diff --git a/tests/integration/observability/test_anthropic_overloaded_failure_signals.py b/tests/integration/observability/test_anthropic_overloaded_failure_signals.py
index 85f452c4a19..3d6414dadd5 100644
--- a/tests/integration/observability/test_anthropic_overloaded_failure_signals.py
+++ b/tests/integration/observability/test_anthropic_overloaded_failure_signals.py
@@ -338,15 +338,15 @@ def test_the_datadog_proxy_failure_log_carries_the_answered_status_and_the_llm_f
 def _datadog_llm_failures(rig: _Rig, aliases: Sequence[str]) -> Mapping[str, Mapping[str, JsonValue]]:
     batches: Final[list[Request]] = []  # mutable-ok: drain() consumes the queue, later polls must keep earlier batches
 
+    def alias_of(message: Mapping[str, JsonValue]) -> str | None:
+        if "user_api_key_dict" in message:
+            return None
+        return next((alias for alias in aliases if _keyed_by(message, alias)), None)
+
     def delivered() -> Mapping[str, Mapping[str, JsonValue]]:
         batches.extend(rig.datadog.drain())
-        return {
-            alias: object_value(message["error_information"])
-            for message in _datadog_messages(batches)
-            if "user_api_key_dict" not in message
-            for alias in aliases
-            if _keyed_by(message, alias)
-        }
+        keyed: Final = ((alias_of(message), message) for message in _datadog_messages(batches))
+        return {alias: object_value(message["error_information"]) for alias, message in keyed if alias is not None}
 
     return eventually(delivered, lambda found: len(found) >= len(aliases), seconds=40, return_last_on_timeout=True)
 
diff --git a/tests/unit/litellm_core_utils/test_streaming_handler.py b/tests/unit/litellm_core_utils/test_streaming_handler.py
index d729674288a..2073c61f2bb 100644
--- a/tests/unit/litellm_core_utils/test_streaming_handler.py
+++ b/tests/unit/litellm_core_utils/test_streaming_handler.py
@@ -9660,23 +9660,24 @@ class _RecordingLogging(Logging):
             messages=[{"role": "user", "content": "Hey"}],
             stream=True,
             call_type="completion",
-            start_time=datetime.datetime.now(),
+            start_time=datetime.datetime(2026, 1, 1, tzinfo=datetime.timezone.utc),
             litellm_call_id="12345",
             function_id="1245",
         )
         self.logged_failures: list[Exception] = []  # mutable-ok: test double accumulating callback arguments
+        self.failure_logged: Final = threading.Event()
 
     def failure_handler(self, exception: Exception, traceback_exception: str, *args: object, **kwargs: object) -> None:
         self.logged_failures.append(exception)
+        self.failure_logged.set()
 
     async def dispatch_attempt_failure_handlers(self, exception: Exception, traceback_exception: str) -> None:
         self.logged_failures.append(exception)
+        self.failure_logged.set()
 
 
 def _assert_failure_callback_got_the_public_exception(logging: _RecordingLogging, raised: MidStreamFallbackError) -> None:
-    deadline: Final = time.monotonic() + 5
-    while not logging.logged_failures and time.monotonic() < deadline:
-        time.sleep(0.01)
+    assert logging.failure_logged.wait(timeout=5), "failure callbacks never ran"
     assert len(logging.logged_failures) == 1, logging.logged_failures
     logged: Final = logging.logged_failures[0]
     assert type(logged) is litellm.InternalServerError, logged