From 670fda122f1f43c60d8668f110d1e86f10e74b62 Mon Sep 17 00:00:00 2001
From: Serein Pfeiffer <s.pfeiffer@klebert-engineering.de>
Date: Thu, 9 Oct 2025 14:17:01 +0200
Subject: [PATCH 1/7] macos: Replace repair script by directly usage of correct
 paths directly in python-wheel.cmake.

---
 python-wheel.cmake      | 15 +++++++++++----
 repair-wheel-macos.bash | 35 -----------------------------------
 2 files changed, 11 insertions(+), 39 deletions(-)
 delete mode 100755 repair-wheel-macos.bash

diff --git a/python-wheel.cmake b/python-wheel.cmake
index d5c4708..dab2ca9 100644
--- a/python-wheel.cmake
+++ b/python-wheel.cmake
@@ -185,10 +185,17 @@ function (add_wheel WHEEL_TARGET)
 
   add_dependencies(wheel ${WHEEL_TARGET}-setup-py)
 
-  set_target_properties(${WHEEL_TARGET} PROPERTIES
-    BUILD_RPATH "\$ORIGIN;" # Override hardcoded RPATH
-    INSTALL_RPATH "\$ORIGIN;"
-  )
+  if(APPLE)
+    set_target_properties(${WHEEL_TARGET} PROPERTIES
+      BUILD_RPATH "@loader_path" # macOS uses @loader_path
+      INSTALL_RPATH "@loader_path"
+    )
+  else()
+    set_target_properties(${WHEEL_TARGET} PROPERTIES
+      BUILD_RPATH "\$ORIGIN;" # Linux uses $ORIGIN
+      INSTALL_RPATH "\$ORIGIN;"
+    )
+  endif()
 endfunction()
 
 function (add_wheel_test TEST_NAME)
diff --git a/repair-wheel-macos.bash b/repair-wheel-macos.bash
deleted file mode 100755
index d1fc3b9..0000000
--- a/repair-wheel-macos.bash
+++ /dev/null
@@ -1,35 +0,0 @@
-#!/usr/bin/env bash
-
-in_whl=$1
-out_dir=$2
-dylib_dirname=$3
-
-set -ex
-cd "$(mktemp -d)"
-unzip "$in_whl"
-
-# Print the contents of the current directory after unzipping
-echo "\nContents of directory after unzipping wheel ..."
-ls -l
-
-# Set the DYLD_FALLBACK_LIBRARY_PATH to include /usr/local/lib
-export DYLD_FALLBACK_LIBRARY_PATH="/usr/local/lib"
-
-# Add all subdirectories in the current directory to DYLD_FALLBACK_LIBRARY_PATH
-for dir in $(find . -type d); do
-    export DYLD_FALLBACK_LIBRARY_PATH="${DYLD_FALLBACK_LIBRARY_PATH}:$(pwd)/$dir"
-done
-
-echo "\nDelocating ..."
-delocate-path -L "$dylib_dirname.dylibs" .
-
-echo "\nRepackaging ..."
-wheel=$(basename "$in_whl")
-zip -r "$wheel" ./*
-mkdir -p "$out_dir"
-mv "$wheel" "$out_dir"
-tempdir=$(pwd)
-cd -
-rm -rf "$tempdir"
-
-echo "\nDone."

From 112ae22fd147f9b189ba9830407744fc9dcacf51 Mon Sep 17 00:00:00 2001
From: Serein Pfeiffer <s.pfeiffer@klebert-engineering.de>
Date: Thu, 9 Oct 2025 14:21:23 +0200
Subject: [PATCH 2/7] macos: Try to extract macos version directly from wheel
 name, if not possible fallback to macosx_deployment_target usage.

---
 change-wheel-tag-macos.py | 40 +++++++++++++++++++++++++++++++--------
 1 file changed, 32 insertions(+), 8 deletions(-)

diff --git a/change-wheel-tag-macos.py b/change-wheel-tag-macos.py
index fa6304f..a849abf 100644
--- a/change-wheel-tag-macos.py
+++ b/change-wheel-tag-macos.py
@@ -4,18 +4,42 @@
 import shutil
 import re
 
-# Read the deployment target
-deployment_target = os.getenv('MACOSX_DEPLOYMENT_TARGET')
-if not deployment_target:
-    sys.exit("MACOSX_DEPLOYMENT_TARGET is not set")
-
 # Find the latest wheel file
 wheel_files = glob.glob(f"{sys.argv[1]}/{sys.argv[2]}*.whl")
+if not wheel_files:
+    sys.exit(f"No wheel files found matching {sys.argv[1]}/{sys.argv[2]}*.whl")
+
 latest_file = max(wheel_files, key=os.path.getctime)
 
+# Extract current macOS version from wheel filename
+match = re.search(r'macosx_(\d+)_(\d+)', latest_file)
+if match:
+    current_version = f"{match.group(1)}_{match.group(2)}"
+else:
+    # Fallback if we can't extract version
+    current_version = None
+
+# Determine target deployment version
+deployment_target = os.getenv('MACOSX_DEPLOYMENT_TARGET')
+if deployment_target:
+    # Use environment variable if set
+    deployment_target = deployment_target.replace(".", "_")
+    print(f"Using MACOSX_DEPLOYMENT_TARGET from environment: {deployment_target}")
+elif current_version:
+    # Keep current version from wheel filename
+    deployment_target = current_version
+    print(f"Auto-detected macOS version from wheel: {deployment_target}")
+else:
+    # Use sensible default (macOS 11.0 - Big Sur, widely compatible)
+    deployment_target = "11_0"
+    print(f"Using default macOS version: {deployment_target}")
+
 # Define the new filename
-deployment_target = deployment_target.replace(".", "_")
 new_filename = re.sub(r'macosx_\d+_\d+', f'macosx_{deployment_target}', latest_file)
 
-# Rename the wheel file
-shutil.move(latest_file, new_filename)
+# Only rename if filename actually changed
+if latest_file != new_filename:
+    print(f"Renaming: {os.path.basename(latest_file)} -> {os.path.basename(new_filename)}")
+    shutil.move(latest_file, new_filename)
+else:
+    print(f"Wheel already has correct tag: {os.path.basename(latest_file)}")

From 268888e3e20db2d6080607d0f4021c08b8826949 Mon Sep 17 00:00:00 2001
From: Serein Pfeiffer <s.pfeiffer@klebert-engineering.de>
Date: Thu, 9 Oct 2025 14:21:59 +0200
Subject: [PATCH 3/7] doc: Update docs to reflect changes reg. macos support.

---
 README.md | 10 +---------
 1 file changed, 1 insertion(+), 9 deletions(-)

diff --git a/README.md b/README.md
index d356a2f..590b83e 100644
--- a/README.md
+++ b/README.md
@@ -187,8 +187,7 @@ jobs:
 
 ### macOS
 
-For macOS, this repo provides the `repair-wheel-macos.bash` script, which controls
-invocations of the `delocate-path` tool which bundles dependencies into your wheel.
+macOS wheels are now built correctly without any post-processing. (Note: Versions prior to 1.1.0 required manual wheel repair with `repair-wheel-macos.bash`, which is no longer needed.)
 
 Use it in your Github action like this:
 
@@ -212,16 +211,9 @@ jobs:
       - name: Build (macOS)
         if: matrix.os == 'macos-13'
         run: |
-          python -m pip install delocate
-          export MACOSX_DEPLOYMENT_TARGET=10.15
           mkdir build && cd build
           cmake ..
           cmake --build .
-          # Important step: Audit the wheels!
-          mv bin/wheel bin/wheel-auditme  # Same as on Linux
-          ./_deps/python-cmake-wheel-src/repair-wheel-macos.bash \
-                "$(pwd)"/bin/wheel-auditme/mapget*.whl \
-                "$(pwd)"/bin/wheel mapget
       - name: Deploy
         uses: actions/upload-artifact@v3
         with:

From b1d399e70ce0b18641bf3efd4822632a48b75506 Mon Sep 17 00:00:00 2001
From: Serein Pfeiffer <s.pfeiffer@klebert-engineering.de>
Date: Thu, 9 Oct 2025 14:23:04 +0200
Subject: [PATCH 4/7] ci: Intro minimal ci configuration which tests
 python-wheel.cmake with a sample project.

---
 .github/workflows/test.yml            | 54 +++++++++++++++
 test-wheel.bash                       |  6 +-
 tests/macos-wheel-test/CMakeLists.txt | 98 +++++++++++++++++++++++++++
 tests/macos-wheel-test/LICENSE        |  1 +
 tests/macos-wheel-test/py_simple.cpp  | 13 ++++
 tests/macos-wheel-test/simple_lib.cpp | 13 ++++
 tests/macos-wheel-test/simple_lib.h   | 11 +++
 tests/macos-wheel-test/test_wheel.py  | 63 +++++++++++++++++
 8 files changed, 258 insertions(+), 1 deletion(-)
 create mode 100644 .github/workflows/test.yml
 create mode 100644 tests/macos-wheel-test/CMakeLists.txt
 create mode 100644 tests/macos-wheel-test/LICENSE
 create mode 100644 tests/macos-wheel-test/py_simple.cpp
 create mode 100644 tests/macos-wheel-test/simple_lib.cpp
 create mode 100644 tests/macos-wheel-test/simple_lib.h
 create mode 100755 tests/macos-wheel-test/test_wheel.py

diff --git a/.github/workflows/test.yml b/.github/workflows/test.yml
new file mode 100644
index 0000000..d2d1979
--- /dev/null
+++ b/.github/workflows/test.yml
@@ -0,0 +1,54 @@
+name: Test
+
+on:
+  push:
+  pull_request:
+
+jobs:
+  test:
+    runs-on: ${{ matrix.os }}
+    strategy:
+      matrix:
+        os: [ubuntu-latest, macos-13, macos-14, windows-latest]
+        python-version: ["3.10", "3.11", "3.12", "3.13"]
+        exclude:
+          # Python 3.10 doesn't have ARM64 builds for macOS
+          - os: macos-14
+            python-version: "3.10"
+    steps:
+      - uses: actions/checkout@v4
+
+      - uses: actions/setup-python@v5
+        with:
+          python-version: ${{ matrix.python-version }}
+          architecture: x64
+
+      - name: Install Python dependencies
+        run: python -m pip install setuptools wheel
+
+      - name: Configure
+        working-directory: tests/macos-wheel-test
+        run: |
+          mkdir build
+          cd build
+          cmake ..
+
+      - name: Build (Linux/macOS)
+        if: runner.os != 'Windows'
+        working-directory: tests/macos-wheel-test/build
+        run: cmake --build .
+
+      - name: Build (Windows)
+        if: runner.os == 'Windows'
+        working-directory: tests/macos-wheel-test/build
+        run: cmake --build . --config Release
+
+      - name: Test (Linux/macOS)
+        if: runner.os != 'Windows'
+        working-directory: tests/macos-wheel-test/build
+        run: ctest --verbose --no-tests=error
+
+      - name: Test (Windows)
+        if: runner.os == 'Windows'
+        working-directory: tests/macos-wheel-test/build
+        run: ctest -C Release --verbose --no-tests=error
diff --git a/test-wheel.bash b/test-wheel.bash
index cba84a0..35ccee2 100755
--- a/test-wheel.bash
+++ b/test-wheel.bash
@@ -59,7 +59,11 @@ while [[ $# -gt 0 ]]; do
       ;;
     -f|--foreground)
       echo "→ Starting foreground task: $2"
-      $2
+      if [[ "$2" == *.py ]] && [[ "$2" != *[[:space:]]* ]]; then
+        python "$2"
+      else
+        $2
+      fi
       shift
       shift
       ;;
diff --git a/tests/macos-wheel-test/CMakeLists.txt b/tests/macos-wheel-test/CMakeLists.txt
new file mode 100644
index 0000000..606aed0
--- /dev/null
+++ b/tests/macos-wheel-test/CMakeLists.txt
@@ -0,0 +1,98 @@
+cmake_minimum_required(VERSION 3.20)
+project(test-macos-wheel VERSION 1.0.0)
+
+set(CMAKE_CXX_STANDARD 17)
+set(CMAKE_CXX_STANDARD_REQUIRED ON)
+
+# Export all symbols on Windows (like zswag does)
+set(CMAKE_WINDOWS_EXPORT_ALL_SYMBOLS ON)
+
+# Enable testing
+enable_testing()
+
+# Include python-wheel.cmake from repository root
+list(APPEND CMAKE_MODULE_PATH "${CMAKE_CURRENT_SOURCE_DIR}/../..")
+include(python-wheel)
+
+# Set wheel output directory
+set(WHEEL_DEPLOY_DIRECTORY "${CMAKE_BINARY_DIR}/wheel")
+
+# Find Python
+find_package(Python3 COMPONENTS Interpreter Development.Module REQUIRED)
+
+# Fetch CPM.cmake
+set(CPM_DOWNLOAD_VERSION 0.40.2)
+if(CPM_SOURCE_CACHE)
+  set(CPM_DOWNLOAD_LOCATION "${CPM_SOURCE_CACHE}/cpm/CPM_${CPM_DOWNLOAD_VERSION}.cmake")
+elseif(DEFINED ENV{CPM_SOURCE_CACHE})
+  set(CPM_DOWNLOAD_LOCATION "$ENV{CPM_SOURCE_CACHE}/cpm/CPM_${CPM_DOWNLOAD_VERSION}.cmake")
+else()
+  set(CPM_DOWNLOAD_LOCATION "${CMAKE_BINARY_DIR}/cmake/CPM_${CPM_DOWNLOAD_VERSION}.cmake")
+endif()
+if(NOT (EXISTS ${CPM_DOWNLOAD_LOCATION}))
+  message(STATUS "Downloading CPM.cmake to ${CPM_DOWNLOAD_LOCATION}")
+  file(DOWNLOAD
+       https://github.com/cpm-cmake/CPM.cmake/releases/download/v${CPM_DOWNLOAD_VERSION}/CPM.cmake
+       ${CPM_DOWNLOAD_LOCATION}
+  )
+endif()
+include(${CPM_DOWNLOAD_LOCATION})
+
+# Fetch pybind11 via CPM
+CPMAddPackage("gh:pybind/pybind11@2.13.6")
+
+# Create simple C++ library
+add_library(simple_lib SHARED
+    simple_lib.cpp
+    simple_lib.h
+)
+
+target_include_directories(simple_lib PUBLIC
+    ${CMAKE_CURRENT_SOURCE_DIR}
+)
+
+# Diagnostic logging for Windows
+if(WIN32)
+    message(STATUS "=== Windows Build Diagnostics ===")
+    message(STATUS "CMAKE_GENERATOR: ${CMAKE_GENERATOR}")
+    message(STATUS "CMAKE_BINARY_DIR: ${CMAKE_BINARY_DIR}")
+    message(STATUS "CMAKE_CONFIGURATION_TYPES: ${CMAKE_CONFIGURATION_TYPES}")
+    get_target_property(simple_lib_output simple_lib RUNTIME_OUTPUT_DIRECTORY)
+    get_target_property(simple_lib_archive simple_lib ARCHIVE_OUTPUT_DIRECTORY)
+    message(STATUS "simple_lib RUNTIME_OUTPUT_DIRECTORY: ${simple_lib_output}")
+    message(STATUS "simple_lib ARCHIVE_OUTPUT_DIRECTORY: ${simple_lib_archive}")
+    message(STATUS "simple_lib will output to: $<TARGET_FILE:simple_lib>")
+    message(STATUS "simple_lib import lib: $<TARGET_LINKER_FILE:simple_lib>")
+endif()
+
+# Create Python module using pybind11
+pybind11_add_module(py_simple
+    py_simple.cpp
+)
+
+target_link_libraries(py_simple PRIVATE simple_lib)
+
+# More diagnostics after linking
+if(WIN32)
+    get_target_property(py_simple_output py_simple RUNTIME_OUTPUT_DIRECTORY)
+    message(STATUS "py_simple RUNTIME_OUTPUT_DIRECTORY: ${py_simple_output}")
+    message(STATUS "py_simple will output to: $<TARGET_FILE:py_simple>")
+    message(STATUS "py_simple will link: $<TARGET_LINKER_FILE:simple_lib>")
+endif()
+
+# Package as wheel using add_wheel()
+add_wheel(py_simple
+    NAME simple_test
+    VERSION "1.0.0"
+    AUTHOR "Test Author"
+    EMAIL "test@example.com"
+    DESCRIPTION "Minimal test wheel for python-cmake-wheel"
+    PYTHON_REQUIRES ">=3.9"
+    TARGET_DEPENDENCIES simple_lib
+)
+
+# Add test to validate wheel functionality
+add_wheel_test(test-simple-wheel
+    WORKING_DIRECTORY "${CMAKE_CURRENT_SOURCE_DIR}"
+    COMMANDS -f "${CMAKE_CURRENT_SOURCE_DIR}/test_wheel.py"
+)
diff --git a/tests/macos-wheel-test/LICENSE b/tests/macos-wheel-test/LICENSE
new file mode 100644
index 0000000..f6d7b04
--- /dev/null
+++ b/tests/macos-wheel-test/LICENSE
@@ -0,0 +1 @@
+MIT License - Test Project
diff --git a/tests/macos-wheel-test/py_simple.cpp b/tests/macos-wheel-test/py_simple.cpp
new file mode 100644
index 0000000..2819c2e
--- /dev/null
+++ b/tests/macos-wheel-test/py_simple.cpp
@@ -0,0 +1,13 @@
+#include <pybind11/pybind11.h>
+#include "simple_lib.h"
+
+namespace py = pybind11;
+
+PYBIND11_MODULE(py_simple, m) {
+    m.doc() = "Simple test library for python-cmake-wheel";
+
+    py::class_<simple::Calculator>(m, "Calculator")
+        .def(py::init<>())
+        .def("add", &simple::Calculator::add, "Add two numbers")
+        .def("multiply", &simple::Calculator::multiply, "Multiply two numbers");
+}
diff --git a/tests/macos-wheel-test/simple_lib.cpp b/tests/macos-wheel-test/simple_lib.cpp
new file mode 100644
index 0000000..2801fd8
--- /dev/null
+++ b/tests/macos-wheel-test/simple_lib.cpp
@@ -0,0 +1,13 @@
+#include "simple_lib.h"
+
+namespace simple {
+
+int Calculator::add(int a, int b) {
+    return a + b;
+}
+
+int Calculator::multiply(int a, int b) {
+    return a * b;
+}
+
+} // namespace simple
diff --git a/tests/macos-wheel-test/simple_lib.h b/tests/macos-wheel-test/simple_lib.h
new file mode 100644
index 0000000..09aefbe
--- /dev/null
+++ b/tests/macos-wheel-test/simple_lib.h
@@ -0,0 +1,11 @@
+#pragma once
+
+namespace simple {
+
+class Calculator {
+public:
+    int add(int a, int b);
+    int multiply(int a, int b);
+};
+
+} // namespace simple
diff --git a/tests/macos-wheel-test/test_wheel.py b/tests/macos-wheel-test/test_wheel.py
new file mode 100755
index 0000000..03ba52d
--- /dev/null
+++ b/tests/macos-wheel-test/test_wheel.py
@@ -0,0 +1,63 @@
+#!/usr/bin/env python3
+"""
+Test script to validate that the simple_test wheel works correctly.
+Tests import, instantiation, and basic functionality.
+"""
+import sys
+
+def test_wheel():
+    """Test that the wheel can be imported and used."""
+    print("Testing simple_test wheel import and functionality...")
+
+    # Debug: Show what's installed
+    import site
+    import os
+    print(f"Site packages: {site.getsitepackages()}")
+    for sp in site.getsitepackages():
+        simple_test_dir = os.path.join(sp, "simple_test")
+        if os.path.exists(simple_test_dir):
+            print(f"Found simple_test in: {simple_test_dir}")
+            print(f"Contents: {os.listdir(simple_test_dir)}")
+        else:
+            print(f"simple_test NOT in: {sp}")
+
+    # Test import
+    try:
+        import simple_test
+        print("[OK] Import successful")
+    except ImportError as e:
+        print(f"[FAIL] Import failed: {e}")
+        import traceback
+        traceback.print_exc()
+        return False
+
+    # Test instantiation
+    try:
+        calc = simple_test.Calculator()
+        print("[OK] Calculator instantiation successful")
+    except Exception as e:
+        print(f"[FAIL] Calculator instantiation failed: {e}")
+        return False
+
+    # Test add method
+    result = calc.add(10, 20)
+    if result == 30:
+        print(f"[OK] Calculator.add(10, 20) = {result}")
+    else:
+        print(f"[FAIL] Calculator.add(10, 20) returned {result}, expected 30")
+        return False
+
+    # Test multiply method
+    result = calc.multiply(5, 6)
+    if result == 30:
+        print(f"[OK] Calculator.multiply(5, 6) = {result}")
+    else:
+        print(f"[FAIL] Calculator.multiply(5, 6) returned {result}, expected 30")
+        return False
+
+    print("\n[OK] All tests passed!")
+    return True
+
+if __name__ == "__main__":
+    success = test_wheel()
+    sys.exit(0 if success else 1)

From 247a3ea89f61251442830dfc2a27f1a4e79b066b Mon Sep 17 00:00:00 2001
From: Serein Pfeiffer <s.pfeiffer@klebert-engineering.de>
Date: Wed, 29 Oct 2025 15:45:15 +0100
Subject: [PATCH 5/7] Use 'delocate' again for transitive dep support, but
 without need for manual fixup script invocation.

---
 README.md                  |  7 ++++---
 python-wheel-globals.cmake | 11 +++++++++++
 python-wheel.cmake         | 14 +++++++++++++-
 3 files changed, 28 insertions(+), 4 deletions(-)

diff --git a/README.md b/README.md
index 590b83e..a254cad 100644
--- a/README.md
+++ b/README.md
@@ -76,8 +76,7 @@ add_wheel(mylib-python-bindings
 
 The `add_wheel` command will create a temporary `setup.py` for your project in the build folder, which bundles the necessary files. The execution of this `setup.py` is attached to the custom target `wheelname-setup-py`. It will be executed when you run `cmake --build .` in your build directory.
 
-**Note: On macOS, when the `MACOSX_DEPLOYMENT_TARGET` env is set, the wheel will be
-tagged with the indicated deployment target version.**
+**Note: On macOS, `delocate` must be installed (`pip install delocate`) for proper handling of library dependencies. The build process automatically invokes `delocate-path` to fix rpaths in bundled libraries, ensuring transitive dependencies work correctly. When `MACOSX_DEPLOYMENT_TARGET` is set, the wheel will be tagged with the indicated deployment target version.**
 
 ## Adding tests
 
@@ -187,7 +186,7 @@ jobs:
 
 ### macOS
 
-macOS wheels are now built correctly without any post-processing. (Note: Versions prior to 1.1.0 required manual wheel repair with `repair-wheel-macos.bash`, which is no longer needed.)
+macOS wheels require `delocate` for proper handling of library dependencies. The build process automatically invokes `delocate-path` to fix rpaths in all bundled libraries, ensuring transitive dependencies (e.g., OpenSSL → libcrypto) work correctly at runtime.
 
 Use it in your Github action like this:
 
@@ -208,6 +207,8 @@ jobs:
         with:
           python-version: ${{ matrix.python-version }}
           architecture: x64
+      - name: Install delocate
+        run: pip install delocate
       - name: Build (macOS)
         if: matrix.os == 'macos-13'
         run: |
diff --git a/python-wheel-globals.cmake b/python-wheel-globals.cmake
index 6479257..0a04edb 100644
--- a/python-wheel-globals.cmake
+++ b/python-wheel-globals.cmake
@@ -5,6 +5,17 @@ if (APPLE)
   set(CMAKE_MACOSX_RPATH ON)
   set(CMAKE_BUILD_WITH_INSTALL_RPATH ON)
   set(CMAKE_INSTALL_RPATH "${CMAKE_INSTALL_RPATH};@loader_path")
+
+  # Check for delocate (required for proper library dependency handling)
+  execute_process(
+    COMMAND "${Python3_EXECUTABLE}" -c "import delocate"
+    RESULT_VARIABLE DELOCATE_CHECK
+    OUTPUT_QUIET
+    ERROR_QUIET
+  )
+  if(NOT DELOCATE_CHECK EQUAL 0)
+    message(FATAL_ERROR "delocate is required for macOS wheel building to handle library dependencies correctly. Install with: pip install delocate")
+  endif()
 endif()
 
 # Guess python wheel filename infixes (abi + platform) to be used
diff --git a/python-wheel.cmake b/python-wheel.cmake
index dab2ca9..8b2be2a 100644
--- a/python-wheel.cmake
+++ b/python-wheel.cmake
@@ -168,9 +168,21 @@ function (add_wheel WHEEL_TARGET)
   configure_file("${PY_WHEEL_SETUP_FILE}" "${SETUP_FILE}")
 
   if(APPLE)
+    # Run delocate-path to fix library dependencies and rpaths
+    add_custom_target(${WHEEL_TARGET}-delocate
+      COMMAND
+        "${Python3_EXECUTABLE}" "-m" "delocate.cmd.delocate_path"
+          "-L" "${WHEEL_NAME}.dylibs"
+          "${WHEEL_PACKAGE_DIR}"
+      COMMENT "Fixing macOS library dependencies with delocate-path"
+    )
+    add_dependencies(${WHEEL_TARGET}-delocate ${WHEEL_TARGET}-copy-files ${WHEEL_TARGET})
+
     set(EXTRA_ARGS COMMAND "${Python3_EXECUTABLE}" "${PY_CHANGE_TAG_FILE}" "${WHEEL_DEPLOY_DIRECTORY}" "${WHEEL_NAME}")
+    set(DELOCATE_DEPENDENCY ${WHEEL_TARGET}-delocate)
   else()
     set(EXTRA_ARGS "")
+    set(DELOCATE_DEPENDENCY ${WHEEL_TARGET}-copy-files)
   endif()
 
   add_custom_target(${WHEEL_TARGET}-setup-py
@@ -181,7 +193,7 @@ function (add_wheel WHEEL_TARGET)
         "-w" "${WHEEL_DEPLOY_DIRECTORY}"
       ${EXTRA_ARGS})
 
-  add_dependencies(${WHEEL_TARGET}-setup-py ${WHEEL_TARGET}-copy-files ${WHEEL_TARGET})
+  add_dependencies(${WHEEL_TARGET}-setup-py ${DELOCATE_DEPENDENCY} ${WHEEL_TARGET})
 
   add_dependencies(wheel ${WHEEL_TARGET}-setup-py)
 

From 222b1ba2784eabb0f297d7f1bb4e6cf0326dcb8c Mon Sep 17 00:00:00 2001
From: Serein Pfeiffer <s.pfeiffer@klebert-engineering.de>
Date: Wed, 29 Oct 2025 15:46:27 +0100
Subject: [PATCH 6/7] test: Add test for wheels with bundled transitive
 dependencies.

---
 tests/transitive-deps-test/CMakeLists.txt    | 94 ++++++++++++++++++++
 tests/transitive-deps-test/LICENSE           | 21 +++++
 tests/transitive-deps-test/README.md         | 40 +++++++++
 tests/transitive-deps-test/lib_a.cpp         |  7 ++
 tests/transitive-deps-test/lib_a.h           | 13 +++
 tests/transitive-deps-test/lib_b.cpp         |  5 ++
 tests/transitive-deps-test/lib_b.h           | 13 +++
 tests/transitive-deps-test/py_transitive.cpp | 16 ++++
 tests/transitive-deps-test/test_wheel.py     | 54 +++++++++++
 9 files changed, 263 insertions(+)
 create mode 100644 tests/transitive-deps-test/CMakeLists.txt
 create mode 100644 tests/transitive-deps-test/LICENSE
 create mode 100644 tests/transitive-deps-test/README.md
 create mode 100644 tests/transitive-deps-test/lib_a.cpp
 create mode 100644 tests/transitive-deps-test/lib_a.h
 create mode 100644 tests/transitive-deps-test/lib_b.cpp
 create mode 100644 tests/transitive-deps-test/lib_b.h
 create mode 100644 tests/transitive-deps-test/py_transitive.cpp
 create mode 100644 tests/transitive-deps-test/test_wheel.py

diff --git a/tests/transitive-deps-test/CMakeLists.txt b/tests/transitive-deps-test/CMakeLists.txt
new file mode 100644
index 0000000..7b2f78c
--- /dev/null
+++ b/tests/transitive-deps-test/CMakeLists.txt
@@ -0,0 +1,94 @@
+cmake_minimum_required(VERSION 3.20)
+project(test-transitive-deps VERSION 1.0.0)
+
+set(CMAKE_CXX_STANDARD 17)
+set(CMAKE_CXX_STANDARD_REQUIRED ON)
+
+# Export all symbols on Windows
+set(CMAKE_WINDOWS_EXPORT_ALL_SYMBOLS ON)
+
+# Enable testing
+enable_testing()
+
+# Include python-wheel.cmake from repository root
+list(APPEND CMAKE_MODULE_PATH "${CMAKE_CURRENT_SOURCE_DIR}/../..")
+include(python-wheel)
+
+# Set wheel output directory
+set(WHEEL_DEPLOY_DIRECTORY "${CMAKE_BINARY_DIR}/wheel")
+
+# Find Python
+find_package(Python3 COMPONENTS Interpreter Development.Module REQUIRED)
+
+# Fetch CPM.cmake
+set(CPM_DOWNLOAD_VERSION 0.40.2)
+if(CPM_SOURCE_CACHE)
+  set(CPM_DOWNLOAD_LOCATION "${CPM_SOURCE_CACHE}/cpm/CPM_${CPM_DOWNLOAD_VERSION}.cmake")
+elseif(DEFINED ENV{CPM_SOURCE_CACHE})
+  set(CPM_DOWNLOAD_LOCATION "$ENV{CPM_SOURCE_CACHE}/cpm/CPM_${CPM_DOWNLOAD_VERSION}.cmake")
+else()
+  set(CPM_DOWNLOAD_LOCATION "${CMAKE_BINARY_DIR}/cmake/CPM_${CPM_DOWNLOAD_VERSION}.cmake")
+endif()
+if(NOT (EXISTS ${CPM_DOWNLOAD_LOCATION}))
+  message(STATUS "Downloading CPM.cmake to ${CPM_DOWNLOAD_LOCATION}")
+  file(DOWNLOAD
+       https://github.com/cpm-cmake/CPM.cmake/releases/download/v${CPM_DOWNLOAD_VERSION}/CPM.cmake
+       ${CPM_DOWNLOAD_LOCATION}
+  )
+endif()
+include(${CPM_DOWNLOAD_LOCATION})
+
+# Fetch pybind11 via CPM
+CPMAddPackage("gh:pybind/pybind11@2.13.6")
+
+# Create lib_b (lowest level dependency)
+add_library(lib_b SHARED
+    lib_b.cpp
+    lib_b.h
+)
+
+target_compile_definitions(lib_b PRIVATE LIB_B_EXPORTS)
+
+target_include_directories(lib_b PUBLIC
+    ${CMAKE_CURRENT_SOURCE_DIR}
+)
+
+# Create lib_a (depends on lib_b)
+add_library(lib_a SHARED
+    lib_a.cpp
+    lib_a.h
+)
+
+target_compile_definitions(lib_a PRIVATE LIB_A_EXPORTS)
+
+target_include_directories(lib_a PUBLIC
+    ${CMAKE_CURRENT_SOURCE_DIR}
+)
+
+target_link_libraries(lib_a PUBLIC lib_b)
+
+# Create Python module using pybind11 (depends on lib_a)
+pybind11_add_module(py_transitive
+    py_transitive.cpp
+)
+
+target_link_libraries(py_transitive PRIVATE lib_a)
+
+# Package as wheel using add_wheel()
+# Note: We include both lib_a and lib_b in TARGET_DEPENDENCIES
+# This tests that delocate properly handles the transitive dependency chain
+add_wheel(py_transitive
+    NAME transitive_test
+    VERSION "1.0.0"
+    AUTHOR "Test Author"
+    EMAIL "test@example.com"
+    DESCRIPTION "Test wheel with transitive library dependencies (lib_a → lib_b)"
+    PYTHON_REQUIRES ">=3.9"
+    TARGET_DEPENDENCIES lib_a lib_b
+)
+
+# Add test to validate wheel functionality
+add_wheel_test(test-transitive-wheel
+    WORKING_DIRECTORY "${CMAKE_CURRENT_SOURCE_DIR}"
+    COMMANDS -f "${CMAKE_CURRENT_SOURCE_DIR}/test_wheel.py"
+)
diff --git a/tests/transitive-deps-test/LICENSE b/tests/transitive-deps-test/LICENSE
new file mode 100644
index 0000000..57a52e2
--- /dev/null
+++ b/tests/transitive-deps-test/LICENSE
@@ -0,0 +1,21 @@
+MIT License
+
+Copyright (c) 2025 Test
+
+Permission is hereby granted, free of charge, to any person obtaining a copy
+of this software and associated documentation files (the "Software"), to deal
+in the Software without restriction, including without limitation the rights
+to use, copy, modify, merge, publish, distribute, sublicense, and/or sell
+copies of the Software, and to permit persons to whom the Software is
+furnished to do so, subject to the following conditions:
+
+The above copyright notice and this permission notice shall be included in all
+copies or substantial portions of the Software.
+
+THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS OR
+IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY,
+FITNESS FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT SHALL THE
+AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM, DAMAGES OR OTHER
+LIABILITY, WHETHER IN AN ACTION OF CONTRACT, TORT OR OTHERWISE, ARISING FROM,
+OUT OF OR IN CONNECTION WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS IN THE
+SOFTWARE.
diff --git a/tests/transitive-deps-test/README.md b/tests/transitive-deps-test/README.md
new file mode 100644
index 0000000..ad24fe8
--- /dev/null
+++ b/tests/transitive-deps-test/README.md
@@ -0,0 +1,40 @@
+# Transitive Dependencies Test
+
+This test validates that `python-cmake-wheel` correctly handles transitive library dependencies on macOS using `delocate`.
+
+## Dependency Chain
+
+```
+py_transitive (Python module)
+    ↓ links to
+lib_a (shared library)
+    ↓ links to
+lib_b (shared library)
+```
+
+## What This Tests
+
+1. **Build**: All three libraries are built and bundled into a wheel
+2. **Delocate**: The `delocate-path` tool should:
+   - Fix rpaths in `py_transitive.so` to use `@loader_path`
+   - Fix rpaths in `lib_a` to use `@loader_path`
+   - Fix rpaths in `lib_b` to use `@loader_path`
+   - Bundle all dependencies into the `.dylibs` directory
+3. **Runtime**: When the wheel is installed and imported:
+   - `py_transitive` can find `lib_a`
+   - `lib_a` can find `lib_b`
+   - Function calls work correctly across all three levels
+
+## Why This Matters
+
+Without proper delocate handling, `lib_a` would still have absolute paths to `lib_b` (e.g., `/usr/local/lib/lib_b.dylib`), causing runtime failures when the wheel is installed in a different environment.
+
+## Running the Test
+
+```bash
+cd tests/transitive-deps-test
+mkdir build && cd build
+cmake ..
+cmake --build .
+ctest
+```
diff --git a/tests/transitive-deps-test/lib_a.cpp b/tests/transitive-deps-test/lib_a.cpp
new file mode 100644
index 0000000..092160f
--- /dev/null
+++ b/tests/transitive-deps-test/lib_a.cpp
@@ -0,0 +1,7 @@
+#include "lib_a.h"
+#include "lib_b.h"
+
+int process_data(int x) {
+    // lib_a uses lib_b internally
+    return compute_value(x) + 5;
+}
diff --git a/tests/transitive-deps-test/lib_a.h b/tests/transitive-deps-test/lib_a.h
new file mode 100644
index 0000000..6851509
--- /dev/null
+++ b/tests/transitive-deps-test/lib_a.h
@@ -0,0 +1,13 @@
+#pragma once
+
+#ifdef _WIN32
+  #ifdef LIB_A_EXPORTS
+    #define LIB_A_API __declspec(dllexport)
+  #else
+    #define LIB_A_API __declspec(dllimport)
+  #endif
+#else
+  #define LIB_A_API __attribute__((visibility("default")))
+#endif
+
+LIB_A_API int process_data(int x);
diff --git a/tests/transitive-deps-test/lib_b.cpp b/tests/transitive-deps-test/lib_b.cpp
new file mode 100644
index 0000000..4e9d289
--- /dev/null
+++ b/tests/transitive-deps-test/lib_b.cpp
@@ -0,0 +1,5 @@
+#include "lib_b.h"
+
+int compute_value(int x) {
+    return x * 2 + 10;
+}
diff --git a/tests/transitive-deps-test/lib_b.h b/tests/transitive-deps-test/lib_b.h
new file mode 100644
index 0000000..27c7645
--- /dev/null
+++ b/tests/transitive-deps-test/lib_b.h
@@ -0,0 +1,13 @@
+#pragma once
+
+#ifdef _WIN32
+  #ifdef LIB_B_EXPORTS
+    #define LIB_B_API __declspec(dllexport)
+  #else
+    #define LIB_B_API __declspec(dllimport)
+  #endif
+#else
+  #define LIB_B_API __attribute__((visibility("default")))
+#endif
+
+LIB_B_API int compute_value(int x);
diff --git a/tests/transitive-deps-test/py_transitive.cpp b/tests/transitive-deps-test/py_transitive.cpp
new file mode 100644
index 0000000..5a2b152
--- /dev/null
+++ b/tests/transitive-deps-test/py_transitive.cpp
@@ -0,0 +1,16 @@
+#include <pybind11/pybind11.h>
+#include "lib_a.h"
+
+namespace py = pybind11;
+
+PYBIND11_MODULE(py_transitive, m) {
+    m.doc() = "Test module with transitive library dependencies";
+
+    m.def("process", &process_data, "Process data using lib_a (which uses lib_b)");
+
+    m.def("test_transitive", []() {
+        // This tests that lib_a can successfully call lib_b
+        int result = process_data(5);
+        return result == 25;  // (5 * 2 + 10) + 5 = 25
+    }, "Test that transitive dependencies work correctly");
+}
diff --git a/tests/transitive-deps-test/test_wheel.py b/tests/transitive-deps-test/test_wheel.py
new file mode 100644
index 0000000..5ff7eb3
--- /dev/null
+++ b/tests/transitive-deps-test/test_wheel.py
@@ -0,0 +1,54 @@
+#!/usr/bin/env python3
+"""Test script for transitive dependency wheel."""
+
+import sys
+
+def test_import():
+    """Test that the module can be imported."""
+    try:
+        import transitive_test
+        print("✓ Module imported successfully")
+        return True
+    except ImportError as e:
+        print(f"✗ Failed to import module: {e}")
+        return False
+
+def test_transitive_deps():
+    """Test that transitive dependencies work correctly."""
+    import transitive_test
+
+    # Test the transitive dependency chain: py_transitive → lib_a → lib_b
+    result = transitive_test.process(5)
+    expected = 25  # (5 * 2 + 10) + 5 = 25
+
+    if result == expected:
+        print(f"✓ Transitive dependency test passed: process(5) = {result}")
+        return True
+    else:
+        print(f"✗ Transitive dependency test failed: expected {expected}, got {result}")
+        return False
+
+def test_built_in_validation():
+    """Test the built-in validation function."""
+    import transitive_test
+
+    if transitive_test.test_transitive():
+        print("✓ Built-in transitive test passed")
+        return True
+    else:
+        print("✗ Built-in transitive test failed")
+        return False
+
+if __name__ == "__main__":
+    all_passed = True
+
+    all_passed &= test_import()
+    all_passed &= test_transitive_deps()
+    all_passed &= test_built_in_validation()
+
+    if all_passed:
+        print("\n✓ All tests passed!")
+        sys.exit(0)
+    else:
+        print("\n✗ Some tests failed")
+        sys.exit(1)

From 62c17617f5a2050435b10e9bc60d1f12a969f19b Mon Sep 17 00:00:00 2001
From: Serein Pfeiffer <s.pfeiffer@klebert-engineering.de>
Date: Wed, 29 Oct 2025 15:53:01 +0100
Subject: [PATCH 7/7] ci: Ensure we install delocate, which is a requirement.

---
 .github/workflows/test.yml | 2 +-
 1 file changed, 1 insertion(+), 1 deletion(-)

diff --git a/.github/workflows/test.yml b/.github/workflows/test.yml
index d2d1979..6712be4 100644
--- a/.github/workflows/test.yml
+++ b/.github/workflows/test.yml
@@ -24,7 +24,7 @@ jobs:
           architecture: x64
 
       - name: Install Python dependencies
-        run: python -m pip install setuptools wheel
+        run: python -m pip install setuptools wheel delocate
 
       - name: Configure
         working-directory: tests/macos-wheel-test