diff --git a/.github/workflows/nightly-validation.yml b/.github/workflows/nightly-validation.yml
index ea372ccd8..73c79704b 100644
--- a/.github/workflows/nightly-validation.yml
+++ b/.github/workflows/nightly-validation.yml
@@ -713,7 +713,7 @@ jobs:
           
           # Create a test path with same length as typical setup-z3 usage
           # This simulates what setup-z3 does: changing to absolute path
-          TEST_PATH="/Users/runner/hostedtoolcache/z3/latest/x64/z3-4.15.5-x64-osx-15.7.3/bin/libz3.dylib"
+          TEST_PATH="/Users/runner/hostedtoolcache/z3/latest/x64/z3-test-dir/bin/libz3.dylib"
           
           # Try to change the install name - this will fail if headerpad is insufficient
           install_name_tool -id "$TEST_PATH" -change "$ORIGINAL_NAME" "$TEST_PATH" libz3.dylib
@@ -765,7 +765,7 @@ jobs:
           
           # Create a test path with same length as typical setup-z3 usage
           # This simulates what setup-z3 does: changing to absolute path
-          TEST_PATH="/Users/runner/hostedtoolcache/z3/latest/arm64/z3-4.15.5-arm64-osx-15.7.3/bin/libz3.dylib"
+          TEST_PATH="/Users/runner/hostedtoolcache/z3/latest/arm64/z3-test-dir/bin/libz3.dylib"
           
           # Try to change the install name - this will fail if headerpad is insufficient
           install_name_tool -id "$TEST_PATH" -change "$ORIGINAL_NAME" "$TEST_PATH" libz3.dylib
diff --git a/scripts/mk_util.py b/scripts/mk_util.py
index 48cdb953a..163056099 100644
--- a/scripts/mk_util.py
+++ b/scripts/mk_util.py
@@ -2749,7 +2749,7 @@ def mk_config():
             CXXFLAGS = '%s -arch arm64' % CXXFLAGS
             LDFLAGS = '%s -arch arm64' % LDFLAGS
             SLIBEXTRAFLAGS = '%s -arch arm64' % SLIBEXTRAFLAGS
-        if IS_OSX and is_ml_enabled():
+        if IS_OSX:
             SLIBFLAGS += ' -Wl,-headerpad_max_install_names'
 
         config.write('PREFIX=%s\n' % PREFIX)
diff --git a/src/CMakeLists.txt b/src/CMakeLists.txt
index 2af9a7170..4b78963f7 100644
--- a/src/CMakeLists.txt
+++ b/src/CMakeLists.txt
@@ -151,6 +151,11 @@ endif()
 # so that if those are also shared libraries they are referenced by `libz3.so`.
 target_link_libraries(libz3 PRIVATE ${Z3_DEPENDENT_LIBS})
 
+# On macOS, add headerpad for install_name_tool compatibility
+if(CMAKE_SYSTEM_NAME STREQUAL "Darwin" AND BUILD_LIBZ3_SHARED)
+  target_link_options(libz3 PRIVATE "-Wl,-headerpad_max_install_names")
+endif()
+
 ################################################################################
 # Create include directory with headers for easier developer integration
 ################################################################################
diff --git a/src/api/java/CMakeLists.txt b/src/api/java/CMakeLists.txt
index 862e25962..df0baa334 100644
--- a/src/api/java/CMakeLists.txt
+++ b/src/api/java/CMakeLists.txt
@@ -50,6 +50,11 @@ target_include_directories(z3java PRIVATE
 )
 # FIXME: Should this library have SONAME and VERSION set?
 
+# On macOS, add headerpad for install_name_tool compatibility
+if(CMAKE_SYSTEM_NAME STREQUAL "Darwin")
+  target_link_options(z3java PRIVATE "-Wl,-headerpad_max_install_names")
+endif()
+
 # This prevents CMake from automatically defining ``z3java_EXPORTS``
 set_property(TARGET z3java PROPERTY DEFINE_SYMBOL "")
 
diff --git a/src/api/julia/CMakeLists.txt b/src/api/julia/CMakeLists.txt
index 952b33fb5..7b246d6fa 100644
--- a/src/api/julia/CMakeLists.txt
+++ b/src/api/julia/CMakeLists.txt
@@ -35,6 +35,11 @@ target_include_directories(z3jl PRIVATE
     "${PROJECT_SOURCE_DIR}/src/api/c++"
 )
 
+# On macOS, add headerpad for install_name_tool compatibility
+if(CMAKE_SYSTEM_NAME STREQUAL "Darwin")
+  target_link_options(z3jl PRIVATE "-Wl,-headerpad_max_install_names")
+endif()
+
 option(Z3_INSTALL_JULIA_BINDINGS "Install Julia bindings when invoking install target" ON)
 if(Z3_INSTALL_JULIA_BINDINGS)
     install(TARGETS z3jl
diff --git a/src/api/ml/CMakeLists.txt b/src/api/ml/CMakeLists.txt
index c7de53faa..1007939cb 100644
--- a/src/api/ml/CMakeLists.txt
+++ b/src/api/ml/CMakeLists.txt
@@ -159,6 +159,8 @@ endif()
 
 if( APPLE )
   # set(ocaml_rpath "@executable_path/../libz3${so_ext}")
+  # Add headerpad for install_name_tool compatibility on macOS
+  list(APPEND c_lib_deps "-Wl,-headerpad_max_install_names")
 elseif( UNIX )
   set(ocaml_rpath "\\$ORIGIN/../libz3${so_ext}")
   list(APPEND c_lib_deps "-dllpath" ${ocaml_rpath})