diff --git a/2.6/stretch/Dockerfile b/2.6/bullseye/Dockerfile
similarity index 98%
rename from 2.6/stretch/Dockerfile
rename to 2.6/bullseye/Dockerfile
index 73f9cfd91..387c39d5b 100644
--- a/2.6/stretch/Dockerfile
+++ b/2.6/bullseye/Dockerfile
@@ -4,7 +4,7 @@
 # PLEASE DO NOT EDIT IT DIRECTLY.
 #
 
-FROM buildpack-deps:stretch
+FROM buildpack-deps:bullseye
 
 # skip installing gem documentation
 RUN set -eux; \
diff --git a/2.6/slim-stretch/Dockerfile b/2.6/slim-bullseye/Dockerfile
similarity index 98%
rename from 2.6/slim-stretch/Dockerfile
rename to 2.6/slim-bullseye/Dockerfile
index 88d1609db..b2aa2cca9 100644
--- a/2.6/slim-stretch/Dockerfile
+++ b/2.6/slim-bullseye/Dockerfile
@@ -4,7 +4,7 @@
 # PLEASE DO NOT EDIT IT DIRECTLY.
 #
 
-FROM debian:stretch-slim
+FROM debian:bullseye-slim
 
 RUN set -eux; \
 	apt-get update; \
@@ -48,6 +48,7 @@ RUN set -eux; \
 		g++ \
 		gcc \
 		libbz2-dev \
+		libgdbm-compat-dev \
 		libglib2.0-dev \
 		libncurses-dev \
 		libreadline-dev \
diff --git a/2.6/slim-buster/Dockerfile b/2.6/slim-buster/Dockerfile
index 0c3b1a98f..1e50d8fd7 100644
--- a/2.6/slim-buster/Dockerfile
+++ b/2.6/slim-buster/Dockerfile
@@ -48,6 +48,7 @@ RUN set -eux; \
 		g++ \
 		gcc \
 		libbz2-dev \
+		libgdbm-compat-dev \
 		libglib2.0-dev \
 		libncurses-dev \
 		libreadline-dev \
@@ -56,8 +57,6 @@ RUN set -eux; \
 		make \
 		wget \
 		xz-utils \
-# https://packages.debian.org/sid/libgdbm-compat-dev (needed for "dbm" core module, but only in Buster+)
-		libgdbm-compat-dev \
 	; \
 	rm -rf /var/lib/apt/lists/*; \
 	\
diff --git a/2.7/bullseye/Dockerfile b/2.7/bullseye/Dockerfile
new file mode 100644
index 000000000..6ebfaa002
--- /dev/null
+++ b/2.7/bullseye/Dockerfile
@@ -0,0 +1,95 @@
+#
+# NOTE: THIS DOCKERFILE IS GENERATED VIA "apply-templates.sh"
+#
+# PLEASE DO NOT EDIT IT DIRECTLY.
+#
+
+FROM buildpack-deps:bullseye
+
+# skip installing gem documentation
+RUN set -eux; \
+	mkdir -p /usr/local/etc; \
+	{ \
+		echo 'install: --no-document'; \
+		echo 'update: --no-document'; \
+	} >> /usr/local/etc/gemrc
+
+ENV LANG C.UTF-8
+ENV RUBY_MAJOR 2.7
+ENV RUBY_VERSION 2.7.4
+ENV RUBY_DOWNLOAD_SHA256 2a80824e0ad6100826b69b9890bf55cfc4cf2b61a1e1330fccbcb30c46cef8d7
+
+# 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 -eux; \
+	\
+	savedAptMark="$(apt-mark showmanual)"; \
+	apt-get update; \
+	apt-get install -y --no-install-recommends \
+		bison \
+		dpkg-dev \
+		libgdbm-dev \
+		ruby \
+	; \
+	rm -rf /var/lib/apt/lists/*; \
+	\
+	wget -O ruby.tar.xz "https://cache.ruby-lang.org/pub/ruby/${RUBY_MAJOR%-rc}/ruby-$RUBY_VERSION.tar.xz"; \
+	echo "$RUBY_DOWNLOAD_SHA256 *ruby.tar.xz" | sha256sum --check --strict; \
+	\
+	mkdir -p /usr/src/ruby; \
+	tar -xJf ruby.tar.xz -C /usr/src/ruby --strip-components=1; \
+	rm ruby.tar.xz; \
+	\
+	cd /usr/src/ruby; \
+	\
+# hack in "ENABLE_PATH_CHECK" disabling to suppress:
+#   warning: Insecure world writable dir
+	{ \
+		echo '#define ENABLE_PATH_CHECK 0'; \
+		echo; \
+		cat file.c; \
+	} > file.c.new; \
+	mv file.c.new file.c; \
+	\
+	autoconf; \
+	gnuArch="$(dpkg-architecture --query DEB_BUILD_GNU_TYPE)"; \
+	./configure \
+		--build="$gnuArch" \
+		--disable-install-doc \
+		--enable-shared \
+	; \
+	make -j "$(nproc)"; \
+	make install; \
+	\
+	apt-mark auto '.*' > /dev/null; \
+	apt-mark manual $savedAptMark > /dev/null; \
+	find /usr/local -type f -executable -not \( -name '*tkinter*' \) -exec ldd '{}' ';' \
+		| awk '/=>/ { print $(NF-1) }' \
+		| sort -u \
+		| grep -vE '^/usr/local/lib/' \
+		| xargs -r dpkg-query --search \
+		| cut -d: -f1 \
+		| sort -u \
+		| xargs -r apt-mark manual \
+	; \
+	apt-get purge -y --auto-remove -o APT::AutoRemove::RecommendsImportant=false; \
+	\
+	cd /; \
+	rm -r /usr/src/ruby; \
+# verify we have no "ruby" packages installed
+	if dpkg -l | grep -i ruby; then exit 1; fi; \
+	[ "$(command -v ruby)" = '/usr/local/bin/ruby' ]; \
+# rough smoke test
+	ruby --version; \
+	gem --version; \
+	bundle --version
+
+# don't create ".bundle" in all our apps
+ENV GEM_HOME /usr/local/bundle
+ENV BUNDLE_SILENCE_ROOT_WARNING=1 \
+	BUNDLE_APP_CONFIG="$GEM_HOME"
+ENV PATH $GEM_HOME/bin:$PATH
+# adjust permissions of a few directories for running "gem install" as an arbitrary user
+RUN mkdir -p "$GEM_HOME" && chmod 777 "$GEM_HOME"
+
+CMD [ "irb" ]
diff --git a/2.7/slim-bullseye/Dockerfile b/2.7/slim-bullseye/Dockerfile
new file mode 100644
index 000000000..05e01bad4
--- /dev/null
+++ b/2.7/slim-bullseye/Dockerfile
@@ -0,0 +1,122 @@
+#
+# NOTE: THIS DOCKERFILE IS GENERATED VIA "apply-templates.sh"
+#
+# PLEASE DO NOT EDIT IT DIRECTLY.
+#
+
+FROM debian:bullseye-slim
+
+RUN set -eux; \
+	apt-get update; \
+	apt-get install -y --no-install-recommends \
+		bzip2 \
+		ca-certificates \
+		libffi-dev \
+		libgmp-dev \
+		libssl-dev \
+		libyaml-dev \
+		procps \
+		zlib1g-dev \
+	; \
+	rm -rf /var/lib/apt/lists/*
+
+# skip installing gem documentation
+RUN set -eux; \
+	mkdir -p /usr/local/etc; \
+	{ \
+		echo 'install: --no-document'; \
+		echo 'update: --no-document'; \
+	} >> /usr/local/etc/gemrc
+
+ENV LANG C.UTF-8
+ENV RUBY_MAJOR 2.7
+ENV RUBY_VERSION 2.7.4
+ENV RUBY_DOWNLOAD_SHA256 2a80824e0ad6100826b69b9890bf55cfc4cf2b61a1e1330fccbcb30c46cef8d7
+
+# 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 -eux; \
+	\
+	savedAptMark="$(apt-mark showmanual)"; \
+	apt-get update; \
+	apt-get install -y --no-install-recommends \
+		bison \
+		dpkg-dev \
+		libgdbm-dev \
+		ruby \
+		autoconf \
+		g++ \
+		gcc \
+		libbz2-dev \
+		libgdbm-compat-dev \
+		libglib2.0-dev \
+		libncurses-dev \
+		libreadline-dev \
+		libxml2-dev \
+		libxslt-dev \
+		make \
+		wget \
+		xz-utils \
+	; \
+	rm -rf /var/lib/apt/lists/*; \
+	\
+	wget -O ruby.tar.xz "https://cache.ruby-lang.org/pub/ruby/${RUBY_MAJOR%-rc}/ruby-$RUBY_VERSION.tar.xz"; \
+	echo "$RUBY_DOWNLOAD_SHA256 *ruby.tar.xz" | sha256sum --check --strict; \
+	\
+	mkdir -p /usr/src/ruby; \
+	tar -xJf ruby.tar.xz -C /usr/src/ruby --strip-components=1; \
+	rm ruby.tar.xz; \
+	\
+	cd /usr/src/ruby; \
+	\
+# hack in "ENABLE_PATH_CHECK" disabling to suppress:
+#   warning: Insecure world writable dir
+	{ \
+		echo '#define ENABLE_PATH_CHECK 0'; \
+		echo; \
+		cat file.c; \
+	} > file.c.new; \
+	mv file.c.new file.c; \
+	\
+	autoconf; \
+	gnuArch="$(dpkg-architecture --query DEB_BUILD_GNU_TYPE)"; \
+	./configure \
+		--build="$gnuArch" \
+		--disable-install-doc \
+		--enable-shared \
+	; \
+	make -j "$(nproc)"; \
+	make install; \
+	\
+	apt-mark auto '.*' > /dev/null; \
+	apt-mark manual $savedAptMark > /dev/null; \
+	find /usr/local -type f -executable -not \( -name '*tkinter*' \) -exec ldd '{}' ';' \
+		| awk '/=>/ { print $(NF-1) }' \
+		| sort -u \
+		| grep -vE '^/usr/local/lib/' \
+		| xargs -r dpkg-query --search \
+		| cut -d: -f1 \
+		| sort -u \
+		| xargs -r apt-mark manual \
+	; \
+	apt-get purge -y --auto-remove -o APT::AutoRemove::RecommendsImportant=false; \
+	\
+	cd /; \
+	rm -r /usr/src/ruby; \
+# verify we have no "ruby" packages installed
+	if dpkg -l | grep -i ruby; then exit 1; fi; \
+	[ "$(command -v ruby)" = '/usr/local/bin/ruby' ]; \
+# rough smoke test
+	ruby --version; \
+	gem --version; \
+	bundle --version
+
+# don't create ".bundle" in all our apps
+ENV GEM_HOME /usr/local/bundle
+ENV BUNDLE_SILENCE_ROOT_WARNING=1 \
+	BUNDLE_APP_CONFIG="$GEM_HOME"
+ENV PATH $GEM_HOME/bin:$PATH
+# adjust permissions of a few directories for running "gem install" as an arbitrary user
+RUN mkdir -p "$GEM_HOME" && chmod 777 "$GEM_HOME"
+
+CMD [ "irb" ]
diff --git a/2.7/slim-buster/Dockerfile b/2.7/slim-buster/Dockerfile
index e63c04726..3b1825a1c 100644
--- a/2.7/slim-buster/Dockerfile
+++ b/2.7/slim-buster/Dockerfile
@@ -48,6 +48,7 @@ RUN set -eux; \
 		g++ \
 		gcc \
 		libbz2-dev \
+		libgdbm-compat-dev \
 		libglib2.0-dev \
 		libncurses-dev \
 		libreadline-dev \
@@ -56,8 +57,6 @@ RUN set -eux; \
 		make \
 		wget \
 		xz-utils \
-# https://packages.debian.org/sid/libgdbm-compat-dev (needed for "dbm" core module, but only in Buster+)
-		libgdbm-compat-dev \
 	; \
 	rm -rf /var/lib/apt/lists/*; \
 	\
diff --git a/3.0/bullseye/Dockerfile b/3.0/bullseye/Dockerfile
new file mode 100644
index 000000000..6cf1732b4
--- /dev/null
+++ b/3.0/bullseye/Dockerfile
@@ -0,0 +1,95 @@
+#
+# NOTE: THIS DOCKERFILE IS GENERATED VIA "apply-templates.sh"
+#
+# PLEASE DO NOT EDIT IT DIRECTLY.
+#
+
+FROM buildpack-deps:bullseye
+
+# skip installing gem documentation
+RUN set -eux; \
+	mkdir -p /usr/local/etc; \
+	{ \
+		echo 'install: --no-document'; \
+		echo 'update: --no-document'; \
+	} >> /usr/local/etc/gemrc
+
+ENV LANG C.UTF-8
+ENV RUBY_MAJOR 3.0
+ENV RUBY_VERSION 3.0.2
+ENV RUBY_DOWNLOAD_SHA256 570e7773100f625599575f363831166d91d49a1ab97d3ab6495af44774155c40
+
+# 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 -eux; \
+	\
+	savedAptMark="$(apt-mark showmanual)"; \
+	apt-get update; \
+	apt-get install -y --no-install-recommends \
+		bison \
+		dpkg-dev \
+		libgdbm-dev \
+		ruby \
+	; \
+	rm -rf /var/lib/apt/lists/*; \
+	\
+	wget -O ruby.tar.xz "https://cache.ruby-lang.org/pub/ruby/${RUBY_MAJOR%-rc}/ruby-$RUBY_VERSION.tar.xz"; \
+	echo "$RUBY_DOWNLOAD_SHA256 *ruby.tar.xz" | sha256sum --check --strict; \
+	\
+	mkdir -p /usr/src/ruby; \
+	tar -xJf ruby.tar.xz -C /usr/src/ruby --strip-components=1; \
+	rm ruby.tar.xz; \
+	\
+	cd /usr/src/ruby; \
+	\
+# hack in "ENABLE_PATH_CHECK" disabling to suppress:
+#   warning: Insecure world writable dir
+	{ \
+		echo '#define ENABLE_PATH_CHECK 0'; \
+		echo; \
+		cat file.c; \
+	} > file.c.new; \
+	mv file.c.new file.c; \
+	\
+	autoconf; \
+	gnuArch="$(dpkg-architecture --query DEB_BUILD_GNU_TYPE)"; \
+	./configure \
+		--build="$gnuArch" \
+		--disable-install-doc \
+		--enable-shared \
+	; \
+	make -j "$(nproc)"; \
+	make install; \
+	\
+	apt-mark auto '.*' > /dev/null; \
+	apt-mark manual $savedAptMark > /dev/null; \
+	find /usr/local -type f -executable -not \( -name '*tkinter*' \) -exec ldd '{}' ';' \
+		| awk '/=>/ { print $(NF-1) }' \
+		| sort -u \
+		| grep -vE '^/usr/local/lib/' \
+		| xargs -r dpkg-query --search \
+		| cut -d: -f1 \
+		| sort -u \
+		| xargs -r apt-mark manual \
+	; \
+	apt-get purge -y --auto-remove -o APT::AutoRemove::RecommendsImportant=false; \
+	\
+	cd /; \
+	rm -r /usr/src/ruby; \
+# verify we have no "ruby" packages installed
+	if dpkg -l | grep -i ruby; then exit 1; fi; \
+	[ "$(command -v ruby)" = '/usr/local/bin/ruby' ]; \
+# rough smoke test
+	ruby --version; \
+	gem --version; \
+	bundle --version
+
+# don't create ".bundle" in all our apps
+ENV GEM_HOME /usr/local/bundle
+ENV BUNDLE_SILENCE_ROOT_WARNING=1 \
+	BUNDLE_APP_CONFIG="$GEM_HOME"
+ENV PATH $GEM_HOME/bin:$PATH
+# adjust permissions of a few directories for running "gem install" as an arbitrary user
+RUN mkdir -p "$GEM_HOME" && chmod 777 "$GEM_HOME"
+
+CMD [ "irb" ]
diff --git a/3.0/slim-bullseye/Dockerfile b/3.0/slim-bullseye/Dockerfile
new file mode 100644
index 000000000..a17b866a8
--- /dev/null
+++ b/3.0/slim-bullseye/Dockerfile
@@ -0,0 +1,122 @@
+#
+# NOTE: THIS DOCKERFILE IS GENERATED VIA "apply-templates.sh"
+#
+# PLEASE DO NOT EDIT IT DIRECTLY.
+#
+
+FROM debian:bullseye-slim
+
+RUN set -eux; \
+	apt-get update; \
+	apt-get install -y --no-install-recommends \
+		bzip2 \
+		ca-certificates \
+		libffi-dev \
+		libgmp-dev \
+		libssl-dev \
+		libyaml-dev \
+		procps \
+		zlib1g-dev \
+	; \
+	rm -rf /var/lib/apt/lists/*
+
+# skip installing gem documentation
+RUN set -eux; \
+	mkdir -p /usr/local/etc; \
+	{ \
+		echo 'install: --no-document'; \
+		echo 'update: --no-document'; \
+	} >> /usr/local/etc/gemrc
+
+ENV LANG C.UTF-8
+ENV RUBY_MAJOR 3.0
+ENV RUBY_VERSION 3.0.2
+ENV RUBY_DOWNLOAD_SHA256 570e7773100f625599575f363831166d91d49a1ab97d3ab6495af44774155c40
+
+# 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 -eux; \
+	\
+	savedAptMark="$(apt-mark showmanual)"; \
+	apt-get update; \
+	apt-get install -y --no-install-recommends \
+		bison \
+		dpkg-dev \
+		libgdbm-dev \
+		ruby \
+		autoconf \
+		g++ \
+		gcc \
+		libbz2-dev \
+		libgdbm-compat-dev \
+		libglib2.0-dev \
+		libncurses-dev \
+		libreadline-dev \
+		libxml2-dev \
+		libxslt-dev \
+		make \
+		wget \
+		xz-utils \
+	; \
+	rm -rf /var/lib/apt/lists/*; \
+	\
+	wget -O ruby.tar.xz "https://cache.ruby-lang.org/pub/ruby/${RUBY_MAJOR%-rc}/ruby-$RUBY_VERSION.tar.xz"; \
+	echo "$RUBY_DOWNLOAD_SHA256 *ruby.tar.xz" | sha256sum --check --strict; \
+	\
+	mkdir -p /usr/src/ruby; \
+	tar -xJf ruby.tar.xz -C /usr/src/ruby --strip-components=1; \
+	rm ruby.tar.xz; \
+	\
+	cd /usr/src/ruby; \
+	\
+# hack in "ENABLE_PATH_CHECK" disabling to suppress:
+#   warning: Insecure world writable dir
+	{ \
+		echo '#define ENABLE_PATH_CHECK 0'; \
+		echo; \
+		cat file.c; \
+	} > file.c.new; \
+	mv file.c.new file.c; \
+	\
+	autoconf; \
+	gnuArch="$(dpkg-architecture --query DEB_BUILD_GNU_TYPE)"; \
+	./configure \
+		--build="$gnuArch" \
+		--disable-install-doc \
+		--enable-shared \
+	; \
+	make -j "$(nproc)"; \
+	make install; \
+	\
+	apt-mark auto '.*' > /dev/null; \
+	apt-mark manual $savedAptMark > /dev/null; \
+	find /usr/local -type f -executable -not \( -name '*tkinter*' \) -exec ldd '{}' ';' \
+		| awk '/=>/ { print $(NF-1) }' \
+		| sort -u \
+		| grep -vE '^/usr/local/lib/' \
+		| xargs -r dpkg-query --search \
+		| cut -d: -f1 \
+		| sort -u \
+		| xargs -r apt-mark manual \
+	; \
+	apt-get purge -y --auto-remove -o APT::AutoRemove::RecommendsImportant=false; \
+	\
+	cd /; \
+	rm -r /usr/src/ruby; \
+# verify we have no "ruby" packages installed
+	if dpkg -l | grep -i ruby; then exit 1; fi; \
+	[ "$(command -v ruby)" = '/usr/local/bin/ruby' ]; \
+# rough smoke test
+	ruby --version; \
+	gem --version; \
+	bundle --version
+
+# don't create ".bundle" in all our apps
+ENV GEM_HOME /usr/local/bundle
+ENV BUNDLE_SILENCE_ROOT_WARNING=1 \
+	BUNDLE_APP_CONFIG="$GEM_HOME"
+ENV PATH $GEM_HOME/bin:$PATH
+# adjust permissions of a few directories for running "gem install" as an arbitrary user
+RUN mkdir -p "$GEM_HOME" && chmod 777 "$GEM_HOME"
+
+CMD [ "irb" ]
diff --git a/3.0/slim-buster/Dockerfile b/3.0/slim-buster/Dockerfile
index 88b4e0242..feef07b49 100644
--- a/3.0/slim-buster/Dockerfile
+++ b/3.0/slim-buster/Dockerfile
@@ -48,6 +48,7 @@ RUN set -eux; \
 		g++ \
 		gcc \
 		libbz2-dev \
+		libgdbm-compat-dev \
 		libglib2.0-dev \
 		libncurses-dev \
 		libreadline-dev \
@@ -56,8 +57,6 @@ RUN set -eux; \
 		make \
 		wget \
 		xz-utils \
-# https://packages.debian.org/sid/libgdbm-compat-dev (needed for "dbm" core module, but only in Buster+)
-		libgdbm-compat-dev \
 	; \
 	rm -rf /var/lib/apt/lists/*; \
 	\
diff --git a/Dockerfile.template b/Dockerfile.template
index dfc9a3247..6798d0248 100644
--- a/Dockerfile.template
+++ b/Dockerfile.template
@@ -103,6 +103,7 @@ RUN set -eux; \
 		g++ \
 		gcc \
 		libbz2-dev \
+		libgdbm-compat-dev \
 		libglib2.0-dev \
 		libncurses-dev \
 		libreadline-dev \
@@ -111,10 +112,6 @@ RUN set -eux; \
 		make \
 		wget \
 		xz-utils \
-{{ if env.variant | endswith("stretch") then "" else ( -}}
-# https://packages.debian.org/sid/libgdbm-compat-dev (needed for "dbm" core module, but only in Buster+)
-		libgdbm-compat-dev \
-{{ ) end -}}
 {{ ) else "" end -}}
 	; \
 	rm -rf /var/lib/apt/lists/*; \
diff --git a/versions.json b/versions.json
index 729a7acb4..c428c8c02 100644
--- a/versions.json
+++ b/versions.json
@@ -2,10 +2,10 @@
   "2.6": {
     "sha256": "8262e4663169c85787fdc9bfbd04d9eb86eb2a4b56d7f98373a8fcaa18e593eb",
     "variants": [
+      "bullseye",
+      "slim-bullseye",
       "buster",
       "slim-buster",
-      "stretch",
-      "slim-stretch",
       "alpine3.14",
       "alpine3.13"
     ],
@@ -14,6 +14,8 @@
   "2.7": {
     "sha256": "2a80824e0ad6100826b69b9890bf55cfc4cf2b61a1e1330fccbcb30c46cef8d7",
     "variants": [
+      "bullseye",
+      "slim-bullseye",
       "buster",
       "slim-buster",
       "alpine3.14",
@@ -24,6 +26,8 @@
   "3.0": {
     "sha256": "570e7773100f625599575f363831166d91d49a1ab97d3ab6495af44774155c40",
     "variants": [
+      "bullseye",
+      "slim-bullseye",
       "buster",
       "slim-buster",
       "alpine3.14",
diff --git a/versions.sh b/versions.sh
index 92290eb34..51d1803e2 100755
--- a/versions.sh
+++ b/versions.sh
@@ -68,10 +68,8 @@ for version in "${versions[@]}"; do
 			sha256: env.shaVal,
 			variants: [
 				(
-					"buster",
-					if env.rcVersion == "2.6" then
-						"stretch"
-					else empty end
+					"bullseye",
+					"buster"
 				| ., "slim-" + .), # https://github.com/docker-library/ruby/pull/142#issuecomment-320012893
 				(
 					"3.14",