diff --git a/2.7/windows/windowsservercore/Dockerfile b/2.7/windows/windowsservercore/Dockerfile
new file mode 100644
index 0000000..901c813
--- /dev/null
+++ b/2.7/windows/windowsservercore/Dockerfile
@@ -0,0 +1,51 @@
+FROM microsoft/windowsservercore
+
+SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop';"]
+
+ENV PYTHON_VERSION 2.7.12
+ENV PYTHON_RELEASE 2.7.12
+
+# if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
+ENV PYTHON_PIP_VERSION 8.1.2
+
+RUN $url = ('https://www.python.org/ftp/python/{0}/python-{1}.amd64.msi' -f $env:PYTHON_RELEASE, $env:PYTHON_VERSION); \
+	Write-Host ('Downloading {0} ...' -f $url); \
+	(New-Object System.Net.WebClient).DownloadFile($url, 'python.msi'); \
+	\
+	Write-Host 'Installing ...'; \
+# https://www.python.org/download/releases/2.4/msi/
+	Start-Process msiexec -Wait \
+		-ArgumentList @( \
+			'/i', \
+			'python.msi', \
+			'/quiet', \
+			'/qn', \
+			'TARGETDIR=C:\Python', \
+			'ALLUSERS=1', \
+			'ADDLOCAL=DefaultFeature,Extensions,TclTk,Tools,PrependPath' \
+		); \
+	\
+# 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.msi -Force; \
+	\
+	$pipInstall = ('pip=={0}' -f $env:PYTHON_PIP_VERSION); \
+	Write-Host ('Installing {0} ...' -f $pipInstall); \
+	(New-Object System.Net.WebClient).DownloadFile('https://bootstrap.pypa.io/get-pip.py', 'get-pip.py'); \
+	python get-pip.py $pipInstall; \
+	Remove-Item get-pip.py -Force; \
+	\
+	Write-Host 'Verifying pip install ...'; \
+	pip --version; \
+	\
+	Write-Host 'Complete.';
+
+# install "virtualenv", since the vast majority of users of this image will want it
+RUN pip install --no-cache-dir virtualenv
+
+CMD ["python"]
diff --git a/3.5/windows/windowsservercore/Dockerfile b/3.5/windows/windowsservercore/Dockerfile
new file mode 100644
index 0000000..917dfb0
--- /dev/null
+++ b/3.5/windows/windowsservercore/Dockerfile
@@ -0,0 +1,52 @@
+#
+# NOTE: THIS DOCKERFILE IS GENERATED VIA "update.sh"
+#
+# PLEASE DO NOT EDIT IT DIRECTLY.
+#
+
+FROM microsoft/windowsservercore
+
+SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop';"]
+
+ENV PYTHON_VERSION 3.5.2
+ENV PYTHON_RELEASE 3.5.2
+
+# if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
+ENV PYTHON_PIP_VERSION 8.1.2
+
+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 $url); \
+	(New-Object System.Net.WebClient).DownloadFile($url, '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_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; \
+	\
+	$pipInstall = ('pip=={0}' -f $env:PYTHON_PIP_VERSION); \
+	Write-Host ('Installing {0} ...' -f $pipInstall); \
+	pip install --no-cache-dir --upgrade $pipInstall; \
+	\
+	Write-Host 'Verifying pip install ...'; \
+	pip --version; \
+	\
+	Write-Host 'Complete.';
+
+CMD ["python"]
diff --git a/3.6/windows/windowsservercore/Dockerfile b/3.6/windows/windowsservercore/Dockerfile
new file mode 100644
index 0000000..ec45dc5
--- /dev/null
+++ b/3.6/windows/windowsservercore/Dockerfile
@@ -0,0 +1,46 @@
+FROM microsoft/windowsservercore
+
+SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop';"]
+
+ENV PYTHON_VERSION 3.6.0a3
+ENV PYTHON_RELEASE 3.6.0
+
+# if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
+ENV PYTHON_PIP_VERSION 8.1.2
+
+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 $url); \
+	(New-Object System.Net.WebClient).DownloadFile($url, '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_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; \
+	\
+	$pipInstall = ('pip=={0}' -f $env:PYTHON_PIP_VERSION); \
+	Write-Host ('Installing {0} ...' -f $pipInstall); \
+	pip install --no-cache-dir --upgrade $pipInstall; \
+	\
+	Write-Host 'Verifying pip install ...'; \
+	pip --version; \
+	\
+	Write-Host 'Complete.';
+
+CMD ["python"]
diff --git a/Dockerfile-windowsservercore.template b/Dockerfile-windowsservercore.template
new file mode 100644
index 0000000..d74d0f9
--- /dev/null
+++ b/Dockerfile-windowsservercore.template
@@ -0,0 +1,46 @@
+FROM microsoft/windowsservercore
+
+SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop';"]
+
+ENV PYTHON_VERSION %%PLACEHOLDER%%
+ENV PYTHON_RELEASE %%PLACEHOLDER%%
+
+# if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
+ENV PYTHON_PIP_VERSION %%PLACEHOLDER%%
+
+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 $url); \
+	(New-Object System.Net.WebClient).DownloadFile($url, '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_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; \
+	\
+	$pipInstall = ('pip=={0}' -f $env:PYTHON_PIP_VERSION); \
+	Write-Host ('Installing {0} ...' -f $pipInstall); \
+	pip install --no-cache-dir --upgrade $pipInstall; \
+	\
+	Write-Host 'Verifying pip install ...'; \
+	pip --version; \
+	\
+	Write-Host 'Complete.';
+
+CMD ["python"]
diff --git a/generate-stackbrew-library.sh b/generate-stackbrew-library.sh
index 8b166f2..92bf0e3 100755
--- a/generate-stackbrew-library.sh
+++ b/generate-stackbrew-library.sh
@@ -67,10 +67,16 @@ for version in "${versions[@]}"; do
 		Directory: $version
 	EOE
 
-	for variant in slim alpine wheezy onbuild; do
-		[ -f "$version/$variant/Dockerfile" ] || continue
+	for v in \
+		slim alpine wheezy onbuild \
+		windows/windowsservercore windows/nanoserver \
+	; do
+		dir="$version/$v"
+		variant="$(basename "$v")"
 
-		commit="$(dirCommit "$version/$variant")"
+		[ -f "$dir/Dockerfile" ] || continue
+
+		commit="$(dirCommit "$dir")"
 
 		variantAliases=( "${versionAliases[@]/%/-$variant}" )
 		variantAliases=( "${variantAliases[@]//latest-/}" )
@@ -79,7 +85,8 @@ for version in "${versions[@]}"; do
 		cat <<-EOE
 			Tags: $(join ', ' "${variantAliases[@]}")
 			GitCommit: $commit
-			Directory: $version/$variant
+			Directory: $dir
 		EOE
+		[ "$variant" = "$v" ] || echo "Constraints: $variant"
 	done
 done
diff --git a/update.sh b/update.sh
index 3a363a6..fae90ae 100755
--- a/update.sh
+++ b/update.sh
@@ -1,5 +1,6 @@
 #!/bin/bash
 set -e
+shopt -s nullglob
 
 declare -A gpgKeys=(
 	# gpg: key 18ADD4FF: public key "Benjamin Peterson <benjamin@python.org>" imported
@@ -65,12 +66,15 @@ for version in "${versions[@]}"; do
 				alpine \
 				slim \
 				onbuild \
+				windows/windowsservercore \
 			; do
 				if [ "$variant" = 'debian' ]; then
 					dir="$version"
 				else
 					dir="$version/$variant"
+					variant="$(basename "$variant")"
 				fi
+				[ -d "$dir" ] || continue
 				template="Dockerfile-$variant.template"
 				{ generated_warning; cat "$template"; } > "$dir/Dockerfile"
 			done
@@ -84,9 +88,10 @@ for version in "${versions[@]}"; do
 			sed -ri \
 				-e 's/^(ENV GPG_KEY) .*/\1 '"${gpgKeys[$version]}"'/' \
 				-e 's/^(ENV PYTHON_VERSION) .*/\1 '"$fullVersion"'/' \
+				-e 's/^(ENV PYTHON_RELEASE) .*/\1 '"${fullVersion%%[a-z]*}"'/' \
 				-e 's/^(ENV PYTHON_PIP_VERSION) .*/\1 '"$pipVersion"'/' \
 				-e 's/^(FROM python):.*/\1:'"$version"'/' \
-				"$version"/{,*/}Dockerfile
+				"$version"/{,*/,*/*/}Dockerfile
 		)
 	fi
 	for variant in wheezy alpine slim; do