diff --git a/relenv/runtime.py b/relenv/runtime.py
index e2beca11..0740be8f 100644
--- a/relenv/runtime.py
+++ b/relenv/runtime.py
@@ -336,6 +336,14 @@ def wrapper(
                 if relocate().is_elf(file):
                     debug(f"Relenv - Found elf {file}")
                     relocate().handle_elf(plat / file, rootdir / "lib", True, rootdir)
+                elif relocate().is_macho(file):
+                    otool_bin = shutil.which("otool")
+                    if otool_bin:
+                        relocate().handle_macho(str(plat / file), str(rootdir), True)
+                    else:
+                        debug(
+                            "The otool command is not available, please run `xcode-select --install`"
+                        )
 
     return wrapper
 
diff --git a/tests/test_verify_build.py b/tests/test_verify_build.py
index 47bbed12..93d96db6 100644
--- a/tests/test_verify_build.py
+++ b/tests/test_verify_build.py
@@ -835,6 +835,44 @@ def find_library(path, search):
     assert valid, p.stdout.decode()
 
 
+@pytest.mark.skip_unless_on_darwin
+@pytest.mark.parametrize("cryptography_version", ["42.0.5", "40.0.1"])
+def test_cryptography_rpath_darwin(pipexec, build, minor_version, cryptography_version):
+    # def find_library(path, search):
+    #    for root, dirs, files in os.walk(path):
+    #        for fname in files:
+    #            if fname.startswith(search) and fname.endswith(".so"):
+    #                return fname
+
+    env = os.environ.copy()
+    env["RELENV_BUILDENV"] = "yes"
+    env["OPENSSL_DIR"] = f"{build}"
+
+    if minor_version == "3.13":
+        env["PYO3_USE_ABI3_FORWARD_COMPATIBILITY"] = "1"
+
+    p = subprocess.run(
+        [
+            str(pipexec),
+            "install",
+            f"cryptography=={cryptography_version}",
+            "--no-cache-dir",
+            "--no-binary=cryptography",
+        ],
+        env=env,
+    )
+    assert p.returncode != 1, "Failed to pip install cryptography"
+    p = subprocess.run(
+        [
+            "otool",
+            "-L",
+            f"{build}/lib/python{minor_version}/site-packages/cryptography/hazmat/bindings/_rust.abi3.so",
+        ],
+        capture_output=True,
+    )
+    assert "/usr/local" not in p.stdout.decode(), p.stdout.decode()
+
+
 @pytest.mark.skip_unless_on_linux
 def test_install_pycurl(pipexec, build):
     _install_ppbt(pipexec)
@@ -1423,9 +1461,12 @@ def test_install_with_target_namespaces(pipexec, build, minor_version, build_ver
 
 
 @pytest.mark.skip_unless_on_linux
-def test_debugpy(pipexec, build, minor_version):
+def test_debugpy(pipexec, build, arch, minor_version):
     if "3.13" in minor_version:
         pytest.xfail("Failes on python 3.13.0")
+    if arch == "arm64":
+        pytest.xfail("Failes on arm64")
+
     p = subprocess.run(
         [
             str(pipexec),