diff --git a/homeassistant/core.py b/homeassistant/core.py
index adeed758555..1d05336e5c4 100644
--- a/homeassistant/core.py
+++ b/homeassistant/core.py
@@ -393,12 +393,28 @@ class HomeAssistant:
         """Block until all pending work is done."""
         # To flush out any call_soon_threadsafe
         await asyncio.sleep(0)
+        start_time: Optional[float] = None
 
         while self._pending_tasks:
             pending = [task for task in self._pending_tasks if not task.done()]
             self._pending_tasks.clear()
             if pending:
                 await self._await_and_log_pending(pending)
+
+                if start_time is None:
+                    # Avoid calling monotonic() until we know
+                    # we may need to start logging blocked tasks.
+                    start_time = 0
+                elif start_time == 0:
+                    # If we have waited twice then we set the start
+                    # time
+                    start_time = monotonic()
+                elif monotonic() - start_time > BLOCK_LOG_TIMEOUT:
+                    # We have waited at least three loops and new tasks
+                    # continue to block. At this point we start
+                    # logging all waiting tasks.
+                    for task in pending:
+                        _LOGGER.debug("Waiting for task: %s", task)
             else:
                 await asyncio.sleep(0)
 
diff --git a/tests/test_core.py b/tests/test_core.py
index c144af86804..12ed00fde2c 100644
--- a/tests/test_core.py
+++ b/tests/test_core.py
@@ -1419,9 +1419,62 @@ async def test_log_blocking_events(hass, caplog):
     hass.async_create_task(_wait_a_bit_1())
     await hass.async_block_till_done()
 
-    with patch.object(ha, "BLOCK_LOG_TIMEOUT", 0.00001):
+    with patch.object(ha, "BLOCK_LOG_TIMEOUT", 0.0001):
         hass.async_create_task(_wait_a_bit_2())
         await hass.async_block_till_done()
 
     assert "_wait_a_bit_2" in caplog.text
     assert "_wait_a_bit_1" not in caplog.text
+
+
+async def test_chained_logging_hits_log_timeout(hass, caplog):
+    """Ensure we log which task is blocking startup when there is a task chain and debug logging is on."""
+    caplog.set_level(logging.DEBUG)
+
+    created = 0
+
+    async def _task_chain_1():
+        nonlocal created
+        created += 1
+        if created > 10:
+            return
+        hass.async_create_task(_task_chain_2())
+
+    async def _task_chain_2():
+        nonlocal created
+        created += 1
+        if created > 10:
+            return
+        hass.async_create_task(_task_chain_1())
+
+    with patch.object(ha, "BLOCK_LOG_TIMEOUT", 0.0001):
+        hass.async_create_task(_task_chain_1())
+        await hass.async_block_till_done()
+
+    assert "_task_chain_" in caplog.text
+
+
+async def test_chained_logging_misses_log_timeout(hass, caplog):
+    """Ensure we do not log which task is blocking startup if we do not hit the timeout."""
+    caplog.set_level(logging.DEBUG)
+
+    created = 0
+
+    async def _task_chain_1():
+        nonlocal created
+        created += 1
+        if created > 10:
+            return
+        hass.async_create_task(_task_chain_2())
+
+    async def _task_chain_2():
+        nonlocal created
+        created += 1
+        if created > 10:
+            return
+        hass.async_create_task(_task_chain_1())
+
+    hass.async_create_task(_task_chain_1())
+    await hass.async_block_till_done()
+
+    assert "_task_chain_" not in caplog.text