diff --git a/litellm/router_utils/cooldown_cache.py b/litellm/router_utils/cooldown_cache.py
index ef29f7d8fd3..4fd433d9391 100644
--- a/litellm/router_utils/cooldown_cache.py
+++ b/litellm/router_utils/cooldown_cache.py
@@ -118,6 +118,7 @@ class CooldownCache:
             )
 
             # Set the cache with a TTL equal to the cooldown time
+            self._drop_in_memory_entry_if_extending(cooldown_key, _cooldown_time)
             self.cooldown_store.set_cache(
                 value=cooldown_data,
                 key=cooldown_key,
@@ -127,6 +128,14 @@ class CooldownCache:
             verbose_logger.error("CooldownCache::add_deployment_to_cooldown - Exception occurred - %s", e)
             raise e
 
+    def _drop_in_memory_entry_if_extending(self, cooldown_key: str, new_cooldown_time: float) -> None:
+        """InMemoryCache keeps a live key's expiry, so a longer cooldown lands only if the entry is deleted first."""
+        current_expiry: Final = self.in_memory_cache.ttl_dict.get(cooldown_key)
+        if current_expiry is None:
+            return
+        if float(current_expiry) < time.time() + float(new_cooldown_time):
+            self.in_memory_cache.delete_cache(cooldown_key)
+
     @staticmethod
     @functools.lru_cache(maxsize=1024)
     def get_cooldown_cache_key(model_id: str) -> str:
diff --git a/tests/unit/router_utils/test_cooldown_cache.py b/tests/unit/router_utils/test_cooldown_cache.py
index 6f90fa8465f..fc59a2054f5 100644
--- a/tests/unit/router_utils/test_cooldown_cache.py
+++ b/tests/unit/router_utils/test_cooldown_cache.py
@@ -582,3 +582,55 @@ class TestCooldownSurvivesUnrelatedCacheTraffic:
         assert [model_id] == [entry[0] for entry in active], (
             "unrelated router cache traffic must not evict a cooldown that is still running"
         )
+
+
+class TestCooldownExtension:
+    """A second failure asking for a longer cooldown must move the deadline out."""
+
+    @staticmethod
+    def _cache() -> CooldownCache:
+        return CooldownCache(cache=DualCache(), default_cooldown_time=60.0)
+
+    def test_longer_cooldown_extends_the_deadline(self):
+        cc = self._cache()
+        key = CooldownCache.get_cooldown_cache_key("dep-a")
+
+        cc.add_deployment_to_cooldown(
+            model_id="dep-a", original_exception=Exception("429"), exception_status=429, cooldown_time=2.0
+        )
+        first_expiry = cc.in_memory_cache.ttl_dict[key]
+
+        started = time.time()
+        cc.add_deployment_to_cooldown(
+            model_id="dep-a", original_exception=Exception("429"), exception_status=429, cooldown_time=60.0
+        )
+        second_expiry = cc.in_memory_cache.ttl_dict[key]
+
+        assert second_expiry > first_expiry, "the longer cooldown was dropped"
+        assert second_expiry - started == pytest.approx(60.0, abs=2.0)
+
+    def test_shorter_cooldown_does_not_cut_an_active_one_short(self):
+        cc = self._cache()
+        key = CooldownCache.get_cooldown_cache_key("dep-b")
+
+        cc.add_deployment_to_cooldown(
+            model_id="dep-b", original_exception=Exception("429"), exception_status=429, cooldown_time=60.0
+        )
+        long_expiry = cc.in_memory_cache.ttl_dict[key]
+
+        cc.add_deployment_to_cooldown(
+            model_id="dep-b", original_exception=Exception("500"), exception_status=500, cooldown_time=1.0
+        )
+
+        assert cc.in_memory_cache.ttl_dict[key] == long_expiry, "a brief cooldown shortened a long one"
+
+    def test_first_cooldown_is_unaffected(self):
+        cc = self._cache()
+        key = CooldownCache.get_cooldown_cache_key("dep-c")
+
+        started = time.time()
+        cc.add_deployment_to_cooldown(
+            model_id="dep-c", original_exception=Exception("429"), exception_status=429, cooldown_time=30.0
+        )
+
+        assert cc.in_memory_cache.ttl_dict[key] - started == pytest.approx(30.0, abs=2.0)