diff --git a/.github/workflows/test-windows.yml b/.github/workflows/test-windows.yml
index 887c7dd9670..8d8cb0b159f 100644
--- a/.github/workflows/test-windows.yml
+++ b/.github/workflows/test-windows.yml
@@ -72,10 +72,10 @@ jobs:
     - name: Install dependencies
       id: install
       run: |
-        7z x winbuild\depends\nasm-2.16.01-win64.zip "-o$env:RUNNER_WORKSPACE\"
-        echo "$env:RUNNER_WORKSPACE\nasm-2.16.01" >> $env:GITHUB_PATH
+        choco install nasm --no-progress
+        echo "C:\Program Files\NASM" >> $env:GITHUB_PATH
 
-        choco install ghostscript --version=10.0.0.20230317
+        choco install ghostscript --version=10.0.0.20230317 --no-progress
         echo "C:\Program Files\gs\gs10.00.0\bin" >> $env:GITHUB_PATH
 
         # Install extra test images
@@ -167,7 +167,6 @@ jobs:
     - name: Build Pillow
       run: |
         $FLAGS="-C raqm=vendor -C fribidi=vendor"
-        if ('${{ github.event_name }}' -ne 'pull_request') { $FLAGS+=" -C imagequant=disable" }
         cmd /c "winbuild\build\build_env.cmd && $env:pythonLocation\python.exe -m pip install -v $FLAGS ."
         & $env:pythonLocation\python.exe selftest.py --installed
       shell: pwsh
@@ -209,47 +208,6 @@ jobs:
         flags: GHA_Windows
         name: ${{ runner.os }} Python ${{ matrix.python-version }}
 
-    - name: Build wheel
-      id: wheel
-      if: "github.event_name != 'pull_request'"
-      run: |
-        mkdir fribidi
-        copy winbuild\build\bin\fribidi* fribidi
-        setlocal EnableDelayedExpansion
-        for %%f in (winbuild\build\license\*) do (
-          set x=%%~nf
-          rem Skip FriBiDi license, it is not included in the wheel.
-          set fribidi=!x:~0,7!
-          if NOT !fribidi!==fribidi (
-            rem Skip imagequant license, it is not included in the wheel.
-            set libimagequant=!x:~0,13!
-            if NOT !libimagequant!==libimagequant (
-              echo. >> LICENSE
-              echo ===== %%~nf ===== >> LICENSE
-              echo. >> LICENSE
-              type %%f >> LICENSE
-            )
-          )
-        )
-        for /f "tokens=3 delims=/" %%a in ("${{ github.ref }}") do echo dist=dist-%%a >> %GITHUB_OUTPUT%
-        call winbuild\\build\\build_env.cmd
-        %pythonLocation%\python.exe -m pip wheel -v -C raqm=vendor -C fribidi=vendor -C imagequant=disable .
-      shell: cmd
-
-    - name: Upload wheel
-      uses: actions/upload-artifact@v3
-      if: "github.event_name != 'pull_request'"
-      with:
-        name: ${{ steps.wheel.outputs.dist }}
-        path: "*.whl"
-
-    - name: Upload fribidi.dll
-      if: "github.event_name != 'pull_request' && matrix.python-version == 3.11"
-      uses: actions/upload-artifact@v3
-      with:
-        name: fribidi
-        path: fribidi\*
-
   success:
     permissions:
       contents: none
diff --git a/.github/workflows/wheels-test.ps1 b/.github/workflows/wheels-test.ps1
new file mode 100644
index 00000000000..f593c722854
--- /dev/null
+++ b/.github/workflows/wheels-test.ps1
@@ -0,0 +1,22 @@
+param ([string]$venv, [string]$pillow="C:\pillow")
+$ErrorActionPreference  = 'Stop'
+$ProgressPreference = 'SilentlyContinue'
+Set-PSDebug -Trace 1
+if ("$venv" -like "*\cibw-run-*\pp*-win_amd64\*") {
+    # unlike CPython, PyPy requires Visual C++ Redistributable to be installed
+    [Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12
+    Invoke-WebRequest -Uri 'https://aka.ms/vs/15/release/vc_redist.x64.exe' -OutFile 'vc_redist.x64.exe'
+    C:\vc_redist.x64.exe /install /quiet /norestart | Out-Null
+}
+$env:path += ";$pillow\winbuild\build\bin\"
+& "$venv\Scripts\activate.ps1"
+& reg add "HKLM\SOFTWARE\Microsoft\Windows NT\CurrentVersion\Image File Execution Options\python.exe" /v "GlobalFlag" /t REG_SZ /d "0x02000000" /f
+cd $pillow
+& python -VV
+if (!$?) { exit $LASTEXITCODE }
+& python selftest.py
+if (!$?) { exit $LASTEXITCODE }
+& python -m pytest -vx Tests\check_wheel.py
+if (!$?) { exit $LASTEXITCODE }
+& python -m pytest -vx Tests
+if (!$?) { exit $LASTEXITCODE }
diff --git a/.github/workflows/wheels-test.sh b/.github/workflows/wheels-test.sh
index 34dfeaf143c..207ec15678b 100755
--- a/.github/workflows/wheels-test.sh
+++ b/.github/workflows/wheels-test.sh
@@ -1,10 +1,6 @@
 #!/bin/bash
 set -e
 
-EXP_CODECS="jpg jpg_2000 libtiff zlib"
-EXP_MODULES="freetype2 littlecms2 pil tkinter webp"
-EXP_FEATURES="fribidi harfbuzz libjpeg_turbo raqm transp_webp webp_anim webp_mux xcb"
-
 if [[ "$OSTYPE" == "darwin"* ]]; then
     brew install fribidi
     export PKG_CONFIG_PATH="/usr/local/opt/openblas/lib/pkgconfig"
@@ -25,21 +21,5 @@ fi
 
 # Runs tests
 python3 selftest.py
+python3 -m pytest Tests/check_wheel.py
 python3 -m pytest
-
-# Test against expected codecs, modules and features
-codecs=$(python3 -c 'from PIL.features import *; print(" ".join(sorted(get_supported_codecs())))')
-if [ "$codecs" != "$EXP_CODECS" ]; then
-    echo "Codecs should be: '$EXP_CODECS'; but are '$codecs'"
-    exit 1
-fi
-modules=$(python3 -c 'from PIL.features import *; print(" ".join(sorted(get_supported_modules())))')
-if [ "$modules" != "$EXP_MODULES" ]; then
-    echo "Modules should be: '$EXP_MODULES'; but are '$modules'"
-    exit 1
-fi
-features=$(python3 -c 'from PIL.features import *; print(" ".join(sorted(get_supported_features())))')
-if [ "$features" != "$EXP_FEATURES" ]; then
-    echo "Features should be: '$EXP_FEATURES'; but are '$features'"
-    exit 1
-fi
diff --git a/.github/workflows/wheels.yml b/.github/workflows/wheels.yml
index 1b141b14fbf..c4737bfc772 100644
--- a/.github/workflows/wheels.yml
+++ b/.github/workflows/wheels.yml
@@ -3,14 +3,20 @@ name: Wheels
 on:
   push:
     paths:
-      - ".github/workflows/wheels*.yml"
+      - ".ci/requirements-cibw.txt"
+      - ".github/workflows/wheel*"
       - "wheels/*"
+      - "winbuild/build_prepare.py"
+      - "winbuild/fribidi.cmake"
     tags:
       - "*"
   pull_request:
     paths:
-      - ".github/workflows/wheels*.yml"
+      - ".ci/requirements-cibw.txt"
+      - ".github/workflows/wheel*"
       - "wheels/*"
+      - "winbuild/build_prepare.py"
+      - "winbuild/fribidi.cmake"
   workflow_dispatch:
 
 permissions:
@@ -63,7 +69,6 @@ jobs:
         env:
           CIBW_ARCHS: ${{ matrix.archs }}
           CIBW_BUILD: ${{ matrix.build }}
-          CIBW_CONFIG_SETTINGS: raqm=enable raqm=vendor fribidi=vendor
           CIBW_MANYLINUX_PYPY_X86_64_IMAGE: ${{ matrix.manylinux }}
           CIBW_MANYLINUX_X86_64_IMAGE: ${{ matrix.manylinux }}
           CIBW_SKIP: pp38-*
@@ -75,6 +80,102 @@ jobs:
           name: dist
           path: ./wheelhouse/*.whl
 
+  windows:
+    name: Windows ${{ matrix.arch }}
+    runs-on: windows-latest
+    strategy:
+      fail-fast: false
+      matrix:
+        include:
+          - arch: x86
+            cibw_arch: x86
+          - arch: x64
+            cibw_arch: AMD64
+          - arch: ARM64
+            cibw_arch: ARM64
+    steps:
+      - uses: actions/checkout@v4
+
+      - name: Checkout extra test images
+        uses: actions/checkout@v4
+        with:
+          repository: python-pillow/test-images
+          path: Tests\test-images
+
+      - uses: actions/setup-python@v4
+        with:
+          python-version: "3.x"
+
+      - name: Prepare for build
+        run: |
+          choco install nasm --no-progress
+          echo "C:\Program Files\NASM" >> $env:GITHUB_PATH
+
+          # Install extra test images
+          xcopy /S /Y Tests\test-images\* Tests\images
+
+          & python.exe -m pip install -r .ci/requirements-cibw.txt
+
+          # Cannot cross-compile FriBiDi (only used for tests)
+          $FLAGS = ("--no-imagequant", "--architecture=${{ matrix.arch }}")
+          if ('${{ matrix.arch }}' -eq 'ARM64') { $FLAGS += "--no-fribidi" }
+          & python.exe winbuild\build_prepare.py -v @FLAGS
+        shell: pwsh
+
+      - name: Build wheels
+        run: |
+          setlocal EnableDelayedExpansion
+          for %%f in (winbuild\build\license\*) do (
+            set x=%%~nf
+            rem Skip FriBiDi license, it is not included in the wheel.
+            set fribidi=!x:~0,7!
+            if NOT !fribidi!==fribidi (
+              rem Skip imagequant license, it is not included in the wheel.
+              set libimagequant=!x:~0,13!
+              if NOT !libimagequant!==libimagequant (
+                echo. >> LICENSE
+                echo ===== %%~nf ===== >> LICENSE
+                echo. >> LICENSE
+                type %%f >> LICENSE
+              )
+            )
+          )
+          call winbuild\\build\\build_env.cmd
+          %pythonLocation%\python.exe -m cibuildwheel . --output-dir wheelhouse
+        env:
+          CIBW_ARCHS: ${{ matrix.cibw_arch }}
+          CIBW_BEFORE_ALL: "{package}\\winbuild\\build\\build_dep_all.cmd"
+          CIBW_CACHE_PATH: "C:\\cibw"
+          CIBW_TEST_SKIP: "*-win_arm64"
+          CIBW_TEST_COMMAND: 'docker run --rm
+            -v {project}:C:\pillow
+            -v C:\cibw:C:\cibw
+            -v %CD%\..\venv-test:%CD%\..\venv-test
+            -e CI -e GITHUB_ACTIONS
+            mcr.microsoft.com/windows/servercore:ltsc2022
+            powershell C:\pillow\.github\workflows\wheels-test.ps1 %CD%\..\venv-test'
+        shell: cmd
+
+      - name: Upload wheels
+        uses: actions/upload-artifact@v3
+        with:
+          name: dist
+          path: ./wheelhouse/*.whl
+
+      - name: Prepare to upload FriBiDi
+        if: "matrix.arch != 'ARM64'"
+        run: |
+          mkdir fribidi\${{ matrix.arch }}
+          copy winbuild\build\bin\fribidi* fribidi\${{ matrix.arch }}
+        shell: cmd
+
+      - name: Upload fribidi.dll
+        if: "matrix.arch != 'ARM64'"
+        uses: actions/upload-artifact@v3
+        with:
+          name: fribidi
+          path: fribidi\*
+
   sdist:
     runs-on: ubuntu-latest
     steps:
@@ -97,7 +198,7 @@ jobs:
   success:
     permissions:
       contents: none
-    needs: [build, sdist]
+    needs: [build, windows, sdist]
     runs-on: ubuntu-latest
     name: Wheels Successful
     steps:
diff --git a/.travis.yml b/.travis.yml
index 4005dbcf036..8f8250809d7 100644
--- a/.travis.yml
+++ b/.travis.yml
@@ -3,7 +3,6 @@ if: tag IS present OR type = api
 env:
   global:
     - CIBW_ARCHS=aarch64
-    - CIBW_CONFIG_SETTINGS="raqm=enable raqm=vendor fribidi=vendor"
     - CIBW_SKIP=pp38-*
 
 language: python
diff --git a/Tests/check_wheel.py b/Tests/check_wheel.py
new file mode 100644
index 00000000000..cc52cb75ebb
--- /dev/null
+++ b/Tests/check_wheel.py
@@ -0,0 +1,41 @@
+import sys
+
+from PIL import features
+
+
+def test_wheel_modules():
+    expected_modules = {"pil", "tkinter", "freetype2", "littlecms2", "webp"}
+
+    # tkinter is not available in cibuildwheel installed CPython on Windows
+    try:
+        import tkinter
+
+        assert tkinter
+    except ImportError:
+        expected_modules.remove("tkinter")
+
+    assert set(features.get_supported_modules()) == expected_modules
+
+
+def test_wheel_codecs():
+    expected_codecs = {"jpg", "jpg_2000", "zlib", "libtiff"}
+
+    assert set(features.get_supported_codecs()) == expected_codecs
+
+
+def test_wheel_features():
+    expected_features = {
+        "webp_anim",
+        "webp_mux",
+        "transp_webp",
+        "raqm",
+        "fribidi",
+        "harfbuzz",
+        "libjpeg_turbo",
+        "xcb",
+    }
+
+    if sys.platform == "win32":
+        expected_features.remove("xcb")
+
+    assert set(features.get_supported_features()) == expected_features
diff --git a/Tests/helper.py b/Tests/helper.py
index aacd9556493..cce7eca3a5a 100644
--- a/Tests/helper.py
+++ b/Tests/helper.py
@@ -5,6 +5,7 @@
 import logging
 import os
 import shutil
+import subprocess
 import sys
 import sysconfig
 import tempfile
@@ -258,11 +259,21 @@ def hopper(mode=None, cache={}):
 
 
 def djpeg_available():
-    return bool(shutil.which("djpeg"))
+    if shutil.which("djpeg"):
+        try:
+            subprocess.check_call(["djpeg", "-version"])
+            return True
+        except subprocess.CalledProcessError:  # pragma: no cover
+            return False
 
 
 def cjpeg_available():
-    return bool(shutil.which("cjpeg"))
+    if shutil.which("cjpeg"):
+        try:
+            subprocess.check_call(["cjpeg", "-version"])
+            return True
+        except subprocess.CalledProcessError:  # pragma: no cover
+            return False
 
 
 def netpbm_available():
diff --git a/Tests/test_imagegrab.py b/Tests/test_imagegrab.py
index f8059eca443..a75cbadc4ad 100644
--- a/Tests/test_imagegrab.py
+++ b/Tests/test_imagegrab.py
@@ -11,6 +11,10 @@
 
 
 class TestImageGrab:
+    @pytest.mark.skipif(
+        os.environ.get("USERNAME") == "ContainerAdministrator",
+        reason="can't grab screen when running in Docker",
+    )
     @pytest.mark.skipif(
         sys.platform not in ("win32", "darwin"), reason="requires Windows or macOS"
     )
diff --git a/pyproject.toml b/pyproject.toml
index 81a51f0d83b..41b5aa87f87 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -88,6 +88,8 @@ version = {attr = "PIL.__version__"}
 
 [tool.cibuildwheel]
 before-all = ".github/workflows/wheels-dependencies.sh"
+build-verbosity = 1
+config-settings = "raqm=enable raqm=vendor fribidi=vendor imagequant=disable"
 test-command = "cd {project} && .github/workflows/wheels-test.sh"
 test-extras = "tests"
 
diff --git a/winbuild/build_prepare.py b/winbuild/build_prepare.py
index 2db646de13c..0d111a8ecdf 100644
--- a/winbuild/build_prepare.py
+++ b/winbuild/build_prepare.py
@@ -586,14 +586,19 @@ def build_dep(name: str) -> str:
 
 def build_dep_all() -> None:
     lines = [r'call "{build_dir}\build_env.cmd"']
+    gha_groups = "GITHUB_ACTIONS" in os.environ
     for dep_name in DEPS:
         print()
         if dep_name in disabled:
             print(f"Skipping disabled dependency {dep_name}")
             continue
         script = build_dep(dep_name)
+        if gha_groups:
+            lines.append(f"@echo ::group::Running {script}")
         lines.append(rf'cmd.exe /c "{{build_dir}}\{script}"')
         lines.append("if errorlevel 1 echo Build failed! && exit /B 1")
+        if gha_groups:
+            lines.append("@echo ::endgroup::")
     print()
     lines.append("@echo All Pillow dependencies built successfully!")
     write_script("build_dep_all.cmd", lines)