diff --git a/.github/workflows/nightly-validation.yml b/.github/workflows/nightly-validation.yml
index 3263207c2..73c79704b 100644
--- a/.github/workflows/nightly-validation.yml
+++ b/.github/workflows/nightly-validation.yml
@@ -672,3 +672,111 @@ jobs:
           $wheel = Get-ChildItem wheels/*.whl | Select-Object -First 1
           pip install $wheel.FullName
           python -c "import z3; x = z3.Int('x'); s = z3.Solver(); s.add(x > 0); print('Result:', s.check()); print('Model:', s.model())"
+
+  # ============================================================================
+  # MACOS DYLIB HEADERPAD VALIDATION
+  # ============================================================================
+
+  validate-macos-headerpad-x64:
+    name: "Validate macOS x64 dylib headerpad"
+    runs-on: macos-13
+    if: ${{ github.event.workflow_run.conclusion == 'success' || github.event_name == 'workflow_dispatch' }}
+    timeout-minutes: 30
+    steps:
+      - name: Checkout code
+        uses: actions/checkout@v6.0.2
+      
+      - name: Download macOS x64 build from release
+        env:
+          GH_TOKEN: ${{ github.token }}
+        run: |
+          TAG="${{ github.event.inputs.release_tag }}"
+          if [ -z "$TAG" ]; then
+            TAG="Nightly"
+          fi
+          gh release download $TAG --pattern "*x64-osx*.zip" --dir downloads
+      
+      - name: Extract build
+        run: |
+          cd downloads
+          unzip *x64-osx*.zip
+          Z3_DIR=$(find . -maxdepth 1 -type d -name "z3-*" | head -n 1)
+          echo "Z3_DIR=$Z3_DIR" >> $GITHUB_ENV
+      
+      - name: Test install_name_tool with headerpad
+        run: |
+          cd downloads/$Z3_DIR/bin
+          
+          # Get the original install name
+          ORIGINAL_NAME=$(otool -D libz3.dylib | tail -n 1)
+          echo "Original install name: $ORIGINAL_NAME"
+          
+          # Create a test path with same length as typical setup-z3 usage
+          # This simulates what setup-z3 does: changing to absolute path
+          TEST_PATH="/Users/runner/hostedtoolcache/z3/latest/x64/z3-test-dir/bin/libz3.dylib"
+          
+          # Try to change the install name - this will fail if headerpad is insufficient
+          install_name_tool -id "$TEST_PATH" -change "$ORIGINAL_NAME" "$TEST_PATH" libz3.dylib
+          
+          # Verify the change was successful
+          NEW_NAME=$(otool -D libz3.dylib | tail -n 1)
+          echo "New install name: $NEW_NAME"
+          
+          if [ "$NEW_NAME" = "$TEST_PATH" ]; then
+            echo "✓ install_name_tool succeeded - headerpad is sufficient"
+          else
+            echo "✗ install_name_tool failed to update install name"
+            exit 1
+          fi
+
+  validate-macos-headerpad-arm64:
+    name: "Validate macOS ARM64 dylib headerpad"
+    runs-on: macos-latest
+    if: ${{ github.event.workflow_run.conclusion == 'success' || github.event_name == 'workflow_dispatch' }}
+    timeout-minutes: 30
+    steps:
+      - name: Checkout code
+        uses: actions/checkout@v6.0.2
+      
+      - name: Download macOS ARM64 build from release
+        env:
+          GH_TOKEN: ${{ github.token }}
+        run: |
+          TAG="${{ github.event.inputs.release_tag }}"
+          if [ -z "$TAG" ]; then
+            TAG="Nightly"
+          fi
+          gh release download $TAG --pattern "*arm64-osx*.zip" --dir downloads
+      
+      - name: Extract build
+        run: |
+          cd downloads
+          unzip *arm64-osx*.zip
+          Z3_DIR=$(find . -maxdepth 1 -type d -name "z3-*" | head -n 1)
+          echo "Z3_DIR=$Z3_DIR" >> $GITHUB_ENV
+      
+      - name: Test install_name_tool with headerpad
+        run: |
+          cd downloads/$Z3_DIR/bin
+          
+          # Get the original install name
+          ORIGINAL_NAME=$(otool -D libz3.dylib | tail -n 1)
+          echo "Original install name: $ORIGINAL_NAME"
+          
+          # Create a test path with same length as typical setup-z3 usage
+          # This simulates what setup-z3 does: changing to absolute path
+          TEST_PATH="/Users/runner/hostedtoolcache/z3/latest/arm64/z3-test-dir/bin/libz3.dylib"
+          
+          # Try to change the install name - this will fail if headerpad is insufficient
+          install_name_tool -id "$TEST_PATH" -change "$ORIGINAL_NAME" "$TEST_PATH" libz3.dylib
+          
+          # Verify the change was successful
+          NEW_NAME=$(otool -D libz3.dylib | tail -n 1)
+          echo "New install name: $NEW_NAME"
+          
+          if [ "$NEW_NAME" = "$TEST_PATH" ]; then
+            echo "✓ install_name_tool succeeded - headerpad is sufficient"
+          else
+            echo "✗ install_name_tool failed to update install name"
+            exit 1
+          fi
diff --git a/.github/workflows/nightly.yml b/.github/workflows/nightly.yml
index 99fb7065d..d15b1e952 100644
--- a/.github/workflows/nightly.yml
+++ b/.github/workflows/nightly.yml
@@ -70,6 +70,106 @@ jobs:
           path: dist/*.zip
           retention-days: 2
 
+  # ============================================================================
+  # VALIDATION STAGE
+  # ============================================================================
+
+  validate-macos-headerpad-x64:
+    name: "Validate macOS x64 dylib headerpad"
+    needs: [mac-build-x64]
+    runs-on: macos-latest
+    timeout-minutes: 15
+    steps:
+      - name: Checkout code
+        uses: actions/checkout@v6.0.2
+      
+      - name: Download macOS x64 Build
+        uses: actions/download-artifact@v7.0.0
+        with:
+          name: macOsBuild
+          path: artifacts
+      
+      - name: Extract build
+        run: |
+          cd artifacts
+          unzip z3-*-x64-osx*.zip
+          Z3_DIR=$(find . -maxdepth 1 -type d -name "z3-*" | head -n 1)
+          echo "Z3_DIR=$Z3_DIR" >> $GITHUB_ENV
+      
+      - name: Test install_name_tool with headerpad
+        run: |
+          cd artifacts/$Z3_DIR/bin
+          
+          # Get the original install name
+          ORIGINAL_NAME=$(otool -D libz3.dylib | tail -n 1)
+          echo "Original install name: $ORIGINAL_NAME"
+          
+          # Create a test path with same length as typical setup-z3 usage
+          # This simulates what setup-z3 does: changing to absolute path
+          TEST_PATH="/Users/runner/hostedtoolcache/z3/latest/x64/z3-test-dir/bin/libz3.dylib"
+          
+          # Try to change the install name - this will fail if headerpad is insufficient
+          install_name_tool -id "$TEST_PATH" -change "$ORIGINAL_NAME" "$TEST_PATH" libz3.dylib
+          
+          # Verify the change was successful
+          NEW_NAME=$(otool -D libz3.dylib | tail -n 1)
+          echo "New install name: $NEW_NAME"
+          
+          if [ "$NEW_NAME" = "$TEST_PATH" ]; then
+            echo "✓ install_name_tool succeeded - headerpad is sufficient"
+          else
+            echo "✗ install_name_tool failed to update install name"
+            exit 1
+          fi
+
+  validate-macos-headerpad-arm64:
+    name: "Validate macOS ARM64 dylib headerpad"
+    needs: [mac-build-arm64]
+    runs-on: macos-latest
+    timeout-minutes: 15
+    steps:
+      - name: Checkout code
+        uses: actions/checkout@v6.0.2
+      
+      - name: Download macOS ARM64 Build
+        uses: actions/download-artifact@v7.0.0
+        with:
+          name: MacArm64
+          path: artifacts
+      
+      - name: Extract build
+        run: |
+          cd artifacts
+          unzip z3-*-arm64-osx*.zip
+          Z3_DIR=$(find . -maxdepth 1 -type d -name "z3-*" | head -n 1)
+          echo "Z3_DIR=$Z3_DIR" >> $GITHUB_ENV
+      
+      - name: Test install_name_tool with headerpad
+        run: |
+          cd artifacts/$Z3_DIR/bin
+          
+          # Get the original install name
+          ORIGINAL_NAME=$(otool -D libz3.dylib | tail -n 1)
+          echo "Original install name: $ORIGINAL_NAME"
+          
+          # Create a test path with same length as typical setup-z3 usage
+          # This simulates what setup-z3 does: changing to absolute path
+          TEST_PATH="/Users/runner/hostedtoolcache/z3/latest/arm64/z3-test-dir/bin/libz3.dylib"
+          
+          # Try to change the install name - this will fail if headerpad is insufficient
+          install_name_tool -id "$TEST_PATH" -change "$ORIGINAL_NAME" "$TEST_PATH" libz3.dylib
+          
+          # Verify the change was successful
+          NEW_NAME=$(otool -D libz3.dylib | tail -n 1)
+          echo "New install name: $NEW_NAME"
+          
+          if [ "$NEW_NAME" = "$TEST_PATH" ]; then
+            echo "✓ install_name_tool succeeded - headerpad is sufficient"
+          else
+            echo "✗ install_name_tool failed to update install name"
+            exit 1
+          fi
+
   ubuntu-build:
     name: "Ubuntu build"
     runs-on: ubuntu-latest
@@ -562,7 +662,9 @@ jobs:
       ubuntu-doc,
       python-package,
       nuget-package-x64,
-      nuget-package-x86
+      nuget-package-x86,
+      validate-macos-headerpad-x64,
+      validate-macos-headerpad-arm64
     ]
     runs-on: ubuntu-latest
     steps:
diff --git a/.github/workflows/release.yml b/.github/workflows/release.yml
index fe727818e..bf6150b1b 100644
--- a/.github/workflows/release.yml
+++ b/.github/workflows/release.yml
@@ -89,6 +89,106 @@ jobs:
           path: dist/*.zip
           retention-days: 7
 
+  # ============================================================================
+  # VALIDATION STAGE
+  # ============================================================================
+
+  validate-macos-headerpad-x64:
+    name: "Validate macOS x64 dylib headerpad"
+    needs: [mac-build-x64]
+    runs-on: macos-15
+    timeout-minutes: 15
+    steps:
+      - name: Checkout code
+        uses: actions/checkout@v6.0.2
+      
+      - name: Download macOS x64 Build
+        uses: actions/download-artifact@v7.0.0
+        with:
+          name: macOsBuild
+          path: artifacts
+      
+      - name: Extract build
+        run: |
+          cd artifacts
+          unzip z3-*-x64-osx*.zip
+          Z3_DIR=$(find . -maxdepth 1 -type d -name "z3-*" | head -n 1)
+          echo "Z3_DIR=$Z3_DIR" >> $GITHUB_ENV
+      
+      - name: Test install_name_tool with headerpad
+        run: |
+          cd artifacts/$Z3_DIR/bin
+          
+          # Get the original install name
+          ORIGINAL_NAME=$(otool -D libz3.dylib | tail -n 1)
+          echo "Original install name: $ORIGINAL_NAME"
+          
+          # Create a test path with same length as typical setup-z3 usage
+          # This simulates what setup-z3 does: changing to absolute path
+          TEST_PATH="/Users/runner/hostedtoolcache/z3/latest/x64/z3-test-dir/bin/libz3.dylib"
+          
+          # Try to change the install name - this will fail if headerpad is insufficient
+          install_name_tool -id "$TEST_PATH" -change "$ORIGINAL_NAME" "$TEST_PATH" libz3.dylib
+          
+          # Verify the change was successful
+          NEW_NAME=$(otool -D libz3.dylib | tail -n 1)
+          echo "New install name: $NEW_NAME"
+          
+          if [ "$NEW_NAME" = "$TEST_PATH" ]; then
+            echo "✓ install_name_tool succeeded - headerpad is sufficient"
+          else
+            echo "✗ install_name_tool failed to update install name"
+            exit 1
+          fi
+
+  validate-macos-headerpad-arm64:
+    name: "Validate macOS ARM64 dylib headerpad"
+    needs: [mac-build-arm64]
+    runs-on: macos-15
+    timeout-minutes: 15
+    steps:
+      - name: Checkout code
+        uses: actions/checkout@v6.0.2
+      
+      - name: Download macOS ARM64 Build
+        uses: actions/download-artifact@v7.0.0
+        with:
+          name: MacArm64
+          path: artifacts
+      
+      - name: Extract build
+        run: |
+          cd artifacts
+          unzip z3-*-arm64-osx*.zip
+          Z3_DIR=$(find . -maxdepth 1 -type d -name "z3-*" | head -n 1)
+          echo "Z3_DIR=$Z3_DIR" >> $GITHUB_ENV
+      
+      - name: Test install_name_tool with headerpad
+        run: |
+          cd artifacts/$Z3_DIR/bin
+          
+          # Get the original install name
+          ORIGINAL_NAME=$(otool -D libz3.dylib | tail -n 1)
+          echo "Original install name: $ORIGINAL_NAME"
+          
+          # Create a test path with same length as typical setup-z3 usage
+          # This simulates what setup-z3 does: changing to absolute path
+          TEST_PATH="/Users/runner/hostedtoolcache/z3/latest/arm64/z3-test-dir/bin/libz3.dylib"
+          
+          # Try to change the install name - this will fail if headerpad is insufficient
+          install_name_tool -id "$TEST_PATH" -change "$ORIGINAL_NAME" "$TEST_PATH" libz3.dylib
+          
+          # Verify the change was successful
+          NEW_NAME=$(otool -D libz3.dylib | tail -n 1)
+          echo "New install name: $NEW_NAME"
+          
+          if [ "$NEW_NAME" = "$TEST_PATH" ]; then
+            echo "✓ install_name_tool succeeded - headerpad is sufficient"
+          else
+            echo "✗ install_name_tool failed to update install name"
+            exit 1
+          fi
+
   ubuntu-build:
     name: "Ubuntu build"
     runs-on: ubuntu-latest
@@ -582,7 +682,9 @@ jobs:
       ubuntu-doc,
       python-package,
       nuget-package-x64,
-      nuget-package-x86
+      nuget-package-x86,
+      validate-macos-headerpad-x64,
+      validate-macos-headerpad-arm64
     ]
     runs-on: ubuntu-latest
     steps:
diff --git a/scripts/mk_util.py b/scripts/mk_util.py
index 864b6e23e..163056099 100644
--- a/scripts/mk_util.py
+++ b/scripts/mk_util.py
@@ -2749,8 +2749,6 @@ def mk_config():
             CXXFLAGS = '%s -arch arm64' % CXXFLAGS
             LDFLAGS = '%s -arch arm64' % LDFLAGS
             SLIBEXTRAFLAGS = '%s -arch arm64' % SLIBEXTRAFLAGS
-        # Add header padding for macOS to allow install_name_tool to modify the dylib
-        # This fixes issues where install_name_tool fails with "larger updated load commands do not fit"
         if IS_OSX:
             SLIBFLAGS += ' -Wl,-headerpad_max_install_names'
 
diff --git a/src/CMakeLists.txt b/src/CMakeLists.txt
index 22b5ce513..65420484e 100644
--- a/src/CMakeLists.txt
+++ b/src/CMakeLists.txt
@@ -155,6 +155,11 @@ 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 Z3_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 5245a62da..9bde1bb20 100644
--- a/src/api/java/CMakeLists.txt
+++ b/src/api/java/CMakeLists.txt
@@ -54,6 +54,11 @@ if (CMAKE_SYSTEM_NAME STREQUAL "Darwin")
 endif()
 # 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 9b34564be..233b0fd59 100644
--- a/src/api/julia/CMakeLists.txt
+++ b/src/api/julia/CMakeLists.txt
@@ -39,6 +39,11 @@ if (CMAKE_SYSTEM_NAME STREQUAL "Darwin")
   target_link_options(z3jl PRIVATE "-Wl,-headerpad_max_install_names")
 endif()
 
+# 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 0e5e92be8..2727c55ed 100644
--- a/src/api/ml/CMakeLists.txt
+++ b/src/api/ml/CMakeLists.txt
@@ -159,8 +159,7 @@ endif()
 
 if( APPLE )
   # set(ocaml_rpath "@executable_path/../libz3${so_ext}")
-  # Add header padding to allow install_name_tool to modify the dylib
-  # This fixes issues where install_name_tool fails with "larger updated load commands do not fit"
+  # Add headerpad for install_name_tool compatibility on macOS
   list(APPEND c_lib_deps "-ldopt" "-Wl,-headerpad_max_install_names")
 elseif( UNIX )
   set(ocaml_rpath "\\$ORIGIN/../libz3${so_ext}")