diff --git a/litellm/router_utils/cooldown_handlers.py b/litellm/router_utils/cooldown_handlers.py
index bef07c68e9e..6e6d4c253e9 100644
--- a/litellm/router_utils/cooldown_handlers.py
+++ b/litellm/router_utils/cooldown_handlers.py
@@ -640,8 +640,13 @@ def cast_exception_status_to_int(exception_status: str | int) -> int:
     return exception_status
 
 
-def is_caller_timeout_408(model_call_details: Mapping[str, object], exception_status: str | int) -> bool:
-    """A 408 that arrives before the caller-set timeout could have fired came from the provider."""
+def is_caller_timeout_408(
+    model_call_details: Mapping[str, object], exception_status: str | int, ended: datetime | None = None
+) -> bool:
+    """A 408 that arrives before the caller-set timeout could have fired came from the provider.
+
+    ``ended`` overrides ``model_call_details["end_time"]`` for callers that run before the
+    failure logger has stamped the current API call's end time."""
     if cast_exception_status_to_int(exception_status) != 408:
         return False
     litellm_params: Final = model_call_details.get("litellm_params")
@@ -649,7 +654,7 @@ def is_caller_timeout_408(model_call_details: Mapping[str, object], exception_st
         return False
     timeout: Final = litellm_params.get("timeout")
     started: Final = model_call_details.get("api_call_start_time") or model_call_details.get("start_time")
-    ended: Final = model_call_details.get("end_time")
-    if not isinstance(timeout, (int, float)) or not isinstance(started, datetime) or not isinstance(ended, datetime):
+    finished: Final = ended if ended is not None else model_call_details.get("end_time")
+    if not isinstance(timeout, (int, float)) or not isinstance(started, datetime) or not isinstance(finished, datetime):
         return False
-    return (ended - started).total_seconds() >= timeout
+    return (finished - started).total_seconds() >= timeout
diff --git a/litellm/router_utils/fallback_event_handlers.py b/litellm/router_utils/fallback_event_handlers.py
index eeea9b9faf8..94164d0ea0c 100644
--- a/litellm/router_utils/fallback_event_handlers.py
+++ b/litellm/router_utils/fallback_event_handlers.py
@@ -2,6 +2,7 @@ import hashlib
 import json
 from collections.abc import Mapping, Sequence
 from dataclasses import dataclass
+from datetime import datetime
 from enum import Enum
 from types import MappingProxyType
 from typing import TYPE_CHECKING, Any, Final
@@ -84,7 +85,11 @@ def _trigger_cooldown_for_failed_deployment(
         # timeout, which litellm.Timeout reports as status 408 regardless of the deployment's
         # actual health. Left unguarded, a caller could force a 408 on every deployment in
         # the fallback chain from a single request with a near-zero timeout.
-        if is_caller_timeout_408(model_call_details, exception_status):
+        if is_caller_timeout_408(
+            model_call_details,
+            exception_status,
+            ended=datetime.now(),  # noqa: DTZ005  # naive to match the logging pipeline's api_call_start_time
+        ):
             verbose_router_logger.debug(
                 "Not triggering cooldown for fallback deployment: a caller-supplied "
                 "x-litellm-timeout caused this 408, not deployment health."
diff --git a/tests/test_litellm/router_utils/test_fallback_event_handlers.py b/tests/test_litellm/router_utils/test_fallback_event_handlers.py
index 783f8da31e9..9318f306c89 100644
--- a/tests/test_litellm/router_utils/test_fallback_event_handlers.py
+++ b/tests/test_litellm/router_utils/test_fallback_event_handlers.py
@@ -956,7 +956,11 @@ class TestTriggerCooldownForFailedDeployment:
         """The proxy's x-litellm-timeout header lets a caller set an arbitrarily short
         timeout, which litellm.Timeout reports as status 408 regardless of the
         deployment's actual health. Without this guard, a caller could force a 408 on
-        every deployment in the fallback chain from a single request."""
+        every deployment in the fallback chain from a single request.
+
+        The failure logger never stamps end_time for a fallback hop (has_logged_async_failure
+        is already set), so model_call_details still carries the previous hop's end_time, which
+        predates this hop's api_call_start_time. The guard must not trust it."""
         mock_router = MagicMock()
         mock_router.cooldown_time = 60.0
         mock_router.get_model_info.return_value = None
@@ -977,7 +981,7 @@ class TestTriggerCooldownForFailedDeployment:
                 model_call_details={
                     "litellm_params": {"client_side_timeout": True, "timeout": 0.5},
                     "api_call_start_time": datetime.now() - timedelta(seconds=1),
-                    "end_time": datetime.now(),
+                    "end_time": datetime.now() - timedelta(seconds=5),
                 },
             )