diff --git a/.github/workflows/ci_sh_def.yml b/.github/workflows/ci_sh_def.yml
index 687c1e4a3..16b21964c 100644
--- a/.github/workflows/ci_sh_def.yml
+++ b/.github/workflows/ci_sh_def.yml
@@ -36,35 +36,38 @@ jobs:
     strategy:
       fail-fast: false
       matrix:
-        runs-on: [ubuntu-latest, windows-latest, macos-latest]
+        runs-on: [ubuntu-latest, windows-2022, macos-latest]
         python:
         - '2.7'
         - '3.5'
         - '3.6'
         - '3.9'
         - '3.10'
-        # - '3.11-dev'
-        - 'pypy-3.7-v7.3.5'
-        # - 'pypy-3.8'
+        - 'pypy-3.7-v7.3.7'
+        - 'pypy-3.8-v7.3.7'
 
         # Items in here will either be added to the build matrix (if not
         # present), or add new keys to an existing matrix element if all the
         # existing keys match.
         #
-        # We support three optional keys: args (both build), args1 (first
-        # build), and args2 (second build).
+        # We support an optional key: args, for cmake args
         include:
           # Just add a key
           - runs-on: ubuntu-latest
-            python: 3.6
+            python: '3.6'
             args: >
               -DPYBIND11_FINDPYTHON=ON
           - runs-on: windows-latest
-            python: 3.6
+            python: '3.6'
             args: >
               -DPYBIND11_FINDPYTHON=ON
           - runs-on: macos-latest
-            python: pypy-2.7
+            python: 'pypy-2.7'
+          # Inject a couple Windows 2019 runs
+          - runs-on: windows-2019
+            python: '3.9'
+          - runs-on: windows-2019
+            python: '2.7'
 
     name: "🐍 ${{ matrix.python }} • ${{ matrix.runs-on }} • x64 ${{ matrix.args }}"
     runs-on: ${{ matrix.runs-on }}
@@ -136,7 +139,7 @@ jobs:
       run: git clean -fdx
 
     # Second build - C++17 mode and in a build directory
-    - name: Configure ${{ matrix.args2 }}
+    - name: Configure C++17
       run: >
         cmake -S . -B build2
         -DPYBIND11_WERROR=ON
@@ -145,7 +148,6 @@ jobs:
         -DCMAKE_CXX_STANDARD=17
         -DCMAKE_CXX_FLAGS="-DPYBIND11_USE_SMART_HOLDER_AS_DEFAULT ${{runner.os == 'Windows' && '/GR /EHsc' || ''}}"
         ${{ matrix.args }}
-        ${{ matrix.args2 }}
 
     - name: Build
       run: cmake --build build2 -j 2
@@ -200,6 +202,7 @@ jobs:
     # setuptools
     - name: Setuptools helpers test
       run: pytest tests/extra_setuptools
+      if: "!(matrix.python == '3.5' && matrix.runs-on == 'windows-2022')"
 
 
   deadsnakes:
diff --git a/.github/workflows/ci_sh_def.yml.patch b/.github/workflows/ci_sh_def.yml.patch
index fc1eb0654..b35ee296d 100644
--- a/.github/workflows/ci_sh_def.yml.patch
+++ b/.github/workflows/ci_sh_def.yml.patch
@@ -1,5 +1,5 @@
---- ci.yml	2021-11-15 14:43:09.035251017 -0800
-+++ ci_sh_def.yml	2021-11-15 15:03:40.563973496 -0800
+--- ci.yml	2021-12-03 11:12:00.501984137 -0800
++++ ci_sh_def.yml	2021-12-03 11:12:25.675660000 -0800
 @@ -1,4 +1,16 @@
 -name: CI
 +# PLEASE KEEP THIS GROUP OF FILES IN SYNC AT ALL TIMES:
@@ -27,7 +27,7 @@
    cancel-in-progress: true
  
  env:
-@@ -103,6 +115,7 @@
+@@ -106,6 +118,7 @@
          -DDOWNLOAD_CATCH=ON
          -DDOWNLOAD_EIGEN=ON
          -DCMAKE_CXX_STANDARD=11
@@ -35,15 +35,15 @@
          ${{ matrix.args }}
  
      - name: Build C++11
-@@ -130,6 +143,7 @@
+@@ -133,6 +146,7 @@
          -DDOWNLOAD_CATCH=ON
          -DDOWNLOAD_EIGEN=ON
          -DCMAKE_CXX_STANDARD=17
 +        -DCMAKE_CXX_FLAGS="-DPYBIND11_USE_SMART_HOLDER_AS_DEFAULT ${{runner.os == 'Windows' && '/GR /EHsc' || ''}}"
          ${{ matrix.args }}
-         ${{ matrix.args2 }}
  
-@@ -152,6 +166,7 @@
+     - name: Build
+@@ -154,6 +168,7 @@
          -DDOWNLOAD_CATCH=ON
          -DDOWNLOAD_EIGEN=ON
          -DCMAKE_CXX_STANDARD=17
@@ -51,7 +51,7 @@
          -DPYBIND11_INTERNALS_VERSION=10000000
          "-DPYBIND11_TEST_OVERRIDE=test_call_policies.cpp;test_gil_scoped.cpp;test_thread.cpp"
          ${{ matrix.args }}
-@@ -252,6 +267,7 @@
+@@ -255,6 +270,7 @@
          -DDOWNLOAD_CATCH=ON
          -DDOWNLOAD_EIGEN=ON
          -DCMAKE_CXX_STANDARD=17
@@ -59,7 +59,7 @@
  
      - name: Build
        run: cmake --build build -j 2
-@@ -306,6 +322,7 @@
+@@ -309,6 +325,7 @@
          -DPYBIND11_WERROR=ON
          -DDOWNLOAD_CATCH=ON
          -DCMAKE_CXX_STANDARD=${{ matrix.std }}
@@ -67,7 +67,7 @@
          -DPYTHON_EXECUTABLE=$(python3 -c "import sys; print(sys.executable)")
  
      - name: Build
-@@ -335,7 +352,8 @@
+@@ -338,7 +355,8 @@
        run: apt-get update && DEBIAN_FRONTEND="noninteractive" apt-get install -y cmake git python3-dev python3-pytest python3-numpy
  
      - name: Configure
@@ -77,7 +77,7 @@
  
      - name: Build
        run: cmake --build build -j2 --verbose
-@@ -415,7 +433,7 @@
+@@ -418,7 +436,7 @@
          cmake3 -S . -B build -DDOWNLOAD_CATCH=ON \
                              -DCMAKE_CXX_STANDARD=11 \
                              -DPYTHON_EXECUTABLE=$(python3 -c "import sys; print(sys.executable)") \
@@ -86,7 +86,7 @@
                              -DPYBIND11_TEST_FILTER="test_smart_ptr.cpp;test_virtual_functions.cpp"
  
      # Building before installing Pip should produce a warning but not an error
-@@ -474,6 +492,7 @@
+@@ -477,6 +495,7 @@
          -DPYBIND11_WERROR=ON
          -DDOWNLOAD_CATCH=ON
          -DCMAKE_CXX_STANDARD=${{ matrix.std }}
@@ -94,7 +94,7 @@
          -DPYTHON_EXECUTABLE=$(python3 -c "import sys; print(sys.executable)")
  
      - name: Build
-@@ -529,6 +548,7 @@
+@@ -532,6 +551,7 @@
          -DDOWNLOAD_CATCH=ON     \
          -DDOWNLOAD_EIGEN=OFF    \
          -DCMAKE_CXX_STANDARD=11             \
@@ -102,7 +102,7 @@
          -DCMAKE_CXX_COMPILER=$(which icpc)  \
          -DPYTHON_EXECUTABLE=$(python3 -c "import sys; print(sys.executable)")
  
-@@ -561,6 +581,7 @@
+@@ -564,6 +584,7 @@
          -DDOWNLOAD_CATCH=ON     \
          -DDOWNLOAD_EIGEN=OFF    \
          -DCMAKE_CXX_STANDARD=17             \
@@ -110,7 +110,7 @@
          -DCMAKE_CXX_COMPILER=$(which icpc)  \
          -DPYTHON_EXECUTABLE=$(python3 -c "import sys; print(sys.executable)")
  
-@@ -633,6 +654,7 @@
+@@ -636,6 +657,7 @@
          -DDOWNLOAD_CATCH=ON
          -DDOWNLOAD_EIGEN=ON
          -DCMAKE_CXX_STANDARD=11
@@ -118,7 +118,7 @@
          -DPYTHON_EXECUTABLE=$(python3 -c "import sys; print(sys.executable)")
  
      - name: Build
-@@ -683,6 +705,7 @@
+@@ -686,6 +708,7 @@
          cmake ../pybind11-tests
          -DDOWNLOAD_CATCH=ON
          -DPYBIND11_WERROR=ON
@@ -126,7 +126,7 @@
          -DPYTHON_EXECUTABLE=$(python3 -c "import sys; print(sys.executable)")
        working-directory: /build-tests
  
-@@ -775,6 +798,7 @@
+@@ -778,6 +801,7 @@
          -DPYBIND11_WERROR=ON
          -DDOWNLOAD_CATCH=ON
          -DDOWNLOAD_EIGEN=ON
@@ -134,7 +134,7 @@
          ${{ matrix.args }}
      - name: Build C++11
        run: cmake --build build -j 2
-@@ -822,6 +846,7 @@
+@@ -825,6 +849,7 @@
          -DPYBIND11_WERROR=ON
          -DDOWNLOAD_CATCH=ON
          -DDOWNLOAD_EIGEN=ON
@@ -142,7 +142,7 @@
  
      - name: Build C++14
        run: cmake --build build -j 2
-@@ -847,11 +872,11 @@
+@@ -850,11 +875,11 @@
            - python: 2.7
              std: 17
              args: >
@@ -156,7 +156,7 @@
  
      steps:
      - uses: actions/checkout@v2
-@@ -920,7 +945,7 @@
+@@ -923,7 +948,7 @@
      - name: Configure C++11
        # LTO leads to many undefined reference like
        # `pybind11::detail::function_call::function_call(pybind11::detail::function_call&&)
@@ -165,7 +165,7 @@
  
      - name: Build C++11
        run: cmake --build build -j 2
-@@ -938,7 +963,7 @@
+@@ -941,7 +966,7 @@
        run: git clean -fdx
  
      - name: Configure C++14
@@ -174,7 +174,7 @@
  
      - name: Build C++14
        run: cmake --build build2 -j 2
-@@ -956,7 +981,7 @@
+@@ -959,7 +984,7 @@
        run: git clean -fdx
  
      - name: Configure C++17