diff --git a/.travis.yml b/.travis.yml
index a730c572b..66d56bc7e 100644
--- a/.travis.yml
+++ b/.travis.yml
@@ -1,44 +1,84 @@
 language: bash
 services: docker
 
-env:
-  - VERSION=3.7 VARIANT=stretch
-  - VERSION=3.7 VARIANT=stretch/slim
-  - VERSION=3.7 VARIANT=alpine3.9
-  - VERSION=3.7 VARIANT=alpine3.8
-  - VERSION=3.6 VARIANT=stretch
-  - VERSION=3.6 VARIANT=stretch/slim
-  - VERSION=3.6 VARIANT=jessie
-  - VERSION=3.6 VARIANT=jessie/slim
-  - VERSION=3.6 VARIANT=alpine3.9
-  - VERSION=3.6 VARIANT=alpine3.8
-  - VERSION=3.5 VARIANT=stretch
-  - VERSION=3.5 VARIANT=stretch/slim
-  - VERSION=3.5 VARIANT=jessie
-  - VERSION=3.5 VARIANT=jessie/slim
-  - VERSION=3.5 VARIANT=alpine3.9
-  - VERSION=3.5 VARIANT=alpine3.8
-  - VERSION=3.4 VARIANT=stretch
-  - VERSION=3.4 VARIANT=stretch/slim
-  - VERSION=3.4 VARIANT=jessie
-  - VERSION=3.4 VARIANT=jessie/slim
-  - VERSION=3.4 VARIANT=wheezy
-  - VERSION=3.4 VARIANT=alpine3.9
-  - VERSION=3.4 VARIANT=alpine3.8
-  - VERSION=2.7 VARIANT=stretch
-  - VERSION=2.7 VARIANT=stretch/slim
-  - VERSION=2.7 VARIANT=jessie
-  - VERSION=2.7 VARIANT=jessie/slim
-  - VERSION=2.7 VARIANT=wheezy
-  - VERSION=2.7 VARIANT=alpine3.9
-  - VERSION=2.7 VARIANT=alpine3.8
+matrix:
+  include:
+    - os: windows
+      dist: 1803-containers
+      env: VERSION=3.7 VARIANT=windows/windowsservercore-1803
+    - os: linux
+      env: VERSION=3.7 VARIANT=stretch
+    - os: linux
+      env: VERSION=3.7 VARIANT=stretch/slim
+    - os: linux
+      env: VERSION=3.7 VARIANT=alpine3.9
+    - os: linux
+      env: VERSION=3.7 VARIANT=alpine3.8
+    - os: windows
+      dist: 1803-containers
+      env: VERSION=3.6 VARIANT=windows/windowsservercore-1803
+    - os: linux
+      env: VERSION=3.6 VARIANT=stretch
+    - os: linux
+      env: VERSION=3.6 VARIANT=stretch/slim
+    - os: linux
+      env: VERSION=3.6 VARIANT=jessie
+    - os: linux
+      env: VERSION=3.6 VARIANT=jessie/slim
+    - os: linux
+      env: VERSION=3.6 VARIANT=alpine3.9
+    - os: linux
+      env: VERSION=3.6 VARIANT=alpine3.8
+    - os: linux
+      env: VERSION=3.5 VARIANT=stretch
+    - os: linux
+      env: VERSION=3.5 VARIANT=stretch/slim
+    - os: linux
+      env: VERSION=3.5 VARIANT=jessie
+    - os: linux
+      env: VERSION=3.5 VARIANT=jessie/slim
+    - os: linux
+      env: VERSION=3.5 VARIANT=alpine3.9
+    - os: linux
+      env: VERSION=3.5 VARIANT=alpine3.8
+    - os: linux
+      env: VERSION=3.4 VARIANT=stretch
+    - os: linux
+      env: VERSION=3.4 VARIANT=stretch/slim
+    - os: linux
+      env: VERSION=3.4 VARIANT=jessie
+    - os: linux
+      env: VERSION=3.4 VARIANT=jessie/slim
+    - os: linux
+      env: VERSION=3.4 VARIANT=wheezy
+    - os: linux
+      env: VERSION=3.4 VARIANT=alpine3.9
+    - os: linux
+      env: VERSION=3.4 VARIANT=alpine3.8
+    - os: windows
+      dist: 1803-containers
+      env: VERSION=2.7 VARIANT=windows/windowsservercore-1803
+    - os: linux
+      env: VERSION=2.7 VARIANT=stretch
+    - os: linux
+      env: VERSION=2.7 VARIANT=stretch/slim
+    - os: linux
+      env: VERSION=2.7 VARIANT=jessie
+    - os: linux
+      env: VERSION=2.7 VARIANT=jessie/slim
+    - os: linux
+      env: VERSION=2.7 VARIANT=wheezy
+    - os: linux
+      env: VERSION=2.7 VARIANT=alpine3.9
+    - os: linux
+      env: VERSION=2.7 VARIANT=alpine3.8
 
 install:
   - git clone https://github.com/docker-library/official-images.git ~/official-images
+  - if [ "$TRAVIS_OS_NAME" = 'linux' ]; then wget -qO- 'https://github.com/tianon/pgp-happy-eyeballs/raw/master/hack-my-builds.sh' | bash; fi
 
 before_script:
   - env | sort
-  - wget -qO- 'https://github.com/tianon/pgp-happy-eyeballs/raw/master/hack-my-builds.sh' | bash
   - cd "$VERSION/$VARIANT"
   - slash='/'; image="python:${VERSION}-${VARIANT//$slash/-}"
 
diff --git a/2.7/windows/windowsservercore-1709/Dockerfile b/2.7/windows/windowsservercore-1709/Dockerfile
index 68595c0b7..25d1b5cfd 100644
--- a/2.7/windows/windowsservercore-1709/Dockerfile
+++ b/2.7/windows/windowsservercore-1709/Dockerfile
@@ -4,7 +4,7 @@
 # PLEASE DO NOT EDIT IT DIRECTLY.
 #
 
-FROM microsoft/windowsservercore:1709
+FROM mcr.microsoft.com/windows/servercore:1709
 
 SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
 
diff --git a/2.7/windows/windowsservercore-1803/Dockerfile b/2.7/windows/windowsservercore-1803/Dockerfile
new file mode 100644
index 000000000..5c46939ed
--- /dev/null
+++ b/2.7/windows/windowsservercore-1803/Dockerfile
@@ -0,0 +1,64 @@
+#
+# NOTE: THIS DOCKERFILE IS GENERATED VIA "update.sh"
+#
+# PLEASE DO NOT EDIT IT DIRECTLY.
+#
+
+FROM mcr.microsoft.com/windows/servercore:1803
+
+SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
+
+ENV PYTHON_VERSION 2.7.15
+ENV PYTHON_RELEASE 2.7.15
+
+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); \
+	[Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12; \
+	Invoke-WebRequest -Uri $url -OutFile '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; \
+	\
+	Write-Host 'Complete.';
+
+# if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
+ENV PYTHON_PIP_VERSION 19.0.2
+
+RUN Write-Host ('Installing pip=={0} ...' -f $env:PYTHON_PIP_VERSION); \
+	[Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12; \
+	Invoke-WebRequest -Uri 'https://bootstrap.pypa.io/get-pip.py' -OutFile 'get-pip.py'; \
+	python get-pip.py \
+		--disable-pip-version-check \
+		--no-cache-dir \
+		('pip=={0}' -f $env:PYTHON_PIP_VERSION) \
+	; \
+	Remove-Item get-pip.py -Force; \
+	\
+	Write-Host 'Verifying pip install ...'; \
+	pip --version; \
+	\
+	Write-Host 'Complete.';
+
+# install "virtualenv", since the vast majority of users of this image will want it
+RUN pip install --no-cache-dir virtualenv
+
+CMD ["python"]
diff --git a/2.7/windows/windowsservercore-1809/Dockerfile b/2.7/windows/windowsservercore-1809/Dockerfile
new file mode 100644
index 000000000..79a9c2f6c
--- /dev/null
+++ b/2.7/windows/windowsservercore-1809/Dockerfile
@@ -0,0 +1,64 @@
+#
+# NOTE: THIS DOCKERFILE IS GENERATED VIA "update.sh"
+#
+# PLEASE DO NOT EDIT IT DIRECTLY.
+#
+
+FROM mcr.microsoft.com/windows/servercore:1809
+
+SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
+
+ENV PYTHON_VERSION 2.7.15
+ENV PYTHON_RELEASE 2.7.15
+
+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); \
+	[Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12; \
+	Invoke-WebRequest -Uri $url -OutFile '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; \
+	\
+	Write-Host 'Complete.';
+
+# if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
+ENV PYTHON_PIP_VERSION 19.0.2
+
+RUN Write-Host ('Installing pip=={0} ...' -f $env:PYTHON_PIP_VERSION); \
+	[Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12; \
+	Invoke-WebRequest -Uri 'https://bootstrap.pypa.io/get-pip.py' -OutFile 'get-pip.py'; \
+	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.';
+
+# 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/2.7/windows/windowsservercore-ltsc2016/Dockerfile b/2.7/windows/windowsservercore-ltsc2016/Dockerfile
index fde56cee1..2fcd7835c 100644
--- a/2.7/windows/windowsservercore-ltsc2016/Dockerfile
+++ b/2.7/windows/windowsservercore-ltsc2016/Dockerfile
@@ -4,7 +4,7 @@
 # PLEASE DO NOT EDIT IT DIRECTLY.
 #
 
-FROM microsoft/windowsservercore:ltsc2016
+FROM mcr.microsoft.com/windows/servercore:ltsc2016
 
 SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
 
diff --git a/3.6/windows/windowsservercore-1709/Dockerfile b/3.6/windows/windowsservercore-1709/Dockerfile
index 244ddaea0..3d8249fbc 100644
--- a/3.6/windows/windowsservercore-1709/Dockerfile
+++ b/3.6/windows/windowsservercore-1709/Dockerfile
@@ -4,7 +4,7 @@
 # PLEASE DO NOT EDIT IT DIRECTLY.
 #
 
-FROM microsoft/windowsservercore:1709
+FROM mcr.microsoft.com/windows/servercore:1709
 
 SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
 
diff --git a/3.6/windows/windowsservercore-1803/Dockerfile b/3.6/windows/windowsservercore-1803/Dockerfile
new file mode 100644
index 000000000..fb0e7b318
--- /dev/null
+++ b/3.6/windows/windowsservercore-1803/Dockerfile
@@ -0,0 +1,62 @@
+#
+# NOTE: THIS DOCKERFILE IS GENERATED VIA "update.sh"
+#
+# PLEASE DO NOT EDIT IT DIRECTLY.
+#
+
+FROM mcr.microsoft.com/windows/servercore:1803
+
+SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
+
+ENV PYTHON_VERSION 3.6.8
+ENV PYTHON_RELEASE 3.6.8
+
+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 19.0.2
+
+RUN Write-Host ('Installing pip=={0} ...' -f $env:PYTHON_PIP_VERSION); \
+	[Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12; \
+	Invoke-WebRequest -Uri 'https://bootstrap.pypa.io/get-pip.py' -OutFile 'get-pip.py'; \
+	python get-pip.py \
+		--disable-pip-version-check \
+		--no-cache-dir \
+		('pip=={0}' -f $env:PYTHON_PIP_VERSION) \
+	; \
+	Remove-Item get-pip.py -Force; \
+	\
+	Write-Host 'Verifying pip install ...'; \
+	pip --version; \
+	\
+	Write-Host 'Complete.';
+
+CMD ["python"]
diff --git a/3.6/windows/windowsservercore-1809/Dockerfile b/3.6/windows/windowsservercore-1809/Dockerfile
new file mode 100644
index 000000000..17b371155
--- /dev/null
+++ b/3.6/windows/windowsservercore-1809/Dockerfile
@@ -0,0 +1,62 @@
+#
+# NOTE: THIS DOCKERFILE IS GENERATED VIA "update.sh"
+#
+# PLEASE DO NOT EDIT IT DIRECTLY.
+#
+
+FROM mcr.microsoft.com/windows/servercore:1809
+
+SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
+
+ENV PYTHON_VERSION 3.6.8
+ENV PYTHON_RELEASE 3.6.8
+
+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 19.0.2
+
+RUN Write-Host ('Installing pip=={0} ...' -f $env:PYTHON_PIP_VERSION); \
+	[Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12; \
+	Invoke-WebRequest -Uri 'https://bootstrap.pypa.io/get-pip.py' -OutFile 'get-pip.py'; \
+	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/windows/windowsservercore-ltsc2016/Dockerfile b/3.6/windows/windowsservercore-ltsc2016/Dockerfile
index ea216cf1b..f50dd7b5b 100644
--- a/3.6/windows/windowsservercore-ltsc2016/Dockerfile
+++ b/3.6/windows/windowsservercore-ltsc2016/Dockerfile
@@ -4,7 +4,7 @@
 # PLEASE DO NOT EDIT IT DIRECTLY.
 #
 
-FROM microsoft/windowsservercore:ltsc2016
+FROM mcr.microsoft.com/windows/servercore:ltsc2016
 
 SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
 
diff --git a/3.7/windows/windowsservercore-1709/Dockerfile b/3.7/windows/windowsservercore-1709/Dockerfile
index 58955c042..93041a22e 100644
--- a/3.7/windows/windowsservercore-1709/Dockerfile
+++ b/3.7/windows/windowsservercore-1709/Dockerfile
@@ -4,7 +4,7 @@
 # PLEASE DO NOT EDIT IT DIRECTLY.
 #
 
-FROM microsoft/windowsservercore:1709
+FROM mcr.microsoft.com/windows/servercore:1709
 
 SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
 
diff --git a/3.7/windows/windowsservercore-1803/Dockerfile b/3.7/windows/windowsservercore-1803/Dockerfile
new file mode 100644
index 000000000..4527d0bd7
--- /dev/null
+++ b/3.7/windows/windowsservercore-1803/Dockerfile
@@ -0,0 +1,62 @@
+#
+# NOTE: THIS DOCKERFILE IS GENERATED VIA "update.sh"
+#
+# PLEASE DO NOT EDIT IT DIRECTLY.
+#
+
+FROM mcr.microsoft.com/windows/servercore:1803
+
+SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
+
+ENV PYTHON_VERSION 3.7.2
+ENV PYTHON_RELEASE 3.7.2
+
+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); \
+	[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 19.0.2
+
+RUN Write-Host ('Installing pip=={0} ...' -f $env:PYTHON_PIP_VERSION); \
+	[Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12; \
+	Invoke-WebRequest -Uri 'https://bootstrap.pypa.io/get-pip.py' -OutFile 'get-pip.py'; \
+	python get-pip.py \
+		--disable-pip-version-check \
+		--no-cache-dir \
+		('pip=={0}' -f $env:PYTHON_PIP_VERSION) \
+	; \
+	Remove-Item get-pip.py -Force; \
+	\
+	Write-Host 'Verifying pip install ...'; \
+	pip --version; \
+	\
+	Write-Host 'Complete.';
+
+CMD ["python"]
diff --git a/3.7/windows/windowsservercore-1809/Dockerfile b/3.7/windows/windowsservercore-1809/Dockerfile
new file mode 100644
index 000000000..83064407a
--- /dev/null
+++ b/3.7/windows/windowsservercore-1809/Dockerfile
@@ -0,0 +1,62 @@
+#
+# NOTE: THIS DOCKERFILE IS GENERATED VIA "update.sh"
+#
+# PLEASE DO NOT EDIT IT DIRECTLY.
+#
+
+FROM mcr.microsoft.com/windows/servercore:1809
+
+SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
+
+ENV PYTHON_VERSION 3.7.2
+ENV PYTHON_RELEASE 3.7.2
+
+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); \
+	[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 19.0.2
+
+RUN Write-Host ('Installing pip=={0} ...' -f $env:PYTHON_PIP_VERSION); \
+	[Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12; \
+	Invoke-WebRequest -Uri 'https://bootstrap.pypa.io/get-pip.py' -OutFile 'get-pip.py'; \
+	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/3.7/windows/windowsservercore-ltsc2016/Dockerfile b/3.7/windows/windowsservercore-ltsc2016/Dockerfile
index bcf40c0d1..ec82e485c 100644
--- a/3.7/windows/windowsservercore-ltsc2016/Dockerfile
+++ b/3.7/windows/windowsservercore-ltsc2016/Dockerfile
@@ -4,7 +4,7 @@
 # PLEASE DO NOT EDIT IT DIRECTLY.
 #
 
-FROM microsoft/windowsservercore:ltsc2016
+FROM mcr.microsoft.com/windows/servercore:ltsc2016
 
 SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
 
diff --git a/Dockerfile-caveman-windowsservercore.template b/Dockerfile-caveman-windowsservercore.template
index e42461bab..f0fe4e606 100644
--- a/Dockerfile-caveman-windowsservercore.template
+++ b/Dockerfile-caveman-windowsservercore.template
@@ -1,4 +1,4 @@
-FROM microsoft/windowsservercore:%%PLACEHOLDER%%
+FROM mcr.microsoft.com/windows/servercore:%%PLACEHOLDER%%
 
 SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
 
diff --git a/Dockerfile-windowsservercore.template b/Dockerfile-windowsservercore.template
index 6570ff653..57b59c266 100644
--- a/Dockerfile-windowsservercore.template
+++ b/Dockerfile-windowsservercore.template
@@ -1,4 +1,4 @@
-FROM microsoft/windowsservercore:%%PLACEHOLDER%%
+FROM mcr.microsoft.com/windows/servercore:%%PLACEHOLDER%%
 
 SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
 
diff --git a/generate-stackbrew-library.sh b/generate-stackbrew-library.sh
index 0b2a9164b..c8b4ecdaa 100755
--- a/generate-stackbrew-library.sh
+++ b/generate-stackbrew-library.sh
@@ -78,8 +78,7 @@ for version in "${versions[@]}"; do
 	for v in \
 		{stretch,jessie,wheezy}{,/slim} \
 		alpine{3.9,3.8} \
-		windows/windowsservercore-{ltsc2016,1709} \
-		windows/nanoserver-{sac2016,1709} \
+		windows/windowsservercore-{ltsc2016,1709,1803,1809} \
 	; do
 		dir="$version/$v"
 		variant="$(basename "$v")"
diff --git a/update.sh b/update.sh
index dc26529a7..c1497035c 100755
--- a/update.sh
+++ b/update.sh
@@ -114,8 +114,7 @@ for version in "${versions[@]}"; do
 	for v in \
 		alpine{3.8,3.9} \
 		{wheezy,jessie,stretch}{/slim,} \
-		windows/nanoserver-{1709,sac2016} \
-		windows/windowsservercore-{1709,ltsc2016} \
+		windows/windowsservercore-{1809,1803,1709,ltsc2016} \
 	; do
 		dir="$version/$v"
 		variant="$(basename "$v")"
@@ -145,7 +144,7 @@ for version in "${versions[@]}"; do
 			-e 's/^(ENV PYTHON_RELEASE) .*/\1 '"${fullVersion%%[a-z]*}"'/' \
 			-e 's/^(ENV PYTHON_PIP_VERSION) .*/\1 '"$pipVersion"'/' \
 			-e 's/^(FROM python):.*/\1:'"$version-$tag"'/' \
-			-e 's!^(FROM (debian|buildpack-deps|alpine|microsoft/[^:]+)):.*!\1:'"$tag"'!' \
+			-e 's!^(FROM (debian|buildpack-deps|alpine|mcr[.]microsoft[.]com/[^:]+)):.*!\1:'"$tag"'!' \
 			"$dir/Dockerfile"
 
 		case "$variant" in
@@ -198,18 +197,24 @@ for version in "${versions[@]}"; do
 		esac
 
 		case "$v" in
-			windows/*-1709) ;; # no AppVeyor support for 1709 yet: https://github.com/appveyor/ci/issues/1885
+			windows/*-1803)
+				travisEnv='\n    - os: windows\n      dist: 1803-containers\n      env: VERSION='"$version VARIANT=$v$travisEnv"
+				;;
+
+			windows/*-1709 | windows/*-1809) ;; # no AppVeyor support for 1709 or 1809 yet: https://github.com/appveyor/ci/issues/1885 and https://github.com/appveyor/ci/issues/2676
+
 			windows/*)
 				appveyorEnv='\n    - version: '"$version"'\n      variant: '"$variant$appveyorEnv"
 				;;
+
 			*)
-				travisEnv='\n  - VERSION='"$version VARIANT=$v$travisEnv"
+				travisEnv='\n    - os: linux\n      env: VERSION='"$version VARIANT=$v$travisEnv"
 				;;
 		esac
 	done
 done
 
-travis="$(awk -v 'RS=\n\n' '$1 == "env:" { $0 = "env:'"$travisEnv"'" } { printf "%s%s", $0, RS }' .travis.yml)"
+travis="$(awk -v 'RS=\n\n' '$1 == "matrix:" { $0 = "matrix:\n  include:'"$travisEnv"'" } { printf "%s%s", $0, RS }' .travis.yml)"
 echo "$travis" > .travis.yml
 
 appveyor="$(awk -v 'RS=\n\n' '$1 == "environment:" { $0 = "environment:\n  matrix:'"$appveyorEnv"'" } { printf "%s%s", $0, RS }' .appveyor.yml)"