/9.2/Dockerfile.musl b/src/engines/jruby/9.2/Dockerfile.musl
index caab212..159c00d 100644
--- a/src/engines/jruby/9.2/Dockerfile.musl
+++ b/src/engines/jruby/9.2/Dockerfile.musl
@@ -46,5 +46,13 @@ ENV PATH /opt/jruby/bin:$PATH
 RUN mkdir -p /opt/jruby/etc \
  && echo -e 'install: --no-document\nupdate: --no-document' >> /opt/jruby/etc/gemrc
 
+## Install a pinned RubyGems and Bundler
+RUN gem update --system 3.3.26
+RUN gem install bundler:2.3.26
+
+# Install additional gems that are in CRuby but missing from the above
+# JRuby install distribution. These are version-pinned for reproducibility.
+RUN gem install rake:13.2.1
+
 # Start IRB as a default
 CMD [ "irb" ]
diff --git a/src/engines/jruby/9.3/Dockerfile.musl b/src/engines/jruby/9.3/Dockerfile.musl
index 5a909e8..191658d 100644
--- a/src/engines/jruby/9.3/Dockerfile.musl
+++ b/src/engines/jruby/9.3/Dockerfile.musl
@@ -46,5 +46,13 @@ ENV PATH /opt/jruby/bin:$PATH
 RUN mkdir -p /opt/jruby/etc \
  && echo -e 'install: --no-document\nupdate: --no-document' >> /opt/jruby/etc/gemrc
 
+## Install a pinned RubyGems and Bundler
+RUN gem update --system 3.3.26
+RUN gem install bundler:2.3.26
+
+# Install additional gems that are in CRuby but missing from the above
+# JRuby install distribution. These are version-pinned for reproducibility.
+RUN gem install rake:13.2.1
+
 # Start IRB as a default
 CMD [ "irb" ]
diff --git a/src/engines/jruby/9.4/Dockerfile.musl b/src/engines/jruby/9.4/Dockerfile.musl
index ba7b1d1..8e18852 100644
--- a/src/engines/jruby/9.4/Dockerfile.musl
+++ b/src/engines/jruby/9.4/Dockerfile.musl
@@ -46,5 +46,13 @@ ENV PATH /opt/jruby/bin:$PATH
 RUN mkdir -p /opt/jruby/etc \
  && echo -e 'install: --no-document\nupdate: --no-document' >> /opt/jruby/etc/gemrc
 
+## Install a pinned RubyGems and Bundler
+RUN gem update --system 3.3.26
+RUN gem install bundler:2.3.26
+
+# Install additional gems that are in CRuby but missing from the above
+# JRuby install distribution. These are version-pinned for reproducibility.
+RUN gem install rake:13.2.1
+
 # Start IRB as a default
 CMD [ "irb" ]
diff --git a/src/engines/ruby/2.1/Dockerfile.musl b/src/engines/ruby/2.1/Dockerfile.musl
index d9acc53..b658f96 100644
--- a/src/engines/ruby/2.1/Dockerfile.musl
+++ b/src/engines/ruby/2.1/Dockerfile.musl
@@ -27,3 +27,11 @@ ARG REPRO_RUN_KEY=0
 # images) should not do `apk update`, instead this base image should be
 # updated by changing the `REPRO_RUN_KEY`.
 RUN true "${REPRO_RUN_KEY}" && apk update
+
+## Install a pinned RubyGems and Bundler
+RUN gem update --system 2.7.11
+RUN gem install bundler --version 1.17.3
+
+# Install additional gems that are in CRuby but missing from the above
+# JRuby install distribution. These are version-pinned for reproducibility.
+RUN gem install rake:12.3.3
diff --git a/src/engines/ruby/2.2/Dockerfile.musl b/src/engines/ruby/2.2/Dockerfile.musl
index a140066..be263cd 100644
--- a/src/engines/ruby/2.2/Dockerfile.musl
+++ b/src/engines/ruby/2.2/Dockerfile.musl
@@ -28,3 +28,11 @@ ARG REPRO_RUN_KEY=0
 # images) should not do `apk update`, instead this base image should be
 # updated by changing the `REPRO_RUN_KEY`.
 RUN true "${REPRO_RUN_KEY}" && apk update
+
+## Install a pinned RubyGems and Bundler
+RUN gem update --system 2.7.11
+RUN gem install bundler --version 1.17.3
+
+# Install additional gems that are in CRuby but missing from the above
+# JRuby install distribution. These are version-pinned for reproducibility.
+RUN gem install rake:13.0.6
diff --git a/src/engines/ruby/2.3/Dockerfile.musl b/src/engines/ruby/2.3/Dockerfile.musl
index 2668347..0aadd04 100644
--- a/src/engines/ruby/2.3/Dockerfile.musl
+++ b/src/engines/ruby/2.3/Dockerfile.musl
@@ -27,3 +27,11 @@ ARG REPRO_RUN_KEY=0
 # images) should not do `apk update`, instead this base image should be
 # updated by changing the `REPRO_RUN_KEY`.
 RUN true "${REPRO_RUN_KEY}" && apk update
+
+## Install a pinned RubyGems and Bundler
+RUN gem update --system 3.3.26
+RUN gem install bundler:2.3.26
+
+# Install additional gems that are in CRuby but missing from the above
+# JRuby install distribution. These are version-pinned for reproducibility.
+RUN gem install rake:13.2.1
diff --git a/src/engines/ruby/2.4/Dockerfile.musl b/src/engines/ruby/2.4/Dockerfile.musl
index ebe9ca4..ee2da59 100644
--- a/src/engines/ruby/2.4/Dockerfile.musl
+++ b/src/engines/ruby/2.4/Dockerfile.musl
@@ -27,3 +27,11 @@ ARG REPRO_RUN_KEY=0
 # images) should not do `apk update`, instead this base image should be
 # updated by changing the `REPRO_RUN_KEY`.
 RUN true "${REPRO_RUN_KEY}" && apk update
+
+## Install a pinned RubyGems and Bundler
+RUN gem update --system 3.3.26
+RUN gem install bundler:2.3.26
+
+# Install additional gems that are in CRuby but missing from the above
+# JRuby install distribution. These are version-pinned for reproducibility.
+RUN gem install rake:13.2.1
diff --git a/src/engines/ruby/2.5/Dockerfile.musl b/src/engines/ruby/2.5/Dockerfile.musl
index 3d9b79a..8edb08f 100644
--- a/src/engines/ruby/2.5/Dockerfile.musl
+++ b/src/engines/ruby/2.5/Dockerfile.musl
@@ -27,3 +27,11 @@ ARG REPRO_RUN_KEY=0
 # images) should not do `apk update`, instead this base image should be
 # updated by changing the `REPRO_RUN_KEY`.
 RUN true "${REPRO_RUN_KEY}" && apk update
+
+## Install a pinned RubyGems and Bundler
+RUN gem update --system 3.3.26
+RUN gem install bundler:2.3.26
+
+# Install additional gems that are in CRuby but missing from the above
+# JRuby install distribution. These are version-pinned for reproducibility.
+RUN gem install rake:13.2.1
diff --git a/src/engines/ruby/2.6/Dockerfile.musl b/src/engines/ruby/2.6/Dockerfile.musl
index 2dbb145..f5856bd 100644
--- a/src/engines/ruby/2.6/Dockerfile.musl
+++ b/src/engines/ruby/2.6/Dockerfile.musl
@@ -27,3 +27,11 @@ ARG REPRO_RUN_KEY=0
 # images) should not do `apk update`, instead this base image should be
 # updated by changing the `REPRO_RUN_KEY`.
 RUN true "${REPRO_RUN_KEY}" && apk update
+
+## Install a pinned RubyGems and Bundler
+RUN gem update --system 3.3.26
+RUN gem install bundler:2.3.26
+
+# Install additional gems that are in CRuby but missing from the above
+# JRuby install distribution. These are version-pinned for reproducibility.
+RUN gem install rake:13.2.1
diff --git a/src/engines/ruby/2.7/Dockerfile.musl b/src/engines/ruby/2.7/Dockerfile.musl
index 1ca4d84..7521b59 100644
--- a/src/engines/ruby/2.7/Dockerfile.musl
+++ b/src/engines/ruby/2.7/Dockerfile.musl
@@ -27,3 +27,11 @@ ARG REPRO_RUN_KEY=0
 # images) should not do `apk update`, instead this base image should be
 # updated by changing the `REPRO_RUN_KEY`.
 RUN true "${REPRO_RUN_KEY}" && apk update
+
+## Install a pinned RubyGems and Bundler
+RUN gem update --system 3.3.26
+RUN gem install bundler:2.3.26
+
+# Install additional gems that are in CRuby but missing from the above
+# JRuby install distribution. These are version-pinned for reproducibility.
+RUN gem install rake:13.2.1
diff --git a/src/engines/ruby/3.0/Dockerfile.musl b/src/engines/ruby/3.0/Dockerfile.musl
index d12b259..3daecac 100644
--- a/src/engines/ruby/3.0/Dockerfile.musl
+++ b/src/engines/ruby/3.0/Dockerfile.musl
@@ -27,3 +27,11 @@ ARG REPRO_RUN_KEY=0
 # images) should not do `apk update`, instead this base image should be
 # updated by changing the `REPRO_RUN_KEY`.
 RUN true "${REPRO_RUN_KEY}" && apk update
+
+## Install a pinned RubyGems and Bundler
+RUN gem update --system 3.3.26
+RUN gem install bundler:2.3.26
+
+# Install additional gems that are in CRuby but missing from the above
+# JRuby install distribution. These are version-pinned for reproducibility.
+RUN gem install rake:13.2.1
diff --git a/src/engines/ruby/3.1/Dockerfile.musl b/src/engines/ruby/3.1/Dockerfile.musl
index 817db6d..a3954eb 100644
--- a/src/engines/ruby/3.1/Dockerfile.musl
+++ b/src/engines/ruby/3.1/Dockerfile.musl
@@ -27,3 +27,11 @@ ARG REPRO_RUN_KEY=0
 # images) should not do `apk update`, instead this base image should be
 # updated by changing the `REPRO_RUN_KEY`.
 RUN true "${REPRO_RUN_KEY}" && apk update
+
+## Install a pinned RubyGems and Bundler
+RUN gem update --system 3.3.26
+RUN gem install bundler:2.3.26
+
+# Install additional gems that are in CRuby but missing from the above
+# JRuby install distribution. These are version-pinned for reproducibility.
+RUN gem install rake:13.2.1
diff --git a/src/engines/ruby/3.2/Dockerfile.musl b/src/engines/ruby/3.2/Dockerfile.musl
index 18f5ff9..8dc80dc 100644
--- a/src/engines/ruby/3.2/Dockerfile.musl
+++ b/src/engines/ruby/3.2/Dockerfile.musl
@@ -27,3 +27,11 @@ ARG REPRO_RUN_KEY=0
 # images) should not do `apk update`, instead this base image should be
 # updated by changing the `REPRO_RUN_KEY`.
 RUN true "${REPRO_RUN_KEY}" && apk update
+
+## Install a pinned RubyGems and Bundler
+RUN gem update --system 3.3.26
+RUN gem install bundler:2.3.26
+
+# Install additional gems that are in CRuby but missing from the above
+# JRuby install distribution. These are version-pinned for reproducibility.
+RUN gem install rake:13.2.1
diff --git a/src/engines/ruby/3.3/Dockerfile.musl b/src/engines/ruby/3.3/Dockerfile.musl
index c46a3d0..d36c9f0 100644
--- a/src/engines/ruby/3.3/Dockerfile.musl
+++ b/src/engines/ruby/3.3/Dockerfile.musl
@@ -27,3 +27,11 @@ ARG REPRO_RUN_KEY=0
 # images) should not do `apk update`, instead this base image should be
 # updated by changing the `REPRO_RUN_KEY`.
 RUN true "${REPRO_RUN_KEY}" && apk update
+
+## Install a pinned RubyGems and Bundler
+RUN gem update --system 3.3.26
+RUN gem install bundler:2.3.26
+
+# Install additional gems that are in CRuby but missing from the above
+# JRuby install distribution. These are version-pinned for reproducibility.
+RUN gem install rake:13.2.1
diff --git a/src/engines/ruby/3.4/Dockerfile.musl b/src/engines/ruby/3.4/Dockerfile.musl
index 0068342..5d6699f 100644
--- a/src/engines/ruby/3.4/Dockerfile.musl
+++ b/src/engines/ruby/3.4/Dockerfile.musl
@@ -27,3 +27,11 @@ ARG REPRO_RUN_KEY=0
 # images) should not do `apk update`, instead this base image should be
 # updated by changing the `REPRO_RUN_KEY`.
 RUN true "${REPRO_RUN_KEY}" && apk update
+
+## Install a pinned RubyGems and Bundler
+RUN gem update --system 3.3.26
+RUN gem install bundler:2.3.26
+
+# Install additional gems that are in CRuby but missing from the above
+# JRuby install distribution. These are version-pinned for reproducibility.
+RUN gem install rake:13.2.1