diff --git a/2.7/windows/windowsservercore-ltsc2025/Dockerfile b/2.7/windows/windowsservercore-ltsc2025/Dockerfile
new file mode 100644
index 0000000..7641ed9
--- /dev/null
+++ b/2.7/windows/windowsservercore-ltsc2025/Dockerfile
@@ -0,0 +1,136 @@
+#
+# NOTE: THIS DOCKERFILE IS GENERATED VIA "apply-templates.sh"
+#
+# PLEASE DO NOT EDIT IT DIRECTLY.
+#
+
+FROM mcr.microsoft.com/windows/servercore:ltsc2025
+
+# $ProgressPreference: https://github.com/PowerShell/PowerShell/issues/2138#issuecomment-251261324
+SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
+
+# https://github.com/docker-library/python/issues/147
+ENV PYTHONIOENCODING UTF-8
+
+# PATH isn't actually set in the Docker image, so we have to set it from within the container
+RUN $newPath = ('C:\pypy;C:\pypy\Scripts;{0}' -f $env:PATH); \
+	Write-Host ('Updating PATH: {0}' -f $newPath); \
+	[Environment]::SetEnvironmentVariable('PATH', $newPath, [EnvironmentVariableTarget]::Machine); \
+	Write-Host 'Complete.'
+# doing this first to share cache across versions more aggressively
+
+# install Microsoft Visual C++ Redistributable
+RUN $url = 'https://download.microsoft.com/download/6/A/A/6AA4EDFF-645B-48C5-81CC-ED5963AEAD48/vc_redist.x64.exe'; \
+	Write-Host ('Downloading {0} ...' -f $url); \
+	Invoke-WebRequest -Uri $url -OutFile 'vc.exe'; \
+	\
+	$sha256 = 'da66717784c192f1004e856bbcf7b3e13b7bf3ea45932c48e4c9b9a50ca80965'; \
+	Write-Host ('Verifying sha256 ({0}) ...' -f $sha256); \
+	if ((Get-FileHash vc.exe -Algorithm sha256).Hash -ne $sha256) { \
+		Write-Host 'FAILED!'; \
+		exit 1; \
+	}; \
+	\
+	Write-Host 'Installing ...'; \
+	Start-Process \
+		-NoNewWindow \
+		-Wait \
+		-FilePath .\vc.exe \
+		-ArgumentList @( \
+			'/install', \
+			'/quiet', \
+			'/norestart' \
+		); \
+	\
+	Write-Host 'Removing ...'; \
+	Remove-Item vc.exe -Force; \
+	\
+	Write-Host 'Complete.'
+
+# Python 2.7.18
+ENV PYPY_VERSION 7.3.17
+
+RUN $url = 'https://downloads.python.org/pypy/pypy2.7-v7.3.17-win64.zip'; \
+	Write-Host ('Downloading {0} ...' -f $url); \
+	Invoke-WebRequest -Uri $url -OutFile 'pypy.zip'; \
+	\
+	$sha256 = '2ce2f4c205819902ee3ea2e80f8fc9ae9b18647bcfc8046ba83fe46b4139f734'; \
+	Write-Host ('Verifying sha256 ({0}) ...' -f $sha256); \
+	if ((Get-FileHash pypy.zip -Algorithm sha256).Hash -ne $sha256) { \
+		Write-Host 'FAILED!'; \
+		exit 1; \
+	}; \
+	\
+	Write-Host 'Expanding ...'; \
+	Expand-Archive pypy.zip -DestinationPath C:\; \
+	\
+	Write-Host 'Removing ...'; \
+	Remove-Item pypy.zip -Force; \
+	\
+	Write-Host 'Renaming ...'; \
+	Rename-Item -Path C:\pypy2.7-v7.3.17-win64 -NewName C:\pypy; \
+	\
+	Write-Host 'Verifying install ("pypy --version") ...'; \
+	pypy --version; \
+	\
+	Write-Host 'Cleanup install ...'; \
+	Get-ChildItem \
+		-Path C:\pypy \
+		-Include @( 'test', 'tests' ) \
+		-Directory \
+		-Recurse \
+		| Remove-Item -Force -Recurse; \
+	Get-ChildItem \
+		-Path C:\pypy \
+		-Include @( '*.pyc', '*.pyo' ) \
+		-File \
+		-Recurse \
+		| Remove-Item -Force; \
+	\
+	Write-Host 'Complete.'
+
+# https://github.com/pypa/get-pip
+ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/3843bff3a0a61da5b63ea0b7d34794c5c51a2f11/get-pip.py
+ENV PYTHON_GET_PIP_SHA256 95c5ee602b2f3cc50ae053d716c3c89bea62c58568f64d7d25924d399b2d5218
+
+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; \
+	}; \
+	\
+	$pipVersion = & pypy -c 'import ensurepip; print(ensurepip._PIP_VERSION)'; \
+	$setuptoolsVersion = & pypy -c 'import ensurepip; print(ensurepip._SETUPTOOLS_VERSION)'; \
+	\
+	Write-Host ('Installing "pip == {0}", "setuptools == {1}" ...' -f $pipVersion, $setuptoolsVersion); \
+	pypy get-pip.py \
+		--disable-pip-version-check \
+		--no-cache-dir \
+		('pip == {0}' -f $pipVersion) \
+		('setuptools == {0}' -f $setuptoolsVersion) \
+	; \
+	Remove-Item get-pip.py -Force; \
+	\
+	Write-Host 'Verifying pip install ...'; \
+	pip --version; \
+	\
+	Write-Host 'Cleanup install ...'; \
+	Get-ChildItem \
+		-Path C:\pypy \
+		-Include @( 'test', 'tests' ) \
+		-Directory \
+		-Recurse \
+		| Remove-Item -Force -Recurse; \
+	Get-ChildItem \
+		-Path C:\pypy \
+		-Include @( '*.pyc', '*.pyo' ) \
+		-File \
+		-Recurse \
+		| Remove-Item -Force; \
+	\
+	Write-Host 'Complete.'
+
+CMD ["pypy"]
diff --git a/3.10/windows/windowsservercore-ltsc2025/Dockerfile b/3.10/windows/windowsservercore-ltsc2025/Dockerfile
new file mode 100644
index 0000000..d448eb4
--- /dev/null
+++ b/3.10/windows/windowsservercore-ltsc2025/Dockerfile
@@ -0,0 +1,133 @@
+#
+# NOTE: THIS DOCKERFILE IS GENERATED VIA "apply-templates.sh"
+#
+# PLEASE DO NOT EDIT IT DIRECTLY.
+#
+
+FROM mcr.microsoft.com/windows/servercore:ltsc2025
+
+# $ProgressPreference: https://github.com/PowerShell/PowerShell/issues/2138#issuecomment-251261324
+SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
+
+# PATH isn't actually set in the Docker image, so we have to set it from within the container
+RUN $newPath = ('C:\pypy;C:\pypy\Scripts;{0}' -f $env:PATH); \
+	Write-Host ('Updating PATH: {0}' -f $newPath); \
+	[Environment]::SetEnvironmentVariable('PATH', $newPath, [EnvironmentVariableTarget]::Machine); \
+	Write-Host 'Complete.'
+# doing this first to share cache across versions more aggressively
+
+# install Microsoft Visual C++ Redistributable
+RUN $url = 'https://download.microsoft.com/download/6/A/A/6AA4EDFF-645B-48C5-81CC-ED5963AEAD48/vc_redist.x64.exe'; \
+	Write-Host ('Downloading {0} ...' -f $url); \
+	Invoke-WebRequest -Uri $url -OutFile 'vc.exe'; \
+	\
+	$sha256 = 'da66717784c192f1004e856bbcf7b3e13b7bf3ea45932c48e4c9b9a50ca80965'; \
+	Write-Host ('Verifying sha256 ({0}) ...' -f $sha256); \
+	if ((Get-FileHash vc.exe -Algorithm sha256).Hash -ne $sha256) { \
+		Write-Host 'FAILED!'; \
+		exit 1; \
+	}; \
+	\
+	Write-Host 'Installing ...'; \
+	Start-Process \
+		-NoNewWindow \
+		-Wait \
+		-FilePath .\vc.exe \
+		-ArgumentList @( \
+			'/install', \
+			'/quiet', \
+			'/norestart' \
+		); \
+	\
+	Write-Host 'Removing ...'; \
+	Remove-Item vc.exe -Force; \
+	\
+	Write-Host 'Complete.'
+
+# Python 3.10.14
+ENV PYPY_VERSION 7.3.17
+
+RUN $url = 'https://downloads.python.org/pypy/pypy3.10-v7.3.17-win64.zip'; \
+	Write-Host ('Downloading {0} ...' -f $url); \
+	Invoke-WebRequest -Uri $url -OutFile 'pypy.zip'; \
+	\
+	$sha256 = 'cab794a03ddda26238c72942ea6f225612e0dc17c76cac6652da83a95024e6e8'; \
+	Write-Host ('Verifying sha256 ({0}) ...' -f $sha256); \
+	if ((Get-FileHash pypy.zip -Algorithm sha256).Hash -ne $sha256) { \
+		Write-Host 'FAILED!'; \
+		exit 1; \
+	}; \
+	\
+	Write-Host 'Expanding ...'; \
+	Expand-Archive pypy.zip -DestinationPath C:\; \
+	\
+	Write-Host 'Removing ...'; \
+	Remove-Item pypy.zip -Force; \
+	\
+	Write-Host 'Renaming ...'; \
+	Rename-Item -Path C:\pypy3.10-v7.3.17-win64 -NewName C:\pypy; \
+	\
+	Write-Host 'Verifying install ("pypy --version") ...'; \
+	pypy --version; \
+	\
+	Write-Host 'Cleanup install ...'; \
+	Get-ChildItem \
+		-Path C:\pypy \
+		-Include @( 'test', 'tests' ) \
+		-Directory \
+		-Recurse \
+		| Remove-Item -Force -Recurse; \
+	Get-ChildItem \
+		-Path C:\pypy \
+		-Include @( '*.pyc', '*.pyo' ) \
+		-File \
+		-Recurse \
+		| Remove-Item -Force; \
+	\
+	Write-Host 'Complete.'
+
+# https://github.com/pypa/get-pip
+ENV PYTHON_GET_PIP_URL https://github.com/pypa/get-pip/raw/3843bff3a0a61da5b63ea0b7d34794c5c51a2f11/get-pip.py
+ENV PYTHON_GET_PIP_SHA256 95c5ee602b2f3cc50ae053d716c3c89bea62c58568f64d7d25924d399b2d5218
+
+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; \
+	}; \
+	\
+	$pipVersion = & pypy -c 'import ensurepip; print(ensurepip._PIP_VERSION)'; \
+	$setuptoolsVersion = & pypy -c 'import ensurepip; print(ensurepip._SETUPTOOLS_VERSION)'; \
+	\
+	Write-Host ('Installing "pip == {0}", "setuptools == {1}" ...' -f $pipVersion, $setuptoolsVersion); \
+	pypy get-pip.py \
+		--disable-pip-version-check \
+		--no-cache-dir \
+		('pip == {0}' -f $pipVersion) \
+		('setuptools == {0}' -f $setuptoolsVersion) \
+	; \
+	Remove-Item get-pip.py -Force; \
+	\
+	Write-Host 'Verifying pip install ...'; \
+	pip --version; \
+	\
+	Write-Host 'Cleanup install ...'; \
+	Get-ChildItem \
+		-Path C:\pypy \
+		-Include @( 'test', 'tests' ) \
+		-Directory \
+		-Recurse \
+		| Remove-Item -Force -Recurse; \
+	Get-ChildItem \
+		-Path C:\pypy \
+		-Include @( '*.pyc', '*.pyo' ) \
+		-File \
+		-Recurse \
+		| Remove-Item -Force; \
+	\
+	Write-Host 'Complete.'
+
+CMD ["pypy"]
diff --git a/versions.json b/versions.json
index 38f4c46..fe8ab90 100644
--- a/versions.json
+++ b/versions.json
@@ -40,6 +40,7 @@
       "slim-bookworm",
       "bullseye",
       "slim-bullseye",
+      "windows/windowsservercore-ltsc2025",
       "windows/windowsservercore-ltsc2022",
       "windows/windowsservercore-1809"
     ],
@@ -86,6 +87,7 @@
       "slim-bookworm",
       "bullseye",
       "slim-bullseye",
+      "windows/windowsservercore-ltsc2025",
       "windows/windowsservercore-ltsc2022",
       "windows/windowsservercore-1809"
     ],
diff --git a/versions.sh b/versions.sh
index a6fea18..68230e3 100755
--- a/versions.sh
+++ b/versions.sh
@@ -117,6 +117,7 @@ for version in "${versions[@]}"; do
 
 				if $doc.arches | keys | any(startswith("windows-")) then
 					(
+						"ltsc2025",
 						"ltsc2022",
 						"1809",
 						empty # trailing comma