diff --git a/asgiref/sync.py b/asgiref/sync.py
index 5406b7d3..92d25112 100644
--- a/asgiref/sync.py
+++ b/asgiref/sync.py
@@ -309,6 +309,11 @@ async def main_wrap(
         if context is not None:
             _restore_context(context[0])
 
+        current_task = asyncio.current_task()
+        if current_task is not None:
+            task_context = SyncToAsync.task_context.get()
+            task_context.append(current_task)
+
         try:
             # If we have an exception, run the function inside the except block
             # after raising it so exc_info is correctly populated.
@@ -324,6 +329,8 @@ async def main_wrap(
         else:
             call_result.set_result(result)
         finally:
+            if current_task is not None:
+                task_context.remove(current_task)
             context[0] = contextvars.copy_context()
 
 
@@ -355,6 +362,10 @@ class SyncToAsync(Generic[_P, _R]):
     # Single-thread executor for thread-sensitive code
     single_thread_executor = ThreadPoolExecutor(max_workers=1)
 
+    task_context: "contextvars.ContextVar[List[asyncio.Task[Any]]]" = (
+        contextvars.ContextVar("task_context", default=[])
+    )
+
     # Maintain a contextvar for the current execution context. Optionally used
     # for thread sensitive mode.
     thread_sensitive_context: "contextvars.ContextVar[ThreadSensitiveContext]" = (
@@ -438,19 +449,35 @@ async def __call__(self, *args: _P.args, **kwargs: _P.kwargs) -> _R:
         child = functools.partial(self.func, *args, **kwargs)
         func = context.run
 
+        # Run the code in the right thread
+        exec_coro = loop.run_in_executor(
+            executor,
+            functools.partial(
+                self.thread_handler,
+                loop,
+                sys.exc_info(),
+                func,
+                child,
+            ),
+        )
+        ret: _R
         try:
-            # Run the code in the right thread
-            ret: _R = await loop.run_in_executor(
-                executor,
-                functools.partial(
-                    self.thread_handler,
-                    loop,
-                    sys.exc_info(),
-                    func,
-                    child,
-                ),
-            )
-
+            ret = await asyncio.shield(exec_coro)
+        except asyncio.CancelledError:
+            tasks = self.task_context.get()
+            cancel_parent = True
+            cancel_parent_force = False
+            for task in tasks:
+                task.cancel()
+            for task in tasks:
+                try:
+                    await task
+                    cancel_parent = False
+                except asyncio.CancelledError:
+                    cancel_parent_force = True
+            if cancel_parent or cancel_parent_force:
+                exec_coro.cancel()
+            ret = await exec_coro
         finally:
             _restore_context(context)
             self.deadlock_context.set(False)
diff --git a/tests/test_sync.py b/tests/test_sync.py
index daed8c4d..a6587f74 100644
--- a/tests/test_sync.py
+++ b/tests/test_sync.py
@@ -852,7 +852,6 @@ def sync_task():
 
 
 @pytest.mark.asyncio
-@pytest.mark.skip(reason="deadlocks")
 async def test_inner_shield_sync_middleware():
     """
     Tests that asyncio.shield is capable of preventing http.disconnect from