diff --git a/src/rdc/services/session_service.py b/src/rdc/services/session_service.py
index 2989026..e233493 100644
--- a/src/rdc/services/session_service.py
+++ b/src/rdc/services/session_service.py
@@ -192,6 +192,7 @@ def open_session(
     max_attempts = 1 if remote_url is not None else 3
     host = "127.0.0.1"
     detail = "unknown error"
+    started = False
     for _attempt in range(max_attempts):
         port = pick_port()
         token = secrets.token_hex(16)
@@ -199,6 +200,7 @@ def open_session(
 
         ok, detail = wait_for_ping(host, port, token, timeout_s=resolved_timeout, proc=proc)
         if ok:
+            started = True
             break
         proc.terminate()
         try:
@@ -207,9 +209,14 @@ def open_session(
             proc.kill()
             proc.wait()
         stderr = _read_daemon_stderr(proc)
+        timed_out = detail.startswith("timeout")
         if stderr:
-            detail = stderr
-    else:
+            # Keep the real reason (timeout, exit code) first; the log tail is context.
+            detail = f"{detail}; daemon log: {stderr}"
+        if timed_out:
+            detail += "; large captures may need a longer --timeout (or RDC_OPEN_TIMEOUT)"
+            break
+    if not started:
         return False, f"error: daemon failed to start ({detail}) -- hint: run 'rdc doctor'"
 
     _discard_daemon_stderr(proc)
diff --git a/tests/unit/test_session_service.py b/tests/unit/test_session_service.py
index 9f47478..a003bf7 100644
--- a/tests/unit/test_session_service.py
+++ b/tests/unit/test_session_service.py
@@ -277,6 +277,33 @@ def test_open_session_all_retries_fail(monkeypatch: pytest.MonkeyPatch, tmp_path
     assert "rdc doctor" in msg
 
 
+def test_open_session_timeout_reports_timeout_first_and_does_not_retry(
+    monkeypatch: pytest.MonkeyPatch, tmp_path: Path
+) -> None:
+    """A startup timeout leads the message, keeps the log as context, and is not retried."""
+    monkeypatch.delenv("RDC_SESSION", raising=False)
+    monkeypatch.setattr(session_service, "load_session", lambda: None)
+    monkeypatch.setattr(session_service, "_renderdoc_available", lambda: False)
+
+    log = tmp_path / "daemon.stderr"
+    log.write_text("GPU match fallback: choosing NVIDIA\n")
+    mock_proc = MagicMock()
+    mock_proc.pid = 999
+    mock_proc._rdc_stderr_path = str(log)
+    starts: list[int] = []
+    monkeypatch.setattr(
+        session_service, "start_daemon", lambda *a, **kw: starts.append(1) or mock_proc
+    )
+    monkeypatch.setattr(session_service, "wait_for_ping", lambda *a, **kw: (False, "timeout (15s)"))
+
+    ok, msg = session_service.open_session(Path("test.rdc"))
+    assert ok is False
+    assert len(starts) == 1
+    assert msg.startswith("error: daemon failed to start (timeout (15s);")
+    assert "--timeout" in msg
+    assert msg.index("timeout (15s)") < msg.index("GPU match fallback")
+
+
 def test_close_session_fallback_kill_on_shutdown_error(
     monkeypatch: pytest.MonkeyPatch, tmp_path: Path
 ) -> None: