diff --git a/hatch_cpp/tests/test_platform_specific.py b/hatch_cpp/tests/test_platform_specific.py
index 34778bd..455d7e1 100644
--- a/hatch_cpp/tests/test_platform_specific.py
+++ b/hatch_cpp/tests/test_platform_specific.py
@@ -345,7 +345,7 @@ def test_link_flags_include_platform_specific_link_args(self):
 
         flags = platform.get_link_flags(library)
         assert "-shared" in flags
-        assert "-Wl,-rpath,$ORIGIN/lib" in flags
+        assert r"-Wl,-rpath,\$ORIGIN/lib" in flags
 
     def test_darwin_platform_uses_darwin_specific_fields(self):
         """Test that darwin platform uses darwin-specific fields."""
diff --git a/hatch_cpp/tests/test_structs.py b/hatch_cpp/tests/test_structs.py
index afa0c25..fa22880 100644
--- a/hatch_cpp/tests/test_structs.py
+++ b/hatch_cpp/tests/test_structs.py
@@ -8,6 +8,7 @@
 from toml import loads
 
 from hatch_cpp import HatchCppBuildConfig, HatchCppBuildPlan, HatchCppLibrary, HatchCppPlatform
+from hatch_cpp.toolchains.common import _normalize_rpath
 
 
 class TestStructs:
@@ -168,3 +169,72 @@ def test_hatch_cpp_vcpkg_env_force_on(self):
         with patch.dict(environ, {"HATCH_CPP_VCPKG": "1"}):
             hatch_build_plan.generate()
             assert "vcpkg" in hatch_build_plan._active_toolchains
+
+
+class TestNormalizeRpath:
+    def test_origin_to_loader_path_on_darwin(self):
+        """$ORIGIN should be translated to @loader_path on macOS."""
+        assert _normalize_rpath("-Wl,-rpath,$ORIGIN", "darwin") == "-Wl,-rpath,@loader_path"
+
+    def test_loader_path_to_origin_on_linux(self):
+        """@loader_path should be translated to (escaped) $ORIGIN on Linux."""
+        result = _normalize_rpath("-Wl,-rpath,@loader_path", "linux")
+        assert result == r"-Wl,-rpath,\$ORIGIN"
+
+    def test_origin_escaped_on_linux(self):
+        """$ORIGIN should be escaped as \\$ORIGIN on Linux for shell safety."""
+        result = _normalize_rpath("-Wl,-rpath,$ORIGIN", "linux")
+        assert result == r"-Wl,-rpath,\$ORIGIN"
+
+    def test_already_escaped_origin_on_darwin(self):
+        """Already-escaped \\$ORIGIN should still translate to @loader_path on macOS."""
+        assert _normalize_rpath(r"-Wl,-rpath,\$ORIGIN", "darwin") == "-Wl,-rpath,@loader_path"
+
+    def test_no_rpath_unchanged(self):
+        """Args without rpath values should pass through unchanged."""
+        assert _normalize_rpath("-lfoo", "linux") == "-lfoo"
+        assert _normalize_rpath("-lfoo", "darwin") == "-lfoo"
+
+    def test_win32_no_transform(self):
+        """Windows should not transform rpath values."""
+        assert _normalize_rpath("$ORIGIN", "win32") == "$ORIGIN"
+        assert _normalize_rpath("@loader_path", "win32") == "@loader_path"
+
+    def test_link_flags_rpath_translation_darwin(self):
+        """Full integration: extra_link_args with $ORIGIN produce @loader_path on macOS."""
+        library = HatchCppLibrary(
+            name="test",
+            sources=["test.cpp"],
+            binding="generic",
+            extra_link_args=["-Wl,-rpath,$ORIGIN"],
+        )
+        platform = HatchCppPlatform(
+            cc="clang",
+            cxx="clang++",
+            ld="ld",
+            platform="darwin",
+            toolchain="clang",
+            disable_ccache=True,
+        )
+        flags = platform.get_link_flags(library)
+        assert "@loader_path" in flags
+        assert "$ORIGIN" not in flags
+
+    def test_link_flags_rpath_escaped_linux(self):
+        """Full integration: extra_link_args with $ORIGIN are shell-escaped on Linux."""
+        library = HatchCppLibrary(
+            name="test",
+            sources=["test.cpp"],
+            binding="generic",
+            extra_link_args=["-Wl,-rpath,$ORIGIN"],
+        )
+        platform = HatchCppPlatform(
+            cc="gcc",
+            cxx="g++",
+            ld="ld",
+            platform="linux",
+            toolchain="gcc",
+            disable_ccache=True,
+        )
+        flags = platform.get_link_flags(library)
+        assert r"\$ORIGIN" in flags
diff --git a/hatch_cpp/toolchains/common.py b/hatch_cpp/toolchains/common.py
index 120ed4a..300f4e8 100644
--- a/hatch_cpp/toolchains/common.py
+++ b/hatch_cpp/toolchains/common.py
@@ -20,6 +20,7 @@
     "PlatformDefaults",
     "HatchCppLibrary",
     "HatchCppPlatform",
+    "_normalize_rpath",
 )
 
 
@@ -207,6 +208,28 @@ def get_effective_undef_macros(self, platform: Platform) -> List[str]:
         return macros
 
 
+def _normalize_rpath(value: str, platform: Platform) -> str:
+    r"""Translate and escape rpath values for the target platform.
+
+    - On macOS (darwin): ``$ORIGIN`` is replaced with ``@loader_path``.
+    - On Linux: ``@loader_path`` is replaced with ``$ORIGIN``, and
+      ``$ORIGIN`` is escaped as ``\$ORIGIN`` so that ``os.system()``
+      (which invokes a shell) passes it through literally.
+    - On Windows: no transformation is applied (Windows does not use
+      rpath).
+    """
+    if platform == "darwin":
+        # Handle already-escaped \$ORIGIN first, then plain $ORIGIN
+        value = value.replace(r"\$ORIGIN", "@loader_path")
+        value = value.replace("$ORIGIN", "@loader_path")
+    elif platform == "linux":
+        # Translate macOS rpath to Linux equivalent
+        value = value.replace("@loader_path", "$ORIGIN")
+        # Escape $ORIGIN for shell safety (os.system runs through bash)
+        value = value.replace("$ORIGIN", r"\$ORIGIN")
+    return value
+
+
 class HatchCppPlatform(BaseModel):
     cc: str
     cxx: str
@@ -336,6 +359,9 @@ def get_link_flags(self, library: HatchCppLibrary, build_type: BuildType = "rele
         effective_libraries = library.get_effective_libraries(self.platform)
         effective_library_dirs = library.get_effective_library_dirs(self.platform)
 
+        # Normalize rpath values ($ORIGIN <-> @loader_path) and escape for shell
+        effective_link_args = [_normalize_rpath(arg, self.platform) for arg in effective_link_args]
+
         if self.toolchain == "gcc":
             flags += " -shared"
             flags += " " + " ".join(effective_link_args)