diff --git a/relocatable.py b/relocatable.py
index dd8b17d..473194e 100644
--- a/relocatable.py
+++ b/relocatable.py
@@ -65,15 +65,37 @@ def patch_path(output_dir: pathlib.Path, patch: str) -> None:
     for root, _, filenames in output_dir.walk():
         for filename in filenames:
             path = root / filename
-            if path.is_symlink():
+            if path.is_symlink() or path.suffix in (".pyc", ".pyo"):
                 continue
             contents = path.read_bytes()
             if placeholder not in contents:
                 continue
-            replacement = target
             if b"\0" in contents:
-                replacement = target.ljust(len(placeholder), b"\0")
-            path.write_bytes(contents.replace(placeholder, replacement))
+                # Pad after the whole string to preserve path suffixes.
+                patched = re.sub(
+                    re.escape(placeholder) + rb"[^\0]*",
+                    lambda match: match[0].replace(placeholder, target).ljust(
+                        len(match[0]), b"\0"
+                    ),
+                    contents,
+                )
+            else:
+                patched = contents.replace(placeholder, target)
+                # shortcut: generated CPython launchers only, extend for other scripts.
+                if match := re.match(
+                    b"#!" + re.escape(placeholder) + rb"(/bin/python[0-9.]*[td]*)\n",
+                    contents,
+                ):
+                    # CPython's launchers need both shell and Python quoting.
+                    executable = target + match[1]
+                    quoted = executable.replace(b"'", b"'\"'\"'").replace(
+                        b"\\", b"'\"\\\\\"'"
+                    )
+                    patched = (
+                        b"#!/bin/sh\n'exec' '" + quoted + b"' \"$0\" \"$@\"\n"
+                        + patched.partition(b"\n")[2]
+                    )
+            path.write_bytes(patched)
             if contents[:4] in MACHO_MAGIC:
                 # Rewriting a Mach-O file invalidates its (ad-hoc) code
                 # signature, and arm64 macOS kills processes that load it.
diff --git a/test_relocatable.py b/test_relocatable.py
new file mode 100644
index 0000000..f13fc85
--- /dev/null
+++ b/test_relocatable.py
@@ -0,0 +1,95 @@
+import json
+import os
+import pathlib
+import py_compile
+import subprocess
+import sys
+import tempfile
+import unittest
+
+from relocatable import patch_path, placeholder_prefix
+
+
+class PatchPathTests(unittest.TestCase):
+    def test_python_shebang(self):
+        with tempfile.TemporaryDirectory() as directory:
+            root = pathlib.Path(directory).resolve()
+            names = (
+                "with spaces",
+                "with\ttab",
+                "with ''' quotes",
+                'with """ quotes',
+                r"with \u backslash",
+                "with $HOME and $(false)",
+                "with café",
+                "x" * (250 - len(os.fsencode(root)) - 1),
+            )
+            for name in names:
+                with self.subTest(name=name):
+                    prefix = root / name
+                    bin_dir = prefix / "bin"
+                    bin_dir.mkdir(parents=True)
+                    interpreter = bin_dir / "python3.16"
+                    interpreter.symlink_to(sys.executable)
+                    script = bin_dir / "pydoc3.16"
+                    script.write_text(
+                        f"#!{placeholder_prefix()}/bin/python3.16\n"
+                        "import json, sys\n"
+                        "print(json.dumps([sys.executable, sys.argv[1:]]))\n",
+                        encoding="utf-8",
+                    )
+                    script.chmod(0o755)
+                    patch_path(prefix, str(prefix))
+                    result = subprocess.run(
+                        [script, "argument with spaces", "$literal"],
+                        env={**os.environ, "PATH": ""},
+                        capture_output=True, text=True, check=True,
+                    )
+                    executable, arguments = json.loads(result.stdout)
+                    self.assertTrue(pathlib.Path(executable).samefile(interpreter))
+                    self.assertEqual(arguments, ["argument with spaces", "$literal"])
+
+    def test_prefix_replacement(self):
+        prefix = placeholder_prefix().encode()
+        target = b"/opt/python"
+        padding = b"\0" * (len(prefix) - len(target))
+        cases = (
+            (prefix + b"/lib", target + b"/lib"),
+            (
+                b"header\0" + prefix + b"/lib\0tail",
+                b"header\0" + target + b"/lib" + padding + b"\0tail",
+            ),
+            (
+                b"\0" + prefix + b"/lib:" + prefix + b"/lib64\0",
+                b"\0" + target + b"/lib:" + target + b"/lib64" + padding * 2 + b"\0",
+            ),
+            (b"\0" + prefix + b"/lib", b"\0" + target + b"/lib" + padding),
+        )
+        with tempfile.TemporaryDirectory() as directory:
+            root = pathlib.Path(directory)
+            path = root / "file"
+            for original, expected in cases:
+                with self.subTest(original=original):
+                    path.write_bytes(original)
+                    patch_path(root, target.decode())
+                    self.assertEqual(path.read_bytes(), expected)
+
+    def test_bytecode_is_unchanged(self):
+        with tempfile.TemporaryDirectory() as directory:
+            root = pathlib.Path(directory)
+            source = root / "module.py"
+            source.write_text("pass\n", encoding="utf-8")
+            for suffix in (".pyc", ".pyo"):
+                with self.subTest(suffix=suffix):
+                    bytecode = root / ("module" + suffix)
+                    py_compile.compile(
+                        str(source), cfile=str(bytecode),
+                        dfile=placeholder_prefix() + "/module.py", doraise=True,
+                    )
+                    original = bytecode.read_bytes()
+                    patch_path(root, "/opt/python")
+                    self.assertEqual(bytecode.read_bytes(), original)
+
+
+if __name__ == "__main__":
+    unittest.main()