diff --git a/ci/docker/python-wheel-windows-test-vs2019.dockerfile b/ci/docker/python-wheel-windows-test-vs2019.dockerfile
index f6f2fd6ad84e4..f2841392b7300 100644
--- a/ci/docker/python-wheel-windows-test-vs2019.dockerfile
+++ b/ci/docker/python-wheel-windows-test-vs2019.dockerfile
@@ -29,7 +29,7 @@ FROM ${base}
 # 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" && setx PYTHON_CMD "C:\Python39\python") & \
-    (if "%python%"=="3.10" setx PYTHON_VERSION "3.10.11" && setx setx PYTHON_CMD "py -3.10") & \
+    (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")
diff --git a/ci/docker/python-wheel-windows-vs2019-base.dockerfile b/ci/docker/python-wheel-windows-vs2019-base.dockerfile
index 1c6d0f2b5215b..1a545b0ba31d1 100644
--- a/ci/docker/python-wheel-windows-vs2019-base.dockerfile
+++ b/ci/docker/python-wheel-windows-vs2019-base.dockerfile
@@ -59,16 +59,16 @@ COPY ci/vcpkg/vcpkg.json arrow/ci/vcpkg/
 # 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
+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
diff --git a/ci/docker/python-wheel-windows-vs2019.dockerfile b/ci/docker/python-wheel-windows-vs2019.dockerfile
index 6f14f9c4f1bfe..6d4ae99e8eefa 100644
--- a/ci/docker/python-wheel-windows-vs2019.dockerfile
+++ b/ci/docker/python-wheel-windows-vs2019.dockerfile
@@ -27,7 +27,7 @@ FROM ${base}
 # 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 PYTHON_CMD "C:\Python39\python") & \
-    (if "%python%"=="3.10" setx PYTHON_VERSION "3.10.11" && setx setx PYTHON_CMD "py -3.10") & \
+    (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")
diff --git a/dev/tasks/python-wheels/github.windows.yml b/dev/tasks/python-wheels/github.windows.yml
index 08ea2a9f305dd..8f04a50979b53 100644
--- a/dev/tasks/python-wheels/github.windows.yml
+++ b/dev/tasks/python-wheels/github.windows.yml
@@ -69,6 +69,8 @@ jobs:
           if errorlevel 1 (
             archery docker build --no-pull %TEST_IMAGE_PREFIX%-wheel-windows-vs2019 || exit /B 1
           )
+          @rem TODO remove this temporary push step
+          archery docker push %TEST_IMAGE_PREFIX%-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
@@ -80,6 +82,10 @@ jobs:
         shell: cmd
         run: |
           cd arrow
+          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 }}