diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index 044312b53..5216e29ca 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -38,6 +38,14 @@ jobs:
             python: 3.7
             arch: x86
             max-cxx-std: 14
+          - runs-on: windows-latest
+            python: 3.6
+            arch: x64
+            max-cxx-std: 17
+          - runs-on: windows-latest
+            python: 3.7
+            arch: x64
+            max-cxx-std: 17
 
         exclude:
             # Currently 32bit only, and we build 64bit
diff --git a/.github/workflows/configure.yml b/.github/workflows/configure.yml
index 96904341d..934b2d73b 100644
--- a/.github/workflows/configure.yml
+++ b/.github/workflows/configure.yml
@@ -1,4 +1,4 @@
-name: Configure
+name: Config
 
 on:
   workflow_dispatch:
@@ -14,63 +14,50 @@ jobs:
     strategy:
       fail-fast: false
       matrix:
-        python:
-        - 2.7
-        - 3.8
+        runs-on: [ubuntu-latest, macos-latest]
+        arch: [x64]
+        cmake: [3.7, 3.18]
 
-    name: CMake ${{ matrix.cmake }} Python ${{ matrix.python }} on ubuntu
-    runs-on: ubuntu-latest
+        include:
+        - runs-on: windows-latest
+          arch: x64
+          cmake: 3.18
+
+        # TODO: 3.8
+        - runs-on: windows-2016
+          arch: x86
+          cmake: 3.11
+
+        - runs-on: windows-2016
+          arch: x86
+          cmake: 3.18
+
+    name: 🐍 3.7 • CMake ${{ matrix.cmake }} • ${{ matrix.runs-on }}
+    runs-on: ${{ matrix.runs-on }}
 
     steps:
     - uses: actions/checkout@v2
 
-    - name: Setup Python ${{ matrix.python }}
+    - name: Setup Python 3.7
       uses: actions/setup-python@v2
       with:
-        python-version: ${{ matrix.python }}
+        python-version: 3.7
+        architecture: ${{ matrix.arch }}
 
     - name: Prepare env
       run: python -m pip install -r tests/requirements.txt
 
+    - name: Setup CMake ${{ matrix.cmake }}
+      uses: jwlawson/actions-setup-cmake@v1.3
+      with:
+        cmake-version: ${{ matrix.cmake }}
+
     - name: Make build directories
-      run: |
-        mkdir build3.7
-        mkdir build3.11
-        mkdir build3.18
+      run: mkdir "build dir"
 
-    - name: Setup CMake 3.7
-      uses: jwlawson/actions-setup-cmake@v1.3
-      with:
-        cmake-version: 3.7
-
-    - name: Configure 3.7
-      working-directory: build3.7
-      run: >
-        cmake ..
-        -DPYBIND11_WERROR=ON
-        -DDOWNLOAD_CATCH=ON
-        -DPYTHON_EXECUTABLE=$(python -c "import sys; print(sys.executable)")
-
-    - name: Setup CMake 3.11
-      uses: jwlawson/actions-setup-cmake@v1.3
-      with:
-        cmake-version: 3.11
-
-    - name: Configure 3.11
-      working-directory: build3.11
-      run: >
-        cmake ..
-        -DPYBIND11_WERROR=ON
-        -DDOWNLOAD_CATCH=ON
-        -DPYTHON_EXECUTABLE=$(python -c "import sys; print(sys.executable)")
-
-    - name: Setup CMake 3.18
-      uses: jwlawson/actions-setup-cmake@v1.3
-      with:
-        cmake-version: 3.18
-
-    - name: Configure 3.18
-      working-directory: build3.18
+    - name: Configure
+      working-directory: build dir
+      shell: bash
       run: >
         cmake ..
         -DPYBIND11_WERROR=ON