diff --git a/3.10/alpine3.21/Dockerfile b/3.10/alpine3.21/Dockerfile
index bde84e689..6cc036e23 100644
--- a/3.10/alpine3.21/Dockerfile
+++ b/3.10/alpine3.21/Dockerfile
@@ -22,8 +22,8 @@ RUN set -eux; \
 	;
 
 ENV GPG_KEY A035C8C19219BA821ECEA86B64E628F8D684696D
-ENV PYTHON_VERSION 3.10.17
-ENV PYTHON_SHA256 4c68050f049d1b4ac5aadd0df5f27941c0350d2a9e7ab0907ee5eb5225d9d6b0
+ENV PYTHON_VERSION 3.10.18
+ENV PYTHON_SHA256 ae665bc678abd9ab6a6e1573d2481625a53719bc517e9a634ed2b9fefae3817f
 
 RUN set -eux; \
 	\
diff --git a/3.10/alpine3.20/Dockerfile b/3.10/alpine3.22/Dockerfile
similarity index 96%
rename from 3.10/alpine3.20/Dockerfile
rename to 3.10/alpine3.22/Dockerfile
index 0fed3b855..b91541a49 100644
--- a/3.10/alpine3.20/Dockerfile
+++ b/3.10/alpine3.22/Dockerfile
@@ -4,7 +4,7 @@
 # PLEASE DO NOT EDIT IT DIRECTLY.
 #
 
-FROM alpine:3.20
+FROM alpine:3.22
 
 # ensure local python is preferred over distribution python
 ENV PATH /usr/local/bin:$PATH
@@ -22,8 +22,8 @@ RUN set -eux; \
 	;
 
 ENV GPG_KEY A035C8C19219BA821ECEA86B64E628F8D684696D
-ENV PYTHON_VERSION 3.10.17
-ENV PYTHON_SHA256 4c68050f049d1b4ac5aadd0df5f27941c0350d2a9e7ab0907ee5eb5225d9d6b0
+ENV PYTHON_VERSION 3.10.18
+ENV PYTHON_SHA256 ae665bc678abd9ab6a6e1573d2481625a53719bc517e9a634ed2b9fefae3817f
 
 RUN set -eux; \
 	\
diff --git a/3.10/bookworm/Dockerfile b/3.10/bookworm/Dockerfile
index 365c28eb3..26a7c1623 100644
--- a/3.10/bookworm/Dockerfile
+++ b/3.10/bookworm/Dockerfile
@@ -25,8 +25,8 @@ RUN set -eux; \
 	rm -rf /var/lib/apt/lists/*
 
 ENV GPG_KEY A035C8C19219BA821ECEA86B64E628F8D684696D
-ENV PYTHON_VERSION 3.10.17
-ENV PYTHON_SHA256 4c68050f049d1b4ac5aadd0df5f27941c0350d2a9e7ab0907ee5eb5225d9d6b0
+ENV PYTHON_VERSION 3.10.18
+ENV PYTHON_SHA256 ae665bc678abd9ab6a6e1573d2481625a53719bc517e9a634ed2b9fefae3817f
 
 RUN set -eux; \
 	\
diff --git a/3.10/bullseye/Dockerfile b/3.10/bullseye/Dockerfile
index df9e90582..965b0995c 100644
--- a/3.10/bullseye/Dockerfile
+++ b/3.10/bullseye/Dockerfile
@@ -25,8 +25,8 @@ RUN set -eux; \
 	rm -rf /var/lib/apt/lists/*
 
 ENV GPG_KEY A035C8C19219BA821ECEA86B64E628F8D684696D
-ENV PYTHON_VERSION 3.10.17
-ENV PYTHON_SHA256 4c68050f049d1b4ac5aadd0df5f27941c0350d2a9e7ab0907ee5eb5225d9d6b0
+ENV PYTHON_VERSION 3.10.18
+ENV PYTHON_SHA256 ae665bc678abd9ab6a6e1573d2481625a53719bc517e9a634ed2b9fefae3817f
 
 RUN set -eux; \
 	\
diff --git a/3.10/slim-bookworm/Dockerfile b/3.10/slim-bookworm/Dockerfile
index 28ea16618..49411c8e6 100644
--- a/3.10/slim-bookworm/Dockerfile
+++ b/3.10/slim-bookworm/Dockerfile
@@ -25,8 +25,8 @@ RUN set -eux; \
 	rm -rf /var/lib/apt/lists/*
 
 ENV GPG_KEY A035C8C19219BA821ECEA86B64E628F8D684696D
-ENV PYTHON_VERSION 3.10.17
-ENV PYTHON_SHA256 4c68050f049d1b4ac5aadd0df5f27941c0350d2a9e7ab0907ee5eb5225d9d6b0
+ENV PYTHON_VERSION 3.10.18
+ENV PYTHON_SHA256 ae665bc678abd9ab6a6e1573d2481625a53719bc517e9a634ed2b9fefae3817f
 
 RUN set -eux; \
 	\
diff --git a/3.10/slim-bullseye/Dockerfile b/3.10/slim-bullseye/Dockerfile
index a8758f729..6d6aa7fe9 100644
--- a/3.10/slim-bullseye/Dockerfile
+++ b/3.10/slim-bullseye/Dockerfile
@@ -25,8 +25,8 @@ RUN set -eux; \
 	rm -rf /var/lib/apt/lists/*
 
 ENV GPG_KEY A035C8C19219BA821ECEA86B64E628F8D684696D
-ENV PYTHON_VERSION 3.10.17
-ENV PYTHON_SHA256 4c68050f049d1b4ac5aadd0df5f27941c0350d2a9e7ab0907ee5eb5225d9d6b0
+ENV PYTHON_VERSION 3.10.18
+ENV PYTHON_SHA256 ae665bc678abd9ab6a6e1573d2481625a53719bc517e9a634ed2b9fefae3817f
 
 RUN set -eux; \
 	\
diff --git a/3.11/alpine3.21/Dockerfile b/3.11/alpine3.21/Dockerfile
index 78e40d489..a164244d7 100644
--- a/3.11/alpine3.21/Dockerfile
+++ b/3.11/alpine3.21/Dockerfile
@@ -22,8 +22,8 @@ RUN set -eux; \
 	;
 
 ENV GPG_KEY A035C8C19219BA821ECEA86B64E628F8D684696D
-ENV PYTHON_VERSION 3.11.12
-ENV PYTHON_SHA256 849da87af4df137710c1796e276a955f7a85c9f971081067c8f565d15c352a09
+ENV PYTHON_VERSION 3.11.13
+ENV PYTHON_SHA256 8fb5f9fbc7609fa822cb31549884575db7fd9657cbffb89510b5d7975963a83a
 
 RUN set -eux; \
 	\
diff --git a/3.11/alpine3.20/Dockerfile b/3.11/alpine3.22/Dockerfile
similarity index 96%
rename from 3.11/alpine3.20/Dockerfile
rename to 3.11/alpine3.22/Dockerfile
index 5d5a0be1a..954cf29ea 100644
--- a/3.11/alpine3.20/Dockerfile
+++ b/3.11/alpine3.22/Dockerfile
@@ -4,7 +4,7 @@
 # PLEASE DO NOT EDIT IT DIRECTLY.
 #
 
-FROM alpine:3.20
+FROM alpine:3.22
 
 # ensure local python is preferred over distribution python
 ENV PATH /usr/local/bin:$PATH
@@ -22,8 +22,8 @@ RUN set -eux; \
 	;
 
 ENV GPG_KEY A035C8C19219BA821ECEA86B64E628F8D684696D
-ENV PYTHON_VERSION 3.11.12
-ENV PYTHON_SHA256 849da87af4df137710c1796e276a955f7a85c9f971081067c8f565d15c352a09
+ENV PYTHON_VERSION 3.11.13
+ENV PYTHON_SHA256 8fb5f9fbc7609fa822cb31549884575db7fd9657cbffb89510b5d7975963a83a
 
 RUN set -eux; \
 	\
diff --git a/3.11/bookworm/Dockerfile b/3.11/bookworm/Dockerfile
index f6a7a9a40..68c68dee3 100644
--- a/3.11/bookworm/Dockerfile
+++ b/3.11/bookworm/Dockerfile
@@ -25,8 +25,8 @@ RUN set -eux; \
 	rm -rf /var/lib/apt/lists/*
 
 ENV GPG_KEY A035C8C19219BA821ECEA86B64E628F8D684696D
-ENV PYTHON_VERSION 3.11.12
-ENV PYTHON_SHA256 849da87af4df137710c1796e276a955f7a85c9f971081067c8f565d15c352a09
+ENV PYTHON_VERSION 3.11.13
+ENV PYTHON_SHA256 8fb5f9fbc7609fa822cb31549884575db7fd9657cbffb89510b5d7975963a83a
 
 RUN set -eux; \
 	\
diff --git a/3.11/bullseye/Dockerfile b/3.11/bullseye/Dockerfile
index 4b7d3f217..1e1f136a3 100644
--- a/3.11/bullseye/Dockerfile
+++ b/3.11/bullseye/Dockerfile
@@ -25,8 +25,8 @@ RUN set -eux; \
 	rm -rf /var/lib/apt/lists/*
 
 ENV GPG_KEY A035C8C19219BA821ECEA86B64E628F8D684696D
-ENV PYTHON_VERSION 3.11.12
-ENV PYTHON_SHA256 849da87af4df137710c1796e276a955f7a85c9f971081067c8f565d15c352a09
+ENV PYTHON_VERSION 3.11.13
+ENV PYTHON_SHA256 8fb5f9fbc7609fa822cb31549884575db7fd9657cbffb89510b5d7975963a83a
 
 RUN set -eux; \
 	\
diff --git a/3.11/slim-bookworm/Dockerfile b/3.11/slim-bookworm/Dockerfile
index 3634bae14..a2538726e 100644
--- a/3.11/slim-bookworm/Dockerfile
+++ b/3.11/slim-bookworm/Dockerfile
@@ -25,8 +25,8 @@ RUN set -eux; \
 	rm -rf /var/lib/apt/lists/*
 
 ENV GPG_KEY A035C8C19219BA821ECEA86B64E628F8D684696D
-ENV PYTHON_VERSION 3.11.12
-ENV PYTHON_SHA256 849da87af4df137710c1796e276a955f7a85c9f971081067c8f565d15c352a09
+ENV PYTHON_VERSION 3.11.13
+ENV PYTHON_SHA256 8fb5f9fbc7609fa822cb31549884575db7fd9657cbffb89510b5d7975963a83a
 
 RUN set -eux; \
 	\
diff --git a/3.11/slim-bullseye/Dockerfile b/3.11/slim-bullseye/Dockerfile
index e89207c9d..5f64e97b3 100644
--- a/3.11/slim-bullseye/Dockerfile
+++ b/3.11/slim-bullseye/Dockerfile
@@ -25,8 +25,8 @@ RUN set -eux; \
 	rm -rf /var/lib/apt/lists/*
 
 ENV GPG_KEY A035C8C19219BA821ECEA86B64E628F8D684696D
-ENV PYTHON_VERSION 3.11.12
-ENV PYTHON_SHA256 849da87af4df137710c1796e276a955f7a85c9f971081067c8f565d15c352a09
+ENV PYTHON_VERSION 3.11.13
+ENV PYTHON_SHA256 8fb5f9fbc7609fa822cb31549884575db7fd9657cbffb89510b5d7975963a83a
 
 RUN set -eux; \
 	\
diff --git a/3.12/alpine3.21/Dockerfile b/3.12/alpine3.21/Dockerfile
index 9b2b2fe71..dc716a395 100644
--- a/3.12/alpine3.21/Dockerfile
+++ b/3.12/alpine3.21/Dockerfile
@@ -22,8 +22,8 @@ RUN set -eux; \
 	;
 
 ENV GPG_KEY 7169605F62C751356D054A26A821E680E5FA6305
-ENV PYTHON_VERSION 3.12.10
-ENV PYTHON_SHA256 07ab697474595e06f06647417d3c7fa97ded07afc1a7e4454c5639919b46eaea
+ENV PYTHON_VERSION 3.12.11
+ENV PYTHON_SHA256 c30bb24b7f1e9a19b11b55a546434f74e739bb4c271a3e3a80ff4380d49f7adb
 
 RUN set -eux; \
 	\
diff --git a/3.12/alpine3.20/Dockerfile b/3.12/alpine3.22/Dockerfile
similarity index 97%
rename from 3.12/alpine3.20/Dockerfile
rename to 3.12/alpine3.22/Dockerfile
index 9519e47a9..e9346935b 100644
--- a/3.12/alpine3.20/Dockerfile
+++ b/3.12/alpine3.22/Dockerfile
@@ -4,7 +4,7 @@
 # PLEASE DO NOT EDIT IT DIRECTLY.
 #
 
-FROM alpine:3.20
+FROM alpine:3.22
 
 # ensure local python is preferred over distribution python
 ENV PATH /usr/local/bin:$PATH
@@ -22,8 +22,8 @@ RUN set -eux; \
 	;
 
 ENV GPG_KEY 7169605F62C751356D054A26A821E680E5FA6305
-ENV PYTHON_VERSION 3.12.10
-ENV PYTHON_SHA256 07ab697474595e06f06647417d3c7fa97ded07afc1a7e4454c5639919b46eaea
+ENV PYTHON_VERSION 3.12.11
+ENV PYTHON_SHA256 c30bb24b7f1e9a19b11b55a546434f74e739bb4c271a3e3a80ff4380d49f7adb
 
 RUN set -eux; \
 	\
diff --git a/3.12/bookworm/Dockerfile b/3.12/bookworm/Dockerfile
index 3c5dadda8..6e1d059e7 100644
--- a/3.12/bookworm/Dockerfile
+++ b/3.12/bookworm/Dockerfile
@@ -25,8 +25,8 @@ RUN set -eux; \
 	rm -rf /var/lib/apt/lists/*
 
 ENV GPG_KEY 7169605F62C751356D054A26A821E680E5FA6305
-ENV PYTHON_VERSION 3.12.10
-ENV PYTHON_SHA256 07ab697474595e06f06647417d3c7fa97ded07afc1a7e4454c5639919b46eaea
+ENV PYTHON_VERSION 3.12.11
+ENV PYTHON_SHA256 c30bb24b7f1e9a19b11b55a546434f74e739bb4c271a3e3a80ff4380d49f7adb
 
 RUN set -eux; \
 	\
diff --git a/3.12/bullseye/Dockerfile b/3.12/bullseye/Dockerfile
index db27cbbe8..b50a5ca4b 100644
--- a/3.12/bullseye/Dockerfile
+++ b/3.12/bullseye/Dockerfile
@@ -25,8 +25,8 @@ RUN set -eux; \
 	rm -rf /var/lib/apt/lists/*
 
 ENV GPG_KEY 7169605F62C751356D054A26A821E680E5FA6305
-ENV PYTHON_VERSION 3.12.10
-ENV PYTHON_SHA256 07ab697474595e06f06647417d3c7fa97ded07afc1a7e4454c5639919b46eaea
+ENV PYTHON_VERSION 3.12.11
+ENV PYTHON_SHA256 c30bb24b7f1e9a19b11b55a546434f74e739bb4c271a3e3a80ff4380d49f7adb
 
 RUN set -eux; \
 	\
diff --git a/3.12/slim-bookworm/Dockerfile b/3.12/slim-bookworm/Dockerfile
index f476f736a..17d0d4871 100644
--- a/3.12/slim-bookworm/Dockerfile
+++ b/3.12/slim-bookworm/Dockerfile
@@ -25,8 +25,8 @@ RUN set -eux; \
 	rm -rf /var/lib/apt/lists/*
 
 ENV GPG_KEY 7169605F62C751356D054A26A821E680E5FA6305
-ENV PYTHON_VERSION 3.12.10
-ENV PYTHON_SHA256 07ab697474595e06f06647417d3c7fa97ded07afc1a7e4454c5639919b46eaea
+ENV PYTHON_VERSION 3.12.11
+ENV PYTHON_SHA256 c30bb24b7f1e9a19b11b55a546434f74e739bb4c271a3e3a80ff4380d49f7adb
 
 RUN set -eux; \
 	\
diff --git a/3.12/slim-bullseye/Dockerfile b/3.12/slim-bullseye/Dockerfile
index 1e5f18c20..5dd6eb97e 100644
--- a/3.12/slim-bullseye/Dockerfile
+++ b/3.12/slim-bullseye/Dockerfile
@@ -25,8 +25,8 @@ RUN set -eux; \
 	rm -rf /var/lib/apt/lists/*
 
 ENV GPG_KEY 7169605F62C751356D054A26A821E680E5FA6305
-ENV PYTHON_VERSION 3.12.10
-ENV PYTHON_SHA256 07ab697474595e06f06647417d3c7fa97ded07afc1a7e4454c5639919b46eaea
+ENV PYTHON_VERSION 3.12.11
+ENV PYTHON_SHA256 c30bb24b7f1e9a19b11b55a546434f74e739bb4c271a3e3a80ff4380d49f7adb
 
 RUN set -eux; \
 	\
diff --git a/3.12/windows/windowsservercore-1809/Dockerfile b/3.12/windows/windowsservercore-1809/Dockerfile
deleted file mode 100644
index aacfeb49e..000000000
--- a/3.12/windows/windowsservercore-1809/Dockerfile
+++ /dev/null
@@ -1,65 +0,0 @@
-#
-# NOTE: THIS DOCKERFILE IS GENERATED VIA "apply-templates.sh"
-#
-# PLEASE DO NOT EDIT IT DIRECTLY.
-#
-
-FROM mcr.microsoft.com/windows/servercore:1809
-
-SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
-
-# https://github.com/docker-library/python/pull/557
-ENV PYTHONIOENCODING UTF-8
-
-ENV PYTHON_VERSION 3.12.10
-ENV PYTHON_SHA256 67b5635e80ea51072b87941312d00ec8927c4db9ba18938f7ad2d27b328b95fb
-
-RUN $url = ('https://www.python.org/ftp/python/{0}/python-{1}-amd64.exe' -f ($env:PYTHON_VERSION -replace '[a-z]+[0-9]*$', ''), $env:PYTHON_VERSION); \
-	Write-Host ('Downloading {0} ...' -f $url); \
-	[Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12; \
-	Invoke-WebRequest -Uri $url -OutFile 'python.exe'; \
-	\
-	Write-Host ('Verifying sha256 ({0}) ...' -f $env:PYTHON_SHA256); \
-	if ((Get-FileHash python.exe -Algorithm sha256).Hash -ne $env:PYTHON_SHA256) { \
-		Write-Host 'FAILED!'; \
-		exit 1; \
-	}; \
-	\
-	Write-Host 'Installing ...'; \
-# https://docs.python.org/3/using/windows.html#installing-without-ui
-	$exitCode = (Start-Process python.exe -Wait -NoNewWindow -PassThru \
-		-ArgumentList @( \
-			'/quiet', \
-			'InstallAllUsers=1', \
-			'TargetDir=C:\Python', \
-			'PrependPath=1', \
-			'Shortcuts=0', \
-			'Include_doc=0', \
-			'Include_pip=1', \
-			'Include_test=0' \
-		) \
-	).ExitCode; \
-	if ($exitCode -ne 0) { \
-		Write-Host ('Running python installer failed with exit code: {0}' -f $exitCode); \
-		Get-ChildItem $env:TEMP | Sort-Object -Descending -Property LastWriteTime | Select-Object -First 1 | Get-Content; \
-		exit $exitCode; \
-	} \
-	\
-# 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; \
-	Remove-Item $env:TEMP/Python*.log -Force; \
-	\
-	$env:PYTHONDONTWRITEBYTECODE = '1'; \
-	\
-	Write-Host 'Verifying pip install ...'; \
-	pip --version; \
-	\
-	Write-Host 'Complete.'
-
-CMD ["python"]
diff --git a/3.12/windows/windowsservercore-ltsc2022/Dockerfile b/3.12/windows/windowsservercore-ltsc2022/Dockerfile
deleted file mode 100644
index f8f537a65..000000000
--- a/3.12/windows/windowsservercore-ltsc2022/Dockerfile
+++ /dev/null
@@ -1,65 +0,0 @@
-#
-# NOTE: THIS DOCKERFILE IS GENERATED VIA "apply-templates.sh"
-#
-# PLEASE DO NOT EDIT IT DIRECTLY.
-#
-
-FROM mcr.microsoft.com/windows/servercore:ltsc2022
-
-SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
-
-# https://github.com/docker-library/python/pull/557
-ENV PYTHONIOENCODING UTF-8
-
-ENV PYTHON_VERSION 3.12.10
-ENV PYTHON_SHA256 67b5635e80ea51072b87941312d00ec8927c4db9ba18938f7ad2d27b328b95fb
-
-RUN $url = ('https://www.python.org/ftp/python/{0}/python-{1}-amd64.exe' -f ($env:PYTHON_VERSION -replace '[a-z]+[0-9]*$', ''), $env:PYTHON_VERSION); \
-	Write-Host ('Downloading {0} ...' -f $url); \
-	[Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12; \
-	Invoke-WebRequest -Uri $url -OutFile 'python.exe'; \
-	\
-	Write-Host ('Verifying sha256 ({0}) ...' -f $env:PYTHON_SHA256); \
-	if ((Get-FileHash python.exe -Algorithm sha256).Hash -ne $env:PYTHON_SHA256) { \
-		Write-Host 'FAILED!'; \
-		exit 1; \
-	}; \
-	\
-	Write-Host 'Installing ...'; \
-# https://docs.python.org/3/using/windows.html#installing-without-ui
-	$exitCode = (Start-Process python.exe -Wait -NoNewWindow -PassThru \
-		-ArgumentList @( \
-			'/quiet', \
-			'InstallAllUsers=1', \
-			'TargetDir=C:\Python', \
-			'PrependPath=1', \
-			'Shortcuts=0', \
-			'Include_doc=0', \
-			'Include_pip=1', \
-			'Include_test=0' \
-		) \
-	).ExitCode; \
-	if ($exitCode -ne 0) { \
-		Write-Host ('Running python installer failed with exit code: {0}' -f $exitCode); \
-		Get-ChildItem $env:TEMP | Sort-Object -Descending -Property LastWriteTime | Select-Object -First 1 | Get-Content; \
-		exit $exitCode; \
-	} \
-	\
-# 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; \
-	Remove-Item $env:TEMP/Python*.log -Force; \
-	\
-	$env:PYTHONDONTWRITEBYTECODE = '1'; \
-	\
-	Write-Host 'Verifying pip install ...'; \
-	pip --version; \
-	\
-	Write-Host 'Complete.'
-
-CMD ["python"]
diff --git a/3.12/windows/windowsservercore-ltsc2025/Dockerfile b/3.12/windows/windowsservercore-ltsc2025/Dockerfile
deleted file mode 100644
index 6e2a0d13f..000000000
--- a/3.12/windows/windowsservercore-ltsc2025/Dockerfile
+++ /dev/null
@@ -1,65 +0,0 @@
-#
-# NOTE: THIS DOCKERFILE IS GENERATED VIA "apply-templates.sh"
-#
-# PLEASE DO NOT EDIT IT DIRECTLY.
-#
-
-FROM mcr.microsoft.com/windows/servercore:ltsc2025
-
-SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
-
-# https://github.com/docker-library/python/pull/557
-ENV PYTHONIOENCODING UTF-8
-
-ENV PYTHON_VERSION 3.12.10
-ENV PYTHON_SHA256 67b5635e80ea51072b87941312d00ec8927c4db9ba18938f7ad2d27b328b95fb
-
-RUN $url = ('https://www.python.org/ftp/python/{0}/python-{1}-amd64.exe' -f ($env:PYTHON_VERSION -replace '[a-z]+[0-9]*$', ''), $env:PYTHON_VERSION); \
-	Write-Host ('Downloading {0} ...' -f $url); \
-	[Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12; \
-	Invoke-WebRequest -Uri $url -OutFile 'python.exe'; \
-	\
-	Write-Host ('Verifying sha256 ({0}) ...' -f $env:PYTHON_SHA256); \
-	if ((Get-FileHash python.exe -Algorithm sha256).Hash -ne $env:PYTHON_SHA256) { \
-		Write-Host 'FAILED!'; \
-		exit 1; \
-	}; \
-	\
-	Write-Host 'Installing ...'; \
-# https://docs.python.org/3/using/windows.html#installing-without-ui
-	$exitCode = (Start-Process python.exe -Wait -NoNewWindow -PassThru \
-		-ArgumentList @( \
-			'/quiet', \
-			'InstallAllUsers=1', \
-			'TargetDir=C:\Python', \
-			'PrependPath=1', \
-			'Shortcuts=0', \
-			'Include_doc=0', \
-			'Include_pip=1', \
-			'Include_test=0' \
-		) \
-	).ExitCode; \
-	if ($exitCode -ne 0) { \
-		Write-Host ('Running python installer failed with exit code: {0}' -f $exitCode); \
-		Get-ChildItem $env:TEMP | Sort-Object -Descending -Property LastWriteTime | Select-Object -First 1 | Get-Content; \
-		exit $exitCode; \
-	} \
-	\
-# 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; \
-	Remove-Item $env:TEMP/Python*.log -Force; \
-	\
-	$env:PYTHONDONTWRITEBYTECODE = '1'; \
-	\
-	Write-Host 'Verifying pip install ...'; \
-	pip --version; \
-	\
-	Write-Host 'Complete.'
-
-CMD ["python"]
diff --git a/3.13/alpine3.21/Dockerfile b/3.13/alpine3.21/Dockerfile
index c289fda11..51bb4f4dd 100644
--- a/3.13/alpine3.21/Dockerfile
+++ b/3.13/alpine3.21/Dockerfile
@@ -17,8 +17,8 @@ RUN set -eux; \
 	;
 
 ENV GPG_KEY 7169605F62C751356D054A26A821E680E5FA6305
-ENV PYTHON_VERSION 3.13.3
-ENV PYTHON_SHA256 40f868bcbdeb8149a3149580bb9bfd407b3321cd48f0be631af955ac92c0e041
+ENV PYTHON_VERSION 3.13.5
+ENV PYTHON_SHA256 93e583f243454e6e9e4588ca2c2662206ad961659863277afcdb96801647d640
 
 RUN set -eux; \
 	\
diff --git a/3.13/alpine3.20/Dockerfile b/3.13/alpine3.22/Dockerfile
similarity index 97%
rename from 3.13/alpine3.20/Dockerfile
rename to 3.13/alpine3.22/Dockerfile
index c3b9eb310..e09ba23c6 100644
--- a/3.13/alpine3.20/Dockerfile
+++ b/3.13/alpine3.22/Dockerfile
@@ -4,7 +4,7 @@
 # PLEASE DO NOT EDIT IT DIRECTLY.
 #
 
-FROM alpine:3.20
+FROM alpine:3.22
 
 # ensure local python is preferred over distribution python
 ENV PATH /usr/local/bin:$PATH
@@ -17,8 +17,8 @@ RUN set -eux; \
 	;
 
 ENV GPG_KEY 7169605F62C751356D054A26A821E680E5FA6305
-ENV PYTHON_VERSION 3.13.3
-ENV PYTHON_SHA256 40f868bcbdeb8149a3149580bb9bfd407b3321cd48f0be631af955ac92c0e041
+ENV PYTHON_VERSION 3.13.5
+ENV PYTHON_SHA256 93e583f243454e6e9e4588ca2c2662206ad961659863277afcdb96801647d640
 
 RUN set -eux; \
 	\
diff --git a/3.13/bookworm/Dockerfile b/3.13/bookworm/Dockerfile
index 4a3f8a2b1..0e7a877df 100644
--- a/3.13/bookworm/Dockerfile
+++ b/3.13/bookworm/Dockerfile
@@ -20,8 +20,8 @@ RUN set -eux; \
 	rm -rf /var/lib/apt/lists/*
 
 ENV GPG_KEY 7169605F62C751356D054A26A821E680E5FA6305
-ENV PYTHON_VERSION 3.13.3
-ENV PYTHON_SHA256 40f868bcbdeb8149a3149580bb9bfd407b3321cd48f0be631af955ac92c0e041
+ENV PYTHON_VERSION 3.13.5
+ENV PYTHON_SHA256 93e583f243454e6e9e4588ca2c2662206ad961659863277afcdb96801647d640
 
 RUN set -eux; \
 	\
diff --git a/3.13/bullseye/Dockerfile b/3.13/bullseye/Dockerfile
index 1267fa3e6..727708bed 100644
--- a/3.13/bullseye/Dockerfile
+++ b/3.13/bullseye/Dockerfile
@@ -20,8 +20,8 @@ RUN set -eux; \
 	rm -rf /var/lib/apt/lists/*
 
 ENV GPG_KEY 7169605F62C751356D054A26A821E680E5FA6305
-ENV PYTHON_VERSION 3.13.3
-ENV PYTHON_SHA256 40f868bcbdeb8149a3149580bb9bfd407b3321cd48f0be631af955ac92c0e041
+ENV PYTHON_VERSION 3.13.5
+ENV PYTHON_SHA256 93e583f243454e6e9e4588ca2c2662206ad961659863277afcdb96801647d640
 
 RUN set -eux; \
 	\
diff --git a/3.13/slim-bookworm/Dockerfile b/3.13/slim-bookworm/Dockerfile
index 15a408ab7..7b83eeb0d 100644
--- a/3.13/slim-bookworm/Dockerfile
+++ b/3.13/slim-bookworm/Dockerfile
@@ -20,8 +20,8 @@ RUN set -eux; \
 	rm -rf /var/lib/apt/lists/*
 
 ENV GPG_KEY 7169605F62C751356D054A26A821E680E5FA6305
-ENV PYTHON_VERSION 3.13.3
-ENV PYTHON_SHA256 40f868bcbdeb8149a3149580bb9bfd407b3321cd48f0be631af955ac92c0e041
+ENV PYTHON_VERSION 3.13.5
+ENV PYTHON_SHA256 93e583f243454e6e9e4588ca2c2662206ad961659863277afcdb96801647d640
 
 RUN set -eux; \
 	\
diff --git a/3.13/slim-bullseye/Dockerfile b/3.13/slim-bullseye/Dockerfile
index 09ba3b8c2..6525ba94b 100644
--- a/3.13/slim-bullseye/Dockerfile
+++ b/3.13/slim-bullseye/Dockerfile
@@ -20,8 +20,8 @@ RUN set -eux; \
 	rm -rf /var/lib/apt/lists/*
 
 ENV GPG_KEY 7169605F62C751356D054A26A821E680E5FA6305
-ENV PYTHON_VERSION 3.13.3
-ENV PYTHON_SHA256 40f868bcbdeb8149a3149580bb9bfd407b3321cd48f0be631af955ac92c0e041
+ENV PYTHON_VERSION 3.13.5
+ENV PYTHON_SHA256 93e583f243454e6e9e4588ca2c2662206ad961659863277afcdb96801647d640
 
 RUN set -eux; \
 	\
diff --git a/3.13/windows/windowsservercore-1809/Dockerfile b/3.13/windows/windowsservercore-1809/Dockerfile
deleted file mode 100644
index 44eecbd41..000000000
--- a/3.13/windows/windowsservercore-1809/Dockerfile
+++ /dev/null
@@ -1,65 +0,0 @@
-#
-# NOTE: THIS DOCKERFILE IS GENERATED VIA "apply-templates.sh"
-#
-# PLEASE DO NOT EDIT IT DIRECTLY.
-#
-
-FROM mcr.microsoft.com/windows/servercore:1809
-
-SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
-
-# https://github.com/docker-library/python/pull/557
-ENV PYTHONIOENCODING UTF-8
-
-ENV PYTHON_VERSION 3.13.3
-ENV PYTHON_SHA256 698f2df46e1a3dd92f393458eea77bd94ef5ff21f0d5bf5cf676f3d28a9b4b6c
-
-RUN $url = ('https://www.python.org/ftp/python/{0}/python-{1}-amd64.exe' -f ($env:PYTHON_VERSION -replace '[a-z]+[0-9]*$', ''), $env:PYTHON_VERSION); \
-	Write-Host ('Downloading {0} ...' -f $url); \
-	[Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12; \
-	Invoke-WebRequest -Uri $url -OutFile 'python.exe'; \
-	\
-	Write-Host ('Verifying sha256 ({0}) ...' -f $env:PYTHON_SHA256); \
-	if ((Get-FileHash python.exe -Algorithm sha256).Hash -ne $env:PYTHON_SHA256) { \
-		Write-Host 'FAILED!'; \
-		exit 1; \
-	}; \
-	\
-	Write-Host 'Installing ...'; \
-# https://docs.python.org/3/using/windows.html#installing-without-ui
-	$exitCode = (Start-Process python.exe -Wait -NoNewWindow -PassThru \
-		-ArgumentList @( \
-			'/quiet', \
-			'InstallAllUsers=1', \
-			'TargetDir=C:\Python', \
-			'PrependPath=1', \
-			'Shortcuts=0', \
-			'Include_doc=0', \
-			'Include_pip=1', \
-			'Include_test=0' \
-		) \
-	).ExitCode; \
-	if ($exitCode -ne 0) { \
-		Write-Host ('Running python installer failed with exit code: {0}' -f $exitCode); \
-		Get-ChildItem $env:TEMP | Sort-Object -Descending -Property LastWriteTime | Select-Object -First 1 | Get-Content; \
-		exit $exitCode; \
-	} \
-	\
-# 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; \
-	Remove-Item $env:TEMP/Python*.log -Force; \
-	\
-	$env:PYTHONDONTWRITEBYTECODE = '1'; \
-	\
-	Write-Host 'Verifying pip install ...'; \
-	pip --version; \
-	\
-	Write-Host 'Complete.'
-
-CMD ["python"]
diff --git a/3.13/windows/windowsservercore-ltsc2022/Dockerfile b/3.13/windows/windowsservercore-ltsc2022/Dockerfile
index fd81d6410..fb7ad9eb4 100644
--- a/3.13/windows/windowsservercore-ltsc2022/Dockerfile
+++ b/3.13/windows/windowsservercore-ltsc2022/Dockerfile
@@ -11,8 +11,8 @@ SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPref
 # https://github.com/docker-library/python/pull/557
 ENV PYTHONIOENCODING UTF-8
 
-ENV PYTHON_VERSION 3.13.3
-ENV PYTHON_SHA256 698f2df46e1a3dd92f393458eea77bd94ef5ff21f0d5bf5cf676f3d28a9b4b6c
+ENV PYTHON_VERSION 3.13.5
+ENV PYTHON_SHA256 c1cb40978b28f696b111c36034a1bdeda17d25e35c74a08ef5e5ff405a63fc20
 
 RUN $url = ('https://www.python.org/ftp/python/{0}/python-{1}-amd64.exe' -f ($env:PYTHON_VERSION -replace '[a-z]+[0-9]*$', ''), $env:PYTHON_VERSION); \
 	Write-Host ('Downloading {0} ...' -f $url); \
diff --git a/3.13/windows/windowsservercore-ltsc2025/Dockerfile b/3.13/windows/windowsservercore-ltsc2025/Dockerfile
index 2f1c1813c..95108cdde 100644
--- a/3.13/windows/windowsservercore-ltsc2025/Dockerfile
+++ b/3.13/windows/windowsservercore-ltsc2025/Dockerfile
@@ -11,8 +11,8 @@ SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPref
 # https://github.com/docker-library/python/pull/557
 ENV PYTHONIOENCODING UTF-8
 
-ENV PYTHON_VERSION 3.13.3
-ENV PYTHON_SHA256 698f2df46e1a3dd92f393458eea77bd94ef5ff21f0d5bf5cf676f3d28a9b4b6c
+ENV PYTHON_VERSION 3.13.5
+ENV PYTHON_SHA256 c1cb40978b28f696b111c36034a1bdeda17d25e35c74a08ef5e5ff405a63fc20
 
 RUN $url = ('https://www.python.org/ftp/python/{0}/python-{1}-amd64.exe' -f ($env:PYTHON_VERSION -replace '[a-z]+[0-9]*$', ''), $env:PYTHON_VERSION); \
 	Write-Host ('Downloading {0} ...' -f $url); \
diff --git a/3.14-rc/alpine3.21/Dockerfile b/3.14-rc/alpine3.21/Dockerfile
index 39b392e95..d11de6427 100644
--- a/3.14-rc/alpine3.21/Dockerfile
+++ b/3.14-rc/alpine3.21/Dockerfile
@@ -16,8 +16,8 @@ RUN set -eux; \
 		tzdata \
 	;
 
-ENV PYTHON_VERSION 3.14.0b1
-ENV PYTHON_SHA256 2ddd30a77c9f62e065ce648664a254b9b0c011bcdaa8c1c2787087e644cbeb39
+ENV PYTHON_VERSION 3.14.0b4
+ENV PYTHON_SHA256 15e123e056abebba6de5e73cfa304459a8c82cafa85d4fc7fc6de80e6a3e1b39
 
 RUN set -eux; \
 	\
diff --git a/3.14-rc/alpine3.20/Dockerfile b/3.14-rc/alpine3.22/Dockerfile
similarity index 96%
rename from 3.14-rc/alpine3.20/Dockerfile
rename to 3.14-rc/alpine3.22/Dockerfile
index 832c5e59b..b15f619ba 100644
--- a/3.14-rc/alpine3.20/Dockerfile
+++ b/3.14-rc/alpine3.22/Dockerfile
@@ -4,7 +4,7 @@
 # PLEASE DO NOT EDIT IT DIRECTLY.
 #
 
-FROM alpine:3.20
+FROM alpine:3.22
 
 # ensure local python is preferred over distribution python
 ENV PATH /usr/local/bin:$PATH
@@ -16,8 +16,8 @@ RUN set -eux; \
 		tzdata \
 	;
 
-ENV PYTHON_VERSION 3.14.0b1
-ENV PYTHON_SHA256 2ddd30a77c9f62e065ce648664a254b9b0c011bcdaa8c1c2787087e644cbeb39
+ENV PYTHON_VERSION 3.14.0b4
+ENV PYTHON_SHA256 15e123e056abebba6de5e73cfa304459a8c82cafa85d4fc7fc6de80e6a3e1b39
 
 RUN set -eux; \
 	\
diff --git a/3.14-rc/bookworm/Dockerfile b/3.14-rc/bookworm/Dockerfile
index b6b99382a..3e041b0df 100644
--- a/3.14-rc/bookworm/Dockerfile
+++ b/3.14-rc/bookworm/Dockerfile
@@ -19,8 +19,8 @@ RUN set -eux; \
 	; \
 	rm -rf /var/lib/apt/lists/*
 
-ENV PYTHON_VERSION 3.14.0b1
-ENV PYTHON_SHA256 2ddd30a77c9f62e065ce648664a254b9b0c011bcdaa8c1c2787087e644cbeb39
+ENV PYTHON_VERSION 3.14.0b4
+ENV PYTHON_SHA256 15e123e056abebba6de5e73cfa304459a8c82cafa85d4fc7fc6de80e6a3e1b39
 
 RUN set -eux; \
 	\
diff --git a/3.14-rc/bullseye/Dockerfile b/3.14-rc/bullseye/Dockerfile
index 34d0fc2a7..95f076100 100644
--- a/3.14-rc/bullseye/Dockerfile
+++ b/3.14-rc/bullseye/Dockerfile
@@ -19,8 +19,8 @@ RUN set -eux; \
 	; \
 	rm -rf /var/lib/apt/lists/*
 
-ENV PYTHON_VERSION 3.14.0b1
-ENV PYTHON_SHA256 2ddd30a77c9f62e065ce648664a254b9b0c011bcdaa8c1c2787087e644cbeb39
+ENV PYTHON_VERSION 3.14.0b4
+ENV PYTHON_SHA256 15e123e056abebba6de5e73cfa304459a8c82cafa85d4fc7fc6de80e6a3e1b39
 
 RUN set -eux; \
 	\
diff --git a/3.14-rc/slim-bookworm/Dockerfile b/3.14-rc/slim-bookworm/Dockerfile
index ff44902a3..1df468d7f 100644
--- a/3.14-rc/slim-bookworm/Dockerfile
+++ b/3.14-rc/slim-bookworm/Dockerfile
@@ -19,8 +19,8 @@ RUN set -eux; \
 	; \
 	rm -rf /var/lib/apt/lists/*
 
-ENV PYTHON_VERSION 3.14.0b1
-ENV PYTHON_SHA256 2ddd30a77c9f62e065ce648664a254b9b0c011bcdaa8c1c2787087e644cbeb39
+ENV PYTHON_VERSION 3.14.0b4
+ENV PYTHON_SHA256 15e123e056abebba6de5e73cfa304459a8c82cafa85d4fc7fc6de80e6a3e1b39
 
 RUN set -eux; \
 	\
diff --git a/3.14-rc/slim-bullseye/Dockerfile b/3.14-rc/slim-bullseye/Dockerfile
index 9cd8ab9de..f39497833 100644
--- a/3.14-rc/slim-bullseye/Dockerfile
+++ b/3.14-rc/slim-bullseye/Dockerfile
@@ -19,8 +19,8 @@ RUN set -eux; \
 	; \
 	rm -rf /var/lib/apt/lists/*
 
-ENV PYTHON_VERSION 3.14.0b1
-ENV PYTHON_SHA256 2ddd30a77c9f62e065ce648664a254b9b0c011bcdaa8c1c2787087e644cbeb39
+ENV PYTHON_VERSION 3.14.0b4
+ENV PYTHON_SHA256 15e123e056abebba6de5e73cfa304459a8c82cafa85d4fc7fc6de80e6a3e1b39
 
 RUN set -eux; \
 	\
diff --git a/3.14-rc/windows/windowsservercore-1809/Dockerfile b/3.14-rc/windows/windowsservercore-1809/Dockerfile
deleted file mode 100644
index 61a8ce521..000000000
--- a/3.14-rc/windows/windowsservercore-1809/Dockerfile
+++ /dev/null
@@ -1,72 +0,0 @@
-#
-# NOTE: THIS DOCKERFILE IS GENERATED VIA "apply-templates.sh"
-#
-# PLEASE DO NOT EDIT IT DIRECTLY.
-#
-
-FROM mcr.microsoft.com/windows/servercore:1809
-
-SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
-
-# https://github.com/docker-library/python/pull/557
-ENV PYTHONIOENCODING UTF-8
-
-ENV PYTHON_VERSION 3.14.0b1
-ENV PYTHON_SHA256 a878026c12b1a606d02f5bbf3ed65aa780ee8272964b8f95d8348ffa2d6ca096
-
-RUN $url = ('https://www.python.org/ftp/python/{0}/python-{1}-amd64.exe' -f ($env:PYTHON_VERSION -replace '[a-z]+[0-9]*$', ''), $env:PYTHON_VERSION); \
-	Write-Host ('Downloading {0} ...' -f $url); \
-	[Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12; \
-	Invoke-WebRequest -Uri $url -OutFile 'python.exe'; \
-	\
-	Write-Host ('Verifying sha256 ({0}) ...' -f $env:PYTHON_SHA256); \
-	if ((Get-FileHash python.exe -Algorithm sha256).Hash -ne $env:PYTHON_SHA256) { \
-		Write-Host 'FAILED!'; \
-		exit 1; \
-	}; \
-	\
-	Write-Host 'Installing ...'; \
-# https://docs.python.org/3/using/windows.html#installing-without-ui
-	$exitCode = (Start-Process python.exe -Wait -NoNewWindow -PassThru \
-		-ArgumentList @( \
-			'/quiet', \
-			'InstallAllUsers=1', \
-			'TargetDir=C:\Python', \
-			'PrependPath=1', \
-			'Shortcuts=0', \
-			'Include_doc=0', \
-			'Include_pip=1', \
-			'Include_test=0' \
-		) \
-	).ExitCode; \
-	if ($exitCode -ne 0) { \
-		Write-Host ('Running python installer failed with exit code: {0}' -f $exitCode); \
-		Get-ChildItem $env:TEMP | Sort-Object -Descending -Property LastWriteTime | Select-Object -First 1 | Get-Content; \
-		exit $exitCode; \
-	} \
-	\
-# 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; \
-	Remove-Item $env:TEMP/Python*.log -Force; \
-	\
-	$env:PYTHONDONTWRITEBYTECODE = '1'; \
-	\
-	Write-Host 'Reinstalling pip to workaround a bug ...'; \
-	# https://github.com/python/cpython/issues/133626
-	# clean up broken pip install
-	Remove-Item -Recurse C:\Python\Lib\site-packages\pip*; \
-	# install pip as pip.exe
-	python -m ensurepip --default-pip -vvv; \
-	\
-	Write-Host 'Verifying pip install ...'; \
-	pip --version; \
-	\
-	Write-Host 'Complete.'
-
-CMD ["python"]
diff --git a/3.14-rc/windows/windowsservercore-ltsc2022/Dockerfile b/3.14-rc/windows/windowsservercore-ltsc2022/Dockerfile
index 75ffda7b0..26953f626 100644
--- a/3.14-rc/windows/windowsservercore-ltsc2022/Dockerfile
+++ b/3.14-rc/windows/windowsservercore-ltsc2022/Dockerfile
@@ -11,8 +11,8 @@ SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPref
 # https://github.com/docker-library/python/pull/557
 ENV PYTHONIOENCODING UTF-8
 
-ENV PYTHON_VERSION 3.14.0b1
-ENV PYTHON_SHA256 a878026c12b1a606d02f5bbf3ed65aa780ee8272964b8f95d8348ffa2d6ca096
+ENV PYTHON_VERSION 3.14.0b4
+ENV PYTHON_SHA256 0f8bbdfd7d1f99a0b8df86278a99e4c0248582b93e9d7d4d6e63e787098dad00
 
 RUN $url = ('https://www.python.org/ftp/python/{0}/python-{1}-amd64.exe' -f ($env:PYTHON_VERSION -replace '[a-z]+[0-9]*$', ''), $env:PYTHON_VERSION); \
 	Write-Host ('Downloading {0} ...' -f $url); \
@@ -57,13 +57,6 @@ RUN $url = ('https://www.python.org/ftp/python/{0}/python-{1}-amd64.exe' -f ($en
 	\
 	$env:PYTHONDONTWRITEBYTECODE = '1'; \
 	\
-	Write-Host 'Reinstalling pip to workaround a bug ...'; \
-	# https://github.com/python/cpython/issues/133626
-	# clean up broken pip install
-	Remove-Item -Recurse C:\Python\Lib\site-packages\pip*; \
-	# install pip as pip.exe
-	python -m ensurepip --default-pip -vvv; \
-	\
 	Write-Host 'Verifying pip install ...'; \
 	pip --version; \
 	\
diff --git a/3.14-rc/windows/windowsservercore-ltsc2025/Dockerfile b/3.14-rc/windows/windowsservercore-ltsc2025/Dockerfile
index ffc2b344d..3e6907a27 100644
--- a/3.14-rc/windows/windowsservercore-ltsc2025/Dockerfile
+++ b/3.14-rc/windows/windowsservercore-ltsc2025/Dockerfile
@@ -11,8 +11,8 @@ SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPref
 # https://github.com/docker-library/python/pull/557
 ENV PYTHONIOENCODING UTF-8
 
-ENV PYTHON_VERSION 3.14.0b1
-ENV PYTHON_SHA256 a878026c12b1a606d02f5bbf3ed65aa780ee8272964b8f95d8348ffa2d6ca096
+ENV PYTHON_VERSION 3.14.0b4
+ENV PYTHON_SHA256 0f8bbdfd7d1f99a0b8df86278a99e4c0248582b93e9d7d4d6e63e787098dad00
 
 RUN $url = ('https://www.python.org/ftp/python/{0}/python-{1}-amd64.exe' -f ($env:PYTHON_VERSION -replace '[a-z]+[0-9]*$', ''), $env:PYTHON_VERSION); \
 	Write-Host ('Downloading {0} ...' -f $url); \
@@ -57,13 +57,6 @@ RUN $url = ('https://www.python.org/ftp/python/{0}/python-{1}-amd64.exe' -f ($en
 	\
 	$env:PYTHONDONTWRITEBYTECODE = '1'; \
 	\
-	Write-Host 'Reinstalling pip to workaround a bug ...'; \
-	# https://github.com/python/cpython/issues/133626
-	# clean up broken pip install
-	Remove-Item -Recurse C:\Python\Lib\site-packages\pip*; \
-	# install pip as pip.exe
-	python -m ensurepip --default-pip -vvv; \
-	\
 	Write-Host 'Verifying pip install ...'; \
 	pip --version; \
 	\
diff --git a/3.9/alpine3.21/Dockerfile b/3.9/alpine3.21/Dockerfile
index a5f0d963f..ec25bdb83 100644
--- a/3.9/alpine3.21/Dockerfile
+++ b/3.9/alpine3.21/Dockerfile
@@ -22,8 +22,8 @@ RUN set -eux; \
 	;
 
 ENV GPG_KEY E3FF2839C048B25C084DEBE9B26995E310250568
-ENV PYTHON_VERSION 3.9.22
-ENV PYTHON_SHA256 8c136d199d3637a1fce98a16adc809c1d83c922d02d41f3614b34f8b6e7d38ec
+ENV PYTHON_VERSION 3.9.23
+ENV PYTHON_SHA256 61a42919e13d539f7673cf11d1c404380e28e540510860b9d242196e165709c9
 
 RUN set -eux; \
 	\
diff --git a/3.9/alpine3.20/Dockerfile b/3.9/alpine3.22/Dockerfile
similarity index 96%
rename from 3.9/alpine3.20/Dockerfile
rename to 3.9/alpine3.22/Dockerfile
index 35e8fef9c..242d08b09 100644
--- a/3.9/alpine3.20/Dockerfile
+++ b/3.9/alpine3.22/Dockerfile
@@ -4,7 +4,7 @@
 # PLEASE DO NOT EDIT IT DIRECTLY.
 #
 
-FROM alpine:3.20
+FROM alpine:3.22
 
 # ensure local python is preferred over distribution python
 ENV PATH /usr/local/bin:$PATH
@@ -22,8 +22,8 @@ RUN set -eux; \
 	;
 
 ENV GPG_KEY E3FF2839C048B25C084DEBE9B26995E310250568
-ENV PYTHON_VERSION 3.9.22
-ENV PYTHON_SHA256 8c136d199d3637a1fce98a16adc809c1d83c922d02d41f3614b34f8b6e7d38ec
+ENV PYTHON_VERSION 3.9.23
+ENV PYTHON_SHA256 61a42919e13d539f7673cf11d1c404380e28e540510860b9d242196e165709c9
 
 RUN set -eux; \
 	\
diff --git a/3.9/bookworm/Dockerfile b/3.9/bookworm/Dockerfile
index 98de1f753..6a6de6111 100644
--- a/3.9/bookworm/Dockerfile
+++ b/3.9/bookworm/Dockerfile
@@ -25,8 +25,8 @@ RUN set -eux; \
 	rm -rf /var/lib/apt/lists/*
 
 ENV GPG_KEY E3FF2839C048B25C084DEBE9B26995E310250568
-ENV PYTHON_VERSION 3.9.22
-ENV PYTHON_SHA256 8c136d199d3637a1fce98a16adc809c1d83c922d02d41f3614b34f8b6e7d38ec
+ENV PYTHON_VERSION 3.9.23
+ENV PYTHON_SHA256 61a42919e13d539f7673cf11d1c404380e28e540510860b9d242196e165709c9
 
 RUN set -eux; \
 	\
diff --git a/3.9/bullseye/Dockerfile b/3.9/bullseye/Dockerfile
index afc057b96..93ee7089e 100644
--- a/3.9/bullseye/Dockerfile
+++ b/3.9/bullseye/Dockerfile
@@ -25,8 +25,8 @@ RUN set -eux; \
 	rm -rf /var/lib/apt/lists/*
 
 ENV GPG_KEY E3FF2839C048B25C084DEBE9B26995E310250568
-ENV PYTHON_VERSION 3.9.22
-ENV PYTHON_SHA256 8c136d199d3637a1fce98a16adc809c1d83c922d02d41f3614b34f8b6e7d38ec
+ENV PYTHON_VERSION 3.9.23
+ENV PYTHON_SHA256 61a42919e13d539f7673cf11d1c404380e28e540510860b9d242196e165709c9
 
 RUN set -eux; \
 	\
diff --git a/3.9/slim-bookworm/Dockerfile b/3.9/slim-bookworm/Dockerfile
index 19b1b68ce..c79cc6009 100644
--- a/3.9/slim-bookworm/Dockerfile
+++ b/3.9/slim-bookworm/Dockerfile
@@ -25,8 +25,8 @@ RUN set -eux; \
 	rm -rf /var/lib/apt/lists/*
 
 ENV GPG_KEY E3FF2839C048B25C084DEBE9B26995E310250568
-ENV PYTHON_VERSION 3.9.22
-ENV PYTHON_SHA256 8c136d199d3637a1fce98a16adc809c1d83c922d02d41f3614b34f8b6e7d38ec
+ENV PYTHON_VERSION 3.9.23
+ENV PYTHON_SHA256 61a42919e13d539f7673cf11d1c404380e28e540510860b9d242196e165709c9
 
 RUN set -eux; \
 	\
diff --git a/3.9/slim-bullseye/Dockerfile b/3.9/slim-bullseye/Dockerfile
index ed73ba93a..27ecb5b30 100644
--- a/3.9/slim-bullseye/Dockerfile
+++ b/3.9/slim-bullseye/Dockerfile
@@ -25,8 +25,8 @@ RUN set -eux; \
 	rm -rf /var/lib/apt/lists/*
 
 ENV GPG_KEY E3FF2839C048B25C084DEBE9B26995E310250568
-ENV PYTHON_VERSION 3.9.22
-ENV PYTHON_SHA256 8c136d199d3637a1fce98a16adc809c1d83c922d02d41f3614b34f8b6e7d38ec
+ENV PYTHON_VERSION 3.9.23
+ENV PYTHON_SHA256 61a42919e13d539f7673cf11d1c404380e28e540510860b9d242196e165709c9
 
 RUN set -eux; \
 	\
diff --git a/versions.json b/versions.json
index a6141223d..a6a698019 100644
--- a/versions.json
+++ b/versions.json
@@ -2,7 +2,7 @@
   "3.10": {
     "checksums": {
       "source": {
-        "sha256": "4c68050f049d1b4ac5aadd0df5f27941c0350d2a9e7ab0907ee5eb5225d9d6b0"
+        "sha256": "ae665bc678abd9ab6a6e1573d2481625a53719bc517e9a634ed2b9fefae3817f"
       }
     },
     "setuptools": {
@@ -13,15 +13,15 @@
       "slim-bookworm",
       "bullseye",
       "slim-bullseye",
-      "alpine3.21",
-      "alpine3.20"
+      "alpine3.22",
+      "alpine3.21"
     ],
-    "version": "3.10.17"
+    "version": "3.10.18"
   },
   "3.11": {
     "checksums": {
       "source": {
-        "sha256": "849da87af4df137710c1796e276a955f7a85c9f971081067c8f565d15c352a09"
+        "sha256": "8fb5f9fbc7609fa822cb31549884575db7fd9657cbffb89510b5d7975963a83a"
       }
     },
     "setuptools": {
@@ -32,18 +32,15 @@
       "slim-bookworm",
       "bullseye",
       "slim-bullseye",
-      "alpine3.21",
-      "alpine3.20"
+      "alpine3.22",
+      "alpine3.21"
     ],
-    "version": "3.11.12"
+    "version": "3.11.13"
   },
   "3.12": {
     "checksums": {
       "source": {
-        "sha256": "07ab697474595e06f06647417d3c7fa97ded07afc1a7e4454c5639919b46eaea"
-      },
-      "windows": {
-        "sha256": "67b5635e80ea51072b87941312d00ec8927c4db9ba18938f7ad2d27b328b95fb"
+        "sha256": "c30bb24b7f1e9a19b11b55a546434f74e739bb4c271a3e3a80ff4380d49f7adb"
       }
     },
     "variants": [
@@ -51,21 +48,18 @@
       "slim-bookworm",
       "bullseye",
       "slim-bullseye",
-      "alpine3.21",
-      "alpine3.20",
-      "windows/windowsservercore-ltsc2025",
-      "windows/windowsservercore-ltsc2022",
-      "windows/windowsservercore-1809"
+      "alpine3.22",
+      "alpine3.21"
     ],
-    "version": "3.12.10"
+    "version": "3.12.11"
   },
   "3.13": {
     "checksums": {
       "source": {
-        "sha256": "40f868bcbdeb8149a3149580bb9bfd407b3321cd48f0be631af955ac92c0e041"
+        "sha256": "93e583f243454e6e9e4588ca2c2662206ad961659863277afcdb96801647d640"
       },
       "windows": {
-        "sha256": "698f2df46e1a3dd92f393458eea77bd94ef5ff21f0d5bf5cf676f3d28a9b4b6c"
+        "sha256": "c1cb40978b28f696b111c36034a1bdeda17d25e35c74a08ef5e5ff405a63fc20"
       }
     },
     "variants": [
@@ -73,21 +67,20 @@
       "slim-bookworm",
       "bullseye",
       "slim-bullseye",
+      "alpine3.22",
       "alpine3.21",
-      "alpine3.20",
       "windows/windowsservercore-ltsc2025",
-      "windows/windowsservercore-ltsc2022",
-      "windows/windowsservercore-1809"
+      "windows/windowsservercore-ltsc2022"
     ],
-    "version": "3.13.3"
+    "version": "3.13.5"
   },
   "3.14-rc": {
     "checksums": {
       "source": {
-        "sha256": "2ddd30a77c9f62e065ce648664a254b9b0c011bcdaa8c1c2787087e644cbeb39"
+        "sha256": "15e123e056abebba6de5e73cfa304459a8c82cafa85d4fc7fc6de80e6a3e1b39"
       },
       "windows": {
-        "sha256": "a878026c12b1a606d02f5bbf3ed65aa780ee8272964b8f95d8348ffa2d6ca096"
+        "sha256": "0f8bbdfd7d1f99a0b8df86278a99e4c0248582b93e9d7d4d6e63e787098dad00"
       }
     },
     "variants": [
@@ -95,18 +88,17 @@
       "slim-bookworm",
       "bullseye",
       "slim-bullseye",
+      "alpine3.22",
       "alpine3.21",
-      "alpine3.20",
       "windows/windowsservercore-ltsc2025",
-      "windows/windowsservercore-ltsc2022",
-      "windows/windowsservercore-1809"
+      "windows/windowsservercore-ltsc2022"
     ],
-    "version": "3.14.0b1"
+    "version": "3.14.0b4"
   },
   "3.9": {
     "checksums": {
       "source": {
-        "sha256": "8c136d199d3637a1fce98a16adc809c1d83c922d02d41f3614b34f8b6e7d38ec"
+        "sha256": "61a42919e13d539f7673cf11d1c404380e28e540510860b9d242196e165709c9"
       }
     },
     "setuptools": {
@@ -117,9 +109,9 @@
       "slim-bookworm",
       "bullseye",
       "slim-bullseye",
-      "alpine3.21",
-      "alpine3.20"
+      "alpine3.22",
+      "alpine3.21"
     ],
-    "version": "3.9.22"
+    "version": "3.9.23"
   }
 }
diff --git a/versions.sh b/versions.sh
index f574d65d2..d4ac179b8 100755
--- a/versions.sh
+++ b/versions.sh
@@ -200,15 +200,14 @@ for version in "${versions[@]}"; do
 					empty
 				| ., "slim-" + .), # https://github.com/docker-library/ruby/pull/142#issuecomment-320012893
 				(
+					"3.22",
 					"3.21",
-					"3.20",
 					empty
 				| "alpine" + .),
 				if env.hasWindows != "" then
 					(
 						"ltsc2025",
 						"ltsc2022",
-						"1809",
 						empty
 					| "windows/windowsservercore-" + .)
 				else empty end