diff --git a/tests/venv_site_packages_libs/importlib_metadata_test.py b/tests/venv_site_packages_libs/importlib_metadata_test.py
index 963d43b6e0..f7bff529cf 100644
--- a/tests/venv_site_packages_libs/importlib_metadata_test.py
+++ b/tests/venv_site_packages_libs/importlib_metadata_test.py
@@ -10,13 +10,47 @@ def test_importlib_metadata_files(self):
             len(files), 0, "importlib.metadata.files returned empty list"
         )
 
-        # Verify it contains some expected files.
-        # The RECORD file lists paths relative to the installation root (site-packages).
-        # whl_with_data1-1.0.data/purelib/data_overlap.py should be installed as data_overlap.py
-        # whl_with_data1-1.0.data/platlib/whl_with_data1/platlib_file.txt should be whl_with_data1/platlib_file.txt
+        expected_paths = [
+            "whl_with_data1-1.0.data/data/bin/data_overlap.sh",
+            "whl_with_data1-1.0.data/data/include/data_overlap.h",
+            "whl_with_data1-1.0.data/data/overlap/both.txt",
+            "whl_with_data1-1.0.data/data/overlap/data1.txt",
+            "whl_with_data1-1.0.data/data/site-packages/data_overlap.py",
+            "whl_with_data1-1.0.data/data/whl_with_data1/data_data_file.txt",
+            "whl_with_data1-1.0.data/data/whl_with_data1/data_data_file.txt",
+            "whl_with_data1-1.0.data/headers/data_overlap.h",
+            "whl_with_data1-1.0.data/headers/overlap/both.h",
+            "whl_with_data1-1.0.data/headers/overlap/header1.h",
+            "whl_with_data1-1.0.data/headers/whl_with_data1/header_file.h",
+            "whl_with_data1-1.0.data/platlib/whl_with_data1/platlib_file.txt",
+            "whl_with_data1-1.0.data/purelib/data_overlap.py",
+            "whl_with_data1-1.0.data/purelib/whl_with_data1/data_file.txt",
+            "whl_with_data1-1.0.data/scripts/data_overlap.sh",
+            "whl_with_data1-1.0.data/scripts/overlap/both.sh",
+            "whl_with_data1-1.0.data/scripts/overlap/script1.sh",
+            "whl_with_data1-1.0.data/scripts/whl_script.sh",
+            "whl_with_data1-1.0.data/scripts/whl_with_data1_script",
+        ]
+        file_paths = sorted(str(f).replace("\\", "/") for f in files)
+        self.assertEqual(file_paths, expected_paths)
 
-        file_names = [f.name for f in files]
-        self.assertIn("data_overlap.py", file_names)
+        for f in files:
+            resolved = f.locate()
+            self.assertTrue(
+                resolved.exists(),
+                f"Expected file {f} (resolved to {resolved}) to exist",
+            )
+            self.assertTrue(
+                resolved.is_file(),
+                f"Expected {resolved} to be a regular file",
+            )
+
+            # Verify file content can be read both as binary and as text
+            content = f.read_binary()
+            self.assertIsNotNone(content)
+
+            text = f.read_text(encoding="utf-8")
+            self.assertIsNotNone(text)
 
 
 if __name__ == "__main__":