From 4ede48c89b8ec80bbd1895357f272c5fb61bc9b6 Mon Sep 17 00:00:00 2001
From: Lysandros Nikolaou <lisandrosnik@gmail.com>
Date: Wed, 8 Jan 2025 12:23:31 +0100
Subject: [PATCH] GH-44421: [Python] Add configuration for building & testing
 free-threaded wheels on Windows (#44804)

### Rationale for this change

There's no blockers anymore for building Windows wheels for the free-threaded build, so this PR adds the necessary configuration to do that.

### What changes are included in this PR?

- Add jobs to build free-threaded wheels on Windows
- Move VCPKG-related stuff to a reusable base job

### Are these changes tested?

No tests required.

### Are there any user-facing changes?

No.

* GitHub Issue: #44421

Lead-authored-by: Antoine Pitrou <antoine@python.org>
Co-authored-by: Lysandros Nikolaou <lisandrosnik@gmail.com>
Signed-off-by: Sutou Kouhei <kou@clear-code.com>
---
 .env                                          |  5 +-
 .pre-commit-config.yaml                       |  2 +-
 ...eaded-wheel-windows-test-vs2019.dockerfile | 52 ++++++++++++
 ...e-threaded-wheel-windows-vs2019.dockerfile | 49 +++++++++++
 ...-wheel-windows-test-vs2019-base.dockerfile | 51 ++++++++++++
 ...ython-wheel-windows-test-vs2019.dockerfile | 56 +++++--------
 ...ython-wheel-windows-vs2019-base.dockerfile | 79 ++++++++++++++++++
 .../python-wheel-windows-vs2019.dockerfile    | 83 +++----------------
 ci/scripts/python_wheel_windows_build.bat     | 19 +++--
 ci/scripts/python_wheel_windows_test.bat      | 14 +---
 dev/tasks/python-wheels/github.windows.yml    | 31 +++++--
 dev/tasks/tasks.yml                           |  8 +-
 docker-compose.yml                            | 73 +++++++++++++---
 13 files changed, 371 insertions(+), 151 deletions(-)
 create mode 100644 ci/docker/python-free-threaded-wheel-windows-test-vs2019.dockerfile
 create mode 100644 ci/docker/python-free-threaded-wheel-windows-vs2019.dockerfile
 create mode 100644 ci/docker/python-wheel-windows-test-vs2019-base.dockerfile
 create mode 100644 ci/docker/python-wheel-windows-vs2019-base.dockerfile

diff --git a/.env b/.env
index 3db2673ae9594..252f59ccfb2e6 100644
--- a/.env
+++ b/.env
@@ -92,10 +92,11 @@ TZ=UTC
 VCPKG="943c5ef1c8f6b5e6ced092b242c8299caae2ff01"    # 2024.04.26 Release
 
 # This must be updated when we update
-# ci/docker/python-wheel-windows-vs2019.dockerfile.
+# ci/docker/python-*-windows-*.dockerfile.
 # This is a workaround for our CI problem that "archery docker build" doesn't
 # use pulled built images in dev/tasks/python-wheels/github.windows.yml.
-PYTHON_WHEEL_WINDOWS_IMAGE_REVISION=2024-08-06
+PYTHON_WHEEL_WINDOWS_IMAGE_REVISION=2025-01-08
+PYTHON_WHEEL_WINDOWS_TEST_IMAGE_REVISION=2025-01-08
 
 # Use conanio/${CONAN_BASE}:{CONAN_VERSION} for "docker compose run --rm conan".
 # See https://github.com/conan-io/conan-docker-tools#readme and
diff --git a/.pre-commit-config.yaml b/.pre-commit-config.yaml
index 27823cae5fa28..e54fe2393cf3d 100644
--- a/.pre-commit-config.yaml
+++ b/.pre-commit-config.yaml
@@ -39,7 +39,7 @@ repos:
         files: >-
           (
           ?^ci/docker/conda-python-emscripten\.dockerfile$|
-          ?^ci/docker/python-wheel-windows-test-vs2019\.dockerfile$|
+          ?^ci/docker/python-.*-wheel-windows-test-vs2019.*\.dockerfile$|
           )
         types: []
   - repo: https://github.com/pycqa/flake8
diff --git a/ci/docker/python-free-threaded-wheel-windows-test-vs2019.dockerfile b/ci/docker/python-free-threaded-wheel-windows-test-vs2019.dockerfile
new file mode 100644
index 0000000000000..4b972999b0475
--- /dev/null
+++ b/ci/docker/python-free-threaded-wheel-windows-test-vs2019.dockerfile
@@ -0,0 +1,52 @@
+# Licensed to the Apache Software Foundation (ASF) under one
+# or more contributor license agreements.  See the NOTICE file
+# distributed with this work for additional information
+# regarding copyright ownership.  The ASF licenses this file
+# to you under the Apache License, Version 2.0 (the
+# "License"); you may not use this file except in compliance
+# with the License.  You may obtain a copy of the License at
+#
+#   http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing,
+# software distributed under the License is distributed on an
+# "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY
+# KIND, either express or implied.  See the License for the
+# specific language governing permissions and limitations
+# under the License.
+
+# NOTE: You must update PYTHON_WHEEL_WINDOWS_TEST_IMAGE_REVISION in .env
+# when you update this file.
+
+ARG base
+# https://github.com/hadolint/hadolint/wiki/DL3006
+# (Hadolint does not expand variables and thinks '${base}' is an untagged image)
+# hadolint ignore=DL3006
+FROM ${base}
+
+ARG python=3.13
+
+SHELL ["powershell", "-NoProfile", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
+RUN $filename = 'python-3.13.1-amd64.exe'; \
+    $url = 'https://www.python.org/ftp/python/3.13.1/' + $filename; \
+    Invoke-WebRequest -Uri $url -OutFile $filename; \
+    Start-Process -FilePath $filename -ArgumentList '/quiet', 'Include_freethreaded=1' -Wait
+
+ENV PYTHON_CMD="py -${python}t"
+
+SHELL ["cmd", "/S", "/C"]
+RUN %PYTHON_CMD% -m pip install -U pip setuptools
+
+COPY python/requirements-wheel-test.txt C:/arrow/python/
+# Cython and Pandas wheels for 3.13 free-threaded are not released yet
+RUN %PYTHON_CMD% -m pip install \
+    --extra-index-url https://pypi.anaconda.org/scientific-python-nightly-wheels/simple \
+    --pre \
+    --prefer-binary \
+    -r C:/arrow/python/requirements-wheel-test.txt
+# cffi-based tests would crash when importing cffi.
+# hadolint ignore=DL3059
+RUN %PYTHON_CMD% -m pip uninstall -y cffi
+
+ENV PYTHON="${python}t"
+ENV PYTHON_GIL=0
diff --git a/ci/docker/python-free-threaded-wheel-windows-vs2019.dockerfile b/ci/docker/python-free-threaded-wheel-windows-vs2019.dockerfile
new file mode 100644
index 0000000000000..adbdccde71dfc
--- /dev/null
+++ b/ci/docker/python-free-threaded-wheel-windows-vs2019.dockerfile
@@ -0,0 +1,49 @@
+# Licensed to the Apache Software Foundation (ASF) under one
+# or more contributor license agreements.  See the NOTICE file
+# distributed with this work for additional information
+# regarding copyright ownership.  The ASF licenses this file
+# to you under the Apache License, Version 2.0 (the
+# "License"); you may not use this file except in compliance
+# with the License.  You may obtain a copy of the License at
+#
+#   http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing,
+# software distributed under the License is distributed on an
+# "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY
+# KIND, either express or implied.  See the License for the
+# specific language governing permissions and limitations
+# under the License.
+
+# NOTE: You must update PYTHON_WHEEL_WINDOWS_IMAGE_REVISION in .env
+# when you update this file.
+
+ARG base
+# https://github.com/hadolint/hadolint/wiki/DL3006
+# (Hadolint does not expand variables and thinks '${base}' is an untagged image)
+# hadolint ignore=DL3006
+FROM ${base}
+
+ARG python=3.13
+
+SHELL ["powershell", "-NoProfile", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
+RUN $filename = 'python-3.13.1-amd64.exe'; \
+    $url = 'https://www.python.org/ftp/python/3.13.1/' + $filename; \
+    Invoke-WebRequest -Uri $url -OutFile $filename; \
+    Start-Process -FilePath $filename -ArgumentList '/quiet', 'Include_freethreaded=1' -Wait
+
+ENV PYTHON_CMD="py -${python}t"
+
+SHELL ["cmd", "/S", "/C"]
+RUN %PYTHON_CMD% -m pip install -U pip setuptools
+
+COPY python/requirements-wheel-build.txt C:/arrow/python/
+# Cython wheels for 3.13 free-threaded are not released yet
+RUN %PYTHON_CMD% -m pip install \
+    --extra-index-url https://pypi.anaconda.org/scientific-python-nightly-wheels/simple \
+    --pre \
+    --prefer-binary \
+    cython
+RUN %PYTHON_CMD% -m pip install -r C:/arrow/python/requirements-wheel-build.txt
+
+ENV PYTHON="${python}t"
diff --git a/ci/docker/python-wheel-windows-test-vs2019-base.dockerfile b/ci/docker/python-wheel-windows-test-vs2019-base.dockerfile
new file mode 100644
index 0000000000000..73a78da30b907
--- /dev/null
+++ b/ci/docker/python-wheel-windows-test-vs2019-base.dockerfile
@@ -0,0 +1,51 @@
+# Licensed to the Apache Software Foundation (ASF) under one
+# or more contributor license agreements.  See the NOTICE file
+# distributed with this work for additional information
+# regarding copyright ownership.  The ASF licenses this file
+# to you under the Apache License, Version 2.0 (the
+# "License"); you may not use this file except in compliance
+# with the License.  You may obtain a copy of the License at
+#
+#   http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing,
+# software distributed under the License is distributed on an
+# "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY
+# KIND, either express or implied.  See the License for the
+# specific language governing permissions and limitations
+# under the License.
+
+# NOTE: You must update PYTHON_WHEEL_WINDOWS_TEST_IMAGE_REVISION in .env
+# when you update this file.
+
+# based on mcr.microsoft.com/windows/servercore:ltsc2019
+# contains choco and vs2019 preinstalled
+FROM abrarov/msvc-2019:2.11.0
+
+# hadolint shell=cmd.exe
+
+# Add unix tools to path
+RUN setx path "%path%;C:\Program Files\Git\usr\bin"
+
+# 1. Remove previous installations of Python from the base image
+# NOTE: a more recent base image (tried with 2.12.1) comes with Python 3.9.7
+# and the MSI installers are failing to remove pip and tcl/tk "products" making
+# the subsequent choco python installation step failing for installing Python
+# version 3.9.* due to existing python version
+# 2. Install Minio for S3 testing.
+RUN wmic product where "name like 'python%%'" call uninstall /nointeractive && \
+    rm -rf Python* && \
+    curl https://dl.min.io/server/minio/release/windows-amd64/archive/minio.RELEASE.2024-09-13T20-26-02Z \
+        --output "C:\Windows\Minio.exe"
+
+# Install archiver to extract xz archives (for timezone database).
+# Install the GCS testbench using a well-known Python version.
+# NOTE: cannot use pipx's `--fetch-missing-python` because of
+# https://github.com/pypa/pipx/issues/1521, therefore download Python ourselves.
+RUN choco install --no-progress -r -y archiver && \
+    choco install -r -y --pre --no-progress python --version=3.11.9
+ENV PIPX_BIN_DIR=C:\\Windows\\
+ENV PIPX_PYTHON="C:\Python311\python.exe"
+COPY ci/scripts/install_gcs_testbench.bat C:/arrow/ci/scripts/
+RUN call "C:\arrow\ci\scripts\install_gcs_testbench.bat" && \
+    storage-testbench -h
diff --git a/ci/docker/python-wheel-windows-test-vs2019.dockerfile b/ci/docker/python-wheel-windows-test-vs2019.dockerfile
index 564bca329f3cb..f80e7ba0fe044 100644
--- a/ci/docker/python-wheel-windows-test-vs2019.dockerfile
+++ b/ci/docker/python-wheel-windows-test-vs2019.dockerfile
@@ -15,49 +15,31 @@
 # specific language governing permissions and limitations
 # under the License.
 
-# NOTE: You must update PYTHON_WHEEL_WINDOWS_IMAGE_REVISION in .env
+# NOTE: You must update PYTHON_WHEEL_WINDOWS_TEST_IMAGE_REVISION in .env
 # when you update this file.
 
-# based on mcr.microsoft.com/windows/servercore:ltsc2019
-# contains choco and vs2019 preinstalled
-FROM abrarov/msvc-2019:2.11.0
+ARG base
+# https://github.com/hadolint/hadolint/wiki/DL3006
+# (Hadolint does not expand variables and thinks '${base}' is an untagged image)
+# hadolint ignore=DL3006
+FROM ${base}
 
 # hadolint shell=cmd.exe
 
-# Add unix tools to path
-RUN setx path "%path%;C:\Program Files\Git\usr\bin"
-
-# 1. Remove previous installations of python from the base image
-# NOTE: a more recent base image (tried with 2.12.1) comes with python 3.9.7
-# and the msi installers are failing to remove pip and tcl/tk "products" making
-# the subsequent choco python installation step failing for installing python
-# version 3.9.* due to existing python version
-# 2. Install Minio for S3 testing.
-RUN wmic product where "name like 'python%%'" call uninstall /nointeractive && \
-    rm -rf Python* && \
-    curl https://dl.min.io/server/minio/release/windows-amd64/archive/minio.RELEASE.2024-09-13T20-26-02Z \
-        --output "C:\Windows\Minio.exe"
-
-# Install the GCS testbench using a well-known Python version.
-# NOTE: cannot use pipx's `--fetch-missing-python` because of
-# https://github.com/pypa/pipx/issues/1521, therefore download Python ourselves.
-RUN choco install -r -y --pre --no-progress python --version=3.11.9
-ENV PIPX_BIN_DIR=C:\\Windows\\
-ENV PIPX_PYTHON="C:\Python311\python.exe"
-COPY ci/scripts/install_gcs_testbench.bat C:/arrow/ci/scripts/
-RUN call "C:\arrow\ci\scripts\install_gcs_testbench.bat" && \
-    storage-testbench -h
-
 # Define the full version number otherwise choco falls back to patch number 0 (3.9 => 3.9.0)
 ARG python=3.9
-RUN (if "%python%"=="3.9" setx PYTHON_VERSION "3.9.13") & \
-    (if "%python%"=="3.10" setx PYTHON_VERSION "3.10.11") & \
-    (if "%python%"=="3.11" setx PYTHON_VERSION "3.11.9") & \
-    (if "%python%"=="3.12" setx PYTHON_VERSION "3.12.5") & \
-    (if "%python%"=="3.13" setx PYTHON_VERSION "3.13.0-rc1")
-
-# Install archiver to extract xz archives
-RUN choco install -r -y --pre --no-progress --force python --version=%PYTHON_VERSION% && \
-    choco install --no-progress -r -y archiver
+RUN (if "%python%"=="3.9" setx PYTHON_VERSION "3.9.13" && setx PYTHON_CMD "C:\Python39\python") & \
+    (if "%python%"=="3.10" setx PYTHON_VERSION "3.10.11" && setx PYTHON_CMD "py -3.10") & \
+    (if "%python%"=="3.11" setx PYTHON_VERSION "3.11.9" && setx PYTHON_CMD "py -3.11") & \
+    (if "%python%"=="3.12" setx PYTHON_VERSION "3.12.8" && setx PYTHON_CMD "py -3.12") & \
+    (if "%python%"=="3.13" setx PYTHON_VERSION "3.13.1" && setx PYTHON_CMD "py -3.13")
+
+# hadolint ignore=DL3059
+RUN choco install -r -y --pre --no-progress --force python --version=%PYTHON_VERSION%
+# hadolint ignore=DL3059
+RUN %PYTHON_CMD% -m pip install -U pip setuptools
+
+COPY python/requirements-wheel-test.txt C:/arrow/python/
+RUN %PYTHON_CMD% -m pip install -r C:/arrow/python/requirements-wheel-test.txt
 
 ENV PYTHON=$python
diff --git a/ci/docker/python-wheel-windows-vs2019-base.dockerfile b/ci/docker/python-wheel-windows-vs2019-base.dockerfile
new file mode 100644
index 0000000000000..bd91f01bf9b6d
--- /dev/null
+++ b/ci/docker/python-wheel-windows-vs2019-base.dockerfile
@@ -0,0 +1,79 @@
+# Licensed to the Apache Software Foundation (ASF) under one
+# or more contributor license agreements.  See the NOTICE file
+# distributed with this work for additional information
+# regarding copyright ownership.  The ASF licenses this file
+# to you under the Apache License, Version 2.0 (the
+# "License"); you may not use this file except in compliance
+# with the License.  You may obtain a copy of the License at
+#
+#   http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing,
+# software distributed under the License is distributed on an
+# "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY
+# KIND, either express or implied.  See the License for the
+# specific language governing permissions and limitations
+# under the License.
+
+# NOTE: You must update PYTHON_WHEEL_WINDOWS_IMAGE_REVISION in .env
+# when you update this file.
+
+# based on mcr.microsoft.com/windows/servercore:ltsc2019
+# contains choco and vs2019 preinstalled
+FROM abrarov/msvc-2019:2.11.0
+
+# Install CMake and Ninja
+ARG cmake=3.31.2
+RUN choco install --no-progress -r -y cmake --version=%cmake% --installargs 'ADD_CMAKE_TO_PATH=System' && \
+    choco install --no-progress -r -y gzip wget ninja
+
+# Add unix tools to path
+RUN setx path "%path%;C:\Program Files\Git\usr\bin"
+
+# Install vcpkg
+#
+# Compiling vcpkg itself from a git tag doesn't work anymore since vcpkg has
+# started to ship precompiled binaries for the vcpkg-tool.
+ARG vcpkg
+COPY ci/vcpkg/*.patch \
+     ci/vcpkg/*windows*.cmake \
+     arrow/ci/vcpkg/
+COPY ci/scripts/install_vcpkg.sh arrow/ci/scripts/
+ENV VCPKG_ROOT=C:\\vcpkg
+RUN bash arrow/ci/scripts/install_vcpkg.sh /c/vcpkg %vcpkg% && \
+    setx PATH "%PATH%;%VCPKG_ROOT%"
+
+# Configure vcpkg and install dependencies
+# NOTE: use windows batch environment notation for build arguments in RUN
+# statements but bash notation in ENV statements
+# VCPKG_FORCE_SYSTEM_BINARIES=1 spare around ~750MB of image size if the system
+# cmake's and ninja's versions are recent enough
+ARG build_type=release
+ENV CMAKE_BUILD_TYPE=${build_type} \
+    VCPKG_OVERLAY_TRIPLETS=C:\\arrow\\ci\\vcpkg \
+    VCPKG_DEFAULT_TRIPLET=amd64-windows-static-md-${build_type} \
+    VCPKG_FEATURE_FLAGS="manifests"
+COPY ci/vcpkg/vcpkg.json arrow/ci/vcpkg/
+# cannot use the S3 feature here because while aws-sdk-cpp=1.9.160 contains
+# ssl related fixes as well as we can patch the vcpkg portfile to support
+# arm machines it hits ARROW-15141 where we would need to fall back to 1.8.186
+# but we cannot patch those portfiles since vcpkg-tool handles the checkout of
+# previous versions => use bundled S3 build
+RUN vcpkg install \
+        --clean-after-build \
+        --x-install-root=%VCPKG_ROOT%\installed \
+        --x-manifest-root=arrow/ci/vcpkg \
+        --x-feature=flight \
+        --x-feature=gcs \
+        --x-feature=json \
+        --x-feature=orc \
+        --x-feature=parquet \
+        --x-feature=s3
+
+# Remove previous installations of Python from the base image
+# NOTE: a more recent base image (tried with 2.12.1) comes with Python 3.9.7
+# and the MSI installers are failing to remove pip and tcl/tk "products" making
+# the subsequent choco python installation step failing for installing Python
+# version 3.9.* due to existing Python version
+RUN wmic product where "name like 'python%%'" call uninstall /nointeractive && \
+    rm -rf Python*
diff --git a/ci/docker/python-wheel-windows-vs2019.dockerfile b/ci/docker/python-wheel-windows-vs2019.dockerfile
index cc8c17efe474e..50e942fd6bd5c 100644
--- a/ci/docker/python-wheel-windows-vs2019.dockerfile
+++ b/ci/docker/python-wheel-windows-vs2019.dockerfile
@@ -18,79 +18,22 @@
 # NOTE: You must update PYTHON_WHEEL_WINDOWS_IMAGE_REVISION in .env
 # when you update this file.
 
-# based on mcr.microsoft.com/windows/servercore:ltsc2019
-# contains choco and vs2019 preinstalled
-FROM abrarov/msvc-2019:2.11.0
-
-# Install CMake and Ninja
-ARG cmake=3.21.4
-RUN choco install --no-progress -r -y cmake --version=%cmake% --installargs 'ADD_CMAKE_TO_PATH=System' && \
-    choco install --no-progress -r -y gzip wget ninja
-
-# Add unix tools to path
-RUN setx path "%path%;C:\Program Files\Git\usr\bin"
-
-# Install vcpkg
-#
-# Compiling vcpkg itself from a git tag doesn't work anymore since vcpkg has
-# started to ship precompiled binaries for the vcpkg-tool.
-ARG vcpkg
-COPY ci/vcpkg/*.patch \
-     ci/vcpkg/*windows*.cmake \
-     arrow/ci/vcpkg/
-COPY ci/scripts/install_vcpkg.sh arrow/ci/scripts/
-ENV VCPKG_ROOT=C:\\vcpkg
-RUN bash arrow/ci/scripts/install_vcpkg.sh /c/vcpkg %vcpkg% && \
-    setx PATH "%PATH%;%VCPKG_ROOT%"
-
-# Configure vcpkg and install dependencies
-# NOTE: use windows batch environment notation for build arguments in RUN
-# statements but bash notation in ENV statements
-# VCPKG_FORCE_SYSTEM_BINARIES=1 spare around ~750MB of image size if the system
-# cmake's and ninja's versions are recent enough
-ARG build_type=release
-ENV CMAKE_BUILD_TYPE=${build_type} \
-    VCPKG_OVERLAY_TRIPLETS=C:\\arrow\\ci\\vcpkg \
-    VCPKG_DEFAULT_TRIPLET=amd64-windows-static-md-${build_type} \
-    VCPKG_FEATURE_FLAGS="manifests"
-COPY ci/vcpkg/vcpkg.json arrow/ci/vcpkg/
-# cannot use the S3 feature here because while aws-sdk-cpp=1.9.160 contains
-# ssl related fixes as well as we can patch the vcpkg portfile to support
-# arm machines it hits ARROW-15141 where we would need to fall back to 1.8.186
-# but we cannot patch those portfiles since vcpkg-tool handles the checkout of
-# previous versions => use bundled S3 build
-RUN vcpkg install \
-        --clean-after-build \
-        --x-install-root=%VCPKG_ROOT%\installed \
-        --x-manifest-root=arrow/ci/vcpkg \
-        --x-feature=flight \
-        --x-feature=gcs \
-        --x-feature=json \
-        --x-feature=orc \
-        --x-feature=parquet \
-        --x-feature=s3
-
-# Remove previous installations of python from the base image
-# NOTE: a more recent base image (tried with 2.12.1) comes with python 3.9.7
-# and the msi installers are failing to remove pip and tcl/tk "products" making
-# the subsequent choco python installation step failing for installing python
-# version 3.9.* due to existing python version
-RUN wmic product where "name like 'python%%'" call uninstall /nointeractive && \
-    rm -rf Python*
+ARG base
+FROM ${base}
 
 # Define the full version number otherwise choco falls back to patch number 0 (3.9 => 3.9.0)
+# Note that Python 3.9 does not come with the "py" launcher
 ARG python=3.9
-RUN (if "%python%"=="3.9" setx PYTHON_VERSION "3.9.13" && setx PATH "%PATH%;C:\Python39;C:\Python39\Scripts") & \
-    (if "%python%"=="3.10" setx PYTHON_VERSION "3.10.11" && setx PATH "%PATH%;C:\Python310;C:\Python310\Scripts") & \
-    (if "%python%"=="3.11" setx PYTHON_VERSION "3.11.9" && setx PATH "%PATH%;C:\Python311;C:\Python311\Scripts") & \
-    (if "%python%"=="3.12" setx PYTHON_VERSION "3.12.5" && setx PATH "%PATH%;C:\Python312;C:\Python312\Scripts") & \
-    (if "%python%"=="3.13" setx PYTHON_VERSION "3.13.0-rc1" && setx PATH "%PATH%;C:\Python313;C:\Python313\Scripts")
+RUN (if "%python%"=="3.9" setx PYTHON_VERSION "3.9.13" && setx PYTHON_CMD "C:\Python39\python") & \
+    (if "%python%"=="3.10" setx PYTHON_VERSION "3.10.11" && setx PYTHON_CMD "py -3.10") & \
+    (if "%python%"=="3.11" setx PYTHON_VERSION "3.11.9" && setx PYTHON_CMD "py -3.11") & \
+    (if "%python%"=="3.12" setx PYTHON_VERSION "3.12.8" && setx PYTHON_CMD "py -3.12") & \
+    (if "%python%"=="3.13" setx PYTHON_VERSION "3.13.1" && setx PYTHON_CMD "py -3.13")
+
 RUN choco install -r -y --pre --no-progress python --version=%PYTHON_VERSION%
-RUN python -m pip install -U pip setuptools
+RUN %PYTHON_CMD% -m pip install -U pip setuptools
 
-COPY python/requirements-wheel-build.txt arrow/python/
-RUN python -m pip install -r arrow/python/requirements-wheel-build.txt
+COPY python/requirements-wheel-build.txt C:/arrow/python/
+RUN %PYTHON_CMD% -m pip install -r C:/arrow/python/requirements-wheel-build.txt
 
-# For debugging purposes
-# RUN wget --no-check-certificate https://github.com/lucasg/Dependencies/releases/download/v1.10/Dependencies_x64_Release.zip
-# RUN unzip Dependencies_x64_Release.zip -d Dependencies && setx path "%path%;C:\Dependencies"
+ENV PYTHON=${python}
diff --git a/ci/scripts/python_wheel_windows_build.bat b/ci/scripts/python_wheel_windows_build.bat
index 999f40980f5d2..9287d2471deec 100644
--- a/ci/scripts/python_wheel_windows_build.bat
+++ b/ci/scripts/python_wheel_windows_build.bat
@@ -19,6 +19,11 @@
 
 echo "Building windows wheel..."
 
+@REM List installed Pythons
+py -0p
+
+%PYTHON_CMD% -m sysconfig || exit /B 1
+
 call "C:\Program Files (x86)\Microsoft Visual Studio\2019\Community\VC\Auxiliary\Build\vcvars64.bat"
 @echo on
 
@@ -27,7 +32,7 @@ choco install -r -y --no-progress vcredist140
 choco upgrade -r -y --no-progress vcredist140
 dir C:\Windows\System32\msvcp140.dll
 
-echo "=== (%PYTHON_VERSION%) Clear output directories and leftovers ==="
+echo "=== (%PYTHON%) Clear output directories and leftovers ==="
 del /s /q C:\arrow-build
 del /s /q C:\arrow-dist
 del /s /q C:\arrow\python\dist
@@ -35,7 +40,7 @@ del /s /q C:\arrow\python\build
 del /s /q C:\arrow\python\pyarrow\*.so
 del /s /q C:\arrow\python\pyarrow\*.so.*
 
-echo "=== (%PYTHON_VERSION%) Building Arrow C++ libraries ==="
+echo "=== (%PYTHON%) Building Arrow C++ libraries ==="
 set ARROW_ACERO=ON
 set ARROW_DATASET=ON
 set ARROW_FLIGHT=ON
@@ -107,8 +112,9 @@ cmake ^
 cmake --build . --config %CMAKE_BUILD_TYPE% --target install || exit /B 1
 popd
 
-echo "=== (%PYTHON_VERSION%) Building wheel ==="
+echo "=== (%PYTHON%) Building wheel ==="
 set PYARROW_BUILD_TYPE=%CMAKE_BUILD_TYPE%
+set PYARROW_BUILD_VERBOSE=1
 set PYARROW_BUNDLE_ARROW_CPP=ON
 set PYARROW_CMAKE_GENERATOR=%CMAKE_GENERATOR%
 set PYARROW_WITH_ACERO=%ARROW_ACERO%
@@ -131,7 +137,7 @@ pushd C:\arrow\python
 cp C:\Windows\System32\msvcp140.dll pyarrow\
 
 @REM Build wheel
-python setup.py bdist_wheel || exit /B 1
+%PYTHON_CMD% setup.py bdist_wheel || exit /B 1
 
 @REM Repair the wheel with delvewheel
 @REM
@@ -141,12 +147,13 @@ python setup.py bdist_wheel || exit /B 1
 @REM
 @REM For now this requires a custom version of delvewheel:
 @REM https://github.com/adang1345/delvewheel/pull/59
-pip install https://github.com/pitrou/delvewheel/archive/refs/heads/fixes-for-arrow.zip || exit /B 1
+%PYTHON_CMD% -m pip install https://github.com/pitrou/delvewheel/archive/refs/heads/fixes-for-arrow.zip || exit /B 1
 
 for /f %%i in ('dir dist\pyarrow-*.whl /B') do (set WHEEL_NAME=%cd%\dist\%%i) || exit /B 1
 echo "Wheel name: %WHEEL_NAME%"
 
-delvewheel repair -vv --mangle-only=msvcp140.dll --no-patch ^
+%PYTHON_CMD% -m delvewheel repair -vv ^
+    --mangle-only=msvcp140.dll --no-patch ^
     -w repaired_wheels %WHEEL_NAME% || exit /B 1
 
 popd
diff --git a/ci/scripts/python_wheel_windows_test.bat b/ci/scripts/python_wheel_windows_test.bat
index 12d35216b1ca5..ffe8b388f93df 100755
--- a/ci/scripts/python_wheel_windows_test.bat
+++ b/ci/scripts/python_wheel_windows_test.bat
@@ -25,28 +25,19 @@ set PYARROW_TEST_GANDIVA=OFF
 set PYARROW_TEST_GCS=ON
 set PYARROW_TEST_HDFS=ON
 set PYARROW_TEST_ORC=ON
+set PYARROW_TEST_PANDAS=ON
 set PYARROW_TEST_PARQUET=ON
 set PYARROW_TEST_PARQUET_ENCRYPTION=ON
 set PYARROW_TEST_SUBSTRAIT=ON
 set PYARROW_TEST_S3=ON
 set PYARROW_TEST_TENSORFLOW=ON
 
-@REM Enable again once https://github.com/scipy/oldest-supported-numpy/pull/27 gets merged
-@REM set PYARROW_TEST_PANDAS=ON
-
 set ARROW_TEST_DATA=C:\arrow\testing\data
 set PARQUET_TEST_DATA=C:\arrow\cpp\submodules\parquet-testing\data
 
 @REM List installed Pythons
 py -0p
 
-set PYTHON_CMD=py -%PYTHON%
-
-%PYTHON_CMD% -m pip install -U pip setuptools || exit /B 1
-
-@REM Install testing dependencies
-%PYTHON_CMD% -m pip install -r C:\arrow\python\requirements-wheel-test.txt || exit /B 1
-
 @REM Install the built wheels
 %PYTHON_CMD% -m pip install --no-index --find-links=C:\arrow\python\repaired_wheels pyarrow || exit /B 1
 
@@ -70,8 +61,9 @@ set PYTHON_CMD=py -%PYTHON%
 @rem Download IANA Timezone Database for ORC C++
 curl https://cygwin.osuosl.org/noarch/release/tzdata/tzdata-2024a-1.tar.xz --output tzdata.tar.xz || exit /B
 mkdir %USERPROFILE%\Downloads\test\tzdata
-arc unarchive tzdata.tar.xz %USERPROFILE%\Downloads\test\tzdata
+arc unarchive tzdata.tar.xz %USERPROFILE%\Downloads\test\tzdata || exit /B
 set TZDIR=%USERPROFILE%\Downloads\test\tzdata\usr\share\zoneinfo
+dir %TZDIR%
 
 @REM Execute unittest
 %PYTHON_CMD% -m pytest -r s --pyargs pyarrow || exit /B 1
diff --git a/dev/tasks/python-wheels/github.windows.yml b/dev/tasks/python-wheels/github.windows.yml
index de0efedbff534..36b25e9819f27 100644
--- a/dev/tasks/python-wheels/github.windows.yml
+++ b/dev/tasks/python-wheels/github.windows.yml
@@ -26,6 +26,7 @@ jobs:
     env:
       # archery uses this environment variable
       PYTHON: "{{ python_version }}"
+      PYTHON_ABI_TAG: "{{ python_abi_tag }}"
       # this is a private repository at the moment (mostly because of licensing
       # consideration of windows images with visual studio), but anyone can
       # recreate the image by manually building it via:
@@ -43,6 +44,19 @@ jobs:
       {{ macros.github_login_ghcr()|indent }}
       {{ macros.github_install_archery()|indent }}
 
+      - name: Prepare
+        shell: bash
+        run: |
+          case "${PYTHON_ABI_TAG}" in
+            *t)
+              test_image_prefix=python-free-threaded
+              ;;
+            *)
+              test_image_prefix=python
+              ;;
+          esac
+          echo "TEST_IMAGE_PREFIX=${test_image_prefix}" >> ${GITHUB_ENV}
+
       - name: Build wheel
         shell: cmd
         run: |
@@ -54,11 +68,11 @@ jobs:
           @rem We can remove this workaround once we find a way to use
           @rem pulled caches when build an image.
           echo on
-          archery docker pull --no-ignore-pull-failures python-wheel-windows-vs2019
+          archery docker pull --no-ignore-pull-failures %TEST_IMAGE_PREFIX%-wheel-windows-vs2019
           if errorlevel 1 (
-            archery docker build --no-pull python-wheel-windows-vs2019 || exit /B 1
+            archery docker build --no-pull %TEST_IMAGE_PREFIX%-wheel-windows-vs2019 || exit /B 1
           )
-          archery docker run --no-build -e SETUPTOOLS_SCM_PRETEND_VERSION={{ arrow.no_rc_version }} python-wheel-windows-vs2019
+          archery docker run --no-build -e SETUPTOOLS_SCM_PRETEND_VERSION={{ arrow.no_rc_version }} %TEST_IMAGE_PREFIX%-wheel-windows-vs2019
 
       - uses: actions/upload-artifact@v4
         with:
@@ -69,16 +83,21 @@ jobs:
         shell: cmd
         run: |
           cd arrow
-          archery docker run python-wheel-windows-test
+          archery docker pull --no-ignore-pull-failures %TEST_IMAGE_PREFIX%-wheel-windows-test
+          if errorlevel 1 (
+            archery docker build --no-pull %TEST_IMAGE_PREFIX%-wheel-windows-test || exit /B 1
+          )
+          archery docker run %TEST_IMAGE_PREFIX%-wheel-windows-test
 
       {{ macros.github_upload_releases("arrow/python/repaired_wheels/*.whl")|indent }}
       {{ macros.github_upload_gemfury("arrow/python/repaired_wheels/*.whl")|indent }}
       {{ macros.github_upload_wheel_scientific_python("arrow/repaired_wheels/repaired_wheels/*.whl")|indent }}
 
       {% if arrow.is_default_branch() %}
-      - name: Push Docker Image
+      - name: Push Docker image
         shell: cmd
         run: |
           cd arrow
-          archery docker push python-wheel-windows-vs2019
+          archery docker push %TEST_IMAGE_PREFIX%-wheel-windows-vs2019
+          archery docker push %TEST_IMAGE_PREFIX%-wheel-windows-test
       {% endif %}
diff --git a/dev/tasks/tasks.yml b/dev/tasks/tasks.yml
index 9f04d33f83ca0..f5b5ab53ebab5 100644
--- a/dev/tasks/tasks.yml
+++ b/dev/tasks/tasks.yml
@@ -445,19 +445,15 @@ tasks:
 
 {############################## Wheel Windows ################################}
 
-# TODO: Remove this when there's NumPy wheels for Windows.
-# See https://github.com/numpy/numpy/issues/26157 for more info.
-{% if abi_tag != "cp313t" %}
-
-  wheel-windows-{{ python_tag }}-amd64:
+  wheel-windows-{{ python_tag }}-{{ abi_tag }}-amd64:
     ci: github
     template: python-wheels/github.windows.yml
     params:
       python_version: "{{ python_version }}"
+      python_abi_tag: "{{ abi_tag }}"
     artifacts:
       - pyarrow-{no_rc_version}-{{ python_tag }}-{{ abi_tag }}-win_amd64.whl
 
-{% endif %}
 {% endfor %}
 
 {############################ Python sdist ####################################}
diff --git a/docker-compose.yml b/docker-compose.yml
index bd9120956330d..5cb96e62c1163 100644
--- a/docker-compose.yml
+++ b/docker-compose.yml
@@ -176,8 +176,12 @@ x-hierarchy:
   - python-free-threaded-wheel-manylinux-test-imports
   - python-wheel-manylinux-test-unittests
   - python-free-threaded-wheel-manylinux-test-unittests
-  - python-wheel-windows-vs2019
-  - python-wheel-windows-test
+  - python-wheel-windows-vs2019-base:
+    - python-wheel-windows-vs2019
+    - python-free-threaded-wheel-windows-vs2019
+  - python-wheel-windows-test-base:
+    - python-wheel-windows-test
+    - python-free-threaded-wheel-windows-test
 
 volumes:
   almalinux-ccache:
@@ -1262,12 +1266,29 @@ services:
       CHECK_UNITTESTS: "ON"
     command: /arrow/ci/scripts/python_wheel_unix_test.sh /arrow
 
+  python-wheel-windows-vs2019-base:
+    image: ${REPO}:python-wheel-windows-vs2019-base-vcpkg-${VCPKG}-${PYTHON_WHEEL_WINDOWS_IMAGE_REVISION}
+    build:
+      args:
+        vcpkg: ${VCPKG}
+      context: .
+      dockerfile: ci/docker/python-wheel-windows-vs2019-base.dockerfile
+      # This should make the pushed images reusable, but the image gets rebuilt.
+      # Uncomment if no local cache is available.
+      # cache_from:
+      #   - abrarov/msvc-2019:2.11.0
+      #   - ${REPO}:python-wheel-windows-vs2019-base-vcpkg-${VCPKG}-${PYTHON_WHEEL_WINDOWS_IMAGE_REVISION}
+    volumes: &python-wheel-windows-vs2019-volumes
+      - type: bind
+        source: .
+        target: "C:/arrow"
+
   python-wheel-windows-vs2019:
     image: ${REPO}:python-${PYTHON}-wheel-windows-vs2019-vcpkg-${VCPKG}-${PYTHON_WHEEL_WINDOWS_IMAGE_REVISION}
     build:
       args:
+        base: ${REPO}:python-wheel-windows-vs2019-base-vcpkg-${VCPKG}-${PYTHON_WHEEL_WINDOWS_IMAGE_REVISION}
         python: ${PYTHON}
-        vcpkg: ${VCPKG}
       context: .
       dockerfile: ci/docker/python-wheel-windows-vs2019.dockerfile
       # This should make the pushed images reusable, but the image gets rebuilt.
@@ -1275,23 +1296,51 @@ services:
       # cache_from:
       #   - abrarov/msvc-2019:2.11.0
       #   - ${REPO}:python-${PYTHON}-wheel-windows-vs2019-vcpkg-${VCPKG}-${PYTHON_WHEEL_WINDOWS_IMAGE_REVISION}
-    volumes:
-      - type: bind
-        source: .
-        target: "C:/arrow"
+    volumes: *python-wheel-windows-vs2019-volumes
     command: arrow\\ci\\scripts\\python_wheel_windows_build.bat
 
+  python-free-threaded-wheel-windows-vs2019:
+    image: ${REPO}:python-${PYTHON}-free-threaded-wheel-windows-vs2019-vcpkg-${VCPKG}-${PYTHON_WHEEL_WINDOWS_IMAGE_REVISION}
+    build:
+      args:
+        base: ${REPO}:python-wheel-windows-vs2019-base-vcpkg-${VCPKG}-${PYTHON_WHEEL_WINDOWS_IMAGE_REVISION}
+        python: ${PYTHON}
+      context: .
+      dockerfile: ci/docker/python-free-threaded-wheel-windows-vs2019.dockerfile
+      # This should make the pushed images reusable, but the image gets rebuilt.
+      # Uncomment if no local cache is available.
+      # cache_from:
+      #   - abrarov/msvc-2019:2.11.0
+      #   - ${REPO}:python-${PYTHON}-free-threaded-wheel-windows-vs2019-vcpkg-${VCPKG}-${PYTHON_WHEEL_WINDOWS_IMAGE_REVISION}
+    volumes: *python-wheel-windows-vs2019-volumes
+    command: arrow\\ci\\scripts\\python_wheel_windows_build.bat
+
+  python-wheel-windows-test-base:
+    image: ${REPO}:python-wheel-windows-test-vs2019-base-${PYTHON_WHEEL_WINDOWS_TEST_IMAGE_REVISION}
+    build:
+      context: .
+      dockerfile: ci/docker/python-wheel-windows-test-vs2019-base.dockerfile
+    volumes: *python-wheel-windows-vs2019-volumes
+
   python-wheel-windows-test:
-    image: ${REPO}:python-${PYTHON}-wheel-windows-test-vs2019-${PYTHON_WHEEL_WINDOWS_IMAGE_REVISION}
+    image: ${REPO}:python-${PYTHON}-wheel-windows-test-vs2019-${PYTHON_WHEEL_WINDOWS_TEST_IMAGE_REVISION}
     build:
       args:
+        base: ${REPO}:python-wheel-windows-test-vs2019-base-${PYTHON_WHEEL_WINDOWS_TEST_IMAGE_REVISION}
         python: ${PYTHON}
       context: .
       dockerfile: ci/docker/python-wheel-windows-test-vs2019.dockerfile
-    volumes:
-      - type: bind
-        source: .
-        target: "C:/arrow"
+    volumes: *python-wheel-windows-vs2019-volumes
+    command: arrow\\ci\\scripts\\python_wheel_windows_test.bat
+
+  python-free-threaded-wheel-windows-test:
+    image: ${REPO}:python-${PYTHON}-free-threaded-wheel-windows-test-vs2019-${PYTHON_WHEEL_WINDOWS_TEST_IMAGE_REVISION}
+    build:
+      args:
+        base: ${REPO}:python-wheel-windows-test-vs2019-base-${PYTHON_WHEEL_WINDOWS_TEST_IMAGE_REVISION}
+      context: .
+      dockerfile: ci/docker/python-free-threaded-wheel-windows-test-vs2019.dockerfile
+    volumes: *python-wheel-windows-vs2019-volumes
     command: arrow\\ci\\scripts\\python_wheel_windows_test.bat
 
   ##############################  Integration #################################