diff --git a/3.12/windows/windowsservercore-ltsc2025/Dockerfile b/3.12/windows/windowsservercore-ltsc2025/Dockerfile
new file mode 100644
index 000000000..24c711bac
--- /dev/null
+++ b/3.12/windows/windowsservercore-ltsc2025/Dockerfile
@@ -0,0 +1,65 @@
+#
+# 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 3.12.8
+ENV PYTHON_SHA256 71bd44e6b0e91c17558963557e4cdb80b483de9b0a0a9717f06cf896f95ab598
+
+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; \
+	\
+	$env:PYTHONDONTWRITEBYTECODE = '1'; \
+	\
+	Write-Host 'Verifying pip install ...'; \
+	pip --version; \
+	\
+	Write-Host 'Complete.'
+
+CMD ["python"]
diff --git a/3.13/windows/windowsservercore-ltsc2025/Dockerfile b/3.13/windows/windowsservercore-ltsc2025/Dockerfile
new file mode 100644
index 000000000..c0fa47f43
--- /dev/null
+++ b/3.13/windows/windowsservercore-ltsc2025/Dockerfile
@@ -0,0 +1,65 @@
+#
+# NOTE: THIS DOCKERFILE IS GENERATED VIA "apply-templates.sh"
+#
+# PLEASE DO NOT EDIT IT DIRECTLY.
+#
+
+FROM mcr.microsoft.com/windows/servercore:ltsc2025
+
+SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
+
+# https://github.com/docker-library/python/pull/557
+ENV PYTHONIOENCODING UTF-8
+
+ENV PYTHON_VERSION 3.13.1
+ENV PYTHON_SHA256 6b33fa9a439a86f553f9f60e538ccabc857d2f308bc77c477c04a46552ade81f
+
+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; \
+	\
+	$env:PYTHONDONTWRITEBYTECODE = '1'; \
+	\
+	Write-Host 'Verifying pip install ...'; \
+	pip --version; \
+	\
+	Write-Host 'Complete.'
+
+CMD ["python"]
diff --git a/3.14-rc/windows/windowsservercore-ltsc2025/Dockerfile b/3.14-rc/windows/windowsservercore-ltsc2025/Dockerfile
new file mode 100644
index 000000000..b4ec7b826
--- /dev/null
+++ b/3.14-rc/windows/windowsservercore-ltsc2025/Dockerfile
@@ -0,0 +1,65 @@
+#
+# NOTE: THIS DOCKERFILE IS GENERATED VIA "apply-templates.sh"
+#
+# PLEASE DO NOT EDIT IT DIRECTLY.
+#
+
+FROM mcr.microsoft.com/windows/servercore:ltsc2025
+
+SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
+
+# https://github.com/docker-library/python/pull/557
+ENV PYTHONIOENCODING UTF-8
+
+ENV PYTHON_VERSION 3.14.0a4
+ENV PYTHON_SHA256 282062869ce0bf0710451280a63b9b98e04e78be2f493010f19b3a2447946d99
+
+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; \
+	\
+	$env:PYTHONDONTWRITEBYTECODE = '1'; \
+	\
+	Write-Host 'Verifying pip install ...'; \
+	pip --version; \
+	\
+	Write-Host 'Complete.'
+
+CMD ["python"]
diff --git a/versions.json b/versions.json
index c80e645e6..a780f99fd 100644
--- a/versions.json
+++ b/versions.json
@@ -53,6 +53,7 @@
       "slim-bullseye",
       "alpine3.21",
       "alpine3.20",
+      "windows/windowsservercore-ltsc2025",
       "windows/windowsservercore-ltsc2022",
       "windows/windowsservercore-1809"
     ],
@@ -74,6 +75,7 @@
       "slim-bullseye",
       "alpine3.21",
       "alpine3.20",
+      "windows/windowsservercore-ltsc2025",
       "windows/windowsservercore-ltsc2022",
       "windows/windowsservercore-1809"
     ],
@@ -95,6 +97,7 @@
       "slim-bullseye",
       "alpine3.21",
       "alpine3.20",
+      "windows/windowsservercore-ltsc2025",
       "windows/windowsservercore-ltsc2022",
       "windows/windowsservercore-1809"
     ],
diff --git a/versions.sh b/versions.sh
index 5b7014ef7..f574d65d2 100755
--- a/versions.sh
+++ b/versions.sh
@@ -206,6 +206,7 @@ for version in "${versions[@]}"; do
 				| "alpine" + .),
 				if env.hasWindows != "" then
 					(
+						"ltsc2025",
 						"ltsc2022",
 						"1809",
 						empty