diff --git a/contrib/web/test_debian_package_docs.py b/contrib/web/test_debian_package_docs.py
new file mode 100644
index 0000000..4c95229
--- /dev/null
+++ b/contrib/web/test_debian_package_docs.py
@@ -0,0 +1,54 @@
+# File: contrib/web/test_debian_package_docs.py
+
+from __future__ import annotations
+
+import unittest
+from pathlib import Path
+
+
+class DebianPackageDocumentationTest(unittest.TestCase):
+    def test_native_website_initialization_creates_site_json(self) -> None:
+        repository = Path(__file__).resolve().parents[2]
+        readme = (repository / "debian" / "README.Debian").read_text(
+            encoding="utf-8"
+        )
+        install_manifest = (
+            repository / "debian" / "activity-relay.install"
+        ).read_text(encoding="utf-8")
+
+        self.assertIn(
+            "contrib/web/site.json.example etc/activity-relay-web",
+            install_manifest,
+        )
+
+        rebuild_wrapper = (
+            repository / "contrib" / "web" / "activity-relay-rebuild-site"
+        ).read_text(encoding="utf-8")
+
+        copy_sequence = (
+            "   cp -an /usr/share/activity-relay/web/. "
+            "/etc/activity-relay-web/\n"
+            "\n"
+            "   cp --update=none \\\n"
+            "       /etc/activity-relay-web/site.json.example \\\n"
+            "       /etc/activity-relay-web/site.json\n"
+        )
+
+        self.assertEqual(readme.count(copy_sequence), 1)
+        self.assertIn(
+            'config_file="${ACTIVITY_RELAY_WEB_CONFIG:-'
+            '/etc/activity-relay-web/site.json}"',
+            rebuild_wrapper,
+        )
+        self.assertLess(
+            readme.index(copy_sequence),
+            readme.index(
+                "Edit /etc/activity-relay-web/site.json and build the site"
+            ),
+        )
+
+
+if __name__ == "__main__":
+    unittest.main()
+
+# EOF: contrib/web/test_debian_package_docs.py
diff --git a/debian/README.Debian b/debian/README.Debian
index ac40402..74cdfd8 100644
--- a/debian/README.Debian
+++ b/debian/README.Debian
@@ -46,6 +46,10 @@ an editable copy without replacing existing files:
 
    cp -an /usr/share/activity-relay/web/. /etc/activity-relay-web/
 
+   cp --update=none \
+       /etc/activity-relay-web/site.json.example \
+       /etc/activity-relay-web/site.json
+
 Edit /etc/activity-relay-web/site.json and build the site with the current
 package-managed source: