From ac76f965e130b2c500e9c14f003e6f7d4bfed177 Mon Sep 17 00:00:00 2001
From: =?UTF-8?q?Ra=C3=BAl=20Cumplido?= <raulcumplido@gmail.com>
Date: Mon, 26 Jan 2026 17:43:16 +0100
Subject: [PATCH 01/13] WIP: [Python] Simplify Windows wheel build ecosystem

---
 ...eaded-wheel-windows-test-vs2022.dockerfile | 16 ++---
 ...-wheel-windows-test-vs2022-base.dockerfile | 65 -------------------
 ...ython-wheel-windows-test-vs2022.dockerfile | 12 ++--
 ...ython-wheel-windows-vs2022-base.dockerfile | 15 +++++
 .../python-wheel-windows-vs2022.dockerfile    |  1 -
 compose.yaml                                  | 12 +---
 6 files changed, 25 insertions(+), 96 deletions(-)
 delete mode 100644 ci/docker/python-wheel-windows-test-vs2022-base.dockerfile

diff --git a/ci/docker/python-free-threaded-wheel-windows-test-vs2022.dockerfile b/ci/docker/python-free-threaded-wheel-windows-test-vs2022.dockerfile
index ab257b271e58..b8940110f149 100644
--- a/ci/docker/python-free-threaded-wheel-windows-test-vs2022.dockerfile
+++ b/ci/docker/python-free-threaded-wheel-windows-test-vs2022.dockerfile
@@ -24,20 +24,12 @@ ARG base
 # hadolint ignore=DL3006
 FROM ${base}
 
-ARG python=3.13
+ARG python=3.10
 
-# hadolint ignore=SC1072
-RUN (if "%python%"=="3.13" setx PYTHON_VERSION "3.13.1") & \
-    (if "%python%"=="3.14" setx PYTHON_VERSION "3.14.0")
+ARG python_variant_suffix=""
+ENV PYTHON_VERSION=${python}${python_variant_suffix}
 
-SHELL ["powershell", "-NoProfile", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
-RUN $version = $env:PYTHON_VERSION; \
-    $filename = 'python-' + $version + '-amd64.exe'; \
-    $url = 'https://www.python.org/ftp/python/' + $version + '/' + $filename; \
-    Invoke-WebRequest -Uri $url -OutFile $filename; \
-    Start-Process -FilePath $filename -ArgumentList '/quiet', 'Include_freethreaded=1' -Wait
-
-ENV PYTHON_CMD="py -${python}t"
+RUN pymanager install %PYTHON_VERSION%
 
 SHELL ["cmd", "/S", "/C"]
 RUN %PYTHON_CMD% -m pip install -U pip setuptools & \
diff --git a/ci/docker/python-wheel-windows-test-vs2022-base.dockerfile b/ci/docker/python-wheel-windows-test-vs2022-base.dockerfile
deleted file mode 100644
index bd1da7b14b37..000000000000
--- a/ci/docker/python-wheel-windows-test-vs2022-base.dockerfile
+++ /dev/null
@@ -1,65 +0,0 @@
-# escape=`
-
-# 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.
-
-FROM mcr.microsoft.com/windows/servercore:ltsc2022
-
-# Ensure we in a command shell and not Powershell
-SHELL ["cmd", "/S", "/C"]
-
-# Install MSVC BuildTools
-#
-# The set of components below (lines starting with --add) is the most minimal
-# set we could find that would still compile Arrow C++.
-RUN `
-    curl -SL --output vs_buildtools.exe https://aka.ms/vs/17/release/vs_buildtools.exe `
-    && (start /w vs_buildtools.exe --quiet --wait --norestart --nocache `
-    --installPath "%ProgramFiles(x86)%\Microsoft Visual Studio\2022\BuildTools" `
-    --add Microsoft.VisualStudio.Component.VC.CoreBuildTools `
-    --add Microsoft.VisualStudio.Component.VC.Tools.x86.x64 `
-    --add Microsoft.VisualStudio.Component.Windows11SDK.26100 `
-    --add Microsoft.VisualStudio.Component.VC.CMake.Project `
-    || IF "%ERRORLEVEL%"=="3010" EXIT 0) `
-    && del /q vs_buildtools.exe
-
-# Install choco CLI
-#
-# We switch into Powershell just for this command and switch back to cmd
-# See https://chocolatey.org/install#completely-offline-install
-SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
-RUN `
-    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'))
-SHELL ["cmd", "/S", "/C"]
-
-# Install git, wget, minio
-RUN choco install --no-progress -r -y git wget
-RUN curl https://dl.min.io/server/minio/release/windows-amd64/archive/minio.RELEASE.2025-01-20T14-49-07Z `
-    --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
diff --git a/ci/docker/python-wheel-windows-test-vs2022.dockerfile b/ci/docker/python-wheel-windows-test-vs2022.dockerfile
index 73a9e167fea6..6fc13c1d123f 100644
--- a/ci/docker/python-wheel-windows-test-vs2022.dockerfile
+++ b/ci/docker/python-wheel-windows-test-vs2022.dockerfile
@@ -26,16 +26,12 @@ FROM ${base}
 
 # hadolint shell=cmd.exe
 
-# Define the full version number otherwise choco falls back to patch number 0 (3.10 => 3.10.0)
 ARG python=3.10
-RUN (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 "3.12.10" && setx PYTHON_CMD "py -3.12") & \
-    (if "%python%"=="3.13" setx PYTHON_VERSION "3.13.9" && setx PYTHON_CMD "py -3.13") & \
-    (if "%python%"=="3.14" setx PYTHON_VERSION "3.14.0" && setx PYTHON_CMD "py -3.14")
 
-# hadolint ignore=DL3059
-RUN choco install -r -y --pre --no-progress --force python --version=%PYTHON_VERSION%
+ARG python_variant_suffix=""
+ENV PYTHON_VERSION=${python}${python_variant_suffix}
+
+RUN pymanager install %PYTHON_VERSION%
 # hadolint ignore=DL3059
 RUN %PYTHON_CMD% -m pip install -U pip setuptools
 
diff --git a/ci/docker/python-wheel-windows-vs2022-base.dockerfile b/ci/docker/python-wheel-windows-vs2022-base.dockerfile
index 426286ebe07d..1d53e863017b 100644
--- a/ci/docker/python-wheel-windows-vs2022-base.dockerfile
+++ b/ci/docker/python-wheel-windows-vs2022-base.dockerfile
@@ -104,6 +104,21 @@ RUN choco install --no-progress -r -y git gzip ninja wget
 # Add UNIX tools to PATH
 RUN setx path "%path%;C:\Program Files\Git\usr\bin"
 
+# Install git, wget, minio
+RUN choco install --no-progress -r -y git wget
+RUN curl https://dl.min.io/server/minio/release/windows-amd64/archive/minio.RELEASE.2025-01-20T14-49-07Z `
+    --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
+
 # Install vcpkg
 #
 # Compiling vcpkg itself from a git tag doesn't work anymore since vcpkg has
diff --git a/ci/docker/python-wheel-windows-vs2022.dockerfile b/ci/docker/python-wheel-windows-vs2022.dockerfile
index e25ebef156c6..0ed5be4939ae 100644
--- a/ci/docker/python-wheel-windows-vs2022.dockerfile
+++ b/ci/docker/python-wheel-windows-vs2022.dockerfile
@@ -21,7 +21,6 @@
 ARG base
 FROM ${base}
 
-# Define the full version number otherwise choco falls back to patch number 0 (3.10 => 3.10.0)
 ARG python=3.10
 
 ARG python_variant_suffix=""
diff --git a/compose.yaml b/compose.yaml
index c99f19e35e0a..edbfa151e291 100644
--- a/compose.yaml
+++ b/compose.yaml
@@ -178,7 +178,6 @@ x-hierarchy:
   - python-wheel-windows-vs2022-base:
     - python-wheel-windows-vs2022
     - python-free-threaded-wheel-windows-vs2022
-  - python-wheel-windows-test-base:
     - python-wheel-windows-test
     - python-free-threaded-wheel-windows-test
 
@@ -1416,18 +1415,11 @@ services:
     volumes: *python-wheel-windows-vs2022-volumes
     command: arrow\\ci\\scripts\\python_wheel_windows_build.bat
 
-  python-wheel-windows-test-base:
-    image: ${REPO}:python-wheel-windows-test-vs2022-base-${PYTHON_WHEEL_WINDOWS_TEST_IMAGE_REVISION}
-    build:
-      context: .
-      dockerfile: ci/docker/python-wheel-windows-test-vs2022-base.dockerfile
-    volumes: *python-wheel-windows-vs2022-volumes
-
   python-wheel-windows-test:
     image: ${REPO}:python-${PYTHON}-wheel-windows-test-vs2022-${PYTHON_WHEEL_WINDOWS_TEST_IMAGE_REVISION}
     build:
       args:
-        base: ${REPO}:python-wheel-windows-test-vs2022-base-${PYTHON_WHEEL_WINDOWS_TEST_IMAGE_REVISION}
+        base: ${REPO}:python-${PYTHON}-wheel-windows-vs2022-vcpkg-${VCPKG}-${PYTHON_WHEEL_WINDOWS_IMAGE_REVISION}
         python: ${PYTHON}
       context: .
       dockerfile: ci/docker/python-wheel-windows-test-vs2022.dockerfile
@@ -1438,7 +1430,7 @@ services:
     image: ${REPO}:python-${PYTHON}-free-threaded-wheel-windows-test-vs2022-${PYTHON_WHEEL_WINDOWS_TEST_IMAGE_REVISION}
     build:
       args:
-        base: ${REPO}:python-wheel-windows-test-vs2022-base-${PYTHON_WHEEL_WINDOWS_TEST_IMAGE_REVISION}
+        base: ${REPO}:python-${PYTHON}-wheel-windows-vs2022-vcpkg-${VCPKG}-${PYTHON_WHEEL_WINDOWS_IMAGE_REVISION}
         python: ${PYTHON}
       context: .
       dockerfile: ci/docker/python-free-threaded-wheel-windows-test-vs2022.dockerfile

From 054b8dc16b93ea88b1c4c2fd7c8fd8d5ce58ece2 Mon Sep 17 00:00:00 2001
From: =?UTF-8?q?Ra=C3=BAl=20Cumplido?= <raulcumplido@gmail.com>
Date: Tue, 27 Jan 2026 14:42:28 +0100
Subject: [PATCH 02/13] Add python_variant_suffix for testing free-threaded

---
 compose.yaml | 1 +
 1 file changed, 1 insertion(+)

diff --git a/compose.yaml b/compose.yaml
index edbfa151e291..1f0e721440d8 100644
--- a/compose.yaml
+++ b/compose.yaml
@@ -1432,6 +1432,7 @@ services:
       args:
         base: ${REPO}:python-${PYTHON}-wheel-windows-vs2022-vcpkg-${VCPKG}-${PYTHON_WHEEL_WINDOWS_IMAGE_REVISION}
         python: ${PYTHON}
+        python_variant_suffix: t
       context: .
       dockerfile: ci/docker/python-free-threaded-wheel-windows-test-vs2022.dockerfile
     volumes: *python-wheel-windows-vs2022-volumes

From a07afbf68f68c58f03744f5c6d5ed0efc130b985 Mon Sep 17 00:00:00 2001
From: =?UTF-8?q?Ra=C3=BAl=20Cumplido?= <raulcumplido@gmail.com>
Date: Tue, 27 Jan 2026 19:47:07 +0100
Subject: [PATCH 03/13] Try upgrading wheel windows image revision

---
 .env | 4 ++--
 1 file changed, 2 insertions(+), 2 deletions(-)

diff --git a/.env b/.env
index 6d64d2847807..6f830ca229b6 100644
--- a/.env
+++ b/.env
@@ -102,8 +102,8 @@ VCPKG="4334d8b4c8916018600212ab4dd4bbdc343065d1"    # 2025.09.17 Release
 # ci/docker/python-*-windows-*.dockerfile or the vcpkg config.
 # 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=2026-01-22
-PYTHON_WHEEL_WINDOWS_TEST_IMAGE_REVISION=2026-01-22
+PYTHON_WHEEL_WINDOWS_IMAGE_REVISION=2026-01-27
+PYTHON_WHEEL_WINDOWS_TEST_IMAGE_REVISION=2026-01-27
 
 # Use conanio/${CONAN_BASE}:{CONAN_VERSION} for "docker compose run --rm conan".
 # See https://github.com/conan-io/conan-docker-tools#readme and

From e1ab7da83dac4ab2001fbf900290f9951fc6fb6f Mon Sep 17 00:00:00 2001
From: =?UTF-8?q?Ra=C3=BAl=20Cumplido?= <raulcumplido@gmail.com>
Date: Wed, 28 Jan 2026 09:34:08 +0100
Subject: [PATCH 04/13] Fix base image

---
 compose.yaml | 2 +-
 1 file changed, 1 insertion(+), 1 deletion(-)

diff --git a/compose.yaml b/compose.yaml
index 1f0e721440d8..029af9d6fa22 100644
--- a/compose.yaml
+++ b/compose.yaml
@@ -1430,7 +1430,7 @@ services:
     image: ${REPO}:python-${PYTHON}-free-threaded-wheel-windows-test-vs2022-${PYTHON_WHEEL_WINDOWS_TEST_IMAGE_REVISION}
     build:
       args:
-        base: ${REPO}:python-${PYTHON}-wheel-windows-vs2022-vcpkg-${VCPKG}-${PYTHON_WHEEL_WINDOWS_IMAGE_REVISION}
+        base: ${REPO}:python-${PYTHON}-free-threaded-wheel-windows-vs2022-vcpkg-${VCPKG}-${PYTHON_WHEEL_WINDOWS_IMAGE_REVISION}
         python: ${PYTHON}
         python_variant_suffix: t
       context: .

From 66650984678b110f6242440f7ff16826fc78ee5a Mon Sep 17 00:00:00 2001
From: =?UTF-8?q?Ra=C3=BAl=20Cumplido?= <raulcumplido@gmail.com>
Date: Wed, 28 Jan 2026 13:05:18 +0100
Subject: [PATCH 05/13] Remove unnecessary change

---
 .../python-free-threaded-wheel-windows-test-vs2022.dockerfile   | 2 +-
 1 file changed, 1 insertion(+), 1 deletion(-)

diff --git a/ci/docker/python-free-threaded-wheel-windows-test-vs2022.dockerfile b/ci/docker/python-free-threaded-wheel-windows-test-vs2022.dockerfile
index b8940110f149..2493dc27c86a 100644
--- a/ci/docker/python-free-threaded-wheel-windows-test-vs2022.dockerfile
+++ b/ci/docker/python-free-threaded-wheel-windows-test-vs2022.dockerfile
@@ -24,7 +24,7 @@ ARG base
 # hadolint ignore=DL3006
 FROM ${base}
 
-ARG python=3.10
+ARG python=3.13
 
 ARG python_variant_suffix=""
 ENV PYTHON_VERSION=${python}${python_variant_suffix}

From 2aa3a1f0c582c20e092d288bab55e2cd7ea48e3e Mon Sep 17 00:00:00 2001
From: =?UTF-8?q?Ra=C3=BAl=20Cumplido?= <raulcumplido@gmail.com>
Date: Wed, 28 Jan 2026 13:24:02 +0100
Subject: [PATCH 06/13] Base for testing images should be the base image not
 the build image

---
 compose.yaml | 4 ++--
 1 file changed, 2 insertions(+), 2 deletions(-)

diff --git a/compose.yaml b/compose.yaml
index 029af9d6fa22..3474643fe6e7 100644
--- a/compose.yaml
+++ b/compose.yaml
@@ -1419,7 +1419,7 @@ services:
     image: ${REPO}:python-${PYTHON}-wheel-windows-test-vs2022-${PYTHON_WHEEL_WINDOWS_TEST_IMAGE_REVISION}
     build:
       args:
-        base: ${REPO}:python-${PYTHON}-wheel-windows-vs2022-vcpkg-${VCPKG}-${PYTHON_WHEEL_WINDOWS_IMAGE_REVISION}
+        base: ${REPO}:python-wheel-windows-vs2022-base-vcpkg-${VCPKG}-${PYTHON_WHEEL_WINDOWS_IMAGE_REVISION}
         python: ${PYTHON}
       context: .
       dockerfile: ci/docker/python-wheel-windows-test-vs2022.dockerfile
@@ -1430,7 +1430,7 @@ services:
     image: ${REPO}:python-${PYTHON}-free-threaded-wheel-windows-test-vs2022-${PYTHON_WHEEL_WINDOWS_TEST_IMAGE_REVISION}
     build:
       args:
-        base: ${REPO}:python-${PYTHON}-free-threaded-wheel-windows-vs2022-vcpkg-${VCPKG}-${PYTHON_WHEEL_WINDOWS_IMAGE_REVISION}
+        base: ${REPO}:python-wheel-windows-vs2022-base-vcpkg-${VCPKG}-${PYTHON_WHEEL_WINDOWS_IMAGE_REVISION}
         python: ${PYTHON}
         python_variant_suffix: t
       context: .

From 1ca2938615416c49f204d489ee10fdcd54d236d7 Mon Sep 17 00:00:00 2001
From: =?UTF-8?q?Ra=C3=BAl=20Cumplido?= <raulcumplido@gmail.com>
Date: Wed, 28 Jan 2026 16:44:43 +0100
Subject: [PATCH 07/13] Dockerfiles for test should specify PYTHON_CMD

---
 .../python-free-threaded-wheel-windows-test-vs2022.dockerfile  | 2 ++
 ci/docker/python-wheel-windows-test-vs2022.dockerfile          | 3 +++
 2 files changed, 5 insertions(+)

diff --git a/ci/docker/python-free-threaded-wheel-windows-test-vs2022.dockerfile b/ci/docker/python-free-threaded-wheel-windows-test-vs2022.dockerfile
index 2493dc27c86a..0ffb08edf8fa 100644
--- a/ci/docker/python-free-threaded-wheel-windows-test-vs2022.dockerfile
+++ b/ci/docker/python-free-threaded-wheel-windows-test-vs2022.dockerfile
@@ -31,6 +31,8 @@ ENV PYTHON_VERSION=${python}${python_variant_suffix}
 
 RUN pymanager install %PYTHON_VERSION%
 
+ENV PYTHON_CMD="py -${python}${python_variant_suffix}"
+
 SHELL ["cmd", "/S", "/C"]
 RUN %PYTHON_CMD% -m pip install -U pip setuptools & \
     if "%python%"=="3.13" ( \
diff --git a/ci/docker/python-wheel-windows-test-vs2022.dockerfile b/ci/docker/python-wheel-windows-test-vs2022.dockerfile
index 6fc13c1d123f..5a5bf1506a67 100644
--- a/ci/docker/python-wheel-windows-test-vs2022.dockerfile
+++ b/ci/docker/python-wheel-windows-test-vs2022.dockerfile
@@ -32,6 +32,9 @@ ARG python_variant_suffix=""
 ENV PYTHON_VERSION=${python}${python_variant_suffix}
 
 RUN pymanager install %PYTHON_VERSION%
+
+ENV PYTHON_CMD="py -${python}${python_variant_suffix}"
+
 # hadolint ignore=DL3059
 RUN %PYTHON_CMD% -m pip install -U pip setuptools
 

From f4d33c277295f961a153eba47f3c308d31b2d9c4 Mon Sep 17 00:00:00 2001
From: =?UTF-8?q?Ra=C3=BAl=20Cumplido?= <raulcumplido@gmail.com>
Date: Thu, 29 Jan 2026 11:47:05 +0100
Subject: [PATCH 08/13] Use pymanager to install Python for GCS testbench

---
 ci/docker/python-wheel-windows-vs2022-base.dockerfile | 6 ++----
 ci/scripts/install_gcs_testbench.bat                  | 9 +++------
 2 files changed, 5 insertions(+), 10 deletions(-)

diff --git a/ci/docker/python-wheel-windows-vs2022-base.dockerfile b/ci/docker/python-wheel-windows-vs2022-base.dockerfile
index 1d53e863017b..8778b85b8297 100644
--- a/ci/docker/python-wheel-windows-vs2022-base.dockerfile
+++ b/ci/docker/python-wheel-windows-vs2022-base.dockerfile
@@ -110,11 +110,9 @@ RUN curl https://dl.min.io/server/minio/release/windows-amd64/archive/minio.RELE
     --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"
+ENV PIPX_PYTHON_VERSION=3.11
+RUN pymanager install %PIPX_PYTHON_VERSION%
 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/scripts/install_gcs_testbench.bat b/ci/scripts/install_gcs_testbench.bat
index d0ceb7be2b69..8b30087064af 100644
--- a/ci/scripts/install_gcs_testbench.bat
+++ b/ci/scripts/install_gcs_testbench.bat
@@ -20,15 +20,12 @@
 set GCS_TESTBENCH_VERSION="v0.55.0"
 
 set PIPX_FLAGS=--verbose
-if NOT "%PIPX_PYTHON%"=="" (
-  set PIPX_FLAGS=--python %PIPX_PYTHON% %PIPX_FLAGS%
-)
 
-python -m pip install -U pipx || exit /B 1
+py -%PIPX_PYTHON_VERSION% -m pip install -U pipx|| exit /B 1
 
 @REM Install GCS testbench %GCS_TESTBENCH_VERSION%
-pipx install %PIPX_FLAGS% ^
+py -%PIPX_PYTHON_VERSION% -m pipx install --python py %PIPX_FLAGS% ^
         "https://github.com/googleapis/storage-testbench/archive/%GCS_TESTBENCH_VERSION%.tar.gz" ^
         || exit /B 1
 
-pipx list --verbose
+py -%PIPX_PYTHON_VERSION% -m pipx list --verbose

From eac026f0fd19b9410d21bf2fd6299ea405476f3f Mon Sep 17 00:00:00 2001
From: =?UTF-8?q?Ra=C3=BAl=20Cumplido?= <raulcumplido@gmail.com>
Date: Fri, 30 Jan 2026 10:52:41 +0100
Subject: [PATCH 09/13] Try removing python installation and see if there's a
 python on the base image

---
 ci/docker/python-wheel-windows-vs2022-base.dockerfile | 3 ---
 ci/scripts/install_gcs_testbench.bat                  | 6 +++---
 2 files changed, 3 insertions(+), 6 deletions(-)

diff --git a/ci/docker/python-wheel-windows-vs2022-base.dockerfile b/ci/docker/python-wheel-windows-vs2022-base.dockerfile
index 8778b85b8297..2973b769e6f7 100644
--- a/ci/docker/python-wheel-windows-vs2022-base.dockerfile
+++ b/ci/docker/python-wheel-windows-vs2022-base.dockerfile
@@ -110,9 +110,6 @@ RUN curl https://dl.min.io/server/minio/release/windows-amd64/archive/minio.RELE
     --output "C:\Windows\Minio.exe"
 
 # Install the GCS testbench using a well-known Python version.
-ENV PIPX_BIN_DIR=C:\\Windows\\
-ENV PIPX_PYTHON_VERSION=3.11
-RUN pymanager install %PIPX_PYTHON_VERSION%
 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/scripts/install_gcs_testbench.bat b/ci/scripts/install_gcs_testbench.bat
index 8b30087064af..b4ed0d9f957a 100644
--- a/ci/scripts/install_gcs_testbench.bat
+++ b/ci/scripts/install_gcs_testbench.bat
@@ -21,11 +21,11 @@ set GCS_TESTBENCH_VERSION="v0.55.0"
 
 set PIPX_FLAGS=--verbose
 
-py -%PIPX_PYTHON_VERSION% -m pip install -U pipx|| exit /B 1
+python -m pip install -U pipx|| exit /B 1
 
 @REM Install GCS testbench %GCS_TESTBENCH_VERSION%
-py -%PIPX_PYTHON_VERSION% -m pipx install --python py %PIPX_FLAGS% ^
+pipx install %PIPX_FLAGS% ^
         "https://github.com/googleapis/storage-testbench/archive/%GCS_TESTBENCH_VERSION%.tar.gz" ^
         || exit /B 1
 
-py -%PIPX_PYTHON_VERSION% -m pipx list --verbose
+pipx list --verbose

From 98410dd6ec394682f870d30527035d216059c7fc Mon Sep 17 00:00:00 2001
From: =?UTF-8?q?Ra=C3=BAl=20Cumplido?= <raulcumplido@gmail.com>
Date: Fri, 30 Jan 2026 15:01:48 +0100
Subject: [PATCH 10/13] Use base image Python instead for gcs

---
 ci/scripts/install_gcs_testbench.bat | 4 ++--
 1 file changed, 2 insertions(+), 2 deletions(-)

diff --git a/ci/scripts/install_gcs_testbench.bat b/ci/scripts/install_gcs_testbench.bat
index b4ed0d9f957a..aa8a1756aa09 100644
--- a/ci/scripts/install_gcs_testbench.bat
+++ b/ci/scripts/install_gcs_testbench.bat
@@ -24,8 +24,8 @@ set PIPX_FLAGS=--verbose
 python -m pip install -U pipx|| exit /B 1
 
 @REM Install GCS testbench %GCS_TESTBENCH_VERSION%
-pipx install %PIPX_FLAGS% ^
+python -m pipx install --fetch-missing-python --python 3.11 %PIPX_FLAGS% ^
         "https://github.com/googleapis/storage-testbench/archive/%GCS_TESTBENCH_VERSION%.tar.gz" ^
         || exit /B 1
 
-pipx list --verbose
+python -m pipx list --verbose
\ No newline at end of file

From a1b065284d4adbee057e4cd5c6f2e1407716b1b3 Mon Sep 17 00:00:00 2001
From: =?UTF-8?q?Ra=C3=BAl=20Cumplido?= <raulcumplido@gmail.com>
Date: Tue, 3 Feb 2026 10:48:28 +0100
Subject: [PATCH 11/13] Revert "Use base image Python instead for gcs"

This reverts commit 98410dd6ec394682f870d30527035d216059c7fc.
---
 ci/scripts/install_gcs_testbench.bat | 4 ++--
 1 file changed, 2 insertions(+), 2 deletions(-)

diff --git a/ci/scripts/install_gcs_testbench.bat b/ci/scripts/install_gcs_testbench.bat
index aa8a1756aa09..b4ed0d9f957a 100644
--- a/ci/scripts/install_gcs_testbench.bat
+++ b/ci/scripts/install_gcs_testbench.bat
@@ -24,8 +24,8 @@ set PIPX_FLAGS=--verbose
 python -m pip install -U pipx|| exit /B 1
 
 @REM Install GCS testbench %GCS_TESTBENCH_VERSION%
-python -m pipx install --fetch-missing-python --python 3.11 %PIPX_FLAGS% ^
+pipx install %PIPX_FLAGS% ^
         "https://github.com/googleapis/storage-testbench/archive/%GCS_TESTBENCH_VERSION%.tar.gz" ^
         || exit /B 1
 
-python -m pipx list --verbose
\ No newline at end of file
+pipx list --verbose

From e4058efb05ac697403f2addd16e38d31745cc26a Mon Sep 17 00:00:00 2001
From: =?UTF-8?q?Ra=C3=BAl=20Cumplido?= <raulcumplido@gmail.com>
Date: Tue, 3 Feb 2026 10:48:36 +0100
Subject: [PATCH 12/13] Revert "Try removing python installation and see if
 there's a python on the base image"

This reverts commit eac026f0fd19b9410d21bf2fd6299ea405476f3f.
---
 ci/docker/python-wheel-windows-vs2022-base.dockerfile | 3 +++
 ci/scripts/install_gcs_testbench.bat                  | 6 +++---
 2 files changed, 6 insertions(+), 3 deletions(-)

diff --git a/ci/docker/python-wheel-windows-vs2022-base.dockerfile b/ci/docker/python-wheel-windows-vs2022-base.dockerfile
index 2973b769e6f7..8778b85b8297 100644
--- a/ci/docker/python-wheel-windows-vs2022-base.dockerfile
+++ b/ci/docker/python-wheel-windows-vs2022-base.dockerfile
@@ -110,6 +110,9 @@ RUN curl https://dl.min.io/server/minio/release/windows-amd64/archive/minio.RELE
     --output "C:\Windows\Minio.exe"
 
 # Install the GCS testbench using a well-known Python version.
+ENV PIPX_BIN_DIR=C:\\Windows\\
+ENV PIPX_PYTHON_VERSION=3.11
+RUN pymanager install %PIPX_PYTHON_VERSION%
 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/scripts/install_gcs_testbench.bat b/ci/scripts/install_gcs_testbench.bat
index b4ed0d9f957a..8b30087064af 100644
--- a/ci/scripts/install_gcs_testbench.bat
+++ b/ci/scripts/install_gcs_testbench.bat
@@ -21,11 +21,11 @@ set GCS_TESTBENCH_VERSION="v0.55.0"
 
 set PIPX_FLAGS=--verbose
 
-python -m pip install -U pipx|| exit /B 1
+py -%PIPX_PYTHON_VERSION% -m pip install -U pipx|| exit /B 1
 
 @REM Install GCS testbench %GCS_TESTBENCH_VERSION%
-pipx install %PIPX_FLAGS% ^
+py -%PIPX_PYTHON_VERSION% -m pipx install --python py %PIPX_FLAGS% ^
         "https://github.com/googleapis/storage-testbench/archive/%GCS_TESTBENCH_VERSION%.tar.gz" ^
         || exit /B 1
 
-pipx list --verbose
+py -%PIPX_PYTHON_VERSION% -m pipx list --verbose

From 796f7c75e85f8743f8ceb4cd4e9926c218a7cb05 Mon Sep 17 00:00:00 2001
From: =?UTF-8?q?Ra=C3=BAl=20Cumplido?= <raulcumplido@gmail.com>
Date: Tue, 3 Feb 2026 10:48:42 +0100
Subject: [PATCH 13/13] Revert "Use pymanager to install Python for GCS
 testbench"

This reverts commit f4d33c277295f961a153eba47f3c308d31b2d9c4.
---
 ci/docker/python-wheel-windows-vs2022-base.dockerfile | 6 ++++--
 ci/scripts/install_gcs_testbench.bat                  | 9 ++++++---
 2 files changed, 10 insertions(+), 5 deletions(-)

diff --git a/ci/docker/python-wheel-windows-vs2022-base.dockerfile b/ci/docker/python-wheel-windows-vs2022-base.dockerfile
index 8778b85b8297..1d53e863017b 100644
--- a/ci/docker/python-wheel-windows-vs2022-base.dockerfile
+++ b/ci/docker/python-wheel-windows-vs2022-base.dockerfile
@@ -110,9 +110,11 @@ RUN curl https://dl.min.io/server/minio/release/windows-amd64/archive/minio.RELE
     --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_VERSION=3.11
-RUN pymanager install %PIPX_PYTHON_VERSION%
+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/scripts/install_gcs_testbench.bat b/ci/scripts/install_gcs_testbench.bat
index 8b30087064af..d0ceb7be2b69 100644
--- a/ci/scripts/install_gcs_testbench.bat
+++ b/ci/scripts/install_gcs_testbench.bat
@@ -20,12 +20,15 @@
 set GCS_TESTBENCH_VERSION="v0.55.0"
 
 set PIPX_FLAGS=--verbose
+if NOT "%PIPX_PYTHON%"=="" (
+  set PIPX_FLAGS=--python %PIPX_PYTHON% %PIPX_FLAGS%
+)
 
-py -%PIPX_PYTHON_VERSION% -m pip install -U pipx|| exit /B 1
+python -m pip install -U pipx || exit /B 1
 
 @REM Install GCS testbench %GCS_TESTBENCH_VERSION%
-py -%PIPX_PYTHON_VERSION% -m pipx install --python py %PIPX_FLAGS% ^
+pipx install %PIPX_FLAGS% ^
         "https://github.com/googleapis/storage-testbench/archive/%GCS_TESTBENCH_VERSION%.tar.gz" ^
         || exit /B 1
 
-py -%PIPX_PYTHON_VERSION% -m pipx list --verbose
+pipx list --verbose