diff --git a/.github/workflows/tests.yaml b/.github/workflows/tests.yaml
index 698298c..ede719d 100644
--- a/.github/workflows/tests.yaml
+++ b/.github/workflows/tests.yaml
@@ -49,8 +49,8 @@ jobs:
     - name: Run tests
       # FIXME: Can this be run without elevated privileges?
       run: |
-        sudo $(command -v pytest)
-        coverage xml
+        sudo --preserve-env $(command -v pytest)
+        coverage xml --omit postroj/winrunner.py
 
     - name: Upload coverage results to Codecov
       uses: codecov/codecov-action@v3
diff --git a/CHANGES.rst b/CHANGES.rst
index 5b28851..7a228d3 100644
--- a/CHANGES.rst
+++ b/CHANGES.rst
@@ -11,6 +11,22 @@ in progress
 - Improve platform guards and naming things
 - Improve central command invocation function
 - Improve documentation
+- Make Windows runner subsystem production ready.
+- Add support for Windows Server Core 2019 and friends, like
+  ``windows/servercore:ltsc2019``, ``windows/nanoserver:1809``, or
+  ``eclipse-temurin:17-jdk``.
+- Add support for Windows Server Core 2016, 2022 and friends, like
+  ``windows/servercore:ltsc2016``, ``windows/servercore:ltsc2022``, or
+  ``windows/nanoserver:ltsc2022``.
+- Improve documentation about the Windows backend
+- Rename environment variables used to control the Windows Docker Machine
+  subsystem. The new names are ``RACKER_WDM_VCPUS``, ``RACKER_WDM_MEMORY``,
+  and ``RACKER_WDM_MACHINE``.
+- Add environment variable ``RACKER_WDM_PROVIDER`` to reconfigure the
+  Vagrant virtualization backend differently than VirtualBox.
+- Documentation: Add use case how to build a Python package within a
+  Windows environment, using Microsoft Visual C++ Build Tools 2015 and
+  Anaconda, both installed using Chocolatey, and ``cibuildwheel``.
 
 
 2022-05-20 0.2.0
diff --git a/README.rst b/README.rst
index 758bff3..0868172 100644
--- a/README.rst
+++ b/README.rst
@@ -109,6 +109,13 @@ another one for Windows.
   `systemd-nspawn`_. Provisioning of additional software is performed using the
   native package manager of the corresponding Linux distribution.
 
+- For running Windows operating systems containers, Racker uses `Vagrant`_,
+  `Docker`_, and `Windows Docker Machine`_. The virtual machine base image is
+  acquired from `Vagrant Cloud`_, container images are acquired from the
+  `Microsoft Container Registry`_. For provisioning additional software, the
+  `Chocolatey`_ package manager is used. All of cmd, PowerShell and Bash are
+  pre-installed on the container images.
+
 
 Operating system coverage
 -------------------------
@@ -132,6 +139,11 @@ Linux
 - SUSE SLES 15 and BCI:latest
 - Ubuntu LTS 20 and 22 (focal, jammy)
 
+Windows
+.......
+- Windows Server Core LTSC 2016, 2019, and 2022
+- Windows Nano Server 1809 and LTSC 2022
+
 
 Prior art
 ---------
@@ -212,6 +224,8 @@ Racker
 The ``racker`` program aims to resemble the semantics of Docker by providing a
 command line interface compatible with the ``docker`` command.
 
+Linux
+-----
 ::
 
     # Invoke the vanilla Docker `hello-world` image.
@@ -244,6 +258,20 @@ command line interface compatible with the ``docker`` command.
     time echo "hello world" | racker run -it --rm fedora:37 cat /dev/stdin > hello
     cat hello
 
+Windows
+-------
+
+An example of a basic command line invocation should get you started,
+especially if you are familiar with the ``docker`` command::
+
+    racker --verbose run --rm --platform=windows/amd64 mcr.microsoft.com/windows/servercore:ltsc2022 -- wmic os get caption
+
+    Caption
+    Microsoft Windows Server 2022 Datacenter
+
+More extensive information, including many examples, can be found at the
+`Racker Windows backend`_ documentation.
+
 
 Postroj
 =======
@@ -429,6 +457,7 @@ Troubleshooting
 .. _Packer: https://www.packer.io/
 .. _Podman: https://podman.io/
 .. _Racker sandbox installation: https://github.com/cicerops/racker/blob/main/doc/sandbox.rst
+.. _Racker Windows backend: https://github.com/cicerops/racker/blob/main/doc/winrunner.rst
 .. _skopeo: https://github.com/containers/skopeo
 .. _systemd: https://www.freedesktop.org/wiki/Software/systemd/
 .. _systemd-nspawn: https://www.freedesktop.org/software/systemd/man/systemd-nspawn.html
diff --git a/doc/cratedb.rst b/doc/cratedb.rst
index 45fc533..ba8a923 100644
--- a/doc/cratedb.rst
+++ b/doc/cratedb.rst
@@ -1,10 +1,53 @@
-#########################
-Using postroj for CrateDB
-#########################
+#######################################
+Using Racker and Postroj for CrateDB CI
+#######################################
 
-.. note::
 
-    This is still a work in progress.
+**********
+racker run
+**********
+
+Purpose: Invoke programs in a Java/OpenJDK environment, within a
+virtualized/dockerized, volatile/ephemeral Windows environment.
+
+Run the CrateDB test suite on OpenJDK 18 (Eclipse Temurin)::
+
+    time racker --verbose run --rm --platform=windows/amd64 eclipse-temurin:18-jdk \
+        "sh -c 'mkdir /c/src; cd /c/src; git clone https://github.com/crate/crate --depth=1; cd crate; ./gradlew --no-daemon --parallel -PtestForks=2 :server:test -Dtests.crate.run-windows-incompatible=false --stacktrace'"
+
+Use the same image, but select a specific operating system version::
+
+    export RACKER_WDM_MACHINE=2019-box
+    racker --verbose run --rm --platform=windows/amd64 eclipse-temurin:18-jdk -- wmic os get caption
+
+Invoke a Java command prompt (JShell) with OpenJDK 18::
+
+    racker --verbose run -it --rm --platform=windows/amd64 eclipse-temurin:18-jdk jshell
+    System.out.println("OS: " + System.getProperty("os.name") + ", version " + System.getProperty("os.version"))
+    System.out.println("Java: " + System.getProperty("java.vendor") + ", version " + System.getProperty("java.version"))
+
+Build CrateDB from source, extract Zip archive, and invoke available programs::
+
+    # Spawn a Windows environment with `cmd` shell.
+    # TODO: Bind-mounting not possible via command line yet, need to touch the code for this.
+    racker --verbose run --rm -it --platform=windows/amd64 eclipse-temurin:18-jdk -- cmd
+
+    # Build CrateDB.
+    cd \crate
+    gradlew clean distZip
+
+    # Extract zip archive.
+    mkdir \tmp
+    cd \tmp
+    unzip \crate\app\build\distributions\crate-5.3.0-SNAPSHOT-327070e3fe.zip
+    cd crate-5.3.0-SNAPSHOT-327070e3fe
+
+    # Run CrateDB and tools.
+    bin\crate
+    # Submit <Ctrl+C> to stop
+
+    bin\crate-node fix-metadata
+    # Send y to the prompt
 
 
 ****************
diff --git a/doc/use-cases/python-on-windows.rst b/doc/use-cases/python-on-windows.rst
new file mode 100644
index 0000000..f9d2adb
--- /dev/null
+++ b/doc/use-cases/python-on-windows.rst
@@ -0,0 +1,74 @@
+###############################
+Use cases for Python on Windows
+###############################
+
+
+*************************
+Build wheels for PyTables
+*************************
+
+About
+=====
+
+DIY, without a hosted CI provider.
+
+How to build a Python wheel package, here PyTables, within a Windows
+environment, using Microsoft Visual C++ Build Tools 2015 and Anaconda, both
+installed using Chocolatey, and ``cibuildwheel``.
+
+References
+==========
+
+- https://github.com/PyTables/PyTables/pull/872#issuecomment-773535041
+- https://github.com/PyTables/PyTables/blob/master/.github/workflows/wheels.yml
+
+Synopsis
+========
+
+.. note::
+
+    The ``windows-pytables-wheel.sh`` program is part of this repository. You
+    will only find it at the designated location when running ``racker`` from
+    the working tree of its Git repository.
+
+    You still can get hold of the program and invoke it, by downloading it from
+    `windows-pytables-wheel.sh`_.
+
+So, let's start by defining the download URL to that file::
+
+    export PAYLOAD_URL=https://raw.githubusercontent.com/cicerops/racker/windows/doc/use-cases/windows-pytables-wheel.sh
+
+Unattended::
+
+    time racker --verbose run --rm --platform=windows/amd64 python:3.9 -- \
+        "sh -c 'wget ${PAYLOAD_URL}; sh windows-pytables-wheel.sh'"
+
+Or, interactively::
+
+    racker --verbose run -it --rm --platform=windows/amd64 python:3.9 -- bash
+    wget ${PAYLOAD_URL}
+    sh windows-pytables-wheel.sh
+
+
+Future
+======
+
+See https://github.com/cicerops/racker/issues/8.
+
+When working on the code base, you can invoke the program directly from
+the repository, after the ``--volume`` option got implemented::
+
+    # Unattended.
+    time racker --verbose run --rm \
+        --volume=C:/Users/amo/dev/cicerops-foss/sources/postroj:C:/racker \
+        --platform=windows/amd64 python:3.9 -- \
+        sh /c/racker/doc/use-cases/windows-pytables-wheel.sh
+
+    # Interactively.
+    racker --verbose run -it --rm \
+        --volume=C:/Users/amo/dev/cicerops-foss/sources/postroj:C:/racker \
+        --platform=windows/amd64 python:3.9 -- bash
+    /c/racker/doc/use-cases/windows-pytables-wheel.sh
+
+
+.. _windows-pytables-wheel.sh: https://raw.githubusercontent.com/cicerops/racker/main/doc/use-cases/windows-pytables-wheel.sh
diff --git a/doc/use-cases/windows-pytables-wheel.sh b/doc/use-cases/windows-pytables-wheel.sh
new file mode 100755
index 0000000..9842ce3
--- /dev/null
+++ b/doc/use-cases/windows-pytables-wheel.sh
@@ -0,0 +1,75 @@
+#!/bin/bash
+#
+# Build wheels for PyTables on Windows. DIY, without a hosted CI provider.
+# https://github.com/cicerops/racker/blob/main/doc/use-cases/python-on-windows.rst
+#
+# Synopsis::
+#
+#   racker --verbose run -it --rm --platform=windows/amd64 python:3.9 -- bash
+#   /c/racker/doc/use-cases/windows-pytables-wheel.sh
+#
+set -e
+
+# Install prerequisites.
+
+# Miniconda - A minimal installer for Anaconda.
+# https://conda.io/miniconda.html
+scoop bucket add extras
+scoop install miniconda3
+#export PATH="$PATH:/c/Users/ContainerAdministrator/scoop/apps/miniconda3/current/condabin"
+#alias conda=conda.bat
+#/c/Users/ContainerAdministrator/scoop/apps/miniconda3/current/condabin/conda.bat init bash
+source /c/Users/ContainerAdministrator/scoop/apps/miniconda3/current/Scripts/activate
+conda --version
+
+# /c/Users/ContainerAdministrator/scoop/apps/miniconda3/4.12.0/Scripts/conda.exe
+
+# TODO: `/AddToPath:1` seems to not work, so adjust `$PATH` manually.
+#export PATH="$PATH:/c/Tools/miniconda3/condabin"
+
+# TODO: At least within Bash, just addressing `conda` does not work.
+#export conda="conda.bat"
+
+
+# Check prerequisites.
+#echo $PATH
+#$conda --version
+# cibuildwheel --version
+
+# Pretend to be on a build matrix.
+export MATRIX_ARCH=win_amd64      # win32
+export MATRIX_ARCH_SUBDIR=win-64  # win-32
+
+# Activate and prepare Anaconda environment for building.
+conda create --yes --name=build
+conda activate build
+conda config --env --set subdir ${MATRIX_ARCH_SUBDIR}
+
+# Install needed libraries.
+conda install --yes blosc bzip2 hdf5 lz4 lzo snappy zstd zlib
+
+# Install cibuildwheel.
+# Build Python wheels for all the platforms on CI with minimal configuration.
+# https://cibuildwheel.readthedocs.io/
+pip install --upgrade cibuildwheel
+
+# Configure cibuildwheel.
+#export CIBW_BUILD="cp36-${MATRIX_ARCH} cp37-${MATRIX_ARCH} cp38-${MATRIX_ARCH} cp39-${MATRIX_ARCH} cp310-${MATRIX_ARCH}"
+export CIBW_BUILD="cp39-${MATRIX_ARCH}"
+#export CIBW_BEFORE_ALL_WINDOWS="conda create --yes --name=build && conda activate build && conda config --env --set subdir ${MATRIX_ARCH_SUBDIR} && conda install --yes blosc bzip2 hdf5 lz4 lzo snappy zstd zlib"
+#export CIBW_ENVIRONMENT_WINDOWS='CONDA_PREFIX="C:\\Miniconda\\envs\\build" PATH="$PATH;C:\\Miniconda\\envs\\build\\Library\\bin"'
+export CIBW_ENVIRONMENT="PYTABLES_NO_EMBEDDED_LIBS=true DISABLE_AVX2=true"
+export CIBW_BEFORE_BUILD="echo $PATH; pip install -r requirements.txt cython>=0.29.21 delvewheel"
+export CIBW_REPAIR_WHEEL_COMMAND_WINDOWS="delvewheel repair -w {dest_dir} {wheel}"
+
+# Debugging.
+# env
+
+# Acquire sources.
+mkdir -p /c/src
+cd /c/src
+test ! -d PyTables && git clone https://github.com/PyTables/PyTables --recursive --depth=1
+cd PyTables
+
+# Build wheel.
+cibuildwheel --platform=windows --output-dir=wheelhouse
diff --git a/doc/winrunner.rst b/doc/winrunner.rst
index de388d9..03baf6f 100644
--- a/doc/winrunner.rst
+++ b/doc/winrunner.rst
@@ -1,17 +1,51 @@
-#################
-postroj winrunner
-#################
+######################
+Racker Windows backend
+######################
+
+
+*****
+About
+*****
+
+Launch an interactive command prompt (cmd, PowerShell, or Bash) within a
+Windows environment (2016, 2019, or 2022), or invoke programs
+non-interactively.
+
+Features
+========
+
+- The subsystem is heavily based on the excellent `Windows Docker Machine`_.
+- The `Scoop`_ package manager is pre-installed on the container images
+  where PowerShell is available. The `Chocolatey`_ package manager can be
+  installed on demand.
+- Programs like ``busybox``, ``curl``, ``git``, ``nano``, and ``wget`` are
+  pre-installed on the container images where `Scoop`_ is available.
+- The `Windows container version compatibility`_ problem is conveniently
+  solved by automatically selecting the right machine matching the requested
+  container image.
+
+
+Use cases
+=========
+
+The first encounter with `Windows Docker Machine`_ was when aiming to run the
+build process of the PyTables Python package within a Windows environment, see
+`Wheels for Windows`_.
+
+The second use case was to run the Java test suite of CrateDB within a Windows
+environment, see `Using Racker and Postroj for CrateDB CI`_.
 
-.. note::
 
-    This is still a work in progress.
 
 
 *****
-About
+Setup
 *****
+::
 
-- https://github.com/PyTables/PyTables/pull/872#issuecomment-773535041
+    # Install VirtualBox, Vagrant, Docker, Python, and Racker.
+    brew install virtualbox vagrant docker python
+    pip install racker
 
 
 ********
@@ -19,63 +53,423 @@ Synopsis
 ********
 ::
 
-    # Basic usage.
-    postroj invoke --system=windows-1809 -- cmd /C echo hello
+    racker --verbose run --rm \
+        --platform=windows/amd64 mcr.microsoft.com/windows/servercore:ltsc2019 -- \
+        wmic os get caption
 
 
-*****
-Setup
-*****
-::
+*************
+Configuration
+*************
 
-    # Install VirtualBox, Vagrant and Docker.
-    brew install virtualbox docker vagrant
+Resources
+=========
 
-    # Install Windows VM with Docker environment.
-    git clone https://github.com/StefanScherer/windows-docker-machine
-    cd windows-docker-machine
+When creating the `Windows Docker Machine`_ virtual machine, the program will
+configure it to use 4 VCPUs and 4 GB system memory by default.
 
-    # Adjust resources.
-    sed -i 's/v.memory = 2048/v.memory = 8192/' Vagrantfile
-    sed -i 's/v.cpus = 2/v.cpus = 8/' Vagrantfile
+In order to adjust those values, use these environment variables before
+invoking the later commands::
 
-    # Run the box.
-    vagrant up --provider virtualbox 2019-box
+    export RACKER_WDM_VCPUS=8
+    export RACKER_WDM_MEMORY=8192
 
+If you want to adjust the values after the initial deployment, you will have to
+reset the `Windows Docker Machine`_ installation directory. For example, it is:
 
-*****
-Usage
-*****
+- On Linux: ``/root/.local/state/racker/windows-docker-machine``
+- On macOS: ``/Users/amo/Library/Application Support/racker/windows-docker-machine``
+
+
+VM provider
+===========
+
+`Vagrant`_ is able to use different providers as virtualization backend. By
+default, Racker selects `VirtualBox`_. In order to change the backend,
+reconfigure this environment variable::
+
+    export RACKER_WDM_PROVIDER=vmware_workstation
+
+Possible values are, in alphabetical order, ``hyperv``, ``virtualbox``,
+``qemu``, ``vmware_fusion``, ``vmware_workstation``.
+
+Please note that this has not been tested with providers other than
+`VirtualBox`_, so we would welcome to receive feedback from the community
+whether this also works well for them on other hypervisors.
+
+
+VM machine
+==========
+
+The architecture of Windows leads to container compatibility requirements that
+are different than on Linux, more background about this detail can be found at
+`Windows container version compatibility`_.
+
+In order to provide appropriate convenience, Racker's launcher subsystem
+inquires the ``os.version`` attribute of the OCI image about the designated
+version of Windows version before starting the container. Based on the version,
+the corresponding Windows Docker Machine host is selected to run the payload
+on. Currently, the supported operating systems are Windows 2016, 2019, and 2022.
+
+Certain container images can still be launched on mismatching operating system
+versions, for example, the `eclipse-temurin`_ container images. By default,
+when possible, the image will be launched on a Windows 2022 machine. If you
+want to explicitly control on which runner host the container will be launched,
+use another environment variable::
+
+    export RACKER_WDM_MACHINE=2019-box
+
+If you receive error messages like ``docker: no matching manifest for
+windows/amd64 10.0.17763 in the manifest list entries.``, reset this setting
+by typing::
+
+    unset RACKER_WDM_MACHINE
+
+Vagrant stores the boxes in this directory:
+
+- On Linux an macOS: ``~/.vagrant.d/boxes``
+- On Windows: ``C:/Users/USERNAME/.vagrant.d/boxes``
+
+The sizes of the three Vagrant boxes are:
 
-Which shell spawns faster?
+- ``StefanScherer/windows_2016_docker``: 11.0 GB
+- ``StefanScherer/windows_2019_docker``: 14.0 GB
+- ``StefanScherer/windows_2022_docker``:  6.4 GB
+
+
+********
+Examples
+********
+
+
+Introduction
+============
+
+For understanding some of the acronyms used in the following section, it is
+good to memorize those:
+
+- LTSC: Long-Term Servicing Channel
+- SAC: Semi-Annual Channel
+
+For more details, see `Overview of System Center release options`_.
+
+
+Choosing a base image
+=====================
+
+Quoting from `Windows Container Base Images`_:
+
+    How do you choose the right base image to build upon? For most users, Windows
+    Server Core and Nanoserver will be the most appropriate image to use. Each
+    base image is briefly described below:
+
+    - ``Nano Server`` is an ultralight Windows offering for new application
+      development.
+    - ``Server Core`` is medium in size and a good option for "lifting and
+      shifting" Windows Server apps.
+    - ``Windows Server`` has full Windows API support, and allows you to use
+      more server features.
+    - ``Windows`` is the largest image and has full Windows API support for
+      workloads.
+
+The examples outlined within this section will use different Windows container
+images. According to the feature set outlined above, their download sizes are
+different.
+
+- Nano Server: 125 MB
+- Server Core: 2.2 GB
+- Windows Server: 4.8 GB
+- Windows: 7.1 GB
+
+Around 2016/2019, it was like https://stefanscherer.github.io/windows-docker-workshop/#20.
+
+
+System information
+==================
+
+Install and run `Winfetch`_::
+
+    racker --verbose run --rm \
+        --platform=windows/amd64 mcr.microsoft.com/windows/servercore:ltsc2022 -- \
+        cmd /C 'scoop install winfetch & winfetch'
+
+.. figure:: https://user-images.githubusercontent.com/453543/173195228-b75c8727-7187-4c38-ae28-f74098dfb450.png
+    :width: 800
+
+With ``ver``, ``reg``, WMI and PowerShell::
+
+    # Both ``ver`` and ``reg`` will be available even on Nano Server.
+    racker --verbose run --rm --platform=windows/amd64 mcr.microsoft.com/windows/servercore:ltsc2016 -- cmd /C ver
+    racker --verbose run --rm --platform=windows/amd64 mcr.microsoft.com/windows/servercore:ltsc2016 -- 'reg query "HKLM\SOFTWARE\Microsoft\Windows NT\CurrentVersion" /v ProductName'
+    racker --verbose run --rm --platform=windows/amd64 mcr.microsoft.com/windows/servercore:ltsc2016 -- 'reg query "HKLM\SOFTWARE\Microsoft\Windows NT\CurrentVersion" /v InstallationType'
+
+    # WMI and PowerShell are not always available.
+    racker --verbose run --rm --platform=windows/amd64 mcr.microsoft.com/windows/servercore:ltsc2016 -- wmic os get caption
+    racker --verbose run --rm --platform=windows/amd64 mcr.microsoft.com/windows/servercore:ltsc2019 -- powershell -Command Get-ComputerInfo
+    racker --verbose run --rm --platform=windows/amd64 mcr.microsoft.com/windows/servercore:ltsc2022 -- powershell -Command Get-ComputerInfo -Property WindowsProductName
+
+With ``busybox``::
+
+    racker --verbose run -it --rm --platform=windows/amd64 mcr.microsoft.com/windows/servercore:ltsc2022 -- cmd
+
+    C:\>busybox nproc
+    6
+
+    C:\>busybox free -m
+                  total        used        free      shared  buff/cache   available
+    Mem:           2048        1422    16774251           0        3591           0
+    Swap:          1664           0        1664
+
+    C:\>busybox df -h
+    Filesystem                Size      Used Available Use% Mounted on
+    C:                       19.9G     83.3M     19.8G   0% C:/
+
+
+Interactive command prompt
 ==========================
+
+Where possible, the operating system images offer three terminal/shell
+programs: cmd, PowerShell, and Bash. To get an interactive shell, run::
+
+    racker --verbose run -it --rm --platform=windows/amd64 mcr.microsoft.com/windows/servercore:ltsc2016 cmd
+    racker --verbose run -it --rm --platform=windows/amd64 mcr.microsoft.com/windows/servercore:ltsc2019 powershell
+    racker --verbose run -it --rm --platform=windows/amd64 mcr.microsoft.com/windows/servercore:ltsc2022 bash
+
+
+Invoke single command
+=====================
 ::
 
-    time docker --context=2019-box run -it --rm openjdk:17-windowsservercore-1809 cmd /C "echo Hello, world."
+    # Run a basic command with cmd, PowerShell, and Bash.
+    racker --verbose run --rm --platform=windows/amd64 mcr.microsoft.com/windows/servercore:ltsc2016 cmd /C echo "Hello, world."
+    racker --verbose run --rm --platform=windows/amd64 mcr.microsoft.com/windows/servercore:ltsc2019 -- 'powershell -Command {echo "Hello, world."}'
+    racker --verbose run --rm --platform=windows/amd64 mcr.microsoft.com/windows/servercore:ltsc2022 'sh -c "echo Hello, world."'
+
+    # Use stdin and stdout, with time keeping.
+    time racker --verbose run --rm --platform=windows/amd64 mcr.microsoft.com/windows/nanoserver:1809 cmd /C echo "Hello, world." > hello
+    cat hello
 
+
+Nano Server
+===========
 ::
 
-    time docker --context=2019-box run -it --rm openjdk:17-windowsservercore-1809 powershell -Command "echo 'Hello, world.'"
+    # Display system version.
+    racker --verbose run --rm --platform=windows/amd64 mcr.microsoft.com/windows/nanoserver:sac2016 cmd /C ver
+    racker --verbose run --rm --platform=windows/amd64 mcr.microsoft.com/windows/nanoserver:1809 cmd /C ver
+    racker --verbose run --rm --platform=windows/amd64 mcr.microsoft.com/windows/nanoserver:ltsc2022 cmd /C ver
 
+    # Interactive shell with cmd.
+    racker --verbose run -it --rm --platform=windows/amd64 mcr.microsoft.com/windows/nanoserver:1809 cmd
 
+    # Interactive shell with PowerShell.
+    racker --verbose run -it --rm --platform=windows/amd64 mcr.microsoft.com/powershell:nanoserver-ltsc2022 pwsh
+
+
+Windows Server
+==============
+::
+
+    racker --verbose run --rm --platform=windows/amd64 mcr.microsoft.com/windows/server:ltsc2022 -- cmd /C ver
+    racker --verbose run --rm --platform=windows/amd64 mcr.microsoft.com/windows/server:ltsc2022 -- wmic os get caption
+    racker --verbose run --rm --platform=windows/amd64 mcr.microsoft.com/windows/server:ltsc2022 -- powershell -Command Get-ComputerInfo -Property WindowsProductName
 
-***********
-Admin guide
-***********
 
+Windows
+=======
 ::
 
-    docker --context=2019-box run -it --rm openjdk:17-windowsservercore-1809 cmd
+    # Windows 10
+    racker --verbose run --rm --platform=windows/amd64 mcr.microsoft.com/windows:1809 -- cmd /C ver
+    racker --verbose run --rm --platform=windows/amd64 mcr.microsoft.com/windows:1809 -- wmic os get caption
+    racker --verbose run --rm --platform=windows/amd64 mcr.microsoft.com/windows:1809 -- powershell -Command Get-ComputerInfo -Property WindowsProductName
+
+    # Untested.
+    racker --verbose run -it --rm --platform=windows/amd64 mcr.microsoft.com/windows:20H2 wmic os get caption
+
+
+Midnight Commander
+==================
+
+Install and run `Midnight Commander`_::
+
+    racker --verbose run -it --rm \
+        --platform=windows/amd64 mcr.microsoft.com/windows/servercore:ltsc2022 -- \
+        cmd /C 'choco install --yes --force mc --install-arguments=/tasks=modifypath & refreshenv & mc'
+
+.. figure:: https://user-images.githubusercontent.com/453543/173195789-9ef87618-5526-4317-99d7-b0dee6ca3970.png
+    :width: 800
+
+
+Python
+======
+
+Select a Windows container image including `Python`_ and launch it.
+
+Display Python version, launched within containers in different environments::
+
+    # Server Core
+    racker --verbose run --rm --platform=windows/amd64 python:2.7 -- python -V
+    racker --verbose run --rm --platform=windows/amd64 python:3.9 -- python -V
+    racker run --rm --platform=windows/amd64 winamd64/python:3.9-windowsservercore-1809 -- python -V
+    racker run --rm --platform=windows/amd64 winamd64/python:3.10-windowsservercore-ltsc2022 -- python -V
+    racker run --rm --platform=windows/amd64 winamd64/python:3.11-rc -- python -V
+
+    # Explicitly select `2019-box` as different host OS.
+    # The default would be to automatically select `2022-box`.
+    RACKER_WDM_MACHINE=2019-box racker --verbose run --rm --platform=windows/amd64 winamd64/python:3.11-rc -- python -V
+
+    # Nano Server
+    racker --verbose run --rm --platform=windows/amd64 stefanscherer/python-windows:nano -- python -V
+
+Display the Zen of Python::
+
+    racker --verbose run --rm --platform=windows/amd64 python:3.9 -- 'python -c "import this"'
+
+Install NumPy and display its configuration::
+
+    racker --verbose run --rm --platform=windows/amd64 python:3.10 -- 'sh -c "pip install numpy; python -c \"import numpy; numpy.show_config()\""'
+
+
+Java
+====
+
+Display Java version, launched within containers in different environments::
+
+    # Eclipse Temurin.
+    racker --verbose run --rm --platform=windows/amd64 eclipse-temurin:16-jdk -- java --version
+    racker --verbose run --rm --platform=windows/amd64 eclipse-temurin:18-jdk -- java --version
+
+    # Oracle OpenJDK.
+    racker --verbose run --rm --platform=windows/amd64 openjdk:8 -- java -version
+    racker --verbose run --rm --platform=windows/amd64 openjdk:8-windowsservercore-ltsc2016 -- java -version
+    racker --verbose run --rm --platform=windows/amd64 openjdk:8-windowsservercore-1809 -- java -version
+    racker --verbose run --rm --platform=windows/amd64 openjdk:19 -- java --version
+
+    # Explicitly select `2019-box` as different host OS.
+    # The default would be to automatically select `2022-box`.
+    RACKER_WDM_MACHINE=2019-box racker --verbose run --rm --platform=windows/amd64 openjdk:19 -- java --version
+
+    # Nano Server
+    racker --verbose run --rm --platform=windows/amd64 openjdk:19-nanoserver -- java --version
+
+
+Invoke a Java command prompt (JShell) with different Java and OS versions::
+
+    racker --verbose run -it --rm --platform=windows/amd64 eclipse-temurin:18-jdk jshell
+    racker --verbose run -it --rm --platform=windows/amd64 openjdk:8-windowsservercore-ltsc2016 jshell
+    racker --verbose run -it --rm --platform=windows/amd64 openjdk:8-windowsservercore-1809 jshell
+    racker --verbose run -it --rm --platform=windows/amd64 openjdk:19-windowsservercore-ltsc2022 jshell
+    System.out.println("OS: " + System.getProperty("os.name") + ", version " + System.getProperty("os.version"))
+    System.out.println("Java: " + System.getProperty("java.vendor") + ", version " + System.getProperty("java.version"))
+    /exit
+
+
+
+******************
+Container handbook
+******************
+
+Inquire system information
+==========================
+
+On systems where ``wmic`` is installed::
+
+    docker --context=2019-box run -it --rm mcr.microsoft.com/windows/servercore:ltsc2019 cmd
     wmic cpu get NumberOfCores
     wmic computersystem get TotalPhysicalMemory
 
-::
+On systems where PowerShell is installed::
 
-    docker --context=2019-box run -it --rm openjdk:17-windowsservercore-1809 powershell
+    docker --context=2019-box run -it --rm mcr.microsoft.com/windows/servercore:ltsc2019 powershell
     Get-ComputerInfo
 
-Terminate an environment::
 
-    docker --context=2019-box ps
-    docker --context=2019-box stop 5e2fe406ccbc
+Manipulating ``PATH``
+=====================
+
+Display the content of the ``PATH`` environment variable::
+
+    echo %PATH%
+    (Get-ItemProperty 'HKLM:\SYSTEM\CurrentControlSet\Control\Session Manager\Environment' -Name Path).Path
+
+Set the content of the ``PATH`` environment variable::
+
+    # Using `setx`.
+    setx PATH "$env:path;$($env:SystemDrive)\Program Files\Git\bin" -m
+
+    # Using PowerShell.
+    [Environment]::SetEnvironmentVariable('Path', $env:Path + ';' + $($env:SystemDrive) + '\Program Files\Git\bin', 'Machine')
+
+
+
+***********
+Admin guide
+***********
+
+
+Terminate a container
+=====================
+
+You will experience situations where the invocation of programs will block your
+terminal and you can't terminate the process using ``CTRL+C``. For example, try
+to run ``wish.exe``.
+
+In such situations, you might want to kill the container. It works like this::
+
+    # Find the container id.
+    docker --context=2022-box ps
+
+    # Terminate or stop the container.
+    docker --context=2022-box kill 08df5fc812f9
+    docker --context=2022-box stop 08df5fc812f9
+
+
+The Docker contexts
+===================
+
+Communication from the Docker CLI to the Docker daemons running on the WDM
+machines is established through Docker contexts.
+
+To list all active contexts, type::
+
+    docker context list
+
+To remove the contexts automatically established by WDM, type::
+
+    docker context rm 2016-box 2019-box 2022-box
+
+
+Installing and using Chocolatey
+===============================
+
+The `Chocolatey`_ package manager can be used to install additional software like
+``git`` and ``bash``::
+
+    racker run -it --rm --platform=windows/amd64 mcr.microsoft.com/windows/servercore:ltsc2019 powershell
+    Set-ExecutionPolicy Bypass -Scope Process -Force; [System.Net.ServicePointManager]::SecurityProtocol = [System.Net.ServicePointManager]::SecurityProtocol -bor 3072; iex ((New-Object System.Net.WebClient).DownloadString('https://community.chocolatey.org/install.ps1'))
+
+    choco install --yes git --package-parameters="/GitAndUnixToolsOnPath /Editor:Nano"
+    iex ((New-Object System.Net.WebClient).DownloadString('https://raw.githubusercontent.com/badrelmers/RefrEnv/main/refrenv.ps1'))
+
+    $ bash --version
+    $ git --version
+
+The whole software catalog can be inquired at `Chocolatey community packages`_.
+
 
+.. _Chocolatey: https://chocolatey.org/
+.. _Chocolatey community packages: https://community.chocolatey.org/packages
+.. _eclipse-temurin: https://hub.docker.com/_/eclipse-temurin
+.. _Midnight Commander: https://en.wikipedia.org/wiki/Midnight_Commander
+.. _Overview of System Center release options: https://docs.microsoft.com/en-us/system-center/ltsc-and-sac-overview
+.. _Python: https://www.python.org/
+.. _Scoop: https://scoop.sh/
+.. _Using Racker and Postroj for CrateDB CI: https://github.com/cicerops/racker/blob/main/doc/cratedb.rst
+.. _Vagrant: https://www.vagrantup.com/
+.. _VirtualBox: https://www.virtualbox.org/
+.. _Windows Container Base Images: https://docs.microsoft.com/en-us/virtualization/windowscontainers/manage-containers/container-base-images
+.. _Windows container version compatibility: https://docs.microsoft.com/en-us/virtualization/windowscontainers/deploy-containers/version-compatibility
+.. _Windows Docker Machine: https://github.com/StefanScherer/windows-docker-machine
+.. _Winfetch: https://github.com/kiedtl/winfetch
+.. _Wheels for Windows: https://github.com/PyTables/PyTables/pull/872#issuecomment-773535041
diff --git a/postroj/cli.py b/postroj/cli.py
index d6583c4..2558dfe 100644
--- a/postroj/cli.py
+++ b/postroj/cli.py
@@ -4,7 +4,7 @@
 
 import click
 
-from postroj import pkgprobe, runner, selftest, winrunner
+from postroj import pkgprobe, selftest
 from postroj.api import pull_multiple_images, pull_single_image
 from postroj.registry import list_images
 from postroj.util import boot
@@ -48,6 +48,5 @@ def cli_pull(ctx: click.Context, name: str, pull_all: bool = False):
 
 cli.add_command(cmd=cli_list_images, name="list-images")
 cli.add_command(cmd=cli_pull, name="pull")
-cli.add_command(cmd=runner.invoke, name="invoke")
 cli.add_command(cmd=pkgprobe.main, name="pkgprobe")
 cli.add_command(cmd=selftest.selftest_main, name="selftest")
diff --git a/postroj/exceptions.py b/postroj/exceptions.py
index 20a7a2b..bfbd69b 100644
--- a/postroj/exceptions.py
+++ b/postroj/exceptions.py
@@ -11,7 +11,7 @@ class ProvisioningError(Exception):
 
 
 class InvalidImageReference(Exception):
-    pass
+    returncode = 1
 
 
 class InvalidPhysicalImage(Exception):
diff --git a/postroj/runner.py b/postroj/runner.py
deleted file mode 100644
index aacb60c..0000000
--- a/postroj/runner.py
+++ /dev/null
@@ -1,38 +0,0 @@
-# -*- coding: utf-8 -*-
-# (c) 2022 Andreas Motl <andreas.motl@cicerops.de>
-import logging
-import sys
-
-import click
-
-from postroj.winrunner import WinRunner
-from racker.cli import racker_run
-
-logger = logging.getLogger(__name__)
-
-
-@click.command()
-@click.option("--system", type=str)
-@click.option("--cpus", type=int)
-@click.option("--memory", type=str)
-@click.option("--mount", type=str)
-@click.argument("command", nargs=-1, type=str)
-@click.pass_context
-def invoke(ctx, system, cpus, memory, mount, command):
-    """
-    Run a command within a designated system environment
-    """
-    # TODO: Propagate and implement `cpus`, `memory` and `mount`. See
-    command = " ".join(command)
-    if system == "windows-1809":
-        runner = WinRunner()
-        runner.setup()
-        runner.start()
-        outcome = runner.run(command)
-        sys.stdout.write(outcome)
-    else:
-        raise NotImplementedError(f'Runtime system "{system}" not supported yet')
-
-
-if __name__ == "__main__":
-    racker_run()
diff --git a/postroj/winrunner.Dockerfile b/postroj/winrunner.Dockerfile
new file mode 100644
index 0000000..6468d74
--- /dev/null
+++ b/postroj/winrunner.Dockerfile
@@ -0,0 +1,46 @@
+# Windows runner Dockerfile for Racker
+# https://github.com/cicerops/racker
+#
+# Provision a Windows operating system image.
+#
+# - Install the Scoop package manager.
+# - Install additional software using Scoop.
+# - https://scoop.sh/
+#
+
+ARG BASE_IMAGE
+
+FROM ${BASE_IMAGE}
+
+# Restore the default Windows shell for correct batch processing.
+SHELL ["cmd", "/S", "/C"]
+
+# Install the Scoop package manager.
+# https://github.com/ScoopInstaller/Install#for-admin
+RUN powershell -Command irm get.scoop.sh -outfile 'scoop-install.ps1'; .\scoop-install.ps1 -RunAsAdmin
+
+# Install/update Aria2 and Git first, to speed up downloads and have it up-to-date.
+RUN scoop install aria2 git
+
+# Install essential and convenience programs.
+RUN scoop install msys2 zip unzip
+
+# Make MSYS2 programs available on the program search path.
+# Note: It is not fully installed. In order to complete it, run `msys2` once.
+RUN powershell $msys_path = $(scoop prefix msys2); [Environment]::SetEnvironmentVariable('Path', $env:Path + ';' + $msys_path + '\usr\bin', 'Machine')
+
+# Display the program search path.
+#RUN powershell echo (Get-ItemProperty 'HKLM:\SYSTEM\CurrentControlSet\Control\Session Manager\Environment' -Name Path).Path
+
+# Rename Windows-native programs in favor of Scoop-installed/FOSS/GNU ones.
+# An alternative would be to manipulate `$PATH`, but that is more tedious.
+RUN sh -c 'test -f /c/Windows/system32/curl && mv /c/Windows/system32/curl /c/Windows/system32/curl-win'
+RUN sh -c 'test -f /c/Windows/system32/convert && mv /c/Windows/system32/convert /c/Windows/system32/convert-ntfs'
+
+# TODO: With PowerShell 7, it is possible to remove the corresponding aliases.
+#Remove-Alias -Name ls
+#Remove-Alias -Name cat
+#Remove-Alias -Name mv
+#Remove-Alias -Name ps
+#Remove-Alias -Name pwd
+#Remove-Alias -Name rm
diff --git a/postroj/winrunner.py b/postroj/winrunner.py
index b4eb124..99584af 100644
--- a/postroj/winrunner.py
+++ b/postroj/winrunner.py
@@ -1,56 +1,180 @@
 # -*- coding: utf-8 -*-
 # (c) 2022 Andreas Motl <andreas.motl@cicerops.de>
 """
-A convenience wrapper around Windows Docker Machine.
+A convenience wrapper around Windows Docker Machine by Stefan Scherer.
 
 https://github.com/StefanScherer/windows-docker-machine
 """
 import json
-import shlex
+import logging
+import os
 import subprocess
+import tempfile
 from pathlib import Path
 from urllib.parse import urlparse
 
-import click
+import appdirs
+import pkg_resources
 
-from postroj.util import port_is_up
+from postroj.exceptions import InvalidImageReference
+from postroj.util import port_is_up, cmd, fix_tty, subprocess_get_error_message
+
+logger = logging.getLogger(__name__)
 
 
 class WinRunner:
 
-    BOX = "2019-box"
+    VAGRANT_PROVIDER = os.environ.get("RACKER_WDM_PROVIDER", "virtualbox")
+    VCPUS = os.environ.get("RACKER_WDM_VCPUS", 4)
+    MEMORY = os.environ.get("RACKER_WDM_MEMORY", 4096)
+
+    def __init__(self, image: str):
+        self.image_base = image
+        self.image_real = "racker-runtime/" + self.image_base.replace("/", "-")
 
-    def __init__(self):
-        self.workdir = Path.home() / "postroj"
-        self.workdir.mkdir(exist_ok=True)
+        self.wdm_machine = None
+        self.choose_wdm_machine()
+        logger.info(f"Using WDM host machine {self.wdm_machine} for launching container image {self.image_base}")
+
+        self.workdir = Path(appdirs.user_state_dir(appname="racker"))
+        self.workdir.mkdir(exist_ok=True, parents=True)
 
         self.wdmdir = self.workdir / "windows-docker-machine"
 
     def setup(self):
+        """
+        Prepare virtual machine and adjust system resources.
+        """
         if not self.wdmdir.exists():
-            click.echo("Installing Windows Docker Machine")
+            logger.info(f"Installing Windows Docker Machine into {self.wdmdir}")
             command = f"""
-                cd {self.workdir}
-                git clone https://github.com/StefanScherer/windows-docker-machine
+                cd '{self.workdir}'
+                git clone https://github.com/cicerops/windows-docker-machine --branch racker
                 cd windows-docker-machine
-                #ls -alF
-                sed -i 's/v.memory = 2048/v.memory = 8192/' Vagrantfile
-                sed -i 's/v.cpus = 2/v.cpus = 8/' Vagrantfile
+                sed -i 's/v.cpus = [0-9]\+/v.cpus = {self.VCPUS}/' Vagrantfile
+                sed -i 's/v.memory = [0-9]\+/v.memory = {self.MEMORY}/' Vagrantfile
+                sed -i 's/v.maxmemory = [0-9]\+/v.maxmemory = {self.MEMORY}/' Vagrantfile
             """
-            run(command, shell=True)
+            hshell(command)
         else:
-            click.echo("Windows Docker Machine already installed")
+            logger.info(f"Windows Docker Machine already installed into {self.wdmdir}")
 
-    def start(self):
+    def choose_wdm_machine(self):
+        """
+        Choose the right virtual machine based on the container image to launch.
+        """
+
+        image = self.image_base
+        if not image.startswith("docker://"):
+            image = f"docker://{image}"
+
+        logger.info(f"Inquiring information about OCI image '{image}'")
+
+        if "RACKER_WDM_MACHINE" in os.environ:
+            self.wdm_machine = os.environ["RACKER_WDM_MACHINE"]
+            return
+
+        # TODO: Cache the response from `skopeo inspect` to avoid the 3-second speed bump.
+        #       https://github.com/cicerops/racker/issues/6
+        command = f"skopeo --override-os=windows inspect --config --raw {image}"
+        try:
+            process = cmd(command, capture=True)
+        except subprocess.CalledProcessError as ex:
+            message = subprocess_get_error_message(exception=ex)
+            message = f"Inquiring information about OCI image '{image}' failed. {message}"
+            logger.error(message)
+            exception = InvalidImageReference(message)
+            exception.returncode = ex.returncode
+            raise exception
+
+        image_info = json.loads(process.stdout)
+        image_os_name = image_info["os"]
+        image_os_version = image_info["os.version"]
+        logger.info(f"Image inquiry said os={image_os_name}, version={image_os_version}")
+
+        if image_os_name != "windows":
+            raise ValueError(f"Container image {image} is not Windows, but {image_os_name} instead")
+
+        # https://docs.microsoft.com/en-us/virtualization/windowscontainers/deploy-containers/version-compatibility
+        # https://stefanscherer.github.io/windows-docker-workshop/#91
+        os_version_box_map = {
+            "10.0.14393": "2016-box",
+            "10.0.16299": "2019-box",   # openjdk:8-windowsservercore-1709
+            "10.0.17134": "2019-box",
+            "10.0.17763": "2019-box",
+            "10.0.19042": "2022-box",
+            "10.0.20348": "2022-box",
+        }
+
+        for os_version, machine in os_version_box_map.items():
+            if image_os_version.startswith(os_version):
+                self.wdm_machine = machine
+
+        if self.wdm_machine is None:
+            raise ValueError(f"Unable to choose WDM host machine for container image {image}, matching OS version {image_os_version}. "
+                             f"Please report this error to https://github.com/cicerops/racker/issues/new.")
+
+    def start(self, provision=False):
+        """
+        Start the "Windows Docker Machine" virtual machine.
+
+        - Launch a virtual machine using Vagrant.
+        - Connect to Docker daemon on virtual machine.
+        - Provision the operating system image with additional software.
+        """
 
         if self.docker_context_online():
-            click.echo("Docker context is online")
+            logger.info("Docker context is online")
+        else:
+            logger.info("Docker context is offline, starting VirtualBox VM with Vagrant")
+            # TODO: The `provision` option flag is not wired in any way yet.
+            #       https://github.com/cicerops/racker/issues/7
+            provision_option = ""
+            if provision:
+                provision_option = "--provision"
+            cmd(f"vagrant up --provider={self.VAGRANT_PROVIDER} {provision_option} {self.wdm_machine}", cwd=self.wdmdir, use_stderr=True)
+
+        logger.info("Pinging Docker context")
+        if not self.docker_context_online():
+            raise IOError(f"Unable to bring up Docker context {self.wdm_machine}")
+
+        # Attention: This can run into 60 second timeouts.
+        # TODO: Use ``with stopit.ThreadingTimeout(timeout) as to_ctx_mgr``.
+        # TODO: Make timeout values configurable.
+        # https://github.com/moby/moby/blob/0e04b514fb/integration-cli/docker_cli_run_test.go
+        cmd(f"docker --context={self.wdm_machine} ps", capture=True)
+
+        # Skip installing software using Chocolatey for specific Windows OS versions.
+        # - Windows Nanoserver does not have PowerShell.
+        # - Windows 2016 croaks like:
+        #   `The command 'cmd /S /C choco install --yes ...' returned a non-zero code: 3221225785`
+        if "nanoserver" in self.image_base or self.wdm_machine == "2016-box":
+            self.image_real = self.image_base
         else:
-            click.echo("Docker context is offline, starting VirtualBox VM with Vagrant")
-            run(f"vagrant up --provider=virtualbox {self.BOX}", cwd=self.wdmdir)
+            self.provision_image()
 
-        click.echo("Pinging Docker context")
-        run("docker --context=2019-box ps")
+    def provision_image(self):
+        """
+        Provide an operating system image by building a Docker image using `winrunner.Dockerfile`.
+
+        - Provision a Windows operating system image with additional software.
+        - Automatically installs the open source version of the Chocolatey package manager.
+        - By default, it automatically installs some programs like `busybox`, `curl`, `git`,
+          `nano`, and `wget`.
+        """
+
+        logger.info(f"Provisioning Docker image for Windows environment based on {self.image_base}")
+        dockerfile = pkg_resources.resource_filename("postroj", "winrunner.Dockerfile")
+        tmpdir = tempfile.mkdtemp()
+        command = f"docker --context={self.wdm_machine} build --platform=windows/amd64 " \
+                  f"--file={dockerfile} --build-arg=BASE_IMAGE={self.image_base} --tag={self.image_real} {tmpdir}"
+        logger.debug(f"Running command: {command}")
+        try:
+            hcmd(command)
+        except subprocess.CalledProcessError:
+            raise
+        finally:
+            os.rmdir(tmpdir)
 
     def cmd(self, command):
         command = f"cmd /C {command}"
@@ -60,45 +184,66 @@ def powershell(self, command):
         command = f"powershell -Command {command}"
         return self.run(command)
 
-    def run(self, command, strip_armor=True, translate_newlines=True):
-        click.echo(f"Running command: {command}")
-        command = f"docker --context={self.BOX} run -it --rm openjdk:17-windowsservercore-1809 {command}"
-        outcome = run(command)
-        if strip_armor:
-            """
-            b'\x1b[2J\x1b[?25l\x1b[m\x1b[H\r\n\r\n...\r\n\x1b[H\x1b]0;C:\\Windows\\system32\\cmd.exe\x00\x07\x1b[?25h\x1b[?25lhello \r\n\x1b[?25h'
-            """
-            prefix = "\x1b[?25h\x1b[?25l"
-            suffix = "\x1b[?25h"
-            cutoff_left = outcome.find(prefix) + len(prefix)
-            cutoff_right = outcome.rfind(suffix)
-            outcome = outcome[cutoff_left:cutoff_right]
-        if translate_newlines:
-            outcome = outcome.replace("\r\n", "\n")
-        # print(outcome.encode())
-        return outcome
+    def run(self, command, interactive: bool = False, tty: bool = False):
+        logger.info(f"Running guest command: {command}")
+
+        option_interactive = ""
+        if interactive or tty:
+            option_interactive = "-it"
+
+        # TODO: Propagate ``--rm`` option appropriately.
+        # TODO: Propagate ``--volume`` option.
+        #       option_volume = "--volume=C:/Users/amo/dev/cicerops-foss/sources/postroj:C:/racker"
+        #       https://github.com/cicerops/racker/issues/8
+        option_volume = ""
+        #option_volume = "--volume=C:/Users/amo/dev/cicerops-foss/sources/postroj:C:/racker"
+        #option_volume = "--volume=C:/Users/amo/dev/panodata/sources/apprise:C:/apprise"
+        #option_volume = "--volume=C:/Users/amo/dev/earthobservations/wetterdienst:C:/wetterdienst"
+        #option_volume = "--volume=C:/Users/amo/dev/crate/sources/crate:C:/crate"
+        command = f"docker --context={self.wdm_machine} run {option_interactive} --rm {option_volume} {self.image_real} {command}"
+
+        # When an interactive prompt is requested, spawn a shell without further ado.
+        if interactive or tty:
+            ccmd(command, use_pty=True)
+
+        # Otherwise, capture stdout and mangle its output.
+        else:
+            outcome = cmd(command)
+            return outcome
 
     def docker_context_online(self):
         """
-        Test if a Docker context is online.
+        Test if the Docker context is online.
         """
-        response = json.loads(run(f"docker context inspect {self.BOX}"))
-        address = urlparse(response[0]["Endpoints"]["docker"]["Host"])
+        logger.info(f"Checking connectivity to Docker daemon in Windows context '{self.wdm_machine}'")
+        try:
+            response = cmd(f"docker context inspect {self.wdm_machine}", capture=True)
+        except:
+            logger.warning(f"Docker context {self.wdm_machine} not online or not created yet")
+            return False
+
+        data = json.loads(response.stdout)
+        address = urlparse(data[0]["Endpoints"]["docker"]["Host"])
+
+        logger.info(f"Checking TCP connectivity to {address.hostname}:{address.port}")
         return port_is_up(address.hostname, address.port)
 
 
-def run(command, shell=False, cwd=None):
-    """
-    Generic routine to run command within container.
-
-    STDERR will be displayed, STDOUT will be captured.
-    """
-    # print(f"Running command: {command}")
-    # command = f"""
-    #    systemd-run --machine={machine} --wait --quiet --pipe {command}
-    # """
-    if shell:
-        output = subprocess.check_output(command, shell=shell, cwd=cwd)
-    else:
-        output = subprocess.check_output(shlex.split(command), cwd=cwd)
-    return output.decode()
+def hcmd(command, cwd=None,  use_stderr=True, silent=False):
+    logger.debug(f"Running command: {command}")
+    return cmd(command, cwd=cwd, use_stderr=use_stderr)
+
+
+def hshell(command, cwd=None):
+    logger.debug(f"Running command: {command}")
+    #return cmd(command, cwd=cwd, passthrough=True).stdout
+    return subprocess.check_output(command, shell=True, cwd=cwd).decode()
+
+
+def ccmd(command, use_pty=False, capture=False):
+    logger.debug(f"Running command: {command}")
+    p = cmd(command=command, use_pty=use_pty, capture=capture)
+    stdout = p.stdout
+    if use_pty:
+        fix_tty()
+    return stdout
diff --git a/pyproject.toml b/pyproject.toml
index b9fb4e7..1404b88 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -20,7 +20,6 @@ markers = [
 [tool.coverage.run]
 omit = [
     "testing/*",
-    "postroj/winrunner.py",
 ]
 
 [tool.coverage.report]
diff --git a/racker/cli.py b/racker/cli.py
index 5ae0c0d..d811c84 100644
--- a/racker/cli.py
+++ b/racker/cli.py
@@ -10,8 +10,9 @@
 
 from postroj.api import pull_curated_image
 from postroj.container import PostrojContainer
-from postroj.exceptions import ProvisioningError
+from postroj.exceptions import ProvisioningError, InvalidImageReference
 from postroj.util import boot, subprocess_get_error_message
+from postroj.winrunner import WinRunner
 from racker.image import ImageLibrary
 
 logger = logging.getLogger(__name__)
@@ -47,10 +48,11 @@ def racker_pull(ctx, name: str):
 @click.option("--interactive", "-i", is_flag=True)
 @click.option("--tty", "-t", is_flag=True)
 @click.option("--rm", is_flag=True)
+@click.option("--platform", type=str, required=False)
 @click.argument("image", type=str, required=False)
 @click.argument("command", nargs=-1, type=str)
 @click.pass_context
-def racker_run(ctx, interactive: bool, tty: bool, rm: bool, image: str, command: str):
+def racker_run(ctx, interactive: bool, tty: bool, rm: bool, platform: str, image: str, command: str):
     """
     Spawn a container and run a command on it.
     Aims to be compatible with `docker run`.
@@ -84,6 +86,45 @@ def racker_run(ctx, interactive: bool, tty: bool, rm: bool, image: str, command:
     if interactive or tty:
         use_pty = True
 
+    # Use a different subsystem for running Windows containers on Linux or
+    # macOS.
+    if platform is None:
+        pass
+
+    elif platform == "windows/amd64":
+        logger.info(f"Preparing runtime environment for platform {platform} and image {image}")
+        try:
+            runner = WinRunner(image=image)
+        except InvalidImageReference as ex:
+            raise SystemExit(ex.returncode)
+        try:
+            with redirect_stdout(sys.stderr):
+                with redirect_stderr(sys.stderr):
+                    runner.setup()
+                    runner.start()
+        except subprocess.CalledProcessError as ex:
+            message = subprocess_get_error_message(exception=ex)
+            logger.critical(f"Launching container failed. {message}")
+            # subprocess_forward_stderr_stdout(exception=ex)
+            raise SystemExit(ex.returncode)
+
+        logger.info(f"Invoking command '{command}' on {image}")
+        try:
+            runner.run(command, interactive=interactive, tty=tty)
+        except subprocess.CalledProcessError as ex:
+            message = subprocess_get_error_message(exception=ex)
+            logger.critical(f"Running command in Windows container on image {image} failed. {message}")
+            raise SystemExit(ex.returncode)
+        return
+
+    else:
+        raise NotImplementedError(f'Runtime for platform "{platform}" not supported yet')
+
+    if sys.platform != "linux":
+        raise NotImplementedError(f"Unable to launch Linux systems on non-Linux machines yet, "
+                                  f"please use the Vagrant setup")
+
+    # Acquire filesystem image.
     # TODO: Add more advanced image registry, maybe using `docker-py`,
     #       resolving image names from postroj-internal images, Docker Hub,
     #       GHCR, etc.
diff --git a/setup.py b/setup.py
index 64668f0..ea9e1a1 100644
--- a/setup.py
+++ b/setup.py
@@ -76,6 +76,7 @@
         ],
     },
     install_requires=[
+        "appdirs>=1,<2",
         "click>=7,<9",
         "furl>=2,<3",
         "subprocess-tee>=0.3,<1",
diff --git a/testing/postroj/test_winrunner.py b/testing/postroj/test_winrunner.py
new file mode 100644
index 0000000..afe378b
--- /dev/null
+++ b/testing/postroj/test_winrunner.py
@@ -0,0 +1,60 @@
+# -*- coding: utf-8 -*-
+# (c) 2022 Andreas Motl <andreas.motl@cicerops.de>
+import pytest
+
+from postroj.winrunner import ccmd, hshell, hcmd
+
+
+def test_hcmd_echo_newline(capfd):
+    process = hcmd("/bin/echo foo", use_stderr=False)
+    assert process.stdout is None
+    assert process.stderr is None
+
+    result = capfd.readouterr()
+    assert result.out == "foo\n"
+    assert result.err == ""
+
+
+def test_hcmd_echo_no_newline(capfd):
+    hcmd("/bin/echo -n foo", use_stderr=False)
+    result = capfd.readouterr()
+    assert result.out == "foo"
+
+
+def test_hshell_echo_newline():
+    output = hshell("/bin/echo foo")
+    assert output == "foo\n"
+
+
+def test_hshell_echo_no_newline():
+    output = hshell("/bin/echo -n foo")
+    assert output == "foo"
+
+
+def test_ccmd_echo_newline():
+    output = ccmd("/bin/echo foo", capture=True)
+    assert output == "foo\n"
+
+
+def test_ccmd_echo_newline_pty(capfd):
+    output = ccmd("/bin/echo foo", capture=True, use_pty=True)
+    assert output is None
+
+    result = capfd.readouterr()
+    assert result.out == "foo\n"
+    assert result.err == ""
+
+
+@pytest.mark.xfail
+def test_ccmd_echo_no_newline():
+    output = ccmd("/bin/echo -n foo", capture=True)
+    assert output == "foo"
+
+
+def test_ccmd_echo_no_newline_pty(capfd):
+    output = ccmd("/bin/echo -n foo", capture=True, use_pty=True)
+    assert output is None
+
+    result = capfd.readouterr()
+    assert result.out == "foo"
+    assert result.err == ""
diff --git a/testing/racker/test_run.py b/testing/racker/test_run.py
index 4edb12c..0af6a6c 100644
--- a/testing/racker/test_run.py
+++ b/testing/racker/test_run.py
@@ -1,9 +1,11 @@
 # -*- coding: utf-8 -*-
 # (c) 2022 Andreas Motl <andreas.motl@cicerops.de>
+import re
 import shlex
 import subprocess
 import sys
 from pathlib import Path
+from unittest import mock
 
 import pytest
 from click._compat import strip_ansi
@@ -12,6 +14,9 @@
 from racker.cli import cli
 
 
+# Currently, this test module effectively runs well on Linux,
+# because it invokes machinery based on `systemd-nspawn`.
+
 if sys.platform != "linux":
     pytest.skip("Skipping Linux-only tests", allow_module_level=True)
 
@@ -104,6 +109,73 @@ def test_run_stdin_stdout(monkeypatch, capsys, delay):
     assert process.stdout == b"foo"
 
 
+@pytest.mark.xfail(reason="Not working within Linux VM on macOS. Reason: "
+                          "Cannot enable nested VT-x/AMD-V without nested-paging and unrestricted guest execution!")
+def test_run_windows_valid_image(capfd, delay):
+    """
+    Request a valid Windows container image.
+
+    Note: This is currently not possible, because somehow VT-x does not work
+          well enough to support this scenario, at least not on macOS Catalina.
+    """
+    runner = CliRunner()
+
+    result = runner.invoke(cli, "run --rm --platform=windows/amd64 mcr.microsoft.com/windows/nanoserver:ltsc2022 -- cmd /C ver", catch_exceptions=False)
+    assert result.exit_code == 0
+
+    captured = capfd.readouterr()
+    assert "Microsoft Windows [Version 10.0.20348.707]" in captured.out
+
+
+def test_run_windows_invalid_image(caplog, delay):
+    """
+    Request an invalid Windows container image and make sure it croaks correctly.
+    """
+    runner = CliRunner()
+
+    result = runner.invoke(cli, "run --rm --platform=windows/amd64 images.example.org/foo/bar:special -- cmd /C ver", catch_exceptions=False)
+    assert result.exit_code == 1
+
+    assert re.match(".*Inquiring information about OCI image .+ failed.*", caplog.text)
+    assert re.match(".*Reason:.*Error parsing image name .* (error )?pinging (container|docker) registry images.example.org.*", caplog.text)
+
+
+def test_run_windows_mocked_noninteractive():
+    """
+    Pretend to launch a Windows container, but don't.
+    Reason: The `WinRunner` machinery has been mocked completely.
+    """
+    runner = CliRunner()
+
+    with mock.patch("racker.cli.WinRunner") as winrunner:
+        result = runner.invoke(cli, "run --rm --platform=windows/amd64 images.example.org/foo/bar:special -- cmd /C ver", catch_exceptions=False)
+    assert result.exit_code == 0
+    assert winrunner.mock_calls == [
+        mock.call(image='images.example.org/foo/bar:special'),
+        mock.call().setup(),
+        mock.call().start(),
+        mock.call().run('cmd /C ver', interactive=False, tty=False),
+    ]
+
+
+def test_run_windows_mocked_interactive():
+    """
+    Pretend to launch a Windows container, but don't.
+    Reason: The `WinRunner` machinery has been mocked completely.
+    """
+    runner = CliRunner()
+
+    with mock.patch("racker.cli.WinRunner") as winrunner:
+        result = runner.invoke(cli, "run -it --rm --platform=windows/amd64 images.example.org/foo/bar:special -- cmd /C ver", catch_exceptions=False)
+    assert result.exit_code == 0
+    assert winrunner.mock_calls == [
+        mock.call(image='images.example.org/foo/bar:special'),
+        mock.call().setup(),
+        mock.call().start(),
+        mock.call().run('cmd /C ver', interactive=True, tty=True),
+    ]
+
+
 # Unfortunately, this fails.
 """
 def test_run_stdin_stdout_original(capfd):
diff --git a/testing/racker/test_run_windows.py b/testing/racker/test_run_windows.py
new file mode 100644
index 0000000..370f359
--- /dev/null
+++ b/testing/racker/test_run_windows.py
@@ -0,0 +1,91 @@
+# -*- coding: utf-8 -*-
+# (c) 2022 Andreas Motl <andreas.motl@cicerops.de>
+import os
+import subprocess
+import sys
+from pathlib import Path
+import shlex
+import socket
+from subprocess import CalledProcessError, CompletedProcess
+
+import pytest
+
+
+# Currently, this test module effectively runs well on macOS.
+# The following snippet skips invocation on both VirtualBox
+# and GitHub Actions.
+
+if "rackerhost-debian11" in socket.gethostname():
+    pytest.skip("Nested virtualization with VT-x fails within "
+                "VirtualBox environment on developer's macOS workstation", allow_module_level=True)
+
+if "GITHUB_ACTIONS" in os.environ:
+    pytest.skip("Installing the Vagrant filesystem image for Windows "
+                "takes too much disk space on GitHub Actions", allow_module_level=True)
+
+
+def run_racker(command: str) -> subprocess.CompletedProcess:
+    program_path = Path(sys.argv[0]).parent
+    racker = program_path / "racker"
+    command = f"{racker} {command}"
+    process = subprocess.run(shlex.split(command), stdout=subprocess.PIPE)
+    process.check_returncode()
+    return process
+
+
+def test_run_windows_cmd_success():
+    """
+    Launch a Windows Nanoserver container and invoke a `cmd` command.
+    """
+    process = run_racker("--verbose run --rm --platform=windows/amd64 mcr.microsoft.com/windows/nanoserver:1809-amd64 cmd /C 'echo Hello, world.'")
+    process.check_returncode()
+    assert process.stdout == b"Hello, world.\r\n"
+
+
+def test_run_windows_cmd_failure():
+    """
+    Check exit code propagation of a failing `cmd` command.
+    """
+    with pytest.raises(CalledProcessError) as ex:
+        run_racker("--verbose run --rm --platform=windows/amd64 mcr.microsoft.com/windows/nanoserver:1809-amd64 cmd /C 'exit 66'")
+    process: CompletedProcess = ex.value
+    assert process.returncode == 66
+
+
+def test_run_windows_powershell_success():
+    """
+    Launch a Windows Server Core container and invoke a PowerShell command.
+    """
+    process = run_racker("--verbose run --rm --platform=windows/amd64 mcr.microsoft.com/windows/servercore:ltsc2019-amd64 -- 'powershell -Command {echo \"Hello, world.\"}'")
+    process.check_returncode()
+    # FIXME: Why does `echo` get echoed here!?
+    assert process.stdout == b"echo Hello, world.\r\n"
+
+
+def test_run_windows_powershell_failure():
+    """
+    Check exit code propagation of a failing PowerShell command.
+    """
+    with pytest.raises(CalledProcessError) as ex:
+        run_racker("--verbose run --rm --platform=windows/amd64 mcr.microsoft.com/windows/servercore:ltsc2019-amd64 -- 'powershell -Command exit 66'")
+    process: CompletedProcess = ex.value
+    assert process.returncode == 66
+
+
+def test_run_windows_bash_success():
+    """
+    Launch a Windows Server Core container and invoke a Bash command.
+    """
+    process = run_racker("--verbose run --rm --platform=windows/amd64 mcr.microsoft.com/windows/servercore:ltsc2019-amd64 -- 'sh -c \"echo Hello, world.\"'")
+    process.check_returncode()
+    assert process.stdout == b"Hello, world.\n"
+
+
+def test_run_windows_bash_failure():
+    """
+    Check exit code propagation of a failing Bash command.
+    """
+    with pytest.raises(CalledProcessError) as ex:
+        run_racker("--verbose run --rm --platform=windows/amd64 mcr.microsoft.com/windows/servercore:ltsc2019-amd64 -- 'sh -c \"exit 66\"'")
+    process: CompletedProcess = ex.value
+    assert process.returncode == 66