diff --git a/.editorconfig b/.editorconfig
index e55d13f9d6..773e887a6b 100644
--- a/.editorconfig
+++ b/.editorconfig
@@ -14,5 +14,5 @@ max_line_length = 88 # Same as Ruff's default
 [*.md]
 trim_trailing_whitespace = false
 
-[*.{yaml,yml,json,toml,clang-format}]
+[*.{yaml,yml,json,toml,clang-format,vcxproj}]
 indent_size = 2
diff --git a/.github/workflows/install-vs-components.py b/.github/workflows/install-vs-components.py
new file mode 100644
index 0000000000..ed2deb62f7
--- /dev/null
+++ b/.github/workflows/install-vs-components.py
@@ -0,0 +1,44 @@
+# See https://github.com/actions/runner-images/issues/9701
+# Adapted from https://github.com/actions/runner-images/issues/9873#issuecomment-2139288682
+
+import os
+import platform
+from itertools import chain
+from subprocess import check_call, check_output
+
+os.chdir("C:/Program Files (x86)/Microsoft Visual Studio/Installer")
+vs_install_path = check_output(
+    (
+        "vswhere.exe",
+        "-latest",
+        "-products",
+        "*",
+        "-requires",
+        "Microsoft.Component.MSBuild",
+        "-property",
+        "installationPath",
+    ),
+    text=True,
+    shell=True,
+).strip()
+components_to_add = (
+    ["Microsoft.VisualStudio.Component.VC.14.29.16.11.ATL.ARM64"]
+    if platform.machine() == "ARM64"
+    else ["Microsoft.VisualStudio.Component.VC.14.29.16.11.ATL"]
+)
+args = (
+    "vs_installer.exe",
+    "modify",
+    "--installPath",
+    vs_install_path,
+    *chain.from_iterable([("--add", component) for component in components_to_add]),
+    "--quiet",
+    "--norestart",
+)
+print(*args)
+
+# Should be run twice for some reason
+print("First run...")
+check_call(args)
+print("Second run...")
+check_call(args)
diff --git a/.github/workflows/main.yml b/.github/workflows/main.yml
index 7aa7724efc..e03b0c0db0 100644
--- a/.github/workflows/main.yml
+++ b/.github/workflows/main.yml
@@ -17,13 +17,13 @@ env:
 jobs:
   test:
     name: Build and test
-    runs-on: windows-2019
-    timeout-minutes: 20
+    runs-on: windows-2022
+    timeout-minutes: 25
     strategy:
       fail-fast: false
       matrix:
         python-version: ["3.8", "3.9", "3.10", "3.11", "3.12", "3.13", "3.14-dev"]
-        architecture: ["x64", "x86"]
+        architecture: [x64, x86]
 
     steps:
       - uses: actions/checkout@v4
@@ -63,14 +63,16 @@ jobs:
           pywin32_postinstall -remove -destination "$UserSite"
 
       # Compilation and registration of the PyCOMTest server dll
-      - name: Set up MSVC
+      - name: Add msbuild to PATH
         uses: microsoft/setup-msbuild@v2
+
+      - name: Install missing Visual Studio components
+        run: python .github\workflows\install-vs-components.py
+
       - name: Build and register the PyCOMTest server dll
         run: |
-          cd com/TestSources/PyCOMTest
-          msbuild .\PyCOMTest.sln -property:Configuration=Release
-          cd x64/Release
-          regsvr32 .\PyCOMTest.dll
+          msbuild com/TestSources/PyCOMTest/PyCOMTest.sln -property:Configuration=Release
+          regsvr32 com/TestSources/PyCOMTest/x64/Release/PyCOMTest.dll
 
       - name: Run tests
         # Run the tests directly from the source dir so support files (eg, .wav files etc)
@@ -92,8 +94,8 @@ jobs:
   # Later, when available, we can add tests using this wheel on ARM64 VMs
   build_arm64:
     name: Cross-compile ARM
-    runs-on: windows-2019
-    timeout-minutes: 20
+    runs-on: windows-2022
+    timeout-minutes: 25
     strategy:
       fail-fast: false
       matrix:
@@ -142,8 +144,8 @@ jobs:
 
   # This job can be run locally by running `pre-commit run`
   checkers:
-    runs-on: windows-2019
-    timeout-minutes: 20
+    runs-on: windows-2022
+    timeout-minutes: 25
     steps:
       - uses: actions/checkout@v4
       - uses: actions/setup-python@v5
@@ -174,8 +176,8 @@ jobs:
         if: ${{ !cancelled() }}
 
   mypy:
-    runs-on: windows-2019
-    timeout-minutes: 20
+    runs-on: windows-2022
+    timeout-minutes: 25
     strategy:
       fail-fast: false
       matrix:
@@ -192,8 +194,8 @@ jobs:
       - run: mypy . --python-version=${{ matrix.python-version }}
 
   pyright:
-    runs-on: windows-2019
-    timeout-minutes: 20
+    runs-on: windows-2022
+    timeout-minutes: 25
     strategy:
       fail-fast: false
       matrix:
diff --git a/com/TestSources/PyCOMTest/PyCOMTest.vcxproj b/com/TestSources/PyCOMTest/PyCOMTest.vcxproj
index 107b6caa14..050d0f6b60 100644
--- a/com/TestSources/PyCOMTest/PyCOMTest.vcxproj
+++ b/com/TestSources/PyCOMTest/PyCOMTest.vcxproj
@@ -22,7 +22,9 @@
     <VCProjectVersion>17.0</VCProjectVersion>
     <ProjectGuid>{8EB3046C-6CE8-4537-9B58-6EDD46E6D632}</ProjectGuid>
     <Keyword>Win32Proj</Keyword>
-    <WindowsTargetPlatformVersion>10.0.22000.0</WindowsTargetPlatformVersion>
+    <!-- Target Windows Server 2022 which GitHub Actions run on -->
+    <!-- https://github.com/actions/runner-images/blob/main/images/windows/Windows2022-Readme.md#windows-server-2022 -->
+    <WindowsTargetPlatformVersion>10.0.20348.0</WindowsTargetPlatformVersion>
   </PropertyGroup>
   <Import Project="$(VCTargetsPath)\Microsoft.Cpp.Default.props" />
   <PropertyGroup Condition="'$(Configuration)|$(Platform)'=='Debug|Win32'" Label="Configuration">
diff --git a/setup.py b/setup.py
index 8a8928988f..4e61136bbd 100644
--- a/setup.py
+++ b/setup.py
@@ -145,7 +145,7 @@ def __init__(
                 # CRYPT_DECRYPT_MESSAGE_PARA.dwflags is in an ifdef for some unknown reason
                 # See github PR #1444 for more details...
                 ("CRYPT_DECRYPT_MESSAGE_PARA_HAS_EXTRA_FIELDS", None),
-                # Minimum Windows version supported (Windows 7 / Windows Server 2008)
+                # Minimum Windows version supported (Windows 7)
                 # https://learn.microsoft.com/en-us/cpp/porting/modifying-winver-and-win32-winnt
                 ("_WIN32_WINNT", hex(0x0601)),
                 ("WINVER", hex(0x0601)),