diff --git a/src/exstruct/core/libreoffice.py b/src/exstruct/core/libreoffice.py
index 82c3176..f697396 100644
--- a/src/exstruct/core/libreoffice.py
+++ b/src/exstruct/core/libreoffice.py
@@ -800,6 +800,9 @@ def _resolve_python_path(soffice_path: Path) -> Path | None:
     return None
 
 
+_MACOS_BUNDLE_MACOS_DIR = Path("/Applications/LibreOffice.app/Contents/MacOS")
+
+
 def _soffice_program_dirs(soffice_path: Path) -> tuple[Path, ...]:
     """Return candidate LibreOffice program directories for the given ``soffice`` path."""
 
@@ -810,6 +813,18 @@ def _soffice_program_dirs(soffice_path: Path) -> tuple[Path, ...]:
         return tuple(program_dirs)
     if resolved_parent not in program_dirs:
         program_dirs.append(resolved_parent)
+    # macOS keeps soffice in Contents/MacOS but the bundled Python in the sibling
+    # Contents/Resources, so the executable's own dir never finds it. Homebrew
+    # compounds this by putting a bash wrapper on PATH that execs into the bundle,
+    # leaving the resolved path outside the bundle entirely -- hence the fixed
+    # bundle location as a last resort.
+    if sys.platform == "darwin":
+        for parent in (*program_dirs, _MACOS_BUNDLE_MACOS_DIR):
+            if parent.name != "MacOS":
+                continue
+            resources_dir = parent.parent / "Resources"
+            if resources_dir.is_dir() and resources_dir not in program_dirs:
+                program_dirs.append(resources_dir)
     return tuple(program_dirs)
 
 
diff --git a/tests/core/test_libreoffice_macos_paths.py b/tests/core/test_libreoffice_macos_paths.py
new file mode 100644
index 0000000..df6fba1
--- /dev/null
+++ b/tests/core/test_libreoffice_macos_paths.py
@@ -0,0 +1,63 @@
+"""macOS keeps LibreOffice's bundled Python outside the soffice executable's dir."""
+
+from __future__ import annotations
+
+from pathlib import Path
+
+import pytest
+
+from exstruct.core import libreoffice
+
+
+def _fake_bundle(root: Path) -> tuple[Path, Path]:
+    """Build a minimal LibreOffice.app layout and return (soffice, python)."""
+    macos_dir = root / "LibreOffice.app" / "Contents" / "MacOS"
+    resources_dir = root / "LibreOffice.app" / "Contents" / "Resources"
+    macos_dir.mkdir(parents=True)
+    resources_dir.mkdir(parents=True)
+    soffice = macos_dir / "soffice"
+    python = resources_dir / "python"
+    soffice.write_text("#!/bin/sh\n")
+    python.write_text("#!/bin/sh\n")
+    return soffice, python
+
+
+def test_program_dirs_include_the_sibling_resources_dir(
+    tmp_path: Path, monkeypatch: pytest.MonkeyPatch
+) -> None:
+    monkeypatch.setattr(libreoffice.sys, "platform", "darwin")
+    soffice, python = _fake_bundle(tmp_path)
+
+    dirs = libreoffice._soffice_program_dirs(soffice)
+
+    assert python.parent in dirs
+    candidates = [c for d in dirs for c in libreoffice._bundled_python_candidates(d)]
+    assert python in candidates
+
+
+def test_program_dirs_fall_back_to_the_bundle_for_a_homebrew_wrapper(
+    tmp_path: Path, monkeypatch: pytest.MonkeyPatch
+) -> None:
+    """Homebrew puts a bash wrapper on PATH, so the resolved path leaves the bundle."""
+    monkeypatch.setattr(libreoffice.sys, "platform", "darwin")
+    _, python = _fake_bundle(tmp_path)
+    monkeypatch.setattr(
+        libreoffice, "_MACOS_BUNDLE_MACOS_DIR", python.parent.parent / "MacOS"
+    )
+    wrapper_dir = tmp_path / "command-wrappers"
+    wrapper_dir.mkdir()
+    wrapper = wrapper_dir / "soffice"
+    wrapper.write_text("#!/bin/bash\n")
+
+    dirs = libreoffice._soffice_program_dirs(wrapper)
+
+    assert python.parent in dirs
+
+
+def test_program_dirs_stay_unchanged_off_macos(
+    tmp_path: Path, monkeypatch: pytest.MonkeyPatch
+) -> None:
+    monkeypatch.setattr(libreoffice.sys, "platform", "linux")
+    soffice, python = _fake_bundle(tmp_path)
+
+    assert python.parent not in libreoffice._soffice_program_dirs(soffice)