diff --git a/.jenkins b/.jenkins
new file mode 100644
index 000000000..e7c74fc4b
--- /dev/null
+++ b/.jenkins
@@ -0,0 +1,270 @@
+def versions = ["3.11", "3.10", "3.9", "3.8", "3.7"]
+
+def generatePublishStage(job) {
+    return {
+        stage("Publish py:${job}") {
+            withDockerRegistry(registry: [credentialsId: 'vio-docker-hub']) {
+                sh "docker push ${imageName}:${job}-${buildArch}"
+                sh "docker push ${imageName}:${job}-slim-${buildArch}"
+            }
+        }
+    }
+}
+
+def generateManifestStage(job) {
+    return {
+        stage("Publish manifest py:${job}") {
+            withDockerRegistry(registry: [credentialsId: 'vio-docker-hub']) {
+                sh "docker manifest create --amend ${imageName}:${job} ${imageName}:${job}-amd64" // ${imageName}:${job}-arm64"
+                sh "docker manifest push --purge ${imageName}:${job}"
+
+                sh "docker manifest create --amend ${imageName}:${job}-slim ${imageName}:${job}-slim-amd64" // ${imageName}:${job}-slim-arm64"
+                sh "docker manifest push --purge ${imageName}:${job}-slim"
+            }
+        }
+    }
+}
+
+def publishStagesMap = versions.collectEntries {
+    ["${it}" : generatePublishStage(it)]
+}
+
+def publishManifestsMap = versions.collectEntries {
+    ["${it}" : generateManifestStage(it)]
+}
+
+pipeline {
+
+    agent any
+
+    environment {
+        imageName = 'vaporio/python'
+    }
+
+    triggers {
+        upstream(upstreamProjects: 'vapor-ware/buildpack-deps/master', threshold: hudson.model.Result.SUCCESS)
+    }
+
+    stages {
+
+        stage('Sync') {
+            steps {
+                sh './update.sh'
+            }
+        }
+
+        stage('Pull Base Images') {
+            // To ensure the build nodes have the latest correct arch builds of the
+            // base images, explicitly pull them here.
+            parallel {
+                stage('amd64') {
+                    steps {
+                        sh "docker pull vaporio/buildpack-deps:bionic"
+                    }
+                }
+
+                // stage('arm64') {
+                //     agent {
+                //         label 'arm64'
+                //     }
+                //     steps {
+                //         sh "docker pull vaporio/buildpack-deps:bionic"
+                //     }
+                // }
+            }
+        }
+
+        stage('py37') {
+            environment {
+                pyVersion = "3.7"
+            }
+            parallel {
+                stage('amd64') {
+                    environment {
+                        buildArch = "amd64"
+                    }
+                    steps {
+                        sh "docker build -t ${imageName}:${pyVersion}-${buildArch} ${pyVersion}/bionic"
+                        sh "docker build -t ${imageName}:${pyVersion}-slim-${buildArch} ${pyVersion}/bionic/lite"
+                    }
+                }
+
+                // stage('arm64') {
+                //     agent {
+                //         label 'arm64'
+                //     }
+                //     environment {
+                //         buildArch = "arm64"
+                //     }
+                //     steps {
+                //         sh "docker build -t ${imageName}:${pyVersion}-${buildArch} ${pyVersion}/bionic"
+                //         sh "docker build -t ${imageName}:${pyVersion}-slim-${buildArch} ${pyVersion}/bionic/lite"
+                //     }
+                // }
+            }
+        }
+
+        stage('py38') {
+            environment {
+                pyVersion = "3.8"
+            }
+            parallel {
+                stage('amd64') {
+                    environment {
+                        buildArch = "amd64"
+                    }
+                    steps {
+                        sh "docker build -t ${imageName}:${pyVersion}-${buildArch} ${pyVersion}/bionic"
+                        sh "docker build -t ${imageName}:${pyVersion}-slim-${buildArch} ${pyVersion}/bionic/lite"
+                    }
+                }
+
+                // stage('arm64') {
+                //     agent {
+                //         label 'arm64'
+                //     }
+                //     environment {
+                //         buildArch = "arm64"
+                //     }
+                //     steps {
+                //         sh "docker build -t ${imageName}:${pyVersion}-${buildArch} ${pyVersion}/bionic"
+                //         sh "docker build -t ${imageName}:${pyVersion}-slim-${buildArch} ${pyVersion}/bionic/lite"
+                //     }
+                // }
+            }
+        }
+
+        stage('py39') {
+            environment {
+                pyVersion = "3.9"
+            }
+            parallel {
+                stage('amd64') {
+                    environment {
+                        buildArch = "amd64"
+                    }
+                    steps {
+                        sh "docker build -t ${imageName}:${pyVersion}-${buildArch} ${pyVersion}/bionic"
+                        sh "docker build -t ${imageName}:${pyVersion}-slim-${buildArch} ${pyVersion}/bionic/lite"
+                    }
+                }
+
+                // stage('arm64') {
+                //     agent {
+                //         label 'arm64'
+                //     }
+                //     environment {
+                //         buildArch = "arm64"
+                //     }
+                //     steps {
+                //         sh "docker build -t ${imageName}:${pyVersion}-${buildArch} ${pyVersion}/bionic"
+                //         sh "docker build -t ${imageName}:${pyVersion}-slim-${buildArch} ${pyVersion}/bionic/lite"
+                //     }
+                // }
+            }
+        }
+
+        stage('py10') {
+            environment {
+                pyVersion = "3.10"
+            }
+            parallel {
+                stage('amd64') {
+                    environment {
+                        buildArch = "amd64"
+                    }
+                    steps {
+                        sh "docker build -t ${imageName}:${pyVersion}-${buildArch} ${pyVersion}/bionic"
+                        sh "docker build -t ${imageName}:${pyVersion}-slim-${buildArch} ${pyVersion}/bionic/lite"
+                    }
+                }
+
+                // stage('arm64') {
+                //     agent {
+                //         label 'arm64'
+                //     }
+                //     environment {
+                //         buildArch = "arm64"
+                //     }
+                //     steps {
+                //         sh "docker build -t ${imageName}:${pyVersion}-${buildArch} ${pyVersion}/bionic"
+                //         sh "docker build -t ${imageName}:${pyVersion}-slim-${buildArch} ${pyVersion}/bionic/lite"
+                //     }
+                // }
+            }
+        }
+
+        stage('py11') {
+            environment {
+                pyVersion = "3.11"
+            }
+            parallel {
+                stage('amd64') {
+                    environment {
+                        buildArch = "amd64"
+                    }
+                    steps {
+                        sh "docker build -t ${imageName}:${pyVersion}-${buildArch} ${pyVersion}/bionic"
+                        sh "docker build -t ${imageName}:${pyVersion}-slim-${buildArch} ${pyVersion}/bionic/lite"
+                    }
+                }
+
+                // stage('arm64') {
+                //     agent {
+                //         label 'arm64'
+                //     }
+                //     environment {
+                //         buildArch = "arm64"
+                //     }
+                //     steps {
+                //         sh "docker build -t ${imageName}:${pyVersion}-${buildArch} ${pyVersion}/bionic"
+                //         sh "docker build -t ${imageName}:${pyVersion}-slim-${buildArch} ${pyVersion}/bionic/lite"
+                //     }
+                // }
+            }
+        }
+
+        stage('Publish Images') {
+            when {
+                branch 'master'
+            }
+            parallel {
+                stage('amd64') {
+                    environment {
+                         buildArch = "amd64"
+                    }
+                    steps {
+                        script {
+                            parallel publishStagesMap
+                        }
+                    }
+                }
+
+                // stage('arm64') {
+                //     agent {
+                //         label 'arm64'
+                //     }
+                //     environment {
+                //         buildArch = "arm64"
+                //     }
+                //     steps {
+                //         script {
+                //             parallel publishStagesMap
+                //         }
+                //     }
+                // }
+            }
+        }
+
+        stage ('Publish Manifests') {
+            when {
+                branch 'master'
+            }
+            steps {
+                script {
+                    parallel publishManifestsMap
+                }
+            }
+        }
+    }
+}
diff --git a/3.10-rc/alpine3.12/Dockerfile b/3.10/alpine3.17/Dockerfile
similarity index 91%
rename from 3.10-rc/alpine3.12/Dockerfile
rename to 3.10/alpine3.17/Dockerfile
index cdf4676f6..21c5f9099 100644
--- a/3.10-rc/alpine3.12/Dockerfile
+++ b/3.10/alpine3.17/Dockerfile
@@ -4,7 +4,7 @@
 # PLEASE DO NOT EDIT IT DIRECTLY.
 #
 
-FROM alpine:3.12
+FROM alpine:3.17
 
 # ensure local python is preferred over distribution python
 ENV PATH /usr/local/bin:$PATH
@@ -18,7 +18,7 @@ ENV LANG C.UTF-8
 RUN apk add --no-cache ca-certificates
 
 ENV GPG_KEY A035C8C19219BA821ECEA86B64E628F8D684696D
-ENV PYTHON_VERSION 3.10.0a1
+ENV PYTHON_VERSION 3.10.9
 
 RUN set -ex \
 	&& apk add --no-cache --virtual .fetch-deps \
@@ -29,7 +29,7 @@ RUN set -ex \
 	&& wget -O python.tar.xz "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz" \
 	&& wget -O python.tar.xz.asc "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz.asc" \
 	&& export GNUPGHOME="$(mktemp -d)" \
-	&& gpg --batch --keyserver ha.pool.sks-keyservers.net --recv-keys "$GPG_KEY" \
+	&& gpg --batch --keyserver hkps://keys.openpgp.org --recv-keys "$GPG_KEY" \
 	&& gpg --batch --verify python.tar.xz.asc python.tar.xz \
 	&& { command -v gpgconf > /dev/null && gpgconf --kill all || :; } \
 	&& rm -rf "$GNUPGHOME" python.tar.xz.asc \
@@ -108,10 +108,10 @@ RUN cd /usr/local/bin \
 	&& ln -s python3-config python-config
 
 # if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
-ENV PYTHON_PIP_VERSION 20.2.3
+ENV PYTHON_PIP_VERSION 22.3.1
 # https://github.com/pypa/get-pip
-ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/fa7dc83944936bf09a0e4cb5d5ec852c0d256599/get-pip.py
-ENV PYTHON_GET_PIP_SHA256 6e0bb0a2c2533361d7f297ed547237caf1b7507f197835974c0dd7eba998c53c
+ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/66030fa03382b4914d4c4d0896961a0bdeeeb274/public/get-pip.py
+ENV PYTHON_GET_PIP_SHA256 1e501cf004eac1b7eb1f97266d28f995ae835d30250bec7f8850562703067dc6
 
 RUN set -ex; \
 	\
diff --git a/3.10/bionic/Dockerfile b/3.10/bionic/Dockerfile
new file mode 100644
index 000000000..f356b0f67
--- /dev/null
+++ b/3.10/bionic/Dockerfile
@@ -0,0 +1,106 @@
+#
+# NOTE: THIS DOCKERFILE IS GENERATED VIA "update.sh"
+#
+# PLEASE DO NOT EDIT IT DIRECTLY.
+#
+
+FROM vaporio/buildpack-deps:bionic
+
+# ensure local python is preferred over distribution python
+ENV PATH /usr/local/bin:$PATH
+
+# http://bugs.python.org/issue19846
+# > At the moment, setting "LANG=C" on a Linux system *fundamentally breaks Python 3*, and that's not OK.
+ENV LANG C.UTF-8
+ENV DEBIAN_FRONTEND noninteractive
+
+# extra dependencies (over what buildpack-deps already includes)
+RUN apt-get update; \
+    apt-get install -y --no-install-recommends \
+		libbluetooth-dev \
+		tk-dev \
+		uuid-dev \
+	&& rm -rf /var/lib/apt/lists/*
+
+ENV GPG_KEY A035C8C19219BA821ECEA86B64E628F8D684696D
+ENV PYTHON_VERSION 3.10.9
+
+RUN set -ex \
+	\
+	&& wget -O python.tar.xz "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz" \
+	&& wget -O python.tar.xz.asc "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz.asc" \
+	&& export GNUPGHOME="$(mktemp -d)" \
+	&& for server in $(shuf -e \
+	        ha.pool.sks-keyservers.net \
+	        hkp://p80.pool.sks-keyservers.net:80 \
+	        keyserver.ubuntu.com \
+	        hkp://keyserver.ubuntu.com:80 \
+	        pgp.mit.edu) ; do \
+	    gpg --batch --keyserver "$server" --recv-keys "$GPG_KEY" && break || : ; \
+	    done \
+	&& gpg --batch --verify python.tar.xz.asc python.tar.xz \
+	&& { command -v gpgconf > /dev/null && gpgconf --kill all || :; } \
+	&& rm -rf "$GNUPGHOME" python.tar.xz.asc \
+	&& mkdir -p /usr/src/python \
+	&& tar -xJC /usr/src/python --strip-components=1 -f python.tar.xz \
+	&& rm python.tar.xz \
+	\
+	&& cd /usr/src/python \
+	&& gnuArch="$(dpkg-architecture --query DEB_BUILD_GNU_TYPE)" \
+	&& ./configure \
+		--build="$gnuArch" \
+		--enable-loadable-sqlite-extensions \
+		--enable-optimizations \
+		--enable-option-checking=fatal \
+		--enable-shared \
+		--with-system-expat \
+		--with-system-ffi \
+		--without-ensurepip \
+	&& make -j "$(nproc)" \
+	&& make install \
+	&& rm -rf /usr/src/python \
+	\
+	&& find /usr/local -depth \
+		\( \
+			\( -type d -a \( -name test -o -name tests -o -name idle_test \) \) \
+			-o \( -type f -a \( -name '*.pyc' -o -name '*.pyo' -o -name '*.a' \) \) \
+		\) -exec rm -rf '{}' + \
+	\
+	&& ldconfig \
+	\
+	&& python3 --version
+
+# make some useful symlinks that are expected to exist
+RUN cd /usr/local/bin \
+	&& ln -s idle3 idle \
+	&& ln -s pydoc3 pydoc \
+	&& ln -s python3 python \
+	&& ln -s python3-config python-config
+
+# if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
+ENV PYTHON_PIP_VERSION 22.3.1
+# https://github.com/pypa/get-pip
+ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/66030fa03382b4914d4c4d0896961a0bdeeeb274/public/get-pip.py
+ENV PYTHON_GET_PIP_SHA256 1e501cf004eac1b7eb1f97266d28f995ae835d30250bec7f8850562703067dc6
+
+RUN set -ex; \
+	\
+	wget -O get-pip.py "$PYTHON_GET_PIP_URL"; \
+	echo "$PYTHON_GET_PIP_SHA256 *get-pip.py" | sha256sum --check --strict -; \
+	\
+	python get-pip.py \
+		--disable-pip-version-check \
+		--no-cache-dir \
+		"pip==$PYTHON_PIP_VERSION" \
+	; \
+	pip --version; \
+	\
+	find /usr/local -depth \
+		\( \
+			\( -type d -a \( -name test -o -name tests -o -name idle_test \) \) \
+			-o \
+			\( -type f -a \( -name '*.pyc' -o -name '*.pyo' \) \) \
+		\) -exec rm -rf '{}' +; \
+	rm -f get-pip.py
+
+CMD ["python3"]
diff --git a/3.10/bionic/lite/Dockerfile b/3.10/bionic/lite/Dockerfile
new file mode 100644
index 000000000..ae43f58c3
--- /dev/null
+++ b/3.10/bionic/lite/Dockerfile
@@ -0,0 +1,151 @@
+#
+# NOTE: THIS DOCKERFILE IS GENERATED VIA "update.sh"
+#
+# PLEASE DO NOT EDIT IT DIRECTLY.
+#
+
+FROM vaporio/foundation:bionic
+
+# ensure local python is preferred over distribution python
+ENV PATH /usr/local/bin:$PATH
+
+# http://bugs.python.org/issue19846
+# > At the moment, setting "LANG=C" on a Linux system *fundamentally breaks Python 3*, and that's not OK.
+ENV LANG C.UTF-8
+ENV DEBIAN_FRONTEND noninteractive
+
+# runtime dependencies
+RUN apt-get update; \
+    apt-get install -y --no-install-recommends \
+		ca-certificates \
+		netbase \
+	&& rm -rf /var/lib/apt/lists/*
+
+ENV GPG_KEY A035C8C19219BA821ECEA86B64E628F8D684696D
+ENV PYTHON_VERSION 3.10.9
+
+RUN set -ex \
+	\
+	&& savedAptMark="$(apt-mark showmanual)" \
+	&& apt-get update && apt-get install -y --no-install-recommends \
+		dpkg-dev \
+		gcc \
+		libbluetooth-dev \
+		libbz2-dev \
+		libc6-dev \
+		libexpat1-dev \
+		libffi-dev \
+		libgdbm-dev \
+		liblzma-dev \
+		libncursesw5-dev \
+		libreadline-dev \
+		libsqlite3-dev \
+		libssl-dev \
+		make \
+		tk-dev \
+		uuid-dev \
+		wget \
+		xz-utils \
+		zlib1g-dev \
+# as of Stretch, "gpg" is no longer included by default
+		$(command -v gpg > /dev/null || echo 'gnupg dirmngr') \
+	\
+	&& wget -O python.tar.xz "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz" \
+	&& wget -O python.tar.xz.asc "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz.asc" \
+	&& export GNUPGHOME="$(mktemp -d)" \
+	&& for server in $(shuf -e \
+	        ha.pool.sks-keyservers.net \
+	        hkp://p80.pool.sks-keyservers.net:80 \
+	        keyserver.ubuntu.com \
+	        hkp://keyserver.ubuntu.com:80 \
+	        pgp.mit.edu) ; do \
+	    gpg --batch --keyserver "$server" --recv-keys "$GPG_KEY" && break || : ; \
+	    done \
+	&& gpg --batch --verify python.tar.xz.asc python.tar.xz \
+	&& { command -v gpgconf > /dev/null && gpgconf --kill all || :; } \
+	&& rm -rf "$GNUPGHOME" python.tar.xz.asc \
+	&& mkdir -p /usr/src/python \
+	&& tar -xJC /usr/src/python --strip-components=1 -f python.tar.xz \
+	&& rm python.tar.xz \
+	\
+	&& cd /usr/src/python \
+	&& gnuArch="$(dpkg-architecture --query DEB_BUILD_GNU_TYPE)" \
+	&& ./configure \
+		--build="$gnuArch" \
+		--enable-loadable-sqlite-extensions \
+		--enable-optimizations \
+		--enable-option-checking=fatal \
+		--enable-shared \
+		--with-system-expat \
+		--with-system-ffi \
+		--without-ensurepip \
+	&& make -j "$(nproc)" \
+		LDFLAGS="-Wl,--strip-all" \
+	&& make install \
+	&& rm -rf /usr/src/python \
+	\
+	&& find /usr/local -depth \
+		\( \
+			\( -type d -a \( -name test -o -name tests -o -name idle_test \) \) \
+			-o \( -type f -a \( -name '*.pyc' -o -name '*.pyo' -o -name '*.a' \) \) \
+		\) -exec rm -rf '{}' + \
+	\
+	&& ldconfig \
+	\
+	&& apt-mark auto '.*' > /dev/null \
+	&& apt-mark manual $savedAptMark \
+	&& find /usr/local -type f -executable -not \( -name '*tkinter*' \) -exec ldd '{}' ';' \
+		| awk '/=>/ { print $(NF-1) }' \
+		| sort -u \
+		| xargs -r dpkg-query --search \
+		| cut -d: -f1 \
+		| sort -u \
+		| xargs -r apt-mark manual \
+	&& apt-get purge -y --auto-remove -o APT::AutoRemove::RecommendsImportant=false \
+	&& rm -rf /var/lib/apt/lists/* \
+	\
+	&& python3 --version
+
+# make some useful symlinks that are expected to exist
+RUN cd /usr/local/bin \
+	&& ln -s idle3 idle \
+	&& ln -s pydoc3 pydoc \
+	&& ln -s python3 python \
+	&& ln -s python3-config python-config
+
+# if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
+ENV PYTHON_PIP_VERSION 22.3.1
+# https://github.com/pypa/get-pip
+ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/66030fa03382b4914d4c4d0896961a0bdeeeb274/public/get-pip.py
+ENV PYTHON_GET_PIP_SHA256 1e501cf004eac1b7eb1f97266d28f995ae835d30250bec7f8850562703067dc6
+
+RUN set -ex; \
+	\
+	savedAptMark="$(apt-mark showmanual)"; \
+	apt-get update; \
+	apt-get install -y --no-install-recommends wget; \
+	\
+	wget -O get-pip.py "$PYTHON_GET_PIP_URL"; \
+	echo "$PYTHON_GET_PIP_SHA256 *get-pip.py" | sha256sum --check --strict -; \
+	\
+	apt-mark auto '.*' > /dev/null; \
+	[ -z "$savedAptMark" ] || apt-mark manual $savedAptMark; \
+	apt-get purge -y --auto-remove -o APT::AutoRemove::RecommendsImportant=false; \
+	rm -rf /var/lib/apt/lists/*; \
+	\
+	python get-pip.py \
+		--disable-pip-version-check \
+		--no-cache-dir \
+		"pip==$PYTHON_PIP_VERSION" \
+	; \
+	pip --version; \
+	\
+	find /usr/local -depth \
+		\( \
+			\( -type d -a \( -name test -o -name tests -o -name idle_test \) \) \
+			-o \
+			\( -type f -a \( -name '*.pyc' -o -name '*.pyo' \) \) \
+		\) -exec rm -rf '{}' +; \
+	rm -f get-pip.py
+
+CMD ["python3"]
diff --git a/3.10-rc/buster/Dockerfile b/3.10/buster/Dockerfile
similarity index 88%
rename from 3.10-rc/buster/Dockerfile
rename to 3.10/buster/Dockerfile
index 521b75c4d..b785f042c 100644
--- a/3.10-rc/buster/Dockerfile
+++ b/3.10/buster/Dockerfile
@@ -21,14 +21,14 @@ RUN apt-get update && apt-get install -y --no-install-recommends \
 	&& rm -rf /var/lib/apt/lists/*
 
 ENV GPG_KEY A035C8C19219BA821ECEA86B64E628F8D684696D
-ENV PYTHON_VERSION 3.10.0a1
+ENV PYTHON_VERSION 3.10.9
 
 RUN set -ex \
 	\
 	&& wget -O python.tar.xz "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz" \
 	&& wget -O python.tar.xz.asc "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz.asc" \
 	&& export GNUPGHOME="$(mktemp -d)" \
-	&& gpg --batch --keyserver ha.pool.sks-keyservers.net --recv-keys "$GPG_KEY" \
+	&& gpg --batch --keyserver hkps://keys.openpgp.org --recv-keys "$GPG_KEY" \
 	&& gpg --batch --verify python.tar.xz.asc python.tar.xz \
 	&& { command -v gpgconf > /dev/null && gpgconf --kill all || :; } \
 	&& rm -rf "$GNUPGHOME" python.tar.xz.asc \
@@ -69,10 +69,10 @@ RUN cd /usr/local/bin \
 	&& ln -s python3-config python-config
 
 # if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
-ENV PYTHON_PIP_VERSION 20.2.3
+ENV PYTHON_PIP_VERSION 22.3.1
 # https://github.com/pypa/get-pip
-ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/fa7dc83944936bf09a0e4cb5d5ec852c0d256599/get-pip.py
-ENV PYTHON_GET_PIP_SHA256 6e0bb0a2c2533361d7f297ed547237caf1b7507f197835974c0dd7eba998c53c
+ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/66030fa03382b4914d4c4d0896961a0bdeeeb274/public/get-pip.py
+ENV PYTHON_GET_PIP_SHA256 1e501cf004eac1b7eb1f97266d28f995ae835d30250bec7f8850562703067dc6
 
 RUN set -ex; \
 	\
diff --git a/3.10-rc/buster/slim/Dockerfile b/3.10/buster/slim/Dockerfile
similarity index 92%
rename from 3.10-rc/buster/slim/Dockerfile
rename to 3.10/buster/slim/Dockerfile
index 3a02d3b83..5dbf09e97 100644
--- a/3.10-rc/buster/slim/Dockerfile
+++ b/3.10/buster/slim/Dockerfile
@@ -20,7 +20,7 @@ RUN apt-get update && apt-get install -y --no-install-recommends \
 	&& rm -rf /var/lib/apt/lists/*
 
 ENV GPG_KEY A035C8C19219BA821ECEA86B64E628F8D684696D
-ENV PYTHON_VERSION 3.10.0a1
+ENV PYTHON_VERSION 3.10.9
 
 RUN set -ex \
 	\
@@ -51,7 +51,7 @@ RUN set -ex \
 	&& wget -O python.tar.xz "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz" \
 	&& wget -O python.tar.xz.asc "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz.asc" \
 	&& export GNUPGHOME="$(mktemp -d)" \
-	&& gpg --batch --keyserver ha.pool.sks-keyservers.net --recv-keys "$GPG_KEY" \
+	&& gpg --batch --keyserver hkps://keys.openpgp.org --recv-keys "$GPG_KEY" \
 	&& gpg --batch --verify python.tar.xz.asc python.tar.xz \
 	&& { command -v gpgconf > /dev/null && gpgconf --kill all || :; } \
 	&& rm -rf "$GNUPGHOME" python.tar.xz.asc \
@@ -105,10 +105,10 @@ RUN cd /usr/local/bin \
 	&& ln -s python3-config python-config
 
 # if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
-ENV PYTHON_PIP_VERSION 20.2.3
+ENV PYTHON_PIP_VERSION 22.3.1
 # https://github.com/pypa/get-pip
-ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/fa7dc83944936bf09a0e4cb5d5ec852c0d256599/get-pip.py
-ENV PYTHON_GET_PIP_SHA256 6e0bb0a2c2533361d7f297ed547237caf1b7507f197835974c0dd7eba998c53c
+ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/66030fa03382b4914d4c4d0896961a0bdeeeb274/public/get-pip.py
+ENV PYTHON_GET_PIP_SHA256 1e501cf004eac1b7eb1f97266d28f995ae835d30250bec7f8850562703067dc6
 
 RUN set -ex; \
 	\
diff --git a/3.10-rc/windows/windowsservercore-1809/Dockerfile b/3.10/windows/windowsservercore-1809/Dockerfile
similarity index 88%
rename from 3.10-rc/windows/windowsservercore-1809/Dockerfile
rename to 3.10/windows/windowsservercore-1809/Dockerfile
index f5e7bca46..d0d0289a3 100644
--- a/3.10-rc/windows/windowsservercore-1809/Dockerfile
+++ b/3.10/windows/windowsservercore-1809/Dockerfile
@@ -8,8 +8,8 @@ FROM mcr.microsoft.com/windows/servercore:1809
 
 SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
 
-ENV PYTHON_VERSION 3.10.0a1
-ENV PYTHON_RELEASE 3.10.0
+ENV PYTHON_VERSION 3.10.9
+ENV PYTHON_RELEASE 3.10.9
 
 RUN $url = ('https://www.python.org/ftp/python/{0}/python-{1}-amd64.exe' -f $env:PYTHON_RELEASE, $env:PYTHON_VERSION); \
 	Write-Host ('Downloading {0} ...' -f $url); \
@@ -42,10 +42,10 @@ RUN $url = ('https://www.python.org/ftp/python/{0}/python-{1}-amd64.exe' -f $env
 	Write-Host 'Complete.'
 
 # if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
-ENV PYTHON_PIP_VERSION 20.2.3
+ENV PYTHON_PIP_VERSION 22.3.1
 # https://github.com/pypa/get-pip
-ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/fa7dc83944936bf09a0e4cb5d5ec852c0d256599/get-pip.py
-ENV PYTHON_GET_PIP_SHA256 6e0bb0a2c2533361d7f297ed547237caf1b7507f197835974c0dd7eba998c53c
+ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/66030fa03382b4914d4c4d0896961a0bdeeeb274/public/get-pip.py
+ENV PYTHON_GET_PIP_SHA256 1e501cf004eac1b7eb1f97266d28f995ae835d30250bec7f8850562703067dc6
 
 RUN Write-Host ('Downloading get-pip.py ({0}) ...' -f $env:PYTHON_GET_PIP_URL); \
 	[Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12; \
diff --git a/3.10-rc/windows/windowsservercore-ltsc2016/Dockerfile b/3.10/windows/windowsservercore-ltsc2016/Dockerfile
similarity index 88%
rename from 3.10-rc/windows/windowsservercore-ltsc2016/Dockerfile
rename to 3.10/windows/windowsservercore-ltsc2016/Dockerfile
index 49d5c175a..6880cfd8b 100644
--- a/3.10-rc/windows/windowsservercore-ltsc2016/Dockerfile
+++ b/3.10/windows/windowsservercore-ltsc2016/Dockerfile
@@ -8,8 +8,8 @@ FROM mcr.microsoft.com/windows/servercore:ltsc2016
 
 SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
 
-ENV PYTHON_VERSION 3.10.0a1
-ENV PYTHON_RELEASE 3.10.0
+ENV PYTHON_VERSION 3.10.9
+ENV PYTHON_RELEASE 3.10.9
 
 RUN $url = ('https://www.python.org/ftp/python/{0}/python-{1}-amd64.exe' -f $env:PYTHON_RELEASE, $env:PYTHON_VERSION); \
 	Write-Host ('Downloading {0} ...' -f $url); \
@@ -42,10 +42,10 @@ RUN $url = ('https://www.python.org/ftp/python/{0}/python-{1}-amd64.exe' -f $env
 	Write-Host 'Complete.'
 
 # if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
-ENV PYTHON_PIP_VERSION 20.2.3
+ENV PYTHON_PIP_VERSION 22.3.1
 # https://github.com/pypa/get-pip
-ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/fa7dc83944936bf09a0e4cb5d5ec852c0d256599/get-pip.py
-ENV PYTHON_GET_PIP_SHA256 6e0bb0a2c2533361d7f297ed547237caf1b7507f197835974c0dd7eba998c53c
+ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/66030fa03382b4914d4c4d0896961a0bdeeeb274/public/get-pip.py
+ENV PYTHON_GET_PIP_SHA256 1e501cf004eac1b7eb1f97266d28f995ae835d30250bec7f8850562703067dc6
 
 RUN Write-Host ('Downloading get-pip.py ({0}) ...' -f $env:PYTHON_GET_PIP_URL); \
 	[Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12; \
diff --git a/3.8/alpine3.11/Dockerfile b/3.11/alpine3.17/Dockerfile
similarity index 89%
rename from 3.8/alpine3.11/Dockerfile
rename to 3.11/alpine3.17/Dockerfile
index 67ab7656f..1da6c5677 100644
--- a/3.8/alpine3.11/Dockerfile
+++ b/3.11/alpine3.17/Dockerfile
@@ -4,7 +4,7 @@
 # PLEASE DO NOT EDIT IT DIRECTLY.
 #
 
-FROM alpine:3.11
+FROM alpine:3.17
 
 # ensure local python is preferred over distribution python
 ENV PATH /usr/local/bin:$PATH
@@ -17,8 +17,8 @@ ENV LANG C.UTF-8
 # other runtime dependencies for Python are installed later
 RUN apk add --no-cache ca-certificates
 
-ENV GPG_KEY E3FF2839C048B25C084DEBE9B26995E310250568
-ENV PYTHON_VERSION 3.8.6
+ENV GPG_KEY A035C8C19219BA821ECEA86B64E628F8D684696D
+ENV PYTHON_VERSION 3.11.1
 
 RUN set -ex \
 	&& apk add --no-cache --virtual .fetch-deps \
@@ -29,7 +29,7 @@ RUN set -ex \
 	&& wget -O python.tar.xz "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz" \
 	&& wget -O python.tar.xz.asc "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz.asc" \
 	&& export GNUPGHOME="$(mktemp -d)" \
-	&& gpg --batch --keyserver ha.pool.sks-keyservers.net --recv-keys "$GPG_KEY" \
+	&& gpg --batch --keyserver hkps://keys.openpgp.org --recv-keys "$GPG_KEY" \
 	&& gpg --batch --verify python.tar.xz.asc python.tar.xz \
 	&& { command -v gpgconf > /dev/null && gpgconf --kill all || :; } \
 	&& rm -rf "$GNUPGHOME" python.tar.xz.asc \
@@ -89,7 +89,6 @@ RUN set -ex \
 		\( \
 			\( -type d -a \( -name test -o -name tests -o -name idle_test \) \) \
 			-o \( -type f -a \( -name '*.pyc' -o -name '*.pyo' -o -name '*.a' \) \) \
-			-o \( -type f -a -name 'wininst-*.exe' \) \
 		\) -exec rm -rf '{}' + \
 	\
 	&& find /usr/local -type f -executable -not \( -name '*tkinter*' \) -exec scanelf --needed --nobanner --format '%n#p' '{}' ';' \
@@ -109,10 +108,10 @@ RUN cd /usr/local/bin \
 	&& ln -s python3-config python-config
 
 # if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
-ENV PYTHON_PIP_VERSION 20.2.3
+ENV PYTHON_PIP_VERSION 22.3.1
 # https://github.com/pypa/get-pip
-ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/fa7dc83944936bf09a0e4cb5d5ec852c0d256599/get-pip.py
-ENV PYTHON_GET_PIP_SHA256 6e0bb0a2c2533361d7f297ed547237caf1b7507f197835974c0dd7eba998c53c
+ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/66030fa03382b4914d4c4d0896961a0bdeeeb274/public/get-pip.py
+ENV PYTHON_GET_PIP_SHA256 1e501cf004eac1b7eb1f97266d28f995ae835d30250bec7f8850562703067dc6
 
 RUN set -ex; \
 	\
diff --git a/3.11/bionic/Dockerfile b/3.11/bionic/Dockerfile
new file mode 100644
index 000000000..85b0f6a39
--- /dev/null
+++ b/3.11/bionic/Dockerfile
@@ -0,0 +1,106 @@
+#
+# NOTE: THIS DOCKERFILE IS GENERATED VIA "update.sh"
+#
+# PLEASE DO NOT EDIT IT DIRECTLY.
+#
+
+FROM vaporio/buildpack-deps:bionic
+
+# ensure local python is preferred over distribution python
+ENV PATH /usr/local/bin:$PATH
+
+# http://bugs.python.org/issue19846
+# > At the moment, setting "LANG=C" on a Linux system *fundamentally breaks Python 3*, and that's not OK.
+ENV LANG C.UTF-8
+ENV DEBIAN_FRONTEND noninteractive
+
+# extra dependencies (over what buildpack-deps already includes)
+RUN apt-get update; \
+    apt-get install -y --no-install-recommends \
+		libbluetooth-dev \
+		tk-dev \
+		uuid-dev \
+	&& rm -rf /var/lib/apt/lists/*
+
+ENV GPG_KEY A035C8C19219BA821ECEA86B64E628F8D684696D
+ENV PYTHON_VERSION 3.11.1
+
+RUN set -ex \
+	\
+	&& wget -O python.tar.xz "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz" \
+	&& wget -O python.tar.xz.asc "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz.asc" \
+	&& export GNUPGHOME="$(mktemp -d)" \
+	&& for server in $(shuf -e \
+	        ha.pool.sks-keyservers.net \
+	        hkp://p80.pool.sks-keyservers.net:80 \
+	        keyserver.ubuntu.com \
+	        hkp://keyserver.ubuntu.com:80 \
+	        pgp.mit.edu) ; do \
+	    gpg --batch --keyserver "$server" --recv-keys "$GPG_KEY" && break || : ; \
+	    done \
+	&& gpg --batch --verify python.tar.xz.asc python.tar.xz \
+	&& { command -v gpgconf > /dev/null && gpgconf --kill all || :; } \
+	&& rm -rf "$GNUPGHOME" python.tar.xz.asc \
+	&& mkdir -p /usr/src/python \
+	&& tar -xJC /usr/src/python --strip-components=1 -f python.tar.xz \
+	&& rm python.tar.xz \
+	\
+	&& cd /usr/src/python \
+	&& gnuArch="$(dpkg-architecture --query DEB_BUILD_GNU_TYPE)" \
+	&& ./configure \
+		--build="$gnuArch" \
+		--enable-loadable-sqlite-extensions \
+		--enable-optimizations \
+		--enable-option-checking=fatal \
+		--enable-shared \
+		--with-system-expat \
+		--with-system-ffi \
+		--without-ensurepip \
+	&& make -j "$(nproc)" \
+	&& make install \
+	&& rm -rf /usr/src/python \
+	\
+	&& find /usr/local -depth \
+		\( \
+			\( -type d -a \( -name test -o -name tests -o -name idle_test \) \) \
+			-o \( -type f -a \( -name '*.pyc' -o -name '*.pyo' -o -name '*.a' \) \) \
+		\) -exec rm -rf '{}' + \
+	\
+	&& ldconfig \
+	\
+	&& python3 --version
+
+# make some useful symlinks that are expected to exist
+RUN cd /usr/local/bin \
+	&& ln -s idle3 idle \
+	&& ln -s pydoc3 pydoc \
+	&& ln -s python3 python \
+	&& ln -s python3-config python-config
+
+# if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
+ENV PYTHON_PIP_VERSION 22.3.1
+# https://github.com/pypa/get-pip
+ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/66030fa03382b4914d4c4d0896961a0bdeeeb274/public/get-pip.py
+ENV PYTHON_GET_PIP_SHA256 1e501cf004eac1b7eb1f97266d28f995ae835d30250bec7f8850562703067dc6
+
+RUN set -ex; \
+	\
+	wget -O get-pip.py "$PYTHON_GET_PIP_URL"; \
+	echo "$PYTHON_GET_PIP_SHA256 *get-pip.py" | sha256sum --check --strict -; \
+	\
+	python get-pip.py \
+		--disable-pip-version-check \
+		--no-cache-dir \
+		"pip==$PYTHON_PIP_VERSION" \
+	; \
+	pip --version; \
+	\
+	find /usr/local -depth \
+		\( \
+			\( -type d -a \( -name test -o -name tests -o -name idle_test \) \) \
+			-o \
+			\( -type f -a \( -name '*.pyc' -o -name '*.pyo' \) \) \
+		\) -exec rm -rf '{}' +; \
+	rm -f get-pip.py
+
+CMD ["python3"]
diff --git a/3.11/bionic/lite/Dockerfile b/3.11/bionic/lite/Dockerfile
new file mode 100644
index 000000000..685c479b1
--- /dev/null
+++ b/3.11/bionic/lite/Dockerfile
@@ -0,0 +1,151 @@
+#
+# NOTE: THIS DOCKERFILE IS GENERATED VIA "update.sh"
+#
+# PLEASE DO NOT EDIT IT DIRECTLY.
+#
+
+FROM vaporio/foundation:bionic
+
+# ensure local python is preferred over distribution python
+ENV PATH /usr/local/bin:$PATH
+
+# http://bugs.python.org/issue19846
+# > At the moment, setting "LANG=C" on a Linux system *fundamentally breaks Python 3*, and that's not OK.
+ENV LANG C.UTF-8
+ENV DEBIAN_FRONTEND noninteractive
+
+# runtime dependencies
+RUN apt-get update; \
+    apt-get install -y --no-install-recommends \
+		ca-certificates \
+		netbase \
+	&& rm -rf /var/lib/apt/lists/*
+
+ENV GPG_KEY A035C8C19219BA821ECEA86B64E628F8D684696D
+ENV PYTHON_VERSION 3.11.1
+
+RUN set -ex \
+	\
+	&& savedAptMark="$(apt-mark showmanual)" \
+	&& apt-get update && apt-get install -y --no-install-recommends \
+		dpkg-dev \
+		gcc \
+		libbluetooth-dev \
+		libbz2-dev \
+		libc6-dev \
+		libexpat1-dev \
+		libffi-dev \
+		libgdbm-dev \
+		liblzma-dev \
+		libncursesw5-dev \
+		libreadline-dev \
+		libsqlite3-dev \
+		libssl-dev \
+		make \
+		tk-dev \
+		uuid-dev \
+		wget \
+		xz-utils \
+		zlib1g-dev \
+# as of Stretch, "gpg" is no longer included by default
+		$(command -v gpg > /dev/null || echo 'gnupg dirmngr') \
+	\
+	&& wget -O python.tar.xz "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz" \
+	&& wget -O python.tar.xz.asc "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz.asc" \
+	&& export GNUPGHOME="$(mktemp -d)" \
+	&& for server in $(shuf -e \
+	        ha.pool.sks-keyservers.net \
+	        hkp://p80.pool.sks-keyservers.net:80 \
+	        keyserver.ubuntu.com \
+	        hkp://keyserver.ubuntu.com:80 \
+	        pgp.mit.edu) ; do \
+	    gpg --batch --keyserver "$server" --recv-keys "$GPG_KEY" && break || : ; \
+	    done \
+	&& gpg --batch --verify python.tar.xz.asc python.tar.xz \
+	&& { command -v gpgconf > /dev/null && gpgconf --kill all || :; } \
+	&& rm -rf "$GNUPGHOME" python.tar.xz.asc \
+	&& mkdir -p /usr/src/python \
+	&& tar -xJC /usr/src/python --strip-components=1 -f python.tar.xz \
+	&& rm python.tar.xz \
+	\
+	&& cd /usr/src/python \
+	&& gnuArch="$(dpkg-architecture --query DEB_BUILD_GNU_TYPE)" \
+	&& ./configure \
+		--build="$gnuArch" \
+		--enable-loadable-sqlite-extensions \
+		--enable-optimizations \
+		--enable-option-checking=fatal \
+		--enable-shared \
+		--with-system-expat \
+		--with-system-ffi \
+		--without-ensurepip \
+	&& make -j "$(nproc)" \
+		LDFLAGS="-Wl,--strip-all" \
+	&& make install \
+	&& rm -rf /usr/src/python \
+	\
+	&& find /usr/local -depth \
+		\( \
+			\( -type d -a \( -name test -o -name tests -o -name idle_test \) \) \
+			-o \( -type f -a \( -name '*.pyc' -o -name '*.pyo' -o -name '*.a' \) \) \
+		\) -exec rm -rf '{}' + \
+	\
+	&& ldconfig \
+	\
+	&& apt-mark auto '.*' > /dev/null \
+	&& apt-mark manual $savedAptMark \
+	&& find /usr/local -type f -executable -not \( -name '*tkinter*' \) -exec ldd '{}' ';' \
+		| awk '/=>/ { print $(NF-1) }' \
+		| sort -u \
+		| xargs -r dpkg-query --search \
+		| cut -d: -f1 \
+		| sort -u \
+		| xargs -r apt-mark manual \
+	&& apt-get purge -y --auto-remove -o APT::AutoRemove::RecommendsImportant=false \
+	&& rm -rf /var/lib/apt/lists/* \
+	\
+	&& python3 --version
+
+# make some useful symlinks that are expected to exist
+RUN cd /usr/local/bin \
+	&& ln -s idle3 idle \
+	&& ln -s pydoc3 pydoc \
+	&& ln -s python3 python \
+	&& ln -s python3-config python-config
+
+# if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
+ENV PYTHON_PIP_VERSION 22.3.1
+# https://github.com/pypa/get-pip
+ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/66030fa03382b4914d4c4d0896961a0bdeeeb274/public/get-pip.py
+ENV PYTHON_GET_PIP_SHA256 1e501cf004eac1b7eb1f97266d28f995ae835d30250bec7f8850562703067dc6
+
+RUN set -ex; \
+	\
+	savedAptMark="$(apt-mark showmanual)"; \
+	apt-get update; \
+	apt-get install -y --no-install-recommends wget; \
+	\
+	wget -O get-pip.py "$PYTHON_GET_PIP_URL"; \
+	echo "$PYTHON_GET_PIP_SHA256 *get-pip.py" | sha256sum --check --strict -; \
+	\
+	apt-mark auto '.*' > /dev/null; \
+	[ -z "$savedAptMark" ] || apt-mark manual $savedAptMark; \
+	apt-get purge -y --auto-remove -o APT::AutoRemove::RecommendsImportant=false; \
+	rm -rf /var/lib/apt/lists/*; \
+	\
+	python get-pip.py \
+		--disable-pip-version-check \
+		--no-cache-dir \
+		"pip==$PYTHON_PIP_VERSION" \
+	; \
+	pip --version; \
+	\
+	find /usr/local -depth \
+		\( \
+			\( -type d -a \( -name test -o -name tests -o -name idle_test \) \) \
+			-o \
+			\( -type f -a \( -name '*.pyc' -o -name '*.pyo' \) \) \
+		\) -exec rm -rf '{}' +; \
+	rm -f get-pip.py
+
+CMD ["python3"]
diff --git a/3.6/jessie/Dockerfile b/3.11/buster/Dockerfile
similarity index 69%
rename from 3.6/jessie/Dockerfile
rename to 3.11/buster/Dockerfile
index 1055f2fd5..3e604d788 100644
--- a/3.6/jessie/Dockerfile
+++ b/3.11/buster/Dockerfile
@@ -4,7 +4,7 @@
 # PLEASE DO NOT EDIT IT DIRECTLY.
 #
 
-FROM buildpack-deps:jessie
+FROM buildpack-deps:buster
 
 # ensure local python is preferred over distribution python
 ENV PATH /usr/local/bin:$PATH
@@ -15,18 +15,20 @@ ENV LANG C.UTF-8
 
 # extra dependencies (over what buildpack-deps already includes)
 RUN apt-get update && apt-get install -y --no-install-recommends \
+		libbluetooth-dev \
 		tk-dev \
+		uuid-dev \
 	&& rm -rf /var/lib/apt/lists/*
 
-ENV GPG_KEY 0D96DF4D4110E5C43FBFB17F2D347EA6AA65421D
-ENV PYTHON_VERSION 3.6.9
+ENV GPG_KEY A035C8C19219BA821ECEA86B64E628F8D684696D
+ENV PYTHON_VERSION 3.11.1
 
 RUN set -ex \
 	\
 	&& wget -O python.tar.xz "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz" \
 	&& wget -O python.tar.xz.asc "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz.asc" \
 	&& export GNUPGHOME="$(mktemp -d)" \
-	&& gpg --batch --keyserver ha.pool.sks-keyservers.net --recv-keys "$GPG_KEY" \
+	&& gpg --batch --keyserver hkps://keys.openpgp.org --recv-keys "$GPG_KEY" \
 	&& gpg --batch --verify python.tar.xz.asc python.tar.xz \
 	&& { command -v gpgconf > /dev/null && gpgconf --kill all || :; } \
 	&& rm -rf "$GNUPGHOME" python.tar.xz.asc \
@@ -40,57 +42,22 @@ RUN set -ex \
 		--build="$gnuArch" \
 		--enable-loadable-sqlite-extensions \
 		--enable-optimizations \
+		--enable-option-checking=fatal \
 		--enable-shared \
 		--with-system-expat \
 		--with-system-ffi \
 		--without-ensurepip \
 	&& make -j "$(nproc)" \
-# https://github.com/docker-library/python/issues/160#issuecomment-509426916
-		PROFILE_TASK='-m test.regrtest --pgo \
-			test_array \
-			test_base64 \
-			test_binascii \
-			test_binhex \
-			test_binop \
-			test_bytes \
-			test_c_locale_coercion \
-			test_class \
-			test_cmath \
-			test_codecs \
-			test_compile \
-			test_complex \
-			test_csv \
-			test_decimal \
-			test_dict \
-			test_float \
-			test_fstring \
-			test_hashlib \
-			test_io \
-			test_iter \
-			test_json \
-			test_long \
-			test_math \
-			test_memoryview \
-			test_pickle \
-			test_re \
-			test_set \
-			test_slice \
-			test_struct \
-			test_threading \
-			test_time \
-			test_traceback \
-			test_unicode \
-		' \
 	&& make install \
-	&& ldconfig \
+	&& rm -rf /usr/src/python \
 	\
 	&& find /usr/local -depth \
 		\( \
 			\( -type d -a \( -name test -o -name tests -o -name idle_test \) \) \
-			-o \
-			\( -type f -a \( -name '*.pyc' -o -name '*.pyo' \) \) \
+			-o \( -type f -a \( -name '*.pyc' -o -name '*.pyo' -o -name '*.a' \) \) \
 		\) -exec rm -rf '{}' + \
-	&& rm -rf /usr/src/python \
+	\
+	&& ldconfig \
 	\
 	&& python3 --version
 
@@ -102,11 +69,15 @@ RUN cd /usr/local/bin \
 	&& ln -s python3-config python-config
 
 # if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
-ENV PYTHON_PIP_VERSION 19.1.1
+ENV PYTHON_PIP_VERSION 22.3.1
+# https://github.com/pypa/get-pip
+ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/66030fa03382b4914d4c4d0896961a0bdeeeb274/public/get-pip.py
+ENV PYTHON_GET_PIP_SHA256 1e501cf004eac1b7eb1f97266d28f995ae835d30250bec7f8850562703067dc6
 
 RUN set -ex; \
 	\
-	wget -O get-pip.py 'https://bootstrap.pypa.io/get-pip.py'; \
+	wget -O get-pip.py "$PYTHON_GET_PIP_URL"; \
+	echo "$PYTHON_GET_PIP_SHA256 *get-pip.py" | sha256sum --check --strict -; \
 	\
 	python get-pip.py \
 		--disable-pip-version-check \
diff --git a/3.6/jessie/slim/Dockerfile b/3.11/buster/slim/Dockerfile
similarity index 77%
rename from 3.6/jessie/slim/Dockerfile
rename to 3.11/buster/slim/Dockerfile
index 62d9646f7..c0cc65e72 100644
--- a/3.6/jessie/slim/Dockerfile
+++ b/3.11/buster/slim/Dockerfile
@@ -4,7 +4,7 @@
 # PLEASE DO NOT EDIT IT DIRECTLY.
 #
 
-FROM debian:jessie-slim
+FROM debian:buster-slim
 
 # ensure local python is preferred over distribution python
 ENV PATH /usr/local/bin:$PATH
@@ -19,8 +19,8 @@ RUN apt-get update && apt-get install -y --no-install-recommends \
 		netbase \
 	&& rm -rf /var/lib/apt/lists/*
 
-ENV GPG_KEY 0D96DF4D4110E5C43FBFB17F2D347EA6AA65421D
-ENV PYTHON_VERSION 3.6.9
+ENV GPG_KEY A035C8C19219BA821ECEA86B64E628F8D684696D
+ENV PYTHON_VERSION 3.11.1
 
 RUN set -ex \
 	\
@@ -28,6 +28,7 @@ RUN set -ex \
 	&& apt-get update && apt-get install -y --no-install-recommends \
 		dpkg-dev \
 		gcc \
+		libbluetooth-dev \
 		libbz2-dev \
 		libc6-dev \
 		libexpat1-dev \
@@ -40,6 +41,7 @@ RUN set -ex \
 		libssl-dev \
 		make \
 		tk-dev \
+		uuid-dev \
 		wget \
 		xz-utils \
 		zlib1g-dev \
@@ -49,7 +51,7 @@ RUN set -ex \
 	&& wget -O python.tar.xz "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz" \
 	&& wget -O python.tar.xz.asc "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz.asc" \
 	&& export GNUPGHOME="$(mktemp -d)" \
-	&& gpg --batch --keyserver ha.pool.sks-keyservers.net --recv-keys "$GPG_KEY" \
+	&& gpg --batch --keyserver hkps://keys.openpgp.org --recv-keys "$GPG_KEY" \
 	&& gpg --batch --verify python.tar.xz.asc python.tar.xz \
 	&& { command -v gpgconf > /dev/null && gpgconf --kill all || :; } \
 	&& rm -rf "$GNUPGHOME" python.tar.xz.asc \
@@ -63,48 +65,22 @@ RUN set -ex \
 		--build="$gnuArch" \
 		--enable-loadable-sqlite-extensions \
 		--enable-optimizations \
+		--enable-option-checking=fatal \
 		--enable-shared \
 		--with-system-expat \
 		--with-system-ffi \
 		--without-ensurepip \
 	&& make -j "$(nproc)" \
-# https://github.com/docker-library/python/issues/160#issuecomment-509426916
-		PROFILE_TASK='-m test.regrtest --pgo \
-			test_array \
-			test_base64 \
-			test_binascii \
-			test_binhex \
-			test_binop \
-			test_bytes \
-			test_c_locale_coercion \
-			test_class \
-			test_cmath \
-			test_codecs \
-			test_compile \
-			test_complex \
-			test_csv \
-			test_decimal \
-			test_dict \
-			test_float \
-			test_fstring \
-			test_hashlib \
-			test_io \
-			test_iter \
-			test_json \
-			test_long \
-			test_math \
-			test_memoryview \
-			test_pickle \
-			test_re \
-			test_set \
-			test_slice \
-			test_struct \
-			test_threading \
-			test_time \
-			test_traceback \
-			test_unicode \
-		' \
+		LDFLAGS="-Wl,--strip-all" \
 	&& make install \
+	&& rm -rf /usr/src/python \
+	\
+	&& find /usr/local -depth \
+		\( \
+			\( -type d -a \( -name test -o -name tests -o -name idle_test \) \) \
+			-o \( -type f -a \( -name '*.pyc' -o -name '*.pyo' -o -name '*.a' \) \) \
+		\) -exec rm -rf '{}' + \
+	\
 	&& ldconfig \
 	\
 	&& apt-mark auto '.*' > /dev/null \
@@ -119,14 +95,6 @@ RUN set -ex \
 	&& apt-get purge -y --auto-remove -o APT::AutoRemove::RecommendsImportant=false \
 	&& rm -rf /var/lib/apt/lists/* \
 	\
-	&& find /usr/local -depth \
-		\( \
-			\( -type d -a \( -name test -o -name tests -o -name idle_test \) \) \
-			-o \
-			\( -type f -a \( -name '*.pyc' -o -name '*.pyo' \) \) \
-		\) -exec rm -rf '{}' + \
-	&& rm -rf /usr/src/python \
-	\
 	&& python3 --version
 
 # make some useful symlinks that are expected to exist
@@ -137,7 +105,10 @@ RUN cd /usr/local/bin \
 	&& ln -s python3-config python-config
 
 # if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
-ENV PYTHON_PIP_VERSION 19.1.1
+ENV PYTHON_PIP_VERSION 22.3.1
+# https://github.com/pypa/get-pip
+ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/66030fa03382b4914d4c4d0896961a0bdeeeb274/public/get-pip.py
+ENV PYTHON_GET_PIP_SHA256 1e501cf004eac1b7eb1f97266d28f995ae835d30250bec7f8850562703067dc6
 
 RUN set -ex; \
 	\
@@ -145,7 +116,8 @@ RUN set -ex; \
 	apt-get update; \
 	apt-get install -y --no-install-recommends wget; \
 	\
-	wget -O get-pip.py 'https://bootstrap.pypa.io/get-pip.py'; \
+	wget -O get-pip.py "$PYTHON_GET_PIP_URL"; \
+	echo "$PYTHON_GET_PIP_SHA256 *get-pip.py" | sha256sum --check --strict -; \
 	\
 	apt-mark auto '.*' > /dev/null; \
 	[ -z "$savedAptMark" ] || apt-mark manual $savedAptMark; \
diff --git a/3.11/windows/windowsservercore-1809/Dockerfile b/3.11/windows/windowsservercore-1809/Dockerfile
new file mode 100644
index 000000000..fe686b3bf
--- /dev/null
+++ b/3.11/windows/windowsservercore-1809/Dockerfile
@@ -0,0 +1,72 @@
+#
+# NOTE: THIS DOCKERFILE IS GENERATED VIA "update.sh"
+#
+# PLEASE DO NOT EDIT IT DIRECTLY.
+#
+
+FROM mcr.microsoft.com/windows/servercore:1809
+
+SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
+
+ENV PYTHON_VERSION 3.11.1
+ENV PYTHON_RELEASE 3.11.1
+
+RUN $url = ('https://www.python.org/ftp/python/{0}/python-{1}-amd64.exe' -f $env:PYTHON_RELEASE, $env:PYTHON_VERSION); \
+	Write-Host ('Downloading {0} ...' -f $url); \
+	[Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12; \
+	Invoke-WebRequest -Uri $url -OutFile 'python.exe'; \
+	\
+	Write-Host 'Installing ...'; \
+# https://docs.python.org/3.5/using/windows.html#installing-without-ui
+	Start-Process python.exe -Wait \
+		-ArgumentList @( \
+			'/quiet', \
+			'InstallAllUsers=1', \
+			'TargetDir=C:\Python', \
+			'PrependPath=1', \
+			'Shortcuts=0', \
+			'Include_doc=0', \
+			'Include_pip=0', \
+			'Include_test=0' \
+		); \
+	\
+# the installer updated PATH, so we should refresh our local value
+	$env:PATH = [Environment]::GetEnvironmentVariable('PATH', [EnvironmentVariableTarget]::Machine); \
+	\
+	Write-Host 'Verifying install ...'; \
+	Write-Host '  python --version'; python --version; \
+	\
+	Write-Host 'Removing ...'; \
+	Remove-Item python.exe -Force; \
+	\
+	Write-Host 'Complete.'
+
+# if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
+ENV PYTHON_PIP_VERSION 22.3.1
+# https://github.com/pypa/get-pip
+ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/66030fa03382b4914d4c4d0896961a0bdeeeb274/public/get-pip.py
+ENV PYTHON_GET_PIP_SHA256 1e501cf004eac1b7eb1f97266d28f995ae835d30250bec7f8850562703067dc6
+
+RUN Write-Host ('Downloading get-pip.py ({0}) ...' -f $env:PYTHON_GET_PIP_URL); \
+	[Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12; \
+	Invoke-WebRequest -Uri $env:PYTHON_GET_PIP_URL -OutFile 'get-pip.py'; \
+	Write-Host ('Verifying sha256 ({0}) ...' -f $env:PYTHON_GET_PIP_SHA256); \
+	if ((Get-FileHash 'get-pip.py' -Algorithm sha256).Hash -ne $env:PYTHON_GET_PIP_SHA256) { \
+		Write-Host 'FAILED!'; \
+		exit 1; \
+	}; \
+	\
+	Write-Host ('Installing pip=={0} ...' -f $env:PYTHON_PIP_VERSION); \
+	python get-pip.py \
+		--disable-pip-version-check \
+		--no-cache-dir \
+		('pip=={0}' -f $env:PYTHON_PIP_VERSION) \
+	; \
+	Remove-Item get-pip.py -Force; \
+	\
+	Write-Host 'Verifying pip install ...'; \
+	pip --version; \
+	\
+	Write-Host 'Complete.'
+
+CMD ["python"]
diff --git a/3.11/windows/windowsservercore-ltsc2016/Dockerfile b/3.11/windows/windowsservercore-ltsc2016/Dockerfile
new file mode 100644
index 000000000..a5562ad93
--- /dev/null
+++ b/3.11/windows/windowsservercore-ltsc2016/Dockerfile
@@ -0,0 +1,72 @@
+#
+# NOTE: THIS DOCKERFILE IS GENERATED VIA "update.sh"
+#
+# PLEASE DO NOT EDIT IT DIRECTLY.
+#
+
+FROM mcr.microsoft.com/windows/servercore:ltsc2016
+
+SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
+
+ENV PYTHON_VERSION 3.11.1
+ENV PYTHON_RELEASE 3.11.1
+
+RUN $url = ('https://www.python.org/ftp/python/{0}/python-{1}-amd64.exe' -f $env:PYTHON_RELEASE, $env:PYTHON_VERSION); \
+	Write-Host ('Downloading {0} ...' -f $url); \
+	[Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12; \
+	Invoke-WebRequest -Uri $url -OutFile 'python.exe'; \
+	\
+	Write-Host 'Installing ...'; \
+# https://docs.python.org/3.5/using/windows.html#installing-without-ui
+	Start-Process python.exe -Wait \
+		-ArgumentList @( \
+			'/quiet', \
+			'InstallAllUsers=1', \
+			'TargetDir=C:\Python', \
+			'PrependPath=1', \
+			'Shortcuts=0', \
+			'Include_doc=0', \
+			'Include_pip=0', \
+			'Include_test=0' \
+		); \
+	\
+# the installer updated PATH, so we should refresh our local value
+	$env:PATH = [Environment]::GetEnvironmentVariable('PATH', [EnvironmentVariableTarget]::Machine); \
+	\
+	Write-Host 'Verifying install ...'; \
+	Write-Host '  python --version'; python --version; \
+	\
+	Write-Host 'Removing ...'; \
+	Remove-Item python.exe -Force; \
+	\
+	Write-Host 'Complete.'
+
+# if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
+ENV PYTHON_PIP_VERSION 22.3.1
+# https://github.com/pypa/get-pip
+ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/66030fa03382b4914d4c4d0896961a0bdeeeb274/public/get-pip.py
+ENV PYTHON_GET_PIP_SHA256 1e501cf004eac1b7eb1f97266d28f995ae835d30250bec7f8850562703067dc6
+
+RUN Write-Host ('Downloading get-pip.py ({0}) ...' -f $env:PYTHON_GET_PIP_URL); \
+	[Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12; \
+	Invoke-WebRequest -Uri $env:PYTHON_GET_PIP_URL -OutFile 'get-pip.py'; \
+	Write-Host ('Verifying sha256 ({0}) ...' -f $env:PYTHON_GET_PIP_SHA256); \
+	if ((Get-FileHash 'get-pip.py' -Algorithm sha256).Hash -ne $env:PYTHON_GET_PIP_SHA256) { \
+		Write-Host 'FAILED!'; \
+		exit 1; \
+	}; \
+	\
+	Write-Host ('Installing pip=={0} ...' -f $env:PYTHON_PIP_VERSION); \
+	python get-pip.py \
+		--disable-pip-version-check \
+		--no-cache-dir \
+		('pip=={0}' -f $env:PYTHON_PIP_VERSION) \
+	; \
+	Remove-Item get-pip.py -Force; \
+	\
+	Write-Host 'Verifying pip install ...'; \
+	pip --version; \
+	\
+	Write-Host 'Complete.'
+
+CMD ["python"]
diff --git a/3.6/alpine3.11/Dockerfile b/3.6/alpine3.11/Dockerfile
deleted file mode 100644
index 61089fc19..000000000
--- a/3.6/alpine3.11/Dockerfile
+++ /dev/null
@@ -1,172 +0,0 @@
-#
-# NOTE: THIS DOCKERFILE IS GENERATED VIA "update.sh"
-#
-# PLEASE DO NOT EDIT IT DIRECTLY.
-#
-
-FROM alpine:3.11
-
-# ensure local python is preferred over distribution python
-ENV PATH /usr/local/bin:$PATH
-
-# http://bugs.python.org/issue19846
-# > At the moment, setting "LANG=C" on a Linux system *fundamentally breaks Python 3*, and that's not OK.
-ENV LANG C.UTF-8
-
-# install ca-certificates so that HTTPS works consistently
-# other runtime dependencies for Python are installed later
-RUN apk add --no-cache ca-certificates
-
-ENV GPG_KEY 0D96DF4D4110E5C43FBFB17F2D347EA6AA65421D
-ENV PYTHON_VERSION 3.6.12
-
-RUN set -ex \
-	&& apk add --no-cache --virtual .fetch-deps \
-		gnupg \
-		tar \
-		xz \
-	\
-	&& wget -O python.tar.xz "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz" \
-	&& wget -O python.tar.xz.asc "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz.asc" \
-	&& export GNUPGHOME="$(mktemp -d)" \
-	&& gpg --batch --keyserver ha.pool.sks-keyservers.net --recv-keys "$GPG_KEY" \
-	&& gpg --batch --verify python.tar.xz.asc python.tar.xz \
-	&& { command -v gpgconf > /dev/null && gpgconf --kill all || :; } \
-	&& rm -rf "$GNUPGHOME" python.tar.xz.asc \
-	&& mkdir -p /usr/src/python \
-	&& tar -xJC /usr/src/python --strip-components=1 -f python.tar.xz \
-	&& rm python.tar.xz \
-	\
-	&& apk add --no-cache --virtual .build-deps  \
-		bluez-dev \
-		bzip2-dev \
-		coreutils \
-		dpkg-dev dpkg \
-		expat-dev \
-		findutils \
-		gcc \
-		gdbm-dev \
-		libc-dev \
-		libffi-dev \
-		libnsl-dev \
-		libtirpc-dev \
-		linux-headers \
-		make \
-		ncurses-dev \
-		openssl-dev \
-		pax-utils \
-		readline-dev \
-		sqlite-dev \
-		tcl-dev \
-		tk \
-		tk-dev \
-		xz-dev \
-		zlib-dev \
-# add build deps before removing fetch deps in case there's overlap
-	&& apk del --no-network .fetch-deps \
-	\
-	&& cd /usr/src/python \
-	&& gnuArch="$(dpkg-architecture --query DEB_BUILD_GNU_TYPE)" \
-	&& ./configure \
-		--build="$gnuArch" \
-		--enable-loadable-sqlite-extensions \
-		--enable-optimizations \
-		--enable-option-checking=fatal \
-		--enable-shared \
-		--with-system-expat \
-		--with-system-ffi \
-		--without-ensurepip \
-	&& make -j "$(nproc)" \
-# set thread stack size to 1MB so we don't segfault before we hit sys.getrecursionlimit()
-# https://github.com/alpinelinux/aports/commit/2026e1259422d4e0cf92391ca2d3844356c649d0
-		EXTRA_CFLAGS="-DTHREAD_STACK_SIZE=0x100000" \
-		LDFLAGS="-Wl,--strip-all" \
-# setting PROFILE_TASK makes "--enable-optimizations" reasonable: https://bugs.python.org/issue36044 / https://github.com/docker-library/python/issues/160#issuecomment-509426916
-		PROFILE_TASK='-m test.regrtest --pgo \
-			test_array \
-			test_base64 \
-			test_binascii \
-			test_binhex \
-			test_binop \
-			test_bytes \
-			test_c_locale_coercion \
-			test_class \
-			test_cmath \
-			test_codecs \
-			test_compile \
-			test_complex \
-			test_csv \
-			test_decimal \
-			test_dict \
-			test_float \
-			test_fstring \
-			test_hashlib \
-			test_io \
-			test_iter \
-			test_json \
-			test_long \
-			test_math \
-			test_memoryview \
-			test_pickle \
-			test_re \
-			test_set \
-			test_slice \
-			test_struct \
-			test_threading \
-			test_time \
-			test_traceback \
-			test_unicode \
-		' \
-	&& make install \
-	&& rm -rf /usr/src/python \
-	\
-	&& find /usr/local -depth \
-		\( \
-			\( -type d -a \( -name test -o -name tests -o -name idle_test \) \) \
-			-o \( -type f -a \( -name '*.pyc' -o -name '*.pyo' -o -name '*.a' \) \) \
-			-o \( -type f -a -name 'wininst-*.exe' \) \
-		\) -exec rm -rf '{}' + \
-	\
-	&& find /usr/local -type f -executable -not \( -name '*tkinter*' \) -exec scanelf --needed --nobanner --format '%n#p' '{}' ';' \
-		| tr ',' '\n' \
-		| sort -u \
-		| awk 'system("[ -e /usr/local/lib/" $1 " ]") == 0 { next } { print "so:" $1 }' \
-		| xargs -rt apk add --no-cache --virtual .python-rundeps \
-	&& apk del --no-network .build-deps \
-	\
-	&& python3 --version
-
-# make some useful symlinks that are expected to exist
-RUN cd /usr/local/bin \
-	&& ln -s idle3 idle \
-	&& ln -s pydoc3 pydoc \
-	&& ln -s python3 python \
-	&& ln -s python3-config python-config
-
-# if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
-ENV PYTHON_PIP_VERSION 20.2.3
-# https://github.com/pypa/get-pip
-ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/fa7dc83944936bf09a0e4cb5d5ec852c0d256599/get-pip.py
-ENV PYTHON_GET_PIP_SHA256 6e0bb0a2c2533361d7f297ed547237caf1b7507f197835974c0dd7eba998c53c
-
-RUN set -ex; \
-	\
-	wget -O get-pip.py "$PYTHON_GET_PIP_URL"; \
-	echo "$PYTHON_GET_PIP_SHA256 *get-pip.py" | sha256sum -c -; \
-	\
-	python get-pip.py \
-		--disable-pip-version-check \
-		--no-cache-dir \
-		"pip==$PYTHON_PIP_VERSION" \
-	; \
-	pip --version; \
-	\
-	find /usr/local -depth \
-		\( \
-			\( -type d -a \( -name test -o -name tests -o -name idle_test \) \) \
-			-o \
-			\( -type f -a \( -name '*.pyc' -o -name '*.pyo' \) \) \
-		\) -exec rm -rf '{}' +; \
-	rm -f get-pip.py
-
-CMD ["python3"]
diff --git a/3.6/alpine3.12/Dockerfile b/3.6/alpine3.12/Dockerfile
deleted file mode 100644
index 9ffd45a75..000000000
--- a/3.6/alpine3.12/Dockerfile
+++ /dev/null
@@ -1,172 +0,0 @@
-#
-# NOTE: THIS DOCKERFILE IS GENERATED VIA "update.sh"
-#
-# PLEASE DO NOT EDIT IT DIRECTLY.
-#
-
-FROM alpine:3.12
-
-# ensure local python is preferred over distribution python
-ENV PATH /usr/local/bin:$PATH
-
-# http://bugs.python.org/issue19846
-# > At the moment, setting "LANG=C" on a Linux system *fundamentally breaks Python 3*, and that's not OK.
-ENV LANG C.UTF-8
-
-# install ca-certificates so that HTTPS works consistently
-# other runtime dependencies for Python are installed later
-RUN apk add --no-cache ca-certificates
-
-ENV GPG_KEY 0D96DF4D4110E5C43FBFB17F2D347EA6AA65421D
-ENV PYTHON_VERSION 3.6.12
-
-RUN set -ex \
-	&& apk add --no-cache --virtual .fetch-deps \
-		gnupg \
-		tar \
-		xz \
-	\
-	&& wget -O python.tar.xz "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz" \
-	&& wget -O python.tar.xz.asc "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz.asc" \
-	&& export GNUPGHOME="$(mktemp -d)" \
-	&& gpg --batch --keyserver ha.pool.sks-keyservers.net --recv-keys "$GPG_KEY" \
-	&& gpg --batch --verify python.tar.xz.asc python.tar.xz \
-	&& { command -v gpgconf > /dev/null && gpgconf --kill all || :; } \
-	&& rm -rf "$GNUPGHOME" python.tar.xz.asc \
-	&& mkdir -p /usr/src/python \
-	&& tar -xJC /usr/src/python --strip-components=1 -f python.tar.xz \
-	&& rm python.tar.xz \
-	\
-	&& apk add --no-cache --virtual .build-deps  \
-		bluez-dev \
-		bzip2-dev \
-		coreutils \
-		dpkg-dev dpkg \
-		expat-dev \
-		findutils \
-		gcc \
-		gdbm-dev \
-		libc-dev \
-		libffi-dev \
-		libnsl-dev \
-		libtirpc-dev \
-		linux-headers \
-		make \
-		ncurses-dev \
-		openssl-dev \
-		pax-utils \
-		readline-dev \
-		sqlite-dev \
-		tcl-dev \
-		tk \
-		tk-dev \
-		xz-dev \
-		zlib-dev \
-# add build deps before removing fetch deps in case there's overlap
-	&& apk del --no-network .fetch-deps \
-	\
-	&& cd /usr/src/python \
-	&& gnuArch="$(dpkg-architecture --query DEB_BUILD_GNU_TYPE)" \
-	&& ./configure \
-		--build="$gnuArch" \
-		--enable-loadable-sqlite-extensions \
-		--enable-optimizations \
-		--enable-option-checking=fatal \
-		--enable-shared \
-		--with-system-expat \
-		--with-system-ffi \
-		--without-ensurepip \
-	&& make -j "$(nproc)" \
-# set thread stack size to 1MB so we don't segfault before we hit sys.getrecursionlimit()
-# https://github.com/alpinelinux/aports/commit/2026e1259422d4e0cf92391ca2d3844356c649d0
-		EXTRA_CFLAGS="-DTHREAD_STACK_SIZE=0x100000" \
-		LDFLAGS="-Wl,--strip-all" \
-# setting PROFILE_TASK makes "--enable-optimizations" reasonable: https://bugs.python.org/issue36044 / https://github.com/docker-library/python/issues/160#issuecomment-509426916
-		PROFILE_TASK='-m test.regrtest --pgo \
-			test_array \
-			test_base64 \
-			test_binascii \
-			test_binhex \
-			test_binop \
-			test_bytes \
-			test_c_locale_coercion \
-			test_class \
-			test_cmath \
-			test_codecs \
-			test_compile \
-			test_complex \
-			test_csv \
-			test_decimal \
-			test_dict \
-			test_float \
-			test_fstring \
-			test_hashlib \
-			test_io \
-			test_iter \
-			test_json \
-			test_long \
-			test_math \
-			test_memoryview \
-			test_pickle \
-			test_re \
-			test_set \
-			test_slice \
-			test_struct \
-			test_threading \
-			test_time \
-			test_traceback \
-			test_unicode \
-		' \
-	&& make install \
-	&& rm -rf /usr/src/python \
-	\
-	&& find /usr/local -depth \
-		\( \
-			\( -type d -a \( -name test -o -name tests -o -name idle_test \) \) \
-			-o \( -type f -a \( -name '*.pyc' -o -name '*.pyo' -o -name '*.a' \) \) \
-			-o \( -type f -a -name 'wininst-*.exe' \) \
-		\) -exec rm -rf '{}' + \
-	\
-	&& find /usr/local -type f -executable -not \( -name '*tkinter*' \) -exec scanelf --needed --nobanner --format '%n#p' '{}' ';' \
-		| tr ',' '\n' \
-		| sort -u \
-		| awk 'system("[ -e /usr/local/lib/" $1 " ]") == 0 { next } { print "so:" $1 }' \
-		| xargs -rt apk add --no-cache --virtual .python-rundeps \
-	&& apk del --no-network .build-deps \
-	\
-	&& python3 --version
-
-# make some useful symlinks that are expected to exist
-RUN cd /usr/local/bin \
-	&& ln -s idle3 idle \
-	&& ln -s pydoc3 pydoc \
-	&& ln -s python3 python \
-	&& ln -s python3-config python-config
-
-# if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
-ENV PYTHON_PIP_VERSION 20.2.3
-# https://github.com/pypa/get-pip
-ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/fa7dc83944936bf09a0e4cb5d5ec852c0d256599/get-pip.py
-ENV PYTHON_GET_PIP_SHA256 6e0bb0a2c2533361d7f297ed547237caf1b7507f197835974c0dd7eba998c53c
-
-RUN set -ex; \
-	\
-	wget -O get-pip.py "$PYTHON_GET_PIP_URL"; \
-	echo "$PYTHON_GET_PIP_SHA256 *get-pip.py" | sha256sum -c -; \
-	\
-	python get-pip.py \
-		--disable-pip-version-check \
-		--no-cache-dir \
-		"pip==$PYTHON_PIP_VERSION" \
-	; \
-	pip --version; \
-	\
-	find /usr/local -depth \
-		\( \
-			\( -type d -a \( -name test -o -name tests -o -name idle_test \) \) \
-			-o \
-			\( -type f -a \( -name '*.pyc' -o -name '*.pyo' \) \) \
-		\) -exec rm -rf '{}' +; \
-	rm -f get-pip.py
-
-CMD ["python3"]
diff --git a/3.7/alpine3.11/Dockerfile b/3.7/alpine3.11/Dockerfile
deleted file mode 100644
index 8e67175e3..000000000
--- a/3.7/alpine3.11/Dockerfile
+++ /dev/null
@@ -1,173 +0,0 @@
-#
-# NOTE: THIS DOCKERFILE IS GENERATED VIA "update.sh"
-#
-# PLEASE DO NOT EDIT IT DIRECTLY.
-#
-
-FROM alpine:3.11
-
-# ensure local python is preferred over distribution python
-ENV PATH /usr/local/bin:$PATH
-
-# http://bugs.python.org/issue19846
-# > At the moment, setting "LANG=C" on a Linux system *fundamentally breaks Python 3*, and that's not OK.
-ENV LANG C.UTF-8
-
-# install ca-certificates so that HTTPS works consistently
-# other runtime dependencies for Python are installed later
-RUN apk add --no-cache ca-certificates
-
-ENV GPG_KEY 0D96DF4D4110E5C43FBFB17F2D347EA6AA65421D
-ENV PYTHON_VERSION 3.7.9
-
-RUN set -ex \
-	&& apk add --no-cache --virtual .fetch-deps \
-		gnupg \
-		tar \
-		xz \
-	\
-	&& wget -O python.tar.xz "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz" \
-	&& wget -O python.tar.xz.asc "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz.asc" \
-	&& export GNUPGHOME="$(mktemp -d)" \
-	&& gpg --batch --keyserver ha.pool.sks-keyservers.net --recv-keys "$GPG_KEY" \
-	&& gpg --batch --verify python.tar.xz.asc python.tar.xz \
-	&& { command -v gpgconf > /dev/null && gpgconf --kill all || :; } \
-	&& rm -rf "$GNUPGHOME" python.tar.xz.asc \
-	&& mkdir -p /usr/src/python \
-	&& tar -xJC /usr/src/python --strip-components=1 -f python.tar.xz \
-	&& rm python.tar.xz \
-	\
-	&& apk add --no-cache --virtual .build-deps  \
-		bluez-dev \
-		bzip2-dev \
-		coreutils \
-		dpkg-dev dpkg \
-		expat-dev \
-		findutils \
-		gcc \
-		gdbm-dev \
-		libc-dev \
-		libffi-dev \
-		libnsl-dev \
-		libtirpc-dev \
-		linux-headers \
-		make \
-		ncurses-dev \
-		openssl-dev \
-		pax-utils \
-		readline-dev \
-		sqlite-dev \
-		tcl-dev \
-		tk \
-		tk-dev \
-		util-linux-dev \
-		xz-dev \
-		zlib-dev \
-# add build deps before removing fetch deps in case there's overlap
-	&& apk del --no-network .fetch-deps \
-	\
-	&& cd /usr/src/python \
-	&& gnuArch="$(dpkg-architecture --query DEB_BUILD_GNU_TYPE)" \
-	&& ./configure \
-		--build="$gnuArch" \
-		--enable-loadable-sqlite-extensions \
-		--enable-optimizations \
-		--enable-option-checking=fatal \
-		--enable-shared \
-		--with-system-expat \
-		--with-system-ffi \
-		--without-ensurepip \
-	&& make -j "$(nproc)" \
-# set thread stack size to 1MB so we don't segfault before we hit sys.getrecursionlimit()
-# https://github.com/alpinelinux/aports/commit/2026e1259422d4e0cf92391ca2d3844356c649d0
-		EXTRA_CFLAGS="-DTHREAD_STACK_SIZE=0x100000" \
-		LDFLAGS="-Wl,--strip-all" \
-# setting PROFILE_TASK makes "--enable-optimizations" reasonable: https://bugs.python.org/issue36044 / https://github.com/docker-library/python/issues/160#issuecomment-509426916
-		PROFILE_TASK='-m test.regrtest --pgo \
-			test_array \
-			test_base64 \
-			test_binascii \
-			test_binhex \
-			test_binop \
-			test_bytes \
-			test_c_locale_coercion \
-			test_class \
-			test_cmath \
-			test_codecs \
-			test_compile \
-			test_complex \
-			test_csv \
-			test_decimal \
-			test_dict \
-			test_float \
-			test_fstring \
-			test_hashlib \
-			test_io \
-			test_iter \
-			test_json \
-			test_long \
-			test_math \
-			test_memoryview \
-			test_pickle \
-			test_re \
-			test_set \
-			test_slice \
-			test_struct \
-			test_threading \
-			test_time \
-			test_traceback \
-			test_unicode \
-		' \
-	&& make install \
-	&& rm -rf /usr/src/python \
-	\
-	&& find /usr/local -depth \
-		\( \
-			\( -type d -a \( -name test -o -name tests -o -name idle_test \) \) \
-			-o \( -type f -a \( -name '*.pyc' -o -name '*.pyo' -o -name '*.a' \) \) \
-			-o \( -type f -a -name 'wininst-*.exe' \) \
-		\) -exec rm -rf '{}' + \
-	\
-	&& find /usr/local -type f -executable -not \( -name '*tkinter*' \) -exec scanelf --needed --nobanner --format '%n#p' '{}' ';' \
-		| tr ',' '\n' \
-		| sort -u \
-		| awk 'system("[ -e /usr/local/lib/" $1 " ]") == 0 { next } { print "so:" $1 }' \
-		| xargs -rt apk add --no-cache --virtual .python-rundeps \
-	&& apk del --no-network .build-deps \
-	\
-	&& python3 --version
-
-# make some useful symlinks that are expected to exist
-RUN cd /usr/local/bin \
-	&& ln -s idle3 idle \
-	&& ln -s pydoc3 pydoc \
-	&& ln -s python3 python \
-	&& ln -s python3-config python-config
-
-# if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
-ENV PYTHON_PIP_VERSION 20.2.3
-# https://github.com/pypa/get-pip
-ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/fa7dc83944936bf09a0e4cb5d5ec852c0d256599/get-pip.py
-ENV PYTHON_GET_PIP_SHA256 6e0bb0a2c2533361d7f297ed547237caf1b7507f197835974c0dd7eba998c53c
-
-RUN set -ex; \
-	\
-	wget -O get-pip.py "$PYTHON_GET_PIP_URL"; \
-	echo "$PYTHON_GET_PIP_SHA256 *get-pip.py" | sha256sum -c -; \
-	\
-	python get-pip.py \
-		--disable-pip-version-check \
-		--no-cache-dir \
-		"pip==$PYTHON_PIP_VERSION" \
-	; \
-	pip --version; \
-	\
-	find /usr/local -depth \
-		\( \
-			\( -type d -a \( -name test -o -name tests -o -name idle_test \) \) \
-			-o \
-			\( -type f -a \( -name '*.pyc' -o -name '*.pyo' \) \) \
-		\) -exec rm -rf '{}' +; \
-	rm -f get-pip.py
-
-CMD ["python3"]
diff --git a/3.7/alpine3.12/Dockerfile b/3.7/alpine3.17/Dockerfile
similarity index 93%
rename from 3.7/alpine3.12/Dockerfile
rename to 3.7/alpine3.17/Dockerfile
index fcd81e039..9f0869360 100644
--- a/3.7/alpine3.12/Dockerfile
+++ b/3.7/alpine3.17/Dockerfile
@@ -4,7 +4,7 @@
 # PLEASE DO NOT EDIT IT DIRECTLY.
 #
 
-FROM alpine:3.12
+FROM alpine:3.17
 
 # ensure local python is preferred over distribution python
 ENV PATH /usr/local/bin:$PATH
@@ -29,7 +29,7 @@ RUN set -ex \
 	&& wget -O python.tar.xz "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz" \
 	&& wget -O python.tar.xz.asc "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz.asc" \
 	&& export GNUPGHOME="$(mktemp -d)" \
-	&& gpg --batch --keyserver ha.pool.sks-keyservers.net --recv-keys "$GPG_KEY" \
+	&& gpg --batch --keyserver hkps://keys.openpgp.org --recv-keys "$GPG_KEY" \
 	&& gpg --batch --verify python.tar.xz.asc python.tar.xz \
 	&& { command -v gpgconf > /dev/null && gpgconf --kill all || :; } \
 	&& rm -rf "$GNUPGHOME" python.tar.xz.asc \
@@ -145,10 +145,10 @@ RUN cd /usr/local/bin \
 	&& ln -s python3-config python-config
 
 # if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
-ENV PYTHON_PIP_VERSION 20.2.3
+ENV PYTHON_PIP_VERSION 22.3.1
 # https://github.com/pypa/get-pip
-ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/fa7dc83944936bf09a0e4cb5d5ec852c0d256599/get-pip.py
-ENV PYTHON_GET_PIP_SHA256 6e0bb0a2c2533361d7f297ed547237caf1b7507f197835974c0dd7eba998c53c
+ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/66030fa03382b4914d4c4d0896961a0bdeeeb274/public/get-pip.py
+ENV PYTHON_GET_PIP_SHA256 1e501cf004eac1b7eb1f97266d28f995ae835d30250bec7f8850562703067dc6
 
 RUN set -ex; \
 	\
diff --git a/3.6/buster/Dockerfile b/3.7/bionic/Dockerfile
similarity index 82%
rename from 3.6/buster/Dockerfile
rename to 3.7/bionic/Dockerfile
index 9db9a7d94..215250d4b 100644
--- a/3.6/buster/Dockerfile
+++ b/3.7/bionic/Dockerfile
@@ -4,7 +4,7 @@
 # PLEASE DO NOT EDIT IT DIRECTLY.
 #
 
-FROM buildpack-deps:buster
+FROM vaporio/buildpack-deps:bionic
 
 # ensure local python is preferred over distribution python
 ENV PATH /usr/local/bin:$PATH
@@ -12,22 +12,32 @@ ENV PATH /usr/local/bin:$PATH
 # http://bugs.python.org/issue19846
 # > At the moment, setting "LANG=C" on a Linux system *fundamentally breaks Python 3*, and that's not OK.
 ENV LANG C.UTF-8
+ENV DEBIAN_FRONTEND noninteractive
 
 # extra dependencies (over what buildpack-deps already includes)
-RUN apt-get update && apt-get install -y --no-install-recommends \
+RUN apt-get update; \
+    apt-get install -y --no-install-recommends \
 		libbluetooth-dev \
 		tk-dev \
+		uuid-dev \
 	&& rm -rf /var/lib/apt/lists/*
 
 ENV GPG_KEY 0D96DF4D4110E5C43FBFB17F2D347EA6AA65421D
-ENV PYTHON_VERSION 3.6.12
+ENV PYTHON_VERSION 3.7.9
 
 RUN set -ex \
 	\
 	&& wget -O python.tar.xz "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz" \
 	&& wget -O python.tar.xz.asc "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz.asc" \
 	&& export GNUPGHOME="$(mktemp -d)" \
-	&& gpg --batch --keyserver ha.pool.sks-keyservers.net --recv-keys "$GPG_KEY" \
+	&& for server in $(shuf -e \
+	        ha.pool.sks-keyservers.net \
+	        hkp://p80.pool.sks-keyservers.net:80 \
+	        keyserver.ubuntu.com \
+	        hkp://keyserver.ubuntu.com:80 \
+	        pgp.mit.edu) ; do \
+	    gpg --batch --keyserver "$server" --recv-keys "$GPG_KEY" && break || : ; \
+	    done \
 	&& gpg --batch --verify python.tar.xz.asc python.tar.xz \
 	&& { command -v gpgconf > /dev/null && gpgconf --kill all || :; } \
 	&& rm -rf "$GNUPGHOME" python.tar.xz.asc \
@@ -105,10 +115,10 @@ RUN cd /usr/local/bin \
 	&& ln -s python3-config python-config
 
 # if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
-ENV PYTHON_PIP_VERSION 20.2.3
+ENV PYTHON_PIP_VERSION 22.3.1
 # https://github.com/pypa/get-pip
-ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/fa7dc83944936bf09a0e4cb5d5ec852c0d256599/get-pip.py
-ENV PYTHON_GET_PIP_SHA256 6e0bb0a2c2533361d7f297ed547237caf1b7507f197835974c0dd7eba998c53c
+ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/66030fa03382b4914d4c4d0896961a0bdeeeb274/public/get-pip.py
+ENV PYTHON_GET_PIP_SHA256 1e501cf004eac1b7eb1f97266d28f995ae835d30250bec7f8850562703067dc6
 
 RUN set -ex; \
 	\
diff --git a/3.6/buster/slim/Dockerfile b/3.7/bionic/lite/Dockerfile
similarity index 86%
rename from 3.6/buster/slim/Dockerfile
rename to 3.7/bionic/lite/Dockerfile
index c65e87814..42532c144 100644
--- a/3.6/buster/slim/Dockerfile
+++ b/3.7/bionic/lite/Dockerfile
@@ -4,7 +4,7 @@
 # PLEASE DO NOT EDIT IT DIRECTLY.
 #
 
-FROM debian:buster-slim
+FROM vaporio/foundation:bionic
 
 # ensure local python is preferred over distribution python
 ENV PATH /usr/local/bin:$PATH
@@ -12,15 +12,17 @@ ENV PATH /usr/local/bin:$PATH
 # http://bugs.python.org/issue19846
 # > At the moment, setting "LANG=C" on a Linux system *fundamentally breaks Python 3*, and that's not OK.
 ENV LANG C.UTF-8
+ENV DEBIAN_FRONTEND noninteractive
 
 # runtime dependencies
-RUN apt-get update && apt-get install -y --no-install-recommends \
+RUN apt-get update; \
+    apt-get install -y --no-install-recommends \
 		ca-certificates \
 		netbase \
 	&& rm -rf /var/lib/apt/lists/*
 
 ENV GPG_KEY 0D96DF4D4110E5C43FBFB17F2D347EA6AA65421D
-ENV PYTHON_VERSION 3.6.12
+ENV PYTHON_VERSION 3.7.9
 
 RUN set -ex \
 	\
@@ -41,6 +43,7 @@ RUN set -ex \
 		libssl-dev \
 		make \
 		tk-dev \
+		uuid-dev \
 		wget \
 		xz-utils \
 		zlib1g-dev \
@@ -50,7 +53,14 @@ RUN set -ex \
 	&& wget -O python.tar.xz "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz" \
 	&& wget -O python.tar.xz.asc "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz.asc" \
 	&& export GNUPGHOME="$(mktemp -d)" \
-	&& gpg --batch --keyserver ha.pool.sks-keyservers.net --recv-keys "$GPG_KEY" \
+	&& for server in $(shuf -e \
+	        ha.pool.sks-keyservers.net \
+	        hkp://p80.pool.sks-keyservers.net:80 \
+	        keyserver.ubuntu.com \
+	        hkp://keyserver.ubuntu.com:80 \
+	        pgp.mit.edu) ; do \
+	    gpg --batch --keyserver "$server" --recv-keys "$GPG_KEY" && break || : ; \
+	    done \
 	&& gpg --batch --verify python.tar.xz.asc python.tar.xz \
 	&& { command -v gpgconf > /dev/null && gpgconf --kill all || :; } \
 	&& rm -rf "$GNUPGHOME" python.tar.xz.asc \
@@ -141,10 +151,10 @@ RUN cd /usr/local/bin \
 	&& ln -s python3-config python-config
 
 # if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
-ENV PYTHON_PIP_VERSION 20.2.3
+ENV PYTHON_PIP_VERSION 22.3.1
 # https://github.com/pypa/get-pip
-ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/fa7dc83944936bf09a0e4cb5d5ec852c0d256599/get-pip.py
-ENV PYTHON_GET_PIP_SHA256 6e0bb0a2c2533361d7f297ed547237caf1b7507f197835974c0dd7eba998c53c
+ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/66030fa03382b4914d4c4d0896961a0bdeeeb274/public/get-pip.py
+ENV PYTHON_GET_PIP_SHA256 1e501cf004eac1b7eb1f97266d28f995ae835d30250bec7f8850562703067dc6
 
 RUN set -ex; \
 	\
diff --git a/3.7/buster/Dockerfile b/3.7/buster/Dockerfile
index be1a8ffbc..c585b4a68 100644
--- a/3.7/buster/Dockerfile
+++ b/3.7/buster/Dockerfile
@@ -28,7 +28,7 @@ RUN set -ex \
 	&& wget -O python.tar.xz "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz" \
 	&& wget -O python.tar.xz.asc "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz.asc" \
 	&& export GNUPGHOME="$(mktemp -d)" \
-	&& gpg --batch --keyserver ha.pool.sks-keyservers.net --recv-keys "$GPG_KEY" \
+	&& gpg --batch --keyserver hkps://keys.openpgp.org --recv-keys "$GPG_KEY" \
 	&& gpg --batch --verify python.tar.xz.asc python.tar.xz \
 	&& { command -v gpgconf > /dev/null && gpgconf --kill all || :; } \
 	&& rm -rf "$GNUPGHOME" python.tar.xz.asc \
@@ -106,10 +106,10 @@ RUN cd /usr/local/bin \
 	&& ln -s python3-config python-config
 
 # if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
-ENV PYTHON_PIP_VERSION 20.2.3
+ENV PYTHON_PIP_VERSION 22.3.1
 # https://github.com/pypa/get-pip
-ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/fa7dc83944936bf09a0e4cb5d5ec852c0d256599/get-pip.py
-ENV PYTHON_GET_PIP_SHA256 6e0bb0a2c2533361d7f297ed547237caf1b7507f197835974c0dd7eba998c53c
+ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/66030fa03382b4914d4c4d0896961a0bdeeeb274/public/get-pip.py
+ENV PYTHON_GET_PIP_SHA256 1e501cf004eac1b7eb1f97266d28f995ae835d30250bec7f8850562703067dc6
 
 RUN set -ex; \
 	\
diff --git a/3.7/buster/slim/Dockerfile b/3.7/buster/slim/Dockerfile
index 33c29de86..dba7f9a05 100644
--- a/3.7/buster/slim/Dockerfile
+++ b/3.7/buster/slim/Dockerfile
@@ -51,7 +51,7 @@ RUN set -ex \
 	&& wget -O python.tar.xz "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz" \
 	&& wget -O python.tar.xz.asc "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz.asc" \
 	&& export GNUPGHOME="$(mktemp -d)" \
-	&& gpg --batch --keyserver ha.pool.sks-keyservers.net --recv-keys "$GPG_KEY" \
+	&& gpg --batch --keyserver hkps://keys.openpgp.org --recv-keys "$GPG_KEY" \
 	&& gpg --batch --verify python.tar.xz.asc python.tar.xz \
 	&& { command -v gpgconf > /dev/null && gpgconf --kill all || :; } \
 	&& rm -rf "$GNUPGHOME" python.tar.xz.asc \
@@ -142,10 +142,10 @@ RUN cd /usr/local/bin \
 	&& ln -s python3-config python-config
 
 # if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
-ENV PYTHON_PIP_VERSION 20.2.3
+ENV PYTHON_PIP_VERSION 22.3.1
 # https://github.com/pypa/get-pip
-ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/fa7dc83944936bf09a0e4cb5d5ec852c0d256599/get-pip.py
-ENV PYTHON_GET_PIP_SHA256 6e0bb0a2c2533361d7f297ed547237caf1b7507f197835974c0dd7eba998c53c
+ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/66030fa03382b4914d4c4d0896961a0bdeeeb274/public/get-pip.py
+ENV PYTHON_GET_PIP_SHA256 1e501cf004eac1b7eb1f97266d28f995ae835d30250bec7f8850562703067dc6
 
 RUN set -ex; \
 	\
diff --git a/3.7/windows/windowsservercore-1809/Dockerfile b/3.7/windows/windowsservercore-1809/Dockerfile
index 38a558010..8176453a3 100644
--- a/3.7/windows/windowsservercore-1809/Dockerfile
+++ b/3.7/windows/windowsservercore-1809/Dockerfile
@@ -42,10 +42,10 @@ RUN $url = ('https://www.python.org/ftp/python/{0}/python-{1}-amd64.exe' -f $env
 	Write-Host 'Complete.'
 
 # if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
-ENV PYTHON_PIP_VERSION 20.2.3
+ENV PYTHON_PIP_VERSION 22.3.1
 # https://github.com/pypa/get-pip
-ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/fa7dc83944936bf09a0e4cb5d5ec852c0d256599/get-pip.py
-ENV PYTHON_GET_PIP_SHA256 6e0bb0a2c2533361d7f297ed547237caf1b7507f197835974c0dd7eba998c53c
+ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/66030fa03382b4914d4c4d0896961a0bdeeeb274/public/get-pip.py
+ENV PYTHON_GET_PIP_SHA256 1e501cf004eac1b7eb1f97266d28f995ae835d30250bec7f8850562703067dc6
 
 RUN Write-Host ('Downloading get-pip.py ({0}) ...' -f $env:PYTHON_GET_PIP_URL); \
 	[Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12; \
diff --git a/3.7/windows/windowsservercore-ltsc2016/Dockerfile b/3.7/windows/windowsservercore-ltsc2016/Dockerfile
index 4da2b22c7..7d2a2c996 100644
--- a/3.7/windows/windowsservercore-ltsc2016/Dockerfile
+++ b/3.7/windows/windowsservercore-ltsc2016/Dockerfile
@@ -42,10 +42,10 @@ RUN $url = ('https://www.python.org/ftp/python/{0}/python-{1}-amd64.exe' -f $env
 	Write-Host 'Complete.'
 
 # if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
-ENV PYTHON_PIP_VERSION 20.2.3
+ENV PYTHON_PIP_VERSION 22.3.1
 # https://github.com/pypa/get-pip
-ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/fa7dc83944936bf09a0e4cb5d5ec852c0d256599/get-pip.py
-ENV PYTHON_GET_PIP_SHA256 6e0bb0a2c2533361d7f297ed547237caf1b7507f197835974c0dd7eba998c53c
+ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/66030fa03382b4914d4c4d0896961a0bdeeeb274/public/get-pip.py
+ENV PYTHON_GET_PIP_SHA256 1e501cf004eac1b7eb1f97266d28f995ae835d30250bec7f8850562703067dc6
 
 RUN Write-Host ('Downloading get-pip.py ({0}) ...' -f $env:PYTHON_GET_PIP_URL); \
 	[Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12; \
diff --git a/3.8/alpine3.12/Dockerfile b/3.8/alpine3.17/Dockerfile
similarity index 91%
rename from 3.8/alpine3.12/Dockerfile
rename to 3.8/alpine3.17/Dockerfile
index 4771c5da6..d9de1483e 100644
--- a/3.8/alpine3.12/Dockerfile
+++ b/3.8/alpine3.17/Dockerfile
@@ -4,7 +4,7 @@
 # PLEASE DO NOT EDIT IT DIRECTLY.
 #
 
-FROM alpine:3.12
+FROM alpine:3.17
 
 # ensure local python is preferred over distribution python
 ENV PATH /usr/local/bin:$PATH
@@ -18,7 +18,7 @@ ENV LANG C.UTF-8
 RUN apk add --no-cache ca-certificates
 
 ENV GPG_KEY E3FF2839C048B25C084DEBE9B26995E310250568
-ENV PYTHON_VERSION 3.8.6
+ENV PYTHON_VERSION 3.8.10
 
 RUN set -ex \
 	&& apk add --no-cache --virtual .fetch-deps \
@@ -29,7 +29,7 @@ RUN set -ex \
 	&& wget -O python.tar.xz "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz" \
 	&& wget -O python.tar.xz.asc "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz.asc" \
 	&& export GNUPGHOME="$(mktemp -d)" \
-	&& gpg --batch --keyserver ha.pool.sks-keyservers.net --recv-keys "$GPG_KEY" \
+	&& gpg --batch --keyserver hkps://keys.openpgp.org --recv-keys "$GPG_KEY" \
 	&& gpg --batch --verify python.tar.xz.asc python.tar.xz \
 	&& { command -v gpgconf > /dev/null && gpgconf --kill all || :; } \
 	&& rm -rf "$GNUPGHOME" python.tar.xz.asc \
@@ -109,10 +109,10 @@ RUN cd /usr/local/bin \
 	&& ln -s python3-config python-config
 
 # if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
-ENV PYTHON_PIP_VERSION 20.2.3
+ENV PYTHON_PIP_VERSION 22.3.1
 # https://github.com/pypa/get-pip
-ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/fa7dc83944936bf09a0e4cb5d5ec852c0d256599/get-pip.py
-ENV PYTHON_GET_PIP_SHA256 6e0bb0a2c2533361d7f297ed547237caf1b7507f197835974c0dd7eba998c53c
+ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/66030fa03382b4914d4c4d0896961a0bdeeeb274/public/get-pip.py
+ENV PYTHON_GET_PIP_SHA256 1e501cf004eac1b7eb1f97266d28f995ae835d30250bec7f8850562703067dc6
 
 RUN set -ex; \
 	\
diff --git a/3.6/stretch/Dockerfile b/3.8/bionic/Dockerfile
similarity index 67%
rename from 3.6/stretch/Dockerfile
rename to 3.8/bionic/Dockerfile
index 91bbdaf6a..8fc314216 100644
--- a/3.6/stretch/Dockerfile
+++ b/3.8/bionic/Dockerfile
@@ -4,7 +4,7 @@
 # PLEASE DO NOT EDIT IT DIRECTLY.
 #
 
-FROM buildpack-deps:stretch
+FROM vaporio/buildpack-deps:bionic
 
 # ensure local python is preferred over distribution python
 ENV PATH /usr/local/bin:$PATH
@@ -12,22 +12,32 @@ ENV PATH /usr/local/bin:$PATH
 # http://bugs.python.org/issue19846
 # > At the moment, setting "LANG=C" on a Linux system *fundamentally breaks Python 3*, and that's not OK.
 ENV LANG C.UTF-8
+ENV DEBIAN_FRONTEND noninteractive
 
 # extra dependencies (over what buildpack-deps already includes)
-RUN apt-get update && apt-get install -y --no-install-recommends \
+RUN apt-get update; \
+    apt-get install -y --no-install-recommends \
 		libbluetooth-dev \
 		tk-dev \
+		uuid-dev \
 	&& rm -rf /var/lib/apt/lists/*
 
-ENV GPG_KEY 0D96DF4D4110E5C43FBFB17F2D347EA6AA65421D
-ENV PYTHON_VERSION 3.6.12
+ENV GPG_KEY E3FF2839C048B25C084DEBE9B26995E310250568
+ENV PYTHON_VERSION 3.8.10
 
 RUN set -ex \
 	\
 	&& wget -O python.tar.xz "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz" \
 	&& wget -O python.tar.xz.asc "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz.asc" \
 	&& export GNUPGHOME="$(mktemp -d)" \
-	&& gpg --batch --keyserver ha.pool.sks-keyservers.net --recv-keys "$GPG_KEY" \
+	&& for server in $(shuf -e \
+	        ha.pool.sks-keyservers.net \
+	        hkp://p80.pool.sks-keyservers.net:80 \
+	        keyserver.ubuntu.com \
+	        hkp://keyserver.ubuntu.com:80 \
+	        pgp.mit.edu) ; do \
+	    gpg --batch --keyserver "$server" --recv-keys "$GPG_KEY" && break || : ; \
+	    done \
 	&& gpg --batch --verify python.tar.xz.asc python.tar.xz \
 	&& { command -v gpgconf > /dev/null && gpgconf --kill all || :; } \
 	&& rm -rf "$GNUPGHOME" python.tar.xz.asc \
@@ -47,42 +57,6 @@ RUN set -ex \
 		--with-system-ffi \
 		--without-ensurepip \
 	&& make -j "$(nproc)" \
-# setting PROFILE_TASK makes "--enable-optimizations" reasonable: https://bugs.python.org/issue36044 / https://github.com/docker-library/python/issues/160#issuecomment-509426916
-		PROFILE_TASK='-m test.regrtest --pgo \
-			test_array \
-			test_base64 \
-			test_binascii \
-			test_binhex \
-			test_binop \
-			test_bytes \
-			test_c_locale_coercion \
-			test_class \
-			test_cmath \
-			test_codecs \
-			test_compile \
-			test_complex \
-			test_csv \
-			test_decimal \
-			test_dict \
-			test_float \
-			test_fstring \
-			test_hashlib \
-			test_io \
-			test_iter \
-			test_json \
-			test_long \
-			test_math \
-			test_memoryview \
-			test_pickle \
-			test_re \
-			test_set \
-			test_slice \
-			test_struct \
-			test_threading \
-			test_time \
-			test_traceback \
-			test_unicode \
-		' \
 	&& make install \
 	&& rm -rf /usr/src/python \
 	\
@@ -105,10 +79,10 @@ RUN cd /usr/local/bin \
 	&& ln -s python3-config python-config
 
 # if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
-ENV PYTHON_PIP_VERSION 20.2.3
+ENV PYTHON_PIP_VERSION 22.3.1
 # https://github.com/pypa/get-pip
-ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/fa7dc83944936bf09a0e4cb5d5ec852c0d256599/get-pip.py
-ENV PYTHON_GET_PIP_SHA256 6e0bb0a2c2533361d7f297ed547237caf1b7507f197835974c0dd7eba998c53c
+ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/66030fa03382b4914d4c4d0896961a0bdeeeb274/public/get-pip.py
+ENV PYTHON_GET_PIP_SHA256 1e501cf004eac1b7eb1f97266d28f995ae835d30250bec7f8850562703067dc6
 
 RUN set -ex; \
 	\
diff --git a/3.6/stretch/slim/Dockerfile b/3.8/bionic/lite/Dockerfile
similarity index 75%
rename from 3.6/stretch/slim/Dockerfile
rename to 3.8/bionic/lite/Dockerfile
index e9db00100..3355b3e4b 100644
--- a/3.6/stretch/slim/Dockerfile
+++ b/3.8/bionic/lite/Dockerfile
@@ -4,7 +4,7 @@
 # PLEASE DO NOT EDIT IT DIRECTLY.
 #
 
-FROM debian:stretch-slim
+FROM vaporio/foundation:bionic
 
 # ensure local python is preferred over distribution python
 ENV PATH /usr/local/bin:$PATH
@@ -12,15 +12,17 @@ ENV PATH /usr/local/bin:$PATH
 # http://bugs.python.org/issue19846
 # > At the moment, setting "LANG=C" on a Linux system *fundamentally breaks Python 3*, and that's not OK.
 ENV LANG C.UTF-8
+ENV DEBIAN_FRONTEND noninteractive
 
 # runtime dependencies
-RUN apt-get update && apt-get install -y --no-install-recommends \
+RUN apt-get update; \
+    apt-get install -y --no-install-recommends \
 		ca-certificates \
 		netbase \
 	&& rm -rf /var/lib/apt/lists/*
 
-ENV GPG_KEY 0D96DF4D4110E5C43FBFB17F2D347EA6AA65421D
-ENV PYTHON_VERSION 3.6.12
+ENV GPG_KEY E3FF2839C048B25C084DEBE9B26995E310250568
+ENV PYTHON_VERSION 3.8.10
 
 RUN set -ex \
 	\
@@ -41,6 +43,7 @@ RUN set -ex \
 		libssl-dev \
 		make \
 		tk-dev \
+		uuid-dev \
 		wget \
 		xz-utils \
 		zlib1g-dev \
@@ -50,7 +53,14 @@ RUN set -ex \
 	&& wget -O python.tar.xz "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz" \
 	&& wget -O python.tar.xz.asc "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz.asc" \
 	&& export GNUPGHOME="$(mktemp -d)" \
-	&& gpg --batch --keyserver ha.pool.sks-keyservers.net --recv-keys "$GPG_KEY" \
+	&& for server in $(shuf -e \
+	        ha.pool.sks-keyservers.net \
+	        hkp://p80.pool.sks-keyservers.net:80 \
+	        keyserver.ubuntu.com \
+	        hkp://keyserver.ubuntu.com:80 \
+	        pgp.mit.edu) ; do \
+	    gpg --batch --keyserver "$server" --recv-keys "$GPG_KEY" && break || : ; \
+	    done \
 	&& gpg --batch --verify python.tar.xz.asc python.tar.xz \
 	&& { command -v gpgconf > /dev/null && gpgconf --kill all || :; } \
 	&& rm -rf "$GNUPGHOME" python.tar.xz.asc \
@@ -71,42 +81,6 @@ RUN set -ex \
 		--without-ensurepip \
 	&& make -j "$(nproc)" \
 		LDFLAGS="-Wl,--strip-all" \
-# setting PROFILE_TASK makes "--enable-optimizations" reasonable: https://bugs.python.org/issue36044 / https://github.com/docker-library/python/issues/160#issuecomment-509426916
-		PROFILE_TASK='-m test.regrtest --pgo \
-			test_array \
-			test_base64 \
-			test_binascii \
-			test_binhex \
-			test_binop \
-			test_bytes \
-			test_c_locale_coercion \
-			test_class \
-			test_cmath \
-			test_codecs \
-			test_compile \
-			test_complex \
-			test_csv \
-			test_decimal \
-			test_dict \
-			test_float \
-			test_fstring \
-			test_hashlib \
-			test_io \
-			test_iter \
-			test_json \
-			test_long \
-			test_math \
-			test_memoryview \
-			test_pickle \
-			test_re \
-			test_set \
-			test_slice \
-			test_struct \
-			test_threading \
-			test_time \
-			test_traceback \
-			test_unicode \
-		' \
 	&& make install \
 	&& rm -rf /usr/src/python \
 	\
@@ -141,10 +115,10 @@ RUN cd /usr/local/bin \
 	&& ln -s python3-config python-config
 
 # if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
-ENV PYTHON_PIP_VERSION 20.2.3
+ENV PYTHON_PIP_VERSION 22.3.1
 # https://github.com/pypa/get-pip
-ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/fa7dc83944936bf09a0e4cb5d5ec852c0d256599/get-pip.py
-ENV PYTHON_GET_PIP_SHA256 6e0bb0a2c2533361d7f297ed547237caf1b7507f197835974c0dd7eba998c53c
+ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/66030fa03382b4914d4c4d0896961a0bdeeeb274/public/get-pip.py
+ENV PYTHON_GET_PIP_SHA256 1e501cf004eac1b7eb1f97266d28f995ae835d30250bec7f8850562703067dc6
 
 RUN set -ex; \
 	\
diff --git a/3.8/buster/Dockerfile b/3.8/buster/Dockerfile
index ea85676a5..76eb0b34e 100644
--- a/3.8/buster/Dockerfile
+++ b/3.8/buster/Dockerfile
@@ -21,14 +21,14 @@ RUN apt-get update && apt-get install -y --no-install-recommends \
 	&& rm -rf /var/lib/apt/lists/*
 
 ENV GPG_KEY E3FF2839C048B25C084DEBE9B26995E310250568
-ENV PYTHON_VERSION 3.8.6
+ENV PYTHON_VERSION 3.8.10
 
 RUN set -ex \
 	\
 	&& wget -O python.tar.xz "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz" \
 	&& wget -O python.tar.xz.asc "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz.asc" \
 	&& export GNUPGHOME="$(mktemp -d)" \
-	&& gpg --batch --keyserver ha.pool.sks-keyservers.net --recv-keys "$GPG_KEY" \
+	&& gpg --batch --keyserver hkps://keys.openpgp.org --recv-keys "$GPG_KEY" \
 	&& gpg --batch --verify python.tar.xz.asc python.tar.xz \
 	&& { command -v gpgconf > /dev/null && gpgconf --kill all || :; } \
 	&& rm -rf "$GNUPGHOME" python.tar.xz.asc \
@@ -70,10 +70,10 @@ RUN cd /usr/local/bin \
 	&& ln -s python3-config python-config
 
 # if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
-ENV PYTHON_PIP_VERSION 20.2.3
+ENV PYTHON_PIP_VERSION 22.3.1
 # https://github.com/pypa/get-pip
-ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/fa7dc83944936bf09a0e4cb5d5ec852c0d256599/get-pip.py
-ENV PYTHON_GET_PIP_SHA256 6e0bb0a2c2533361d7f297ed547237caf1b7507f197835974c0dd7eba998c53c
+ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/66030fa03382b4914d4c4d0896961a0bdeeeb274/public/get-pip.py
+ENV PYTHON_GET_PIP_SHA256 1e501cf004eac1b7eb1f97266d28f995ae835d30250bec7f8850562703067dc6
 
 RUN set -ex; \
 	\
diff --git a/3.8/buster/slim/Dockerfile b/3.8/buster/slim/Dockerfile
index 74fee143e..a33d6cc38 100644
--- a/3.8/buster/slim/Dockerfile
+++ b/3.8/buster/slim/Dockerfile
@@ -20,7 +20,7 @@ RUN apt-get update && apt-get install -y --no-install-recommends \
 	&& rm -rf /var/lib/apt/lists/*
 
 ENV GPG_KEY E3FF2839C048B25C084DEBE9B26995E310250568
-ENV PYTHON_VERSION 3.8.6
+ENV PYTHON_VERSION 3.8.10
 
 RUN set -ex \
 	\
@@ -51,7 +51,7 @@ RUN set -ex \
 	&& wget -O python.tar.xz "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz" \
 	&& wget -O python.tar.xz.asc "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz.asc" \
 	&& export GNUPGHOME="$(mktemp -d)" \
-	&& gpg --batch --keyserver ha.pool.sks-keyservers.net --recv-keys "$GPG_KEY" \
+	&& gpg --batch --keyserver hkps://keys.openpgp.org --recv-keys "$GPG_KEY" \
 	&& gpg --batch --verify python.tar.xz.asc python.tar.xz \
 	&& { command -v gpgconf > /dev/null && gpgconf --kill all || :; } \
 	&& rm -rf "$GNUPGHOME" python.tar.xz.asc \
@@ -106,10 +106,10 @@ RUN cd /usr/local/bin \
 	&& ln -s python3-config python-config
 
 # if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
-ENV PYTHON_PIP_VERSION 20.2.3
+ENV PYTHON_PIP_VERSION 22.3.1
 # https://github.com/pypa/get-pip
-ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/fa7dc83944936bf09a0e4cb5d5ec852c0d256599/get-pip.py
-ENV PYTHON_GET_PIP_SHA256 6e0bb0a2c2533361d7f297ed547237caf1b7507f197835974c0dd7eba998c53c
+ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/66030fa03382b4914d4c4d0896961a0bdeeeb274/public/get-pip.py
+ENV PYTHON_GET_PIP_SHA256 1e501cf004eac1b7eb1f97266d28f995ae835d30250bec7f8850562703067dc6
 
 RUN set -ex; \
 	\
diff --git a/3.8/windows/windowsservercore-1809/Dockerfile b/3.8/windows/windowsservercore-1809/Dockerfile
index 9c2f6d4cb..a4167beb4 100644
--- a/3.8/windows/windowsservercore-1809/Dockerfile
+++ b/3.8/windows/windowsservercore-1809/Dockerfile
@@ -8,8 +8,8 @@ FROM mcr.microsoft.com/windows/servercore:1809
 
 SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
 
-ENV PYTHON_VERSION 3.8.6
-ENV PYTHON_RELEASE 3.8.6
+ENV PYTHON_VERSION 3.8.10
+ENV PYTHON_RELEASE 3.8.10
 
 RUN $url = ('https://www.python.org/ftp/python/{0}/python-{1}-amd64.exe' -f $env:PYTHON_RELEASE, $env:PYTHON_VERSION); \
 	Write-Host ('Downloading {0} ...' -f $url); \
@@ -42,10 +42,10 @@ RUN $url = ('https://www.python.org/ftp/python/{0}/python-{1}-amd64.exe' -f $env
 	Write-Host 'Complete.'
 
 # if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
-ENV PYTHON_PIP_VERSION 20.2.3
+ENV PYTHON_PIP_VERSION 22.3.1
 # https://github.com/pypa/get-pip
-ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/fa7dc83944936bf09a0e4cb5d5ec852c0d256599/get-pip.py
-ENV PYTHON_GET_PIP_SHA256 6e0bb0a2c2533361d7f297ed547237caf1b7507f197835974c0dd7eba998c53c
+ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/66030fa03382b4914d4c4d0896961a0bdeeeb274/public/get-pip.py
+ENV PYTHON_GET_PIP_SHA256 1e501cf004eac1b7eb1f97266d28f995ae835d30250bec7f8850562703067dc6
 
 RUN Write-Host ('Downloading get-pip.py ({0}) ...' -f $env:PYTHON_GET_PIP_URL); \
 	[Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12; \
diff --git a/3.8/windows/windowsservercore-ltsc2016/Dockerfile b/3.8/windows/windowsservercore-ltsc2016/Dockerfile
index 30f335a31..beeb9201c 100644
--- a/3.8/windows/windowsservercore-ltsc2016/Dockerfile
+++ b/3.8/windows/windowsservercore-ltsc2016/Dockerfile
@@ -8,8 +8,8 @@ FROM mcr.microsoft.com/windows/servercore:ltsc2016
 
 SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
 
-ENV PYTHON_VERSION 3.8.6
-ENV PYTHON_RELEASE 3.8.6
+ENV PYTHON_VERSION 3.8.10
+ENV PYTHON_RELEASE 3.8.10
 
 RUN $url = ('https://www.python.org/ftp/python/{0}/python-{1}-amd64.exe' -f $env:PYTHON_RELEASE, $env:PYTHON_VERSION); \
 	Write-Host ('Downloading {0} ...' -f $url); \
@@ -42,10 +42,10 @@ RUN $url = ('https://www.python.org/ftp/python/{0}/python-{1}-amd64.exe' -f $env
 	Write-Host 'Complete.'
 
 # if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
-ENV PYTHON_PIP_VERSION 20.2.3
+ENV PYTHON_PIP_VERSION 22.3.1
 # https://github.com/pypa/get-pip
-ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/fa7dc83944936bf09a0e4cb5d5ec852c0d256599/get-pip.py
-ENV PYTHON_GET_PIP_SHA256 6e0bb0a2c2533361d7f297ed547237caf1b7507f197835974c0dd7eba998c53c
+ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/66030fa03382b4914d4c4d0896961a0bdeeeb274/public/get-pip.py
+ENV PYTHON_GET_PIP_SHA256 1e501cf004eac1b7eb1f97266d28f995ae835d30250bec7f8850562703067dc6
 
 RUN Write-Host ('Downloading get-pip.py ({0}) ...' -f $env:PYTHON_GET_PIP_URL); \
 	[Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12; \
diff --git a/3.9/alpine3.12/Dockerfile b/3.9/alpine3.17/Dockerfile
similarity index 91%
rename from 3.9/alpine3.12/Dockerfile
rename to 3.9/alpine3.17/Dockerfile
index c810b8cfa..d71c83f79 100644
--- a/3.9/alpine3.12/Dockerfile
+++ b/3.9/alpine3.17/Dockerfile
@@ -4,7 +4,7 @@
 # PLEASE DO NOT EDIT IT DIRECTLY.
 #
 
-FROM alpine:3.12
+FROM alpine:3.17
 
 # ensure local python is preferred over distribution python
 ENV PATH /usr/local/bin:$PATH
@@ -18,7 +18,7 @@ ENV LANG C.UTF-8
 RUN apk add --no-cache ca-certificates
 
 ENV GPG_KEY E3FF2839C048B25C084DEBE9B26995E310250568
-ENV PYTHON_VERSION 3.9.0
+ENV PYTHON_VERSION 3.9.13
 
 RUN set -ex \
 	&& apk add --no-cache --virtual .fetch-deps \
@@ -29,7 +29,7 @@ RUN set -ex \
 	&& wget -O python.tar.xz "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz" \
 	&& wget -O python.tar.xz.asc "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz.asc" \
 	&& export GNUPGHOME="$(mktemp -d)" \
-	&& gpg --batch --keyserver ha.pool.sks-keyservers.net --recv-keys "$GPG_KEY" \
+	&& gpg --batch --keyserver hkps://keys.openpgp.org --recv-keys "$GPG_KEY" \
 	&& gpg --batch --verify python.tar.xz.asc python.tar.xz \
 	&& { command -v gpgconf > /dev/null && gpgconf --kill all || :; } \
 	&& rm -rf "$GNUPGHOME" python.tar.xz.asc \
@@ -108,10 +108,10 @@ RUN cd /usr/local/bin \
 	&& ln -s python3-config python-config
 
 # if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
-ENV PYTHON_PIP_VERSION 20.2.3
+ENV PYTHON_PIP_VERSION 22.3.1
 # https://github.com/pypa/get-pip
-ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/fa7dc83944936bf09a0e4cb5d5ec852c0d256599/get-pip.py
-ENV PYTHON_GET_PIP_SHA256 6e0bb0a2c2533361d7f297ed547237caf1b7507f197835974c0dd7eba998c53c
+ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/66030fa03382b4914d4c4d0896961a0bdeeeb274/public/get-pip.py
+ENV PYTHON_GET_PIP_SHA256 1e501cf004eac1b7eb1f97266d28f995ae835d30250bec7f8850562703067dc6
 
 RUN set -ex; \
 	\
diff --git a/3.9/bionic/Dockerfile b/3.9/bionic/Dockerfile
new file mode 100644
index 000000000..7e5a2dd02
--- /dev/null
+++ b/3.9/bionic/Dockerfile
@@ -0,0 +1,106 @@
+#
+# NOTE: THIS DOCKERFILE IS GENERATED VIA "update.sh"
+#
+# PLEASE DO NOT EDIT IT DIRECTLY.
+#
+
+FROM vaporio/buildpack-deps:bionic
+
+# ensure local python is preferred over distribution python
+ENV PATH /usr/local/bin:$PATH
+
+# http://bugs.python.org/issue19846
+# > At the moment, setting "LANG=C" on a Linux system *fundamentally breaks Python 3*, and that's not OK.
+ENV LANG C.UTF-8
+ENV DEBIAN_FRONTEND noninteractive
+
+# extra dependencies (over what buildpack-deps already includes)
+RUN apt-get update; \
+    apt-get install -y --no-install-recommends \
+		libbluetooth-dev \
+		tk-dev \
+		uuid-dev \
+	&& rm -rf /var/lib/apt/lists/*
+
+ENV GPG_KEY E3FF2839C048B25C084DEBE9B26995E310250568
+ENV PYTHON_VERSION 3.9.13
+
+RUN set -ex \
+	\
+	&& wget -O python.tar.xz "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz" \
+	&& wget -O python.tar.xz.asc "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz.asc" \
+	&& export GNUPGHOME="$(mktemp -d)" \
+	&& for server in $(shuf -e \
+	        ha.pool.sks-keyservers.net \
+	        hkp://p80.pool.sks-keyservers.net:80 \
+	        keyserver.ubuntu.com \
+	        hkp://keyserver.ubuntu.com:80 \
+	        pgp.mit.edu) ; do \
+	    gpg --batch --keyserver "$server" --recv-keys "$GPG_KEY" && break || : ; \
+	    done \
+	&& gpg --batch --verify python.tar.xz.asc python.tar.xz \
+	&& { command -v gpgconf > /dev/null && gpgconf --kill all || :; } \
+	&& rm -rf "$GNUPGHOME" python.tar.xz.asc \
+	&& mkdir -p /usr/src/python \
+	&& tar -xJC /usr/src/python --strip-components=1 -f python.tar.xz \
+	&& rm python.tar.xz \
+	\
+	&& cd /usr/src/python \
+	&& gnuArch="$(dpkg-architecture --query DEB_BUILD_GNU_TYPE)" \
+	&& ./configure \
+		--build="$gnuArch" \
+		--enable-loadable-sqlite-extensions \
+		--enable-optimizations \
+		--enable-option-checking=fatal \
+		--enable-shared \
+		--with-system-expat \
+		--with-system-ffi \
+		--without-ensurepip \
+	&& make -j "$(nproc)" \
+	&& make install \
+	&& rm -rf /usr/src/python \
+	\
+	&& find /usr/local -depth \
+		\( \
+			\( -type d -a \( -name test -o -name tests -o -name idle_test \) \) \
+			-o \( -type f -a \( -name '*.pyc' -o -name '*.pyo' -o -name '*.a' \) \) \
+		\) -exec rm -rf '{}' + \
+	\
+	&& ldconfig \
+	\
+	&& python3 --version
+
+# make some useful symlinks that are expected to exist
+RUN cd /usr/local/bin \
+	&& ln -s idle3 idle \
+	&& ln -s pydoc3 pydoc \
+	&& ln -s python3 python \
+	&& ln -s python3-config python-config
+
+# if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
+ENV PYTHON_PIP_VERSION 22.3.1
+# https://github.com/pypa/get-pip
+ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/66030fa03382b4914d4c4d0896961a0bdeeeb274/public/get-pip.py
+ENV PYTHON_GET_PIP_SHA256 1e501cf004eac1b7eb1f97266d28f995ae835d30250bec7f8850562703067dc6
+
+RUN set -ex; \
+	\
+	wget -O get-pip.py "$PYTHON_GET_PIP_URL"; \
+	echo "$PYTHON_GET_PIP_SHA256 *get-pip.py" | sha256sum --check --strict -; \
+	\
+	python get-pip.py \
+		--disable-pip-version-check \
+		--no-cache-dir \
+		"pip==$PYTHON_PIP_VERSION" \
+	; \
+	pip --version; \
+	\
+	find /usr/local -depth \
+		\( \
+			\( -type d -a \( -name test -o -name tests -o -name idle_test \) \) \
+			-o \
+			\( -type f -a \( -name '*.pyc' -o -name '*.pyo' \) \) \
+		\) -exec rm -rf '{}' +; \
+	rm -f get-pip.py
+
+CMD ["python3"]
diff --git a/3.9/bionic/lite/Dockerfile b/3.9/bionic/lite/Dockerfile
new file mode 100644
index 000000000..5bd78e82d
--- /dev/null
+++ b/3.9/bionic/lite/Dockerfile
@@ -0,0 +1,151 @@
+#
+# NOTE: THIS DOCKERFILE IS GENERATED VIA "update.sh"
+#
+# PLEASE DO NOT EDIT IT DIRECTLY.
+#
+
+FROM vaporio/foundation:bionic
+
+# ensure local python is preferred over distribution python
+ENV PATH /usr/local/bin:$PATH
+
+# http://bugs.python.org/issue19846
+# > At the moment, setting "LANG=C" on a Linux system *fundamentally breaks Python 3*, and that's not OK.
+ENV LANG C.UTF-8
+ENV DEBIAN_FRONTEND noninteractive
+
+# runtime dependencies
+RUN apt-get update; \
+    apt-get install -y --no-install-recommends \
+		ca-certificates \
+		netbase \
+	&& rm -rf /var/lib/apt/lists/*
+
+ENV GPG_KEY E3FF2839C048B25C084DEBE9B26995E310250568
+ENV PYTHON_VERSION 3.9.13
+
+RUN set -ex \
+	\
+	&& savedAptMark="$(apt-mark showmanual)" \
+	&& apt-get update && apt-get install -y --no-install-recommends \
+		dpkg-dev \
+		gcc \
+		libbluetooth-dev \
+		libbz2-dev \
+		libc6-dev \
+		libexpat1-dev \
+		libffi-dev \
+		libgdbm-dev \
+		liblzma-dev \
+		libncursesw5-dev \
+		libreadline-dev \
+		libsqlite3-dev \
+		libssl-dev \
+		make \
+		tk-dev \
+		uuid-dev \
+		wget \
+		xz-utils \
+		zlib1g-dev \
+# as of Stretch, "gpg" is no longer included by default
+		$(command -v gpg > /dev/null || echo 'gnupg dirmngr') \
+	\
+	&& wget -O python.tar.xz "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz" \
+	&& wget -O python.tar.xz.asc "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz.asc" \
+	&& export GNUPGHOME="$(mktemp -d)" \
+	&& for server in $(shuf -e \
+	        ha.pool.sks-keyservers.net \
+	        hkp://p80.pool.sks-keyservers.net:80 \
+	        keyserver.ubuntu.com \
+	        hkp://keyserver.ubuntu.com:80 \
+	        pgp.mit.edu) ; do \
+	    gpg --batch --keyserver "$server" --recv-keys "$GPG_KEY" && break || : ; \
+	    done \
+	&& gpg --batch --verify python.tar.xz.asc python.tar.xz \
+	&& { command -v gpgconf > /dev/null && gpgconf --kill all || :; } \
+	&& rm -rf "$GNUPGHOME" python.tar.xz.asc \
+	&& mkdir -p /usr/src/python \
+	&& tar -xJC /usr/src/python --strip-components=1 -f python.tar.xz \
+	&& rm python.tar.xz \
+	\
+	&& cd /usr/src/python \
+	&& gnuArch="$(dpkg-architecture --query DEB_BUILD_GNU_TYPE)" \
+	&& ./configure \
+		--build="$gnuArch" \
+		--enable-loadable-sqlite-extensions \
+		--enable-optimizations \
+		--enable-option-checking=fatal \
+		--enable-shared \
+		--with-system-expat \
+		--with-system-ffi \
+		--without-ensurepip \
+	&& make -j "$(nproc)" \
+		LDFLAGS="-Wl,--strip-all" \
+	&& make install \
+	&& rm -rf /usr/src/python \
+	\
+	&& find /usr/local -depth \
+		\( \
+			\( -type d -a \( -name test -o -name tests -o -name idle_test \) \) \
+			-o \( -type f -a \( -name '*.pyc' -o -name '*.pyo' -o -name '*.a' \) \) \
+		\) -exec rm -rf '{}' + \
+	\
+	&& ldconfig \
+	\
+	&& apt-mark auto '.*' > /dev/null \
+	&& apt-mark manual $savedAptMark \
+	&& find /usr/local -type f -executable -not \( -name '*tkinter*' \) -exec ldd '{}' ';' \
+		| awk '/=>/ { print $(NF-1) }' \
+		| sort -u \
+		| xargs -r dpkg-query --search \
+		| cut -d: -f1 \
+		| sort -u \
+		| xargs -r apt-mark manual \
+	&& apt-get purge -y --auto-remove -o APT::AutoRemove::RecommendsImportant=false \
+	&& rm -rf /var/lib/apt/lists/* \
+	\
+	&& python3 --version
+
+# make some useful symlinks that are expected to exist
+RUN cd /usr/local/bin \
+	&& ln -s idle3 idle \
+	&& ln -s pydoc3 pydoc \
+	&& ln -s python3 python \
+	&& ln -s python3-config python-config
+
+# if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
+ENV PYTHON_PIP_VERSION 22.3.1
+# https://github.com/pypa/get-pip
+ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/66030fa03382b4914d4c4d0896961a0bdeeeb274/public/get-pip.py
+ENV PYTHON_GET_PIP_SHA256 1e501cf004eac1b7eb1f97266d28f995ae835d30250bec7f8850562703067dc6
+
+RUN set -ex; \
+	\
+	savedAptMark="$(apt-mark showmanual)"; \
+	apt-get update; \
+	apt-get install -y --no-install-recommends wget; \
+	\
+	wget -O get-pip.py "$PYTHON_GET_PIP_URL"; \
+	echo "$PYTHON_GET_PIP_SHA256 *get-pip.py" | sha256sum --check --strict -; \
+	\
+	apt-mark auto '.*' > /dev/null; \
+	[ -z "$savedAptMark" ] || apt-mark manual $savedAptMark; \
+	apt-get purge -y --auto-remove -o APT::AutoRemove::RecommendsImportant=false; \
+	rm -rf /var/lib/apt/lists/*; \
+	\
+	python get-pip.py \
+		--disable-pip-version-check \
+		--no-cache-dir \
+		"pip==$PYTHON_PIP_VERSION" \
+	; \
+	pip --version; \
+	\
+	find /usr/local -depth \
+		\( \
+			\( -type d -a \( -name test -o -name tests -o -name idle_test \) \) \
+			-o \
+			\( -type f -a \( -name '*.pyc' -o -name '*.pyo' \) \) \
+		\) -exec rm -rf '{}' +; \
+	rm -f get-pip.py
+
+CMD ["python3"]
diff --git a/3.9/buster/Dockerfile b/3.9/buster/Dockerfile
index 1fe2d7e46..0985946ba 100644
--- a/3.9/buster/Dockerfile
+++ b/3.9/buster/Dockerfile
@@ -21,14 +21,14 @@ RUN apt-get update && apt-get install -y --no-install-recommends \
 	&& rm -rf /var/lib/apt/lists/*
 
 ENV GPG_KEY E3FF2839C048B25C084DEBE9B26995E310250568
-ENV PYTHON_VERSION 3.9.0
+ENV PYTHON_VERSION 3.9.13
 
 RUN set -ex \
 	\
 	&& wget -O python.tar.xz "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz" \
 	&& wget -O python.tar.xz.asc "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz.asc" \
 	&& export GNUPGHOME="$(mktemp -d)" \
-	&& gpg --batch --keyserver ha.pool.sks-keyservers.net --recv-keys "$GPG_KEY" \
+	&& gpg --batch --keyserver hkps://keys.openpgp.org --recv-keys "$GPG_KEY" \
 	&& gpg --batch --verify python.tar.xz.asc python.tar.xz \
 	&& { command -v gpgconf > /dev/null && gpgconf --kill all || :; } \
 	&& rm -rf "$GNUPGHOME" python.tar.xz.asc \
@@ -69,10 +69,10 @@ RUN cd /usr/local/bin \
 	&& ln -s python3-config python-config
 
 # if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
-ENV PYTHON_PIP_VERSION 20.2.3
+ENV PYTHON_PIP_VERSION 22.3.1
 # https://github.com/pypa/get-pip
-ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/fa7dc83944936bf09a0e4cb5d5ec852c0d256599/get-pip.py
-ENV PYTHON_GET_PIP_SHA256 6e0bb0a2c2533361d7f297ed547237caf1b7507f197835974c0dd7eba998c53c
+ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/66030fa03382b4914d4c4d0896961a0bdeeeb274/public/get-pip.py
+ENV PYTHON_GET_PIP_SHA256 1e501cf004eac1b7eb1f97266d28f995ae835d30250bec7f8850562703067dc6
 
 RUN set -ex; \
 	\
diff --git a/3.9/buster/slim/Dockerfile b/3.9/buster/slim/Dockerfile
index 070e9cad2..38206f8c6 100644
--- a/3.9/buster/slim/Dockerfile
+++ b/3.9/buster/slim/Dockerfile
@@ -20,7 +20,7 @@ RUN apt-get update && apt-get install -y --no-install-recommends \
 	&& rm -rf /var/lib/apt/lists/*
 
 ENV GPG_KEY E3FF2839C048B25C084DEBE9B26995E310250568
-ENV PYTHON_VERSION 3.9.0
+ENV PYTHON_VERSION 3.9.13
 
 RUN set -ex \
 	\
@@ -51,7 +51,7 @@ RUN set -ex \
 	&& wget -O python.tar.xz "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz" \
 	&& wget -O python.tar.xz.asc "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz.asc" \
 	&& export GNUPGHOME="$(mktemp -d)" \
-	&& gpg --batch --keyserver ha.pool.sks-keyservers.net --recv-keys "$GPG_KEY" \
+	&& gpg --batch --keyserver hkps://keys.openpgp.org --recv-keys "$GPG_KEY" \
 	&& gpg --batch --verify python.tar.xz.asc python.tar.xz \
 	&& { command -v gpgconf > /dev/null && gpgconf --kill all || :; } \
 	&& rm -rf "$GNUPGHOME" python.tar.xz.asc \
@@ -105,10 +105,10 @@ RUN cd /usr/local/bin \
 	&& ln -s python3-config python-config
 
 # if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
-ENV PYTHON_PIP_VERSION 20.2.3
+ENV PYTHON_PIP_VERSION 22.3.1
 # https://github.com/pypa/get-pip
-ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/fa7dc83944936bf09a0e4cb5d5ec852c0d256599/get-pip.py
-ENV PYTHON_GET_PIP_SHA256 6e0bb0a2c2533361d7f297ed547237caf1b7507f197835974c0dd7eba998c53c
+ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/66030fa03382b4914d4c4d0896961a0bdeeeb274/public/get-pip.py
+ENV PYTHON_GET_PIP_SHA256 1e501cf004eac1b7eb1f97266d28f995ae835d30250bec7f8850562703067dc6
 
 RUN set -ex; \
 	\
diff --git a/3.9/windows/windowsservercore-1809/Dockerfile b/3.9/windows/windowsservercore-1809/Dockerfile
index 072f3d114..173b87f84 100644
--- a/3.9/windows/windowsservercore-1809/Dockerfile
+++ b/3.9/windows/windowsservercore-1809/Dockerfile
@@ -8,8 +8,8 @@ FROM mcr.microsoft.com/windows/servercore:1809
 
 SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
 
-ENV PYTHON_VERSION 3.9.0
-ENV PYTHON_RELEASE 3.9.0
+ENV PYTHON_VERSION 3.9.13
+ENV PYTHON_RELEASE 3.9.13
 
 RUN $url = ('https://www.python.org/ftp/python/{0}/python-{1}-amd64.exe' -f $env:PYTHON_RELEASE, $env:PYTHON_VERSION); \
 	Write-Host ('Downloading {0} ...' -f $url); \
@@ -42,10 +42,10 @@ RUN $url = ('https://www.python.org/ftp/python/{0}/python-{1}-amd64.exe' -f $env
 	Write-Host 'Complete.'
 
 # if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
-ENV PYTHON_PIP_VERSION 20.2.3
+ENV PYTHON_PIP_VERSION 22.3.1
 # https://github.com/pypa/get-pip
-ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/fa7dc83944936bf09a0e4cb5d5ec852c0d256599/get-pip.py
-ENV PYTHON_GET_PIP_SHA256 6e0bb0a2c2533361d7f297ed547237caf1b7507f197835974c0dd7eba998c53c
+ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/66030fa03382b4914d4c4d0896961a0bdeeeb274/public/get-pip.py
+ENV PYTHON_GET_PIP_SHA256 1e501cf004eac1b7eb1f97266d28f995ae835d30250bec7f8850562703067dc6
 
 RUN Write-Host ('Downloading get-pip.py ({0}) ...' -f $env:PYTHON_GET_PIP_URL); \
 	[Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12; \
diff --git a/3.9/windows/windowsservercore-ltsc2016/Dockerfile b/3.9/windows/windowsservercore-ltsc2016/Dockerfile
index c47255313..995939de4 100644
--- a/3.9/windows/windowsservercore-ltsc2016/Dockerfile
+++ b/3.9/windows/windowsservercore-ltsc2016/Dockerfile
@@ -8,8 +8,8 @@ FROM mcr.microsoft.com/windows/servercore:ltsc2016
 
 SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
 
-ENV PYTHON_VERSION 3.9.0
-ENV PYTHON_RELEASE 3.9.0
+ENV PYTHON_VERSION 3.9.13
+ENV PYTHON_RELEASE 3.9.13
 
 RUN $url = ('https://www.python.org/ftp/python/{0}/python-{1}-amd64.exe' -f $env:PYTHON_RELEASE, $env:PYTHON_VERSION); \
 	Write-Host ('Downloading {0} ...' -f $url); \
@@ -42,10 +42,10 @@ RUN $url = ('https://www.python.org/ftp/python/{0}/python-{1}-amd64.exe' -f $env
 	Write-Host 'Complete.'
 
 # if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
-ENV PYTHON_PIP_VERSION 20.2.3
+ENV PYTHON_PIP_VERSION 22.3.1
 # https://github.com/pypa/get-pip
-ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/fa7dc83944936bf09a0e4cb5d5ec852c0d256599/get-pip.py
-ENV PYTHON_GET_PIP_SHA256 6e0bb0a2c2533361d7f297ed547237caf1b7507f197835974c0dd7eba998c53c
+ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/66030fa03382b4914d4c4d0896961a0bdeeeb274/public/get-pip.py
+ENV PYTHON_GET_PIP_SHA256 1e501cf004eac1b7eb1f97266d28f995ae835d30250bec7f8850562703067dc6
 
 RUN Write-Host ('Downloading get-pip.py ({0}) ...' -f $env:PYTHON_GET_PIP_URL); \
 	[Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12; \
diff --git a/Dockerfile-alpine.template b/Dockerfile-alpine.template
index b387d1928..bb342d1d9 100644
--- a/Dockerfile-alpine.template
+++ b/Dockerfile-alpine.template
@@ -23,7 +23,7 @@ RUN set -ex \
 	&& wget -O python.tar.xz "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz" \
 	&& wget -O python.tar.xz.asc "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz.asc" \
 	&& export GNUPGHOME="$(mktemp -d)" \
-	&& gpg --batch --keyserver ha.pool.sks-keyservers.net --recv-keys "$GPG_KEY" \
+	&& gpg --batch --keyserver hkps://keys.openpgp.org --recv-keys "$GPG_KEY" \
 	&& gpg --batch --verify python.tar.xz.asc python.tar.xz \
 	&& { command -v gpgconf > /dev/null && gpgconf --kill all || :; } \
 	&& rm -rf "$GNUPGHOME" python.tar.xz.asc \
diff --git a/Dockerfile-caveman-lite.template b/Dockerfile-caveman-lite.template
new file mode 100644
index 000000000..09792dce4
--- /dev/null
+++ b/Dockerfile-caveman-lite.template
@@ -0,0 +1,128 @@
+FROM vaporio/foundation:%%PLACEHOLDER%%
+
+# ensure local python is preferred over distribution python
+ENV PATH /usr/local/bin:$PATH
+
+# http://bugs.python.org/issue19846
+# > At the moment, setting "LANG=C" on a Linux system *fundamentally breaks Python 3*, and that's not OK.
+ENV LANG C.UTF-8
+# https://github.com/docker-library/python/issues/147
+ENV PYTHONIOENCODING UTF-8
+
+# runtime dependencies
+RUN apt-get update && apt-get install -y --no-install-recommends \
+		ca-certificates \
+		netbase \
+	&& rm -rf /var/lib/apt/lists/*
+
+ENV GPG_KEY %%PLACEHOLDER%%
+ENV PYTHON_VERSION %%PLACEHOLDER%%
+
+RUN set -ex \
+	\
+	&& export DEBIAN_FRONTEND=noninteractive; \
+    export DEBCONF_NONINTERACTIVE_SEEN=true; \
+    echo 'tzdata tzdata/Areas select Etc' | debconf-set-selections; \
+    echo 'tzdata tzdata/Zones/Etc select UTC' | debconf-set-selections \
+	&& savedAptMark="$(apt-mark showmanual)" \
+	&& apt-get update && apt-get install -y --no-install-recommends \
+		dpkg-dev \
+		gcc \
+		libbz2-dev \
+		libc6-dev \
+		libdb-dev \
+		libgdbm-dev \
+		libncursesw5-dev \
+		libreadline-dev \
+		libsqlite3-dev \
+		libssl-dev \
+		make \
+		tk-dev \
+		wget \
+		xz-utils \
+		zlib1g-dev \
+# as of Stretch, "gpg" is no longer included by default
+		$(command -v gpg > /dev/null || echo 'gnupg dirmngr') \
+	\
+	&& wget -O python.tar.xz "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz" \
+	&& wget -O python.tar.xz.asc "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz.asc" \
+	&& export GNUPGHOME="$(mktemp -d)" \
+	&& for server in $(shuf -e \
+	        ha.pool.sks-keyservers.net \
+	        hkp://p80.pool.sks-keyservers.net:80 \
+	        keyserver.ubuntu.com \
+	        hkp://keyserver.ubuntu.com:80 \
+	        pgp.mit.edu) ; do \
+	    gpg --batch --keyserver "$server" --recv-keys "$GPG_KEY" && break || : ; \
+	    done \
+	&& gpg --batch --verify python.tar.xz.asc python.tar.xz \
+	&& { command -v gpgconf > /dev/null && gpgconf --kill all || :; } \
+	&& rm -rf "$GNUPGHOME" python.tar.xz.asc \
+	&& mkdir -p /usr/src/python \
+	&& tar -xJC /usr/src/python --strip-components=1 -f python.tar.xz \
+	&& rm python.tar.xz \
+	\
+	&& cd /usr/src/python \
+	&& gnuArch="$(dpkg-architecture --query DEB_BUILD_GNU_TYPE)" \
+	&& ./configure \
+		--build="$gnuArch" \
+		--enable-shared \
+		--enable-unicode=ucs4 \
+	&& make -j "$(nproc)" \
+	&& make install \
+	&& ldconfig \
+	\
+	&& apt-mark auto '.*' > /dev/null \
+	&& apt-mark manual $savedAptMark \
+	&& find /usr/local -type f -executable -not \( -name '*tkinter*' \) -exec ldd '{}' ';' \
+		| awk '/=>/ { print $(NF-1) }' \
+		| sort -u \
+		| 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 \
+	&& rm -rf /var/lib/apt/lists/* \
+	\
+	&& find /usr/local -depth \
+		\( \
+			\( -type d -a \( -name test -o -name tests \) \) \
+			-o \
+			\( -type f -a \( -name '*.pyc' -o -name '*.pyo' \) \) \
+		\) -exec rm -rf '{}' + \
+	&& rm -rf /usr/src/python \
+	\
+	&& python2 --version
+
+# if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
+ENV PYTHON_PIP_VERSION %%PLACEHOLDER%%
+
+RUN set -ex; \
+	\
+	savedAptMark="$(apt-mark showmanual)"; \
+	apt-get update; \
+	apt-get install -y --no-install-recommends wget; \
+	\
+	wget -O get-pip.py 'https://bootstrap.pypa.io/get-pip.py'; \
+	\
+	apt-mark auto '.*' > /dev/null; \
+	[ -z "$savedAptMark" ] || apt-mark manual $savedAptMark; \
+	apt-get purge -y --auto-remove -o APT::AutoRemove::RecommendsImportant=false; \
+	rm -rf /var/lib/apt/lists/*; \
+	\
+	python get-pip.py \
+		--disable-pip-version-check \
+		--no-cache-dir \
+		"pip==$PYTHON_PIP_VERSION" \
+	; \
+	pip --version; \
+	\
+	find /usr/local -depth \
+		\( \
+			\( -type d -a \( -name test -o -name tests \) \) \
+			-o \
+			\( -type f -a \( -name '*.pyc' -o -name '*.pyo' \) \) \
+		\) -exec rm -rf '{}' +; \
+	rm -f get-pip.py
+
+CMD ["python2"]
diff --git a/Dockerfile-caveman-ubuntu.template b/Dockerfile-caveman-ubuntu.template
new file mode 100644
index 000000000..2d9fa7e3c
--- /dev/null
+++ b/Dockerfile-caveman-ubuntu.template
@@ -0,0 +1,89 @@
+FROM vaporio/buildpack-deps:%%PLACEHOLDER%%
+
+# ensure local python is preferred over distribution python
+ENV PATH /usr/local/bin:$PATH
+
+# http://bugs.python.org/issue19846
+# > At the moment, setting "LANG=C" on a Linux system *fundamentally breaks Python 3*, and that's not OK.
+ENV LANG C.UTF-8
+# https://github.com/docker-library/python/issues/147
+ENV PYTHONIOENCODING UTF-8
+
+# extra dependencies (over what buildpack-deps already includes)
+RUN export DEBIAN_FRONTEND=noninteractive; \
+    export DEBCONF_NONINTERACTIVE_SEEN=true; \
+    echo 'tzdata tzdata/Areas select Etc' | debconf-set-selections; \
+    echo 'tzdata tzdata/Zones/Etc select UTC' | debconf-set-selections; \
+    apt-get update -y && apt-get install -y --no-install-recommends \
+        tk-dev \
+    && rm -rf /var/lib/apt/lists/*
+
+ENV GPG_KEY %%PLACEHOLDER%%
+ENV PYTHON_VERSION %%PLACEHOLDER%%
+
+RUN set -ex \
+	\
+	&& wget -O python.tar.xz "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz" \
+	&& wget -O python.tar.xz.asc "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz.asc" \
+	&& export GNUPGHOME="$(mktemp -d)" \
+	&& for server in $(shuf -e \
+	        ha.pool.sks-keyservers.net \
+	        hkp://p80.pool.sks-keyservers.net:80 \
+	        keyserver.ubuntu.com \
+	        hkp://keyserver.ubuntu.com:80 \
+	        pgp.mit.edu) ; do \
+	    gpg --batch --keyserver "$server" --recv-keys "$GPG_KEY" && break || : ; \
+	    done \
+	&& gpg --batch --verify python.tar.xz.asc python.tar.xz \
+	&& { command -v gpgconf > /dev/null && gpgconf --kill all || :; } \
+	&& rm -rf "$GNUPGHOME" python.tar.xz.asc \
+	&& mkdir -p /usr/src/python \
+	&& tar -xJC /usr/src/python --strip-components=1 -f python.tar.xz \
+	&& rm python.tar.xz \
+	\
+	&& cd /usr/src/python \
+	&& gnuArch="$(dpkg-architecture --query DEB_BUILD_GNU_TYPE)" \
+	&& ./configure \
+		--build="$gnuArch" \
+		--enable-shared \
+		--enable-unicode=ucs4 \
+	&& make -j "$(nproc)" \
+	&& make install \
+	&& ldconfig \
+	\
+	&& find /usr/local -depth \
+		\( \
+			\( -type d -a \( -name test -o -name tests \) \) \
+			-o \
+			\( -type f -a \( -name '*.pyc' -o -name '*.pyo' \) \) \
+		\) -exec rm -rf '{}' + \
+	&& rm -rf /usr/src/python \
+	\
+	&& python2 --version
+
+# if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
+ENV PYTHON_PIP_VERSION %%PLACEHOLDER%%
+
+RUN set -ex; \
+	\
+	wget -O get-pip.py 'https://bootstrap.pypa.io/get-pip.py'; \
+	\
+	python get-pip.py \
+		--disable-pip-version-check \
+		--no-cache-dir \
+		"pip==$PYTHON_PIP_VERSION" \
+	; \
+	pip --version; \
+	\
+	find /usr/local -depth \
+		\( \
+			\( -type d -a \( -name test -o -name tests \) \) \
+			-o \
+			\( -type f -a \( -name '*.pyc' -o -name '*.pyo' \) \) \
+		\) -exec rm -rf '{}' +; \
+	rm -f get-pip.py
+
+# install "virtualenv", since the vast majority of users of this image will want it
+RUN pip install --no-cache-dir virtualenv
+
+CMD ["python2"]
diff --git a/Dockerfile-debian.template b/Dockerfile-debian.template
index 6f0b37388..858d6e1e9 100644
--- a/Dockerfile-debian.template
+++ b/Dockerfile-debian.template
@@ -22,7 +22,7 @@ RUN set -ex \
 	&& wget -O python.tar.xz "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz" \
 	&& wget -O python.tar.xz.asc "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz.asc" \
 	&& export GNUPGHOME="$(mktemp -d)" \
-	&& gpg --batch --keyserver ha.pool.sks-keyservers.net --recv-keys "$GPG_KEY" \
+	&& gpg --batch --keyserver hkps://keys.openpgp.org --recv-keys "$GPG_KEY" \
 	&& gpg --batch --verify python.tar.xz.asc python.tar.xz \
 	&& { command -v gpgconf > /dev/null && gpgconf --kill all || :; } \
 	&& rm -rf "$GNUPGHOME" python.tar.xz.asc \
diff --git a/3.7/stretch/slim/Dockerfile b/Dockerfile-lite.template
similarity index 87%
rename from 3.7/stretch/slim/Dockerfile
rename to Dockerfile-lite.template
index e5503c57a..9761f8025 100644
--- a/3.7/stretch/slim/Dockerfile
+++ b/Dockerfile-lite.template
@@ -1,10 +1,4 @@
-#
-# NOTE: THIS DOCKERFILE IS GENERATED VIA "update.sh"
-#
-# PLEASE DO NOT EDIT IT DIRECTLY.
-#
-
-FROM debian:stretch-slim
+FROM vaporio/foundation:%%PLACEHOLDER%%
 
 # ensure local python is preferred over distribution python
 ENV PATH /usr/local/bin:$PATH
@@ -12,15 +6,17 @@ ENV PATH /usr/local/bin:$PATH
 # http://bugs.python.org/issue19846
 # > At the moment, setting "LANG=C" on a Linux system *fundamentally breaks Python 3*, and that's not OK.
 ENV LANG C.UTF-8
+ENV DEBIAN_FRONTEND noninteractive
 
 # runtime dependencies
-RUN apt-get update && apt-get install -y --no-install-recommends \
+RUN apt-get update; \
+    apt-get install -y --no-install-recommends \
 		ca-certificates \
 		netbase \
 	&& rm -rf /var/lib/apt/lists/*
 
-ENV GPG_KEY 0D96DF4D4110E5C43FBFB17F2D347EA6AA65421D
-ENV PYTHON_VERSION 3.7.9
+ENV GPG_KEY %%PLACEHOLDER%%
+ENV PYTHON_VERSION %%PLACEHOLDER%%
 
 RUN set -ex \
 	\
@@ -51,7 +47,14 @@ RUN set -ex \
 	&& wget -O python.tar.xz "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz" \
 	&& wget -O python.tar.xz.asc "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz.asc" \
 	&& export GNUPGHOME="$(mktemp -d)" \
-	&& gpg --batch --keyserver ha.pool.sks-keyservers.net --recv-keys "$GPG_KEY" \
+	&& for server in $(shuf -e \
+	        ha.pool.sks-keyservers.net \
+	        hkp://p80.pool.sks-keyservers.net:80 \
+	        keyserver.ubuntu.com \
+	        hkp://keyserver.ubuntu.com:80 \
+	        pgp.mit.edu) ; do \
+	    gpg --batch --keyserver "$server" --recv-keys "$GPG_KEY" && break || : ; \
+	    done \
 	&& gpg --batch --verify python.tar.xz.asc python.tar.xz \
 	&& { command -v gpgconf > /dev/null && gpgconf --kill all || :; } \
 	&& rm -rf "$GNUPGHOME" python.tar.xz.asc \
@@ -142,10 +145,10 @@ RUN cd /usr/local/bin \
 	&& ln -s python3-config python-config
 
 # if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
-ENV PYTHON_PIP_VERSION 20.2.3
+ENV PYTHON_PIP_VERSION %%PLACEHOLDER%%
 # https://github.com/pypa/get-pip
-ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/fa7dc83944936bf09a0e4cb5d5ec852c0d256599/get-pip.py
-ENV PYTHON_GET_PIP_SHA256 6e0bb0a2c2533361d7f297ed547237caf1b7507f197835974c0dd7eba998c53c
+ENV PYTHON_GET_PIP_URL %%PLACEHOLDER%%
+ENV PYTHON_GET_PIP_SHA256 %%PLACEHOLDER%%
 
 RUN set -ex; \
 	\
diff --git a/Dockerfile-slim.template b/Dockerfile-slim.template
index 7c079a426..43cd698af 100644
--- a/Dockerfile-slim.template
+++ b/Dockerfile-slim.template
@@ -45,7 +45,7 @@ RUN set -ex \
 	&& wget -O python.tar.xz "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz" \
 	&& wget -O python.tar.xz.asc "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz.asc" \
 	&& export GNUPGHOME="$(mktemp -d)" \
-	&& gpg --batch --keyserver ha.pool.sks-keyservers.net --recv-keys "$GPG_KEY" \
+	&& gpg --batch --keyserver hkps://keys.openpgp.org --recv-keys "$GPG_KEY" \
 	&& gpg --batch --verify python.tar.xz.asc python.tar.xz \
 	&& { command -v gpgconf > /dev/null && gpgconf --kill all || :; } \
 	&& rm -rf "$GNUPGHOME" python.tar.xz.asc \
diff --git a/3.7/stretch/Dockerfile b/Dockerfile-ubuntu.template
similarity index 83%
rename from 3.7/stretch/Dockerfile
rename to Dockerfile-ubuntu.template
index 7d4f97bf4..a40927382 100644
--- a/3.7/stretch/Dockerfile
+++ b/Dockerfile-ubuntu.template
@@ -1,10 +1,4 @@
-#
-# NOTE: THIS DOCKERFILE IS GENERATED VIA "update.sh"
-#
-# PLEASE DO NOT EDIT IT DIRECTLY.
-#
-
-FROM buildpack-deps:stretch
+FROM vaporio/buildpack-deps:%%PLACEHOLDER%%
 
 # ensure local python is preferred over distribution python
 ENV PATH /usr/local/bin:$PATH
@@ -12,23 +6,32 @@ ENV PATH /usr/local/bin:$PATH
 # http://bugs.python.org/issue19846
 # > At the moment, setting "LANG=C" on a Linux system *fundamentally breaks Python 3*, and that's not OK.
 ENV LANG C.UTF-8
+ENV DEBIAN_FRONTEND noninteractive
 
 # extra dependencies (over what buildpack-deps already includes)
-RUN apt-get update && apt-get install -y --no-install-recommends \
+RUN apt-get update; \
+    apt-get install -y --no-install-recommends \
 		libbluetooth-dev \
 		tk-dev \
 		uuid-dev \
 	&& rm -rf /var/lib/apt/lists/*
 
-ENV GPG_KEY 0D96DF4D4110E5C43FBFB17F2D347EA6AA65421D
-ENV PYTHON_VERSION 3.7.9
+ENV GPG_KEY %%PLACEHOLDER%%
+ENV PYTHON_VERSION %%PLACEHOLDER%%
 
 RUN set -ex \
 	\
 	&& wget -O python.tar.xz "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz" \
 	&& wget -O python.tar.xz.asc "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz.asc" \
 	&& export GNUPGHOME="$(mktemp -d)" \
-	&& gpg --batch --keyserver ha.pool.sks-keyservers.net --recv-keys "$GPG_KEY" \
+	&& for server in $(shuf -e \
+	        ha.pool.sks-keyservers.net \
+	        hkp://p80.pool.sks-keyservers.net:80 \
+	        keyserver.ubuntu.com \
+	        hkp://keyserver.ubuntu.com:80 \
+	        pgp.mit.edu) ; do \
+	    gpg --batch --keyserver "$server" --recv-keys "$GPG_KEY" && break || : ; \
+	    done \
 	&& gpg --batch --verify python.tar.xz.asc python.tar.xz \
 	&& { command -v gpgconf > /dev/null && gpgconf --kill all || :; } \
 	&& rm -rf "$GNUPGHOME" python.tar.xz.asc \
@@ -106,10 +109,10 @@ RUN cd /usr/local/bin \
 	&& ln -s python3-config python-config
 
 # if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
-ENV PYTHON_PIP_VERSION 20.2.3
+ENV PYTHON_PIP_VERSION %%PLACEHOLDER%%
 # https://github.com/pypa/get-pip
-ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/fa7dc83944936bf09a0e4cb5d5ec852c0d256599/get-pip.py
-ENV PYTHON_GET_PIP_SHA256 6e0bb0a2c2533361d7f297ed547237caf1b7507f197835974c0dd7eba998c53c
+ENV PYTHON_GET_PIP_URL %%PLACEHOLDER%%
+ENV PYTHON_GET_PIP_SHA256 %%PLACEHOLDER%%
 
 RUN set -ex; \
 	\
diff --git a/generate-stackbrew-library.sh b/generate-stackbrew-library.sh
index d28d08391..334aa4149 100755
--- a/generate-stackbrew-library.sh
+++ b/generate-stackbrew-library.sh
@@ -2,15 +2,14 @@
 set -Eeuo pipefail
 
 declare -A aliases=(
-	[3.10-rc]='rc'
-	[3.9]='3 latest'
+	[3.11]='3 latest'
 )
 
 defaultDebianSuite='buster' # TODO buster
 declare -A debianSuites=(
 	#[3.8-rc]='buster'
 )
-defaultAlpineVersion='3.12'
+defaultAlpineVersion='3.17'
 
 self="$(basename "$BASH_SOURCE")"
 cd "$(dirname "$(readlink -f "$BASH_SOURCE")")"
@@ -79,7 +78,7 @@ for version in "${versions[@]}"; do
 
 	for v in \
 		{buster,stretch}{,/slim} \
-		alpine{3.12,3.11} \
+		alpine{3.17,3.16} \
 		windows/windowsservercore-{ltsc2016,1809} \
 	; do
 		dir="$version/$v"
diff --git a/update.sh b/update.sh
index 08521a84b..926be5fec 100755
--- a/update.sh
+++ b/update.sh
@@ -1,13 +1,10 @@
 #!/usr/bin/env bash
+set -x
 set -Eeuo pipefail
 shopt -s nullglob
 
 # https://www.python.org/downloads/23Introduction (under "OpenPGP Public Keys")
 declare -A gpgKeys=(
-	# gpg: key AA65421D: public key "Ned Deily (Python release signing key) <nad@acm.org>" imported
-	[3.6]='0D96DF4D4110E5C43FBFB17F2D347EA6AA65421D'
-	# https://www.python.org/dev/peps/pep-0494/#release-manager-and-crew
-
 	# gpg: key AA65421D: public key "Ned Deily (Python release signing key) <nad@acm.org>" imported
 	[3.7]='0D96DF4D4110E5C43FBFB17F2D347EA6AA65421D'
 	# https://www.python.org/dev/peps/pep-0537/#release-manager-and-crew
@@ -23,6 +20,10 @@ declare -A gpgKeys=(
 	# gpg: key 64E628F8D684696D: public key "Pablo Galindo Salgado <pablogsal@gmail.com>" imported
 	[3.10]='A035C8C19219BA821ECEA86B64E628F8D684696D'
 	# https://www.python.org/dev/peps/pep-0619/#release-manager-and-crew
+
+	# gpg: key 64E628F8D684696D: public key "Pablo Galindo Salgado <pablogsal@gmail.com>" imported
+	[3.11]='A035C8C19219BA821ECEA86B64E628F8D684696D'
+	# https://www.python.org/dev/peps/pep-0664/#release-manager-and-crew
 )
 
 cd "$(dirname "$(readlink -f "$BASH_SOURCE")")"
@@ -34,8 +35,8 @@ fi
 versions=( "${versions[@]%/}" )
 
 pipVersion="$(curl -fsSL 'https://pypi.org/pypi/pip/json' | jq -r .info.version)"
-getPipCommit="$(curl -fsSL 'https://github.com/pypa/get-pip/commits/master/get-pip.py.atom' | tac|tac | awk -F '[[:space:]]*[<>/]+' '$2 == "id" && $3 ~ /Commit/ { print $4; exit }')"
-getPipUrl="https://github.com/pypa/get-pip/raw/$getPipCommit/get-pip.py"
+getPipCommit="$(curl -fsSL 'https://github.com/pypa/get-pip/commits/main/public/get-pip.py.atom' | tac|tac | awk -F '[[:space:]]*[<>/]+' '$2 == "id" && $3 ~ /Commit/ { print $4; exit }')"
+getPipUrl="https://github.com/pypa/get-pip/raw/$getPipCommit/public/get-pip.py"
 getPipSha256="$(curl -fsSL "$getPipUrl" | sha256sum | cut -d' ' -f1)"
 
 generated_warning() {
@@ -132,9 +133,10 @@ for version in "${versions[@]}"; do
 	echo "$version: $fullVersion"
 
 	for v in \
-		alpine{3.11,3.12} \
+		alpine{3.16,3.17} \
 		{stretch,buster}{/slim,} \
 		windows/windowsservercore-{1809,ltsc2016} \
+		bionic{/lite,} \
 	; do
 		dir="$version/$v"
 		variant="$(basename "$v")"
@@ -143,8 +145,10 @@ for version in "${versions[@]}"; do
 
 		case "$variant" in
 			slim) template="$variant"; tag="$(basename "$(dirname "$dir")")" ;;
+			lite) template="$variant"; tag="$(basename "$(dirname "$dir")")" ;;
 			windowsservercore-*) template='windowsservercore'; tag="${variant#*-}" ;;
 			alpine*) template='alpine'; tag="${variant#alpine}" ;;
+			bionic) template='ubuntu'; tag="$variant" ;;
 			*) template='debian'; tag="$variant" ;;
 		esac
 		if [ "$variant" = 'slim' ]; then
@@ -163,21 +167,9 @@ for version in "${versions[@]}"; do
 			-e 's!^(ENV PYTHON_GET_PIP_URL) .*!\1 '"$getPipUrl"'!' \
 			-e 's!^(ENV PYTHON_GET_PIP_SHA256) .*!\1 '"$getPipSha256"'!' \
 			-e 's/^(FROM python):.*/\1:'"$version-$tag"'/' \
-			-e 's!^(FROM (debian|buildpack-deps|alpine|mcr[.]microsoft[.]com/[^:]+)):.*!\1:'"$tag"'!' \
+			-e 's!^(FROM (debian|buildpack-deps|vaporio/foundation|vaporio/buildpack-deps|alpine|mcr[.]microsoft[.]com/[^:]+)):.*!\1:'"$tag"'!' \
 			"$dir/Dockerfile"
 
-		case "$rcVersion/$v" in
-			# https://bugs.python.org/issue11063, https://bugs.python.org/issue20519 (Python 3.7.0+)
-			# A new native _uuid module improves uuid import time and avoids using ctypes.
-			# This requires the development libuuid headers.
-			3.6/alpine*)
-				sed -ri -e '/util-linux-dev/d' "$dir/Dockerfile"
-				;;
-			3.6/*)
-				sed -ri -e '/uuid-dev/d' "$dir/Dockerfile"
-				;;
-		esac
-
 		major="${rcVersion%%.*}"
 		minor="${rcVersion#$major.}"
 		minor="${minor%%.*}"