diff --git a/Dockerfile.bionic b/Dockerfile.bionic
index 2e7006f..427cf2b 100644
--- a/Dockerfile.bionic
+++ b/Dockerfile.bionic
@@ -19,7 +19,7 @@ RUN rm -f /bin/sh && \
     cp /etc/gemrc /root/.gemrc && \
     cp /etc/gemrc /package/.gemrc
 
-ADD vendor/ruby-build-20200722.tar.gz /tmp
+ADD vendor/ruby-build-20211203.tar.gz /tmp
 
 RUN mkdir -p /opt/puppet-omnibus/embedded && \
     export MAKE_OPTS="-j3 -s" && \
@@ -28,7 +28,7 @@ RUN mkdir -p /opt/puppet-omnibus/embedded && \
     export RUBY_CONFIGURE_OPTS="--without-gdbm --without-dbm \
     --with-readline-dir=/usr/lib/x86_64-linux-gnu --with-openssl-dir=/usr/lib/x86_64-linux-gnu \
     --disable-install-doc --without-tcl --without-tk" && \
-    /tmp/ruby-build-20200722/bin/ruby-build -p 2.2.10 /opt/puppet-omnibus/embedded
+    /tmp/ruby-build-20211203/bin/ruby-build -p 2.2.10 /opt/puppet-omnibus/embedded
 
 RUN /opt/puppet-omnibus/embedded/bin/gem install rubygems-update -v '<3' && \
     /opt/puppet-omnibus/embedded/bin/update_rubygems && \
diff --git a/Dockerfile.focal b/Dockerfile.focal
index cf7de45..40363f0 100644
--- a/Dockerfile.focal
+++ b/Dockerfile.focal
@@ -19,7 +19,7 @@ RUN rm -f /bin/sh && \
     cp /etc/gemrc /root/.gemrc && \
     cp /etc/gemrc /package/.gemrc
 
-ADD vendor/ruby-build-20200722.tar.gz /tmp
+ADD vendor/ruby-build-20211203.tar.gz /tmp
 
 RUN mkdir -p /opt/puppet-omnibus/embedded && \
     export MAKE_OPTS="-j3 -s" && \
@@ -28,7 +28,7 @@ RUN mkdir -p /opt/puppet-omnibus/embedded && \
     export RUBY_CONFIGURE_OPTS="--without-gdbm --without-dbm \
     --with-readline-dir=/usr/lib/x86_64-linux-gnu --with-openssl-dir=/usr/lib/x86_64-linux-gnu \
     --disable-install-doc --without-tcl --without-tk" && \
-    /tmp/ruby-build-20200722/bin/ruby-build -p 2.4.10 /opt/puppet-omnibus/embedded
+    /tmp/ruby-build-20211203/bin/ruby-build -p 2.4.10 /opt/puppet-omnibus/embedded
 
 RUN /opt/puppet-omnibus/embedded/bin/gem install rubygems-update -v '<3' && \
     /opt/puppet-omnibus/embedded/bin/update_rubygems && \
diff --git a/Dockerfile.jammy b/Dockerfile.jammy
new file mode 100644
index 0000000..2958aa3
--- /dev/null
+++ b/Dockerfile.jammy
@@ -0,0 +1,44 @@
+FROM docker-dev.yelpcorp.com/jammy_yelp:latest
+
+RUN apt-get update && \
+    DEBIAN_FRONTEND=noninteractive apt-get --yes --force-yes install \
+      autoconf bison build-essential curl fakeroot gawk git-core libffi-dev \
+      libffi7 libgdbm-dev libncurses5-dev libpcre3-dev \
+      libreadline-dev libsqlite3-dev libxml2-dev libxslt1-dev \
+      pkg-config ruby screen sudo wget zlib1g zlib1g-dev && \
+    apt-get clean
+
+RUN rm -f /bin/sh && \
+    ln -s /bin/bash /bin/sh && \
+    touch "/etc/default/puppet" && \
+    mkdir -p /opt /package /etc/puppet /var/lib/puppet /var/cache/omnibus && \
+    echo 'gem: --no-document' > /etc/gemrc && \
+    echo 'install: --no-ri --no-rdoc' >> /etc/gemrc && \
+    echo 'update: --no-ri --no-rdoc' >> /etc/gemrc && \
+    cp /etc/gemrc /.gemrc && \
+    cp /etc/gemrc /root/.gemrc && \
+    cp /etc/gemrc /package/.gemrc
+
+ADD vendor/ruby-build-20211203.tar.gz /tmp
+
+# PEREL-2701: Download and install libssl-dev 1.1 from impish, since jammy
+# moves to 3.0 and Ruby doesn't support that at all yet. Jammy does include a
+# runtime edition of 1.1 in libssl1.1 though, just doesn't have development headers
+#
+# Admittedly, this is a hack, and hopefully the situation here is better later
+# on in jammy's release.
+RUN wget http://mirrors.kernel.org/ubuntu/pool/main/o/openssl/libssl-dev_1.1.1l-1ubuntu1_amd64.deb
+RUN dpkg -i libssl-dev_1.1.1l-1ubuntu1_amd64.deb
+
+RUN mkdir -p /opt/puppet-omnibus/embedded && \
+    export MAKE_OPTS="-j3 -s" && \
+    export RUBY_CFLAGS=-Os && \
+    export RUBY_BUILD_CACHE_PATH=/tmp && \
+    export RUBY_CONFIGURE_OPTS="--without-gdbm --without-dbm \
+    --with-readline-dir=/usr/lib/x86_64-linux-gnu --with-openssl-dir=/usr/lib/x86_64-linux-gnu \
+    --disable-install-doc --without-tcl --without-tk" && \
+    /tmp/ruby-build-20211203/bin/ruby-build -p 2.4.10 /opt/puppet-omnibus/embedded
+
+RUN /opt/puppet-omnibus/embedded/bin/gem install rubygems-update -v '<3' && \
+    /opt/puppet-omnibus/embedded/bin/update_rubygems && \
+    rm -rf /opt/puppet-omnibus/embedded/share/*
diff --git a/Dockerfile.trusty b/Dockerfile.trusty
index eec3bec..ad0f3ed 100644
--- a/Dockerfile.trusty
+++ b/Dockerfile.trusty
@@ -19,14 +19,14 @@ RUN rm -f /bin/sh && \
     cp /etc/gemrc /root/.gemrc && \
     cp /etc/gemrc /package/.gemrc
 
-ADD vendor/ruby-build-20200722.tar.gz /tmp
+ADD vendor/ruby-build-20211203.tar.gz /tmp
 
 RUN mkdir -p /opt/puppet-omnibus/embedded && \
     export MAKE_OPTS="-j3 -s" && \
     export RUBY_CFLAGS=-Os && \
     export RUBY_BUILD_CACHE_PATH=/tmp && \
     export RUBY_CONFIGURE_OPTS="--without-gdbm --without-dbm --disable-install-doc --without-tcl --without-tk" && \
-    /tmp/ruby-build-20200722/bin/ruby-build -p 2.2.10 /opt/puppet-omnibus/embedded
+    /tmp/ruby-build-20211203/bin/ruby-build -p 2.2.10 /opt/puppet-omnibus/embedded
 
 RUN /opt/puppet-omnibus/embedded/bin/gem install rubygems-update -v '<3' && \
     /opt/puppet-omnibus/embedded/bin/update_rubygems && \
diff --git a/Dockerfile.xenial b/Dockerfile.xenial
index 18ed0d4..f429fe6 100644
--- a/Dockerfile.xenial
+++ b/Dockerfile.xenial
@@ -19,14 +19,14 @@ RUN rm -f /bin/sh && \
     cp /etc/gemrc /root/.gemrc && \
     cp /etc/gemrc /package/.gemrc
 
-ADD vendor/ruby-build-20200722.tar.gz /tmp
+ADD vendor/ruby-build-20211203.tar.gz /tmp
 
 RUN mkdir -p /opt/puppet-omnibus/embedded && \
     export MAKE_OPTS="-j3 -s" && \
     export RUBY_CFLAGS=-Os && \
     export RUBY_BUILD_CACHE_PATH=/tmp && \
     export RUBY_CONFIGURE_OPTS="--without-gdbm --without-dbm --disable-install-doc --without-tcl --without-tk" && \
-    /tmp/ruby-build-20200722/bin/ruby-build -p 2.2.10 /opt/puppet-omnibus/embedded
+    /tmp/ruby-build-20211203/bin/ruby-build -p 2.2.10 /opt/puppet-omnibus/embedded
 
 RUN /opt/puppet-omnibus/embedded/bin/gem install rubygems-update -v '<3' && \
     /opt/puppet-omnibus/embedded/bin/update_rubygems && \
diff --git a/Makefile b/Makefile
index 003c3cf..356508d 100644
--- a/Makefile
+++ b/Makefile
@@ -51,7 +51,7 @@ itest: require_os package
 		-v `pwd`/itest:/itest:ro \
 		-v `pwd`/dist:/dist:ro \
 		docker-dev.yelpcorp.com/$(OS)_yelp \
-		/itest/$(OS).sh \
+		/itest/ubuntu.sh \
 		/dist/$(OS)/$(PACKAGE_NAME)_$(VERSION)-$(PKG_ITERATION)_amd64.deb \
 		$(VERSION)
 
diff --git a/itest/bionic.sh b/itest/bionic.sh
deleted file mode 120000
index f215cf2..0000000
--- a/itest/bionic.sh
+++ /dev/null
@@ -1 +0,0 @@
-ubuntu.sh
\ No newline at end of file
diff --git a/itest/focal.sh b/itest/focal.sh
deleted file mode 120000
index f215cf2..0000000
--- a/itest/focal.sh
+++ /dev/null
@@ -1 +0,0 @@
-ubuntu.sh
\ No newline at end of file
diff --git a/itest/lucid.sh b/itest/lucid.sh
deleted file mode 120000
index f215cf2..0000000
--- a/itest/lucid.sh
+++ /dev/null
@@ -1 +0,0 @@
-ubuntu.sh
\ No newline at end of file
diff --git a/itest/trusty.sh b/itest/trusty.sh
deleted file mode 120000
index f215cf2..0000000
--- a/itest/trusty.sh
+++ /dev/null
@@ -1 +0,0 @@
-ubuntu.sh
\ No newline at end of file
diff --git a/itest/xenial.sh b/itest/xenial.sh
deleted file mode 120000
index f215cf2..0000000
--- a/itest/xenial.sh
+++ /dev/null
@@ -1 +0,0 @@
-ubuntu.sh
\ No newline at end of file
diff --git a/vendor/ruby-build-20200722.tar.gz b/vendor/ruby-build-20200722.tar.gz
deleted file mode 100644
index 4dc4aca..0000000
Binary files a/vendor/ruby-build-20200722.tar.gz and /dev/null differ
diff --git a/vendor/ruby-build-20211203.tar.gz b/vendor/ruby-build-20211203.tar.gz
new file mode 100644
index 0000000..c0bd76a
Binary files /dev/null and b/vendor/ruby-build-20211203.tar.gz differ