diff --git a/hermes_cli/web_server.py b/hermes_cli/web_server.py
index f17936cc83..b74fe7b64f 100644
--- a/hermes_cli/web_server.py
+++ b/hermes_cli/web_server.py
@@ -1353,11 +1353,18 @@ def _on_server_started(
     _best_effort("host rendezvous publish", lambda: _publish_host_rendezvous(host, actual_port))
 
     _write_dashboard_ready_file(actual_port)
-    # Port-discovery sentinel parsed by the Desktop spawn (matches either
-    # token). Written to fd 1: tui_gateway.server redirects sys.stdout to
-    # stderr at import, and the Desktop watches child.stdout (#96282).
-    ready_token = "HERMES_BACKEND_READY" if headless else "HERMES_DASHBOARD_READY"
-    _write_machine_sentinel_line(f"{ready_token} port={actual_port}")
+    # Port-discovery sentinel parsed by the Desktop spawn. Written to fd 1:
+    # tui_gateway.server redirects sys.stdout to stderr at import, and the
+    # Desktop watches child.stdout (#96282). A headless `serve` announces the
+    # neutral token FIRST and the legacy HERMES_DASHBOARD_READY one after it:
+    # a packaged Desktop artifact whose parser predates the neutral token
+    # (#60772) still matches the legacy sentinel, while current parsers match
+    # either. The legacy `dashboard` backend keeps its own single token.
+    if headless:
+        _write_machine_sentinel_line(f"HERMES_BACKEND_READY port={actual_port}")
+        _write_machine_sentinel_line(f"HERMES_DASHBOARD_READY port={actual_port}")
+    else:
+        _write_machine_sentinel_line(f"HERMES_DASHBOARD_READY port={actual_port}")
     if headless:
         # Auth-gated JSON-RPC/WS only — announce the bind, not a URL. flush:
         # a piped stdout otherwise surfaces this minutes after the sentinel.
diff --git a/tests/hermes_cli/test_serve_port_in_use.py b/tests/hermes_cli/test_serve_port_in_use.py
index 59a207c575..4a0382c08e 100644
--- a/tests/hermes_cli/test_serve_port_in_use.py
+++ b/tests/hermes_cli/test_serve_port_in_use.py
@@ -216,3 +216,46 @@ def test_ready_sentinel_arrives_on_stdout_not_stderr(tmp_path):
             proc.wait(timeout=30)
         except subprocess.TimeoutExpired:
             proc.kill()
+
+
+def test_headless_serve_announces_both_ready_tokens(tmp_path):
+    """#60772 — a headless ``serve`` must announce BOTH ready tokens.
+
+    The packaged Desktop artifact can be older than the Python backend (the
+    CLI-only ``hermes update`` path does not rebuild the packaged app). Its
+    readiness parser may still match only the legacy ``HERMES_DASHBOARD_READY``
+    line; a backend that announces only ``HERMES_BACKEND_READY`` then boots
+    healthily and gets killed after the port-announcement timeout — the exact
+    artifact-skew signature in #60772. The neutral token must come first so
+    current parsers match it before the legacy one.
+    """
+    probe = socket.socket(socket.AF_INET, socket.SOCK_STREAM)
+    probe.bind(("127.0.0.1", 0))
+    port = probe.getsockname()[1]
+    probe.close()
+
+    proc = _spawn_serve(port, tmp_path)
+    try:
+        # Read past the NEUTRAL token to the legacy one: _read_until stops at
+        # its token, so waiting for the legacy line proves BOTH were written
+        # (the neutral one precedes it) without a timing race.
+        ready, lines = _read_until(proc, f"HERMES_DASHBOARD_READY port={port}")
+        out = "".join(lines)
+        assert ready, (
+            f"legacy token missing (a stale packaged Desktop would time out); output:\n{out}"
+        )
+        # The neutral token must come first: current parsers stop at their
+        # first hit, and they should bind to the newer contract.
+        assert f"HERMES_BACKEND_READY port={port}" in out
+        backend_at = out.index(f"HERMES_BACKEND_READY port={port}")
+        legacy_at = out.index(f"HERMES_DASHBOARD_READY port={port}")
+        assert backend_at < legacy_at
+        # Exactly one of each — never a loop of announcements.
+        assert out.count("HERMES_BACKEND_READY port=") == 1
+        assert out.count("HERMES_DASHBOARD_READY port=") == 1
+    finally:
+        proc.terminate()
+        try:
+            proc.wait(timeout=30)
+        except subprocess.TimeoutExpired:
+            proc.kill()