diff --git a/src/phoenix/server/api/helpers/playground_clients.py b/src/phoenix/server/api/helpers/playground_clients.py
index 6d481c68b2..76a96f6205 100644
--- a/src/phoenix/server/api/helpers/playground_clients.py
+++ b/src/phoenix/server/api/helpers/playground_clients.py
@@ -132,7 +132,7 @@ async def wrapper(*args: Any, **kwargs: Any) -> GenericType:
                 request_start_time = time.time()
                 maybe_coroutine = fn(*args, **kwargs)
                 if inspect.isawaitable(maybe_coroutine):
-                    return await maybe_coroutine  # type: ignore
+                    return await maybe_coroutine  # type: ignore[no-any-return]
                 else:
                     return maybe_coroutine
             except self._rate_limit_error:
@@ -144,10 +144,11 @@ async def wrapper(*args: Any, **kwargs: Any) -> GenericType:
                             try:
                                 request_start_time = time.time()
                                 await self._throttler.async_wait_until_ready()
-                                if inspect.iscoroutinefunction(fn):
-                                    return await fn(*args, **kwargs)  # type: ignore
+                                maybe_coroutine = fn(*args, **kwargs)
+                                if inspect.isawaitable(maybe_coroutine):
+                                    return await maybe_coroutine  # type: ignore[no-any-return]
                                 else:
-                                    return fn(*args, **kwargs)
+                                    return maybe_coroutine
                             except self._rate_limit_error:
                                 self._throttler.on_rate_limit_error(
                                     request_start_time, verbose=self._verbose
diff --git a/src/phoenix/server/api/subscriptions.py b/src/phoenix/server/api/subscriptions.py
index 1c34611675..72b6a3a1fc 100644
--- a/src/phoenix/server/api/subscriptions.py
+++ b/src/phoenix/server/api/subscriptions.py
@@ -1,11 +1,11 @@
 import asyncio
 import logging
-from asyncio import FIRST_COMPLETED, Queue, QueueEmpty, Task, create_task, wait, wait_for
 from collections.abc import AsyncIterator, Iterator
 from datetime import datetime, timedelta, timezone
 from typing import (
     Any,
     AsyncGenerator,
+    Coroutine,
     Iterable,
     Mapping,
     Optional,
@@ -287,7 +287,7 @@ async def chat_completion_over_dataset(
             experiment=to_gql_experiment(experiment)
         )  # eagerly yields experiment so it can be linked by consumers of the subscription
 
-        results: Queue[ChatCompletionResult] = Queue()
+        results: asyncio.Queue[ChatCompletionResult] = asyncio.Queue()
         not_started: list[tuple[DatasetExampleID, ChatStream]] = [
             (
                 GlobalID(DatasetExample.__name__, str(revision.dataset_example_id)),
@@ -303,7 +303,11 @@ async def chat_completion_over_dataset(
             for revision in revisions
         ]
         in_progress: list[
-            tuple[Optional[DatasetExampleID], ChatStream, Task[ChatCompletionSubscriptionPayload]]
+            tuple[
+                Optional[DatasetExampleID],
+                ChatStream,
+                asyncio.Task[ChatCompletionSubscriptionPayload],
+            ]
         ] = []
         max_in_progress = 3
         write_batch_size = 10
@@ -315,7 +319,9 @@ async def chat_completion_over_dataset(
                 task = _create_task_with_timeout(stream)
                 in_progress.append((ex_id, stream, task))
             async_tasks_to_run = [task for _, _, task in in_progress]
-            completed_tasks, _ = await wait(async_tasks_to_run, return_when=FIRST_COMPLETED)
+            completed_tasks, _ = await asyncio.wait(
+                async_tasks_to_run, return_when=asyncio.FIRST_COMPLETED
+            )
             for completed_task in completed_tasks:
                 idx = [task for _, _, task in in_progress].index(completed_task)
                 example_id, stream, _ = in_progress[idx]
@@ -327,7 +333,7 @@ async def chat_completion_over_dataset(
                     del in_progress[idx]  # removes timed-out stream
                     if example_id is not None:
                         yield ChatCompletionSubscriptionError(
-                            message="Timed out", dataset_example_id=example_id
+                            message="Playground task timed out", dataset_example_id=example_id
                         )
                 except Exception as error:
                     del in_progress[idx]  # removes failed stream
@@ -368,7 +374,7 @@ async def _stream_chat_completion_over_dataset_example(
     input: ChatCompletionOverDatasetInput,
     llm_client: PlaygroundStreamingClient,
     revision: models.DatasetExampleRevision,
-    results: Queue[ChatCompletionResult],
+    results: asyncio.Queue[ChatCompletionResult],
     experiment_id: int,
     project_id: int,
 ) -> ChatStream:
@@ -470,23 +476,52 @@ def _is_result_payloads_stream(
 
 def _create_task_with_timeout(
     iterable: AsyncIterator[GenericType], timeout_in_seconds: int = 90
-) -> Task[GenericType]:
-    return create_task(wait_for(_as_coroutine(iterable), timeout=timeout_in_seconds))
+) -> asyncio.Task[GenericType]:
+    return asyncio.create_task(
+        _wait_for(
+            _as_coroutine(iterable),
+            timeout=timeout_in_seconds,
+            timeout_message="Playground task timed out",
+        )
+    )
+
+
+async def _wait_for(
+    coro: Coroutine[None, None, GenericType],
+    timeout: float,
+    timeout_message: Optional[str] = None,
+) -> GenericType:
+    """
+    A function that imitates asyncio.wait_for, but allows the task to be
+    cancelled with a custom message.
+    """
+    task = asyncio.create_task(coro)
+    done, pending = await asyncio.wait([task], timeout=timeout)
+    assert len(done) + len(pending) == 1
+    if done:
+        task = done.pop()
+        return task.result()
+    task = pending.pop()
+    task.cancel(msg=timeout_message)
+    try:
+        return await task
+    except asyncio.CancelledError:
+        raise asyncio.TimeoutError()
 
 
-async def _drain(queue: Queue[GenericType]) -> list[GenericType]:
+async def _drain(queue: asyncio.Queue[GenericType]) -> list[GenericType]:
     values: list[GenericType] = []
     while not queue.empty():
         values.append(await queue.get())
     return values
 
 
-def _drain_no_wait(queue: Queue[GenericType]) -> list[GenericType]:
+def _drain_no_wait(queue: asyncio.Queue[GenericType]) -> list[GenericType]:
     values: list[GenericType] = []
     while True:
         try:
             values.append(queue.get_nowait())
-        except QueueEmpty:
+        except asyncio.QueueEmpty:
             break
     return values