diff --git a/tests/tools/test_computer_use.py b/tests/tools/test_computer_use.py
index 85f62e4e3c7..01e022d80e8 100644
--- a/tests/tools/test_computer_use.py
+++ b/tests/tools/test_computer_use.py
@@ -2867,3 +2867,66 @@ class TestCuaToolCoverageExpansion:
         backend.call_tool("get_cursor_position")
         name, args = backend._session.call_tool.call_args.args
         assert args == {"session": backend._session_id}
+
+
+class TestStartupTimeoutPhaseDetail:
+    """Issue #57025: the ready-timeout error must report which startup phase
+    wedged, so 'doctor passes but wrapper times out' reports are diagnosable."""
+
+    def test_timeout_error_includes_startup_phase(self):
+        import threading
+        from typing import Any, cast
+        from unittest.mock import MagicMock
+        from tools.computer_use.cua_backend import _CuaDriverSession
+
+        session = cast(Any, _CuaDriverSession.__new__(_CuaDriverSession))
+        session._lock = threading.Lock()
+        session._ready_event = threading.Event()  # never set → timeout path
+        session._setup_error = None
+        session._shutdown_event = None
+        session._startup_phase = "mcp-initialize"
+        session._signal_shutdown_locked = lambda: None
+
+        fake_bridge = MagicMock()
+        fake_bridge._loop = MagicMock()
+        session._bridge = fake_bridge
+
+        import asyncio
+        from unittest.mock import patch as _patch
+        with _patch.object(session._ready_event, "wait", return_value=False), \
+             _patch.object(asyncio, "run_coroutine_threadsafe", return_value=MagicMock()), \
+             _patch.object(_CuaDriverSession, "_lifecycle_coro", lambda self: None):
+            try:
+                session._start_lifecycle_locked()
+                assert False, "expected RuntimeError"
+            except RuntimeError as e:
+                msg = str(e)
+                assert "stuck in phase: mcp-initialize" in msg
+                assert "computer-use doctor" in msg
+
+    def test_timeout_error_defaults_to_unknown_phase(self):
+        import threading
+        from typing import Any, cast
+        from unittest.mock import MagicMock, patch as _patch
+        import asyncio
+        from tools.computer_use.cua_backend import _CuaDriverSession
+
+        session = cast(Any, _CuaDriverSession.__new__(_CuaDriverSession))
+        session._lock = threading.Lock()
+        session._ready_event = threading.Event()
+        session._setup_error = None
+        session._shutdown_event = None
+        # no _startup_phase attribute at all
+        session._signal_shutdown_locked = lambda: None
+        fake_bridge = MagicMock()
+        fake_bridge._loop = MagicMock()
+        session._bridge = fake_bridge
+
+        with _patch.object(session._ready_event, "wait", return_value=False), \
+             _patch.object(asyncio, "run_coroutine_threadsafe", return_value=MagicMock()), \
+             _patch.object(_CuaDriverSession, "_lifecycle_coro", lambda self: None):
+            try:
+                session._start_lifecycle_locked()
+                assert False, "expected RuntimeError"
+            except RuntimeError as e:
+                assert "stuck in phase: unknown" in str(e)
diff --git a/tools/computer_use/cua_backend.py b/tools/computer_use/cua_backend.py
index 34c25d43207..4a926a9caaf 100644
--- a/tools/computer_use/cua_backend.py
+++ b/tools/computer_use/cua_backend.py
@@ -576,6 +576,10 @@ class _CuaDriverSession:
         # primitive belongs to the correct loop.
         self._shutdown_event = asyncio.Event()
         _t0 = _time.monotonic()
+        # Phase marker surfaced by the ready-timeout error (issue #57025):
+        # when startup wedges, the caller reports HOW FAR it got instead of
+        # an opaque "never reached ready".
+        self._startup_phase = "binary-check"
 
         try:
             if not cua_driver_binary_available():
@@ -584,6 +588,7 @@ class _CuaDriverSession:
             # Surface 8: ask cua-driver itself which subcommand spawns
             # the MCP server, instead of hardcoding ["mcp"]. Falls back
             # transparently for older drivers / any discovery failure.
+            self._startup_phase = "manifest-discovery"
             command, args = _resolve_mcp_invocation(_CUA_DRIVER_CMD)
             _t_manifest = _time.monotonic()
             params = StdioServerParameters(
@@ -595,14 +600,17 @@ class _CuaDriverSession:
             )
 
             async with stdio_client(params) as (read, write):
+                self._startup_phase = "mcp-initialize"
                 async with ClientSession(read, write) as session:
                     await session.initialize()
                     _t_init = _time.monotonic()
                     # Populate capabilities + capability_version BEFORE
                     # exposing the session to callers, so the first
                     # tool call already sees them.
+                    self._startup_phase = "capability-discovery"
                     await self._populate_capabilities(session)
                     self._session = session
+                    self._startup_phase = "ready"
                     self._ready_event.set()
                     logger.info(
                         "cua-driver session ready in %.1fs "
@@ -691,7 +699,17 @@ class _CuaDriverSession:
         if not self._ready_event.wait(timeout=30.0):
             # Best-effort: signal shutdown if the future is still alive.
             self._signal_shutdown_locked()
-            raise RuntimeError("cua-driver session never reached ready (timeout 30s)")
+            # Surface which startup phase wedged (issue #57025) — "doctor
+            # passes but the wrapper times out" reports are undiagnosable
+            # from a bare "never reached ready".
+            phase = getattr(self, "_startup_phase", "unknown")
+            from hermes_constants import display_hermes_home
+            raise RuntimeError(
+                "cua-driver session never reached ready (timeout 30s; "
+                f"stuck in phase: {phase}). "
+                "Run `hermes computer-use doctor` and check "
+                f"{display_hermes_home()}/logs/agent.log for the phase timings."
+            )
         # If setup failed, the lifecycle coroutine set _setup_error
         # before setting _ready_event. Re-raise it on the caller's thread.
         if self._setup_error is not None: