diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index adbbf626f..bd99ddd33 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -1037,3 +1037,70 @@ jobs:
 
       - name: Clean directory
         run: git clean -fdx
+
+  macos_brew_install_llvm:
+    name: "macos-latest • brew install llvm"
+    runs-on: macos-latest
+
+    env:
+      # https://apple.stackexchange.com/questions/227026/how-to-install-recent-clang-with-homebrew
+      LDFLAGS: '-L/usr/local/opt/llvm/lib -Wl,-rpath,/usr/local/opt/llvm/lib'
+
+    steps:
+      - name: Update PATH
+        run: echo "/usr/local/opt/llvm/bin" >> $GITHUB_PATH
+
+      - name: Show env
+        run: env
+
+      - name: Checkout
+        uses: actions/checkout@v3
+
+      - name: Show Clang++ version before brew install llvm
+        run: clang++ --version
+
+      - name: brew install llvm
+        run: brew install llvm
+
+      - name: Show Clang++ version after brew install llvm
+        run: clang++ --version
+
+      - name: Update CMake
+        uses: jwlawson/actions-setup-cmake@v1.13
+
+      - name: Run pip installs
+        run: |
+          python3 -m pip install --upgrade pip
+          python3 -m pip install -r tests/requirements.txt
+          python3 -m pip install numpy
+          python3 -m pip install scipy
+
+      - name: Show CMake version
+        run: cmake --version
+
+      - name: CMake Configure
+        run: >
+          cmake -S . -B .
+          -DCMAKE_VERBOSE_MAKEFILE=ON
+          -DPYBIND11_WERROR=ON
+          -DPYBIND11_SIMPLE_GIL_MANAGEMENT=OFF
+          -DDOWNLOAD_CATCH=ON
+          -DDOWNLOAD_EIGEN=ON
+          -DCMAKE_CXX_COMPILER=clang++
+          -DCMAKE_CXX_STANDARD=17
+          -DPYTHON_EXECUTABLE=$(python3 -c "import sys; print(sys.executable)")
+
+      - name: Build
+        run: cmake --build . -j 2
+
+      - name: Python tests
+        run: cmake --build . --target pytest -j 2
+
+      - name: C++ tests
+        run: cmake --build . --target cpptest -j 2
+
+      - name: Interface test
+        run: cmake --build . --target test_cmake_build -j 2
+
+      - name: Clean directory
+        run: git clean -fdx
diff --git a/tests/test_exceptions.py b/tests/test_exceptions.py
index 7eb1a9d62..0d2c80814 100644
--- a/tests/test_exceptions.py
+++ b/tests/test_exceptions.py
@@ -4,6 +4,7 @@ import pytest
 
 import env
 import pybind11_cross_module_tests as cm
+import pybind11_tests  # noqa: F401
 from pybind11_tests import exceptions as m
 
 
@@ -72,9 +73,9 @@ def test_cross_module_exceptions(msg):
 
 # TODO: FIXME
 @pytest.mark.xfail(
-    "env.PYPY and env.MACOS",
+    "env.MACOS and (env.PYPY or pybind11_tests.compiler_info.startswith('Homebrew Clang'))",
     raises=RuntimeError,
-    reason="Expected failure with PyPy and libc++ (Issue #2847 & PR #2999)",
+    reason="See Issue #2847, PR #2999, PR #4324",
 )
 def test_cross_module_exception_translator():
     with pytest.raises(KeyError):
diff --git a/tools/pybind11NewTools.cmake b/tools/pybind11NewTools.cmake
index 9e13daf1a..5a6a0cb8b 100644
--- a/tools/pybind11NewTools.cmake
+++ b/tools/pybind11NewTools.cmake
@@ -235,7 +235,7 @@ function(pybind11_add_module target_name)
 
   # Use case-insensitive comparison to match the result of $<CONFIG:cfgs>
   string(TOUPPER "${CMAKE_BUILD_TYPE}" uppercase_CMAKE_BUILD_TYPE)
-  if(NOT MSVC AND NOT ${uppercase_CMAKE_BUILD_TYPE} MATCHES DEBUG|RELWITHDEBINFO)
+  if(NOT MSVC AND NOT "${uppercase_CMAKE_BUILD_TYPE}" MATCHES DEBUG|RELWITHDEBINFO)
     # Strip unnecessary sections of the binary on Linux/macOS
     pybind11_strip(${target_name})
   endif()
diff --git a/tools/pybind11Tools.cmake b/tools/pybind11Tools.cmake
index 0dc61d399..66ad00a47 100644
--- a/tools/pybind11Tools.cmake
+++ b/tools/pybind11Tools.cmake
@@ -214,7 +214,7 @@ function(pybind11_add_module target_name)
 
   # Use case-insensitive comparison to match the result of $<CONFIG:cfgs>
   string(TOUPPER "${CMAKE_BUILD_TYPE}" uppercase_CMAKE_BUILD_TYPE)
-  if(NOT MSVC AND NOT ${uppercase_CMAKE_BUILD_TYPE} MATCHES DEBUG|RELWITHDEBINFO)
+  if(NOT MSVC AND NOT "${uppercase_CMAKE_BUILD_TYPE}" MATCHES DEBUG|RELWITHDEBINFO)
     pybind11_strip(${target_name})
   endif()