diff --git a/azure_functions_worker/dispatcher.py b/azure_functions_worker/dispatcher.py
index e230a289d..cf177f930 100644
--- a/azure_functions_worker/dispatcher.py
+++ b/azure_functions_worker/dispatcher.py
@@ -24,20 +24,21 @@
 from . import functions
 from . import loader
 from . import protos
+from .bindings.shared_memory_data_transfer import SharedMemoryManager
 from .constants import (PYTHON_THREADPOOL_THREAD_COUNT,
                         PYTHON_THREADPOOL_THREAD_COUNT_DEFAULT,
                         PYTHON_THREADPOOL_THREAD_COUNT_MAX_37,
                         PYTHON_THREADPOOL_THREAD_COUNT_MIN,
                         PYTHON_ENABLE_DEBUG_LOGGING)
+from .extension import ExtensionManager
 from .logging import disable_console_logging, enable_console_logging
+from .logging import enable_debug_logging_recommendation
 from .logging import (logger, error_logger, is_system_log_category,
                       CONSOLE_LOG_PREFIX)
-from .extension import ExtensionManager
 from .utils.common import get_app_setting, is_envvar_true
-from .utils.tracing import marshall_exception_trace
 from .utils.dependency import DependencyManager
+from .utils.tracing import marshall_exception_trace
 from .utils.wrappers import disable_feature_by
-from .bindings.shared_memory_data_transfer import SharedMemoryManager
 
 _TRUE = "true"
 
@@ -262,6 +263,7 @@ async def _handle__worker_init_request(self, req):
         logger.info('Received WorkerInitRequest, '
                     'python version %s, worker version %s, request ID %s',
                     sys.version, __version__, self.request_id)
+        enable_debug_logging_recommendation()
 
         worker_init_request = req.worker_init_request
         host_capabilities = worker_init_request.capabilities
@@ -459,6 +461,7 @@ async def _handle__function_environment_reload_request(self, req):
         try:
             logger.info('Received FunctionEnvironmentReloadRequest, '
                         'request ID: %s', self.request_id)
+            enable_debug_logging_recommendation()
 
             func_env_reload_request = req.function_environment_reload_request
 
diff --git a/azure_functions_worker/logging.py b/azure_functions_worker/logging.py
index 01a4373a5..4f8fac2ea 100644
--- a/azure_functions_worker/logging.py
+++ b/azure_functions_worker/logging.py
@@ -76,6 +76,11 @@ def enable_console_logging() -> None:
         logger.addHandler(handler)
 
 
+def enable_debug_logging_recommendation():
+    logging.info("To enable debug level logging, please refer to "
+                 "https://aka.ms/python-enable-debug-logging")
+
+
 def is_system_log_category(ctg: str) -> bool:
     """Check if the logging namespace belongs to system logs. Category starts
     with the following name will be treated as system logs.
diff --git a/tests/unittests/test_dispatcher.py b/tests/unittests/test_dispatcher.py
index 2d5960a1c..2b6c3bfa0 100644
--- a/tests/unittests/test_dispatcher.py
+++ b/tests/unittests/test_dispatcher.py
@@ -69,6 +69,36 @@ async def test_dispatcher_initialize_worker_logging(self):
                 1
             )
 
+            self.assertEqual(
+                len([l for l in r.logs if l.message.startswith(
+                    'To enable debug level logging'
+                )]),
+                1
+            )
+
+    async def test_dispatcher_environment_reload_logging(self):
+        """Test if the sync threadpool will pick up app setting in placeholder
+        mode (Linux Consumption)
+        """
+        async with self._ctrl as host:
+            await self._check_if_function_is_ok(host)
+
+            # Reload environment variable on specialization
+            r = await host.reload_environment(environment={})
+            self.assertEqual(
+                len([l for l in r.logs if l.message.startswith(
+                    'Received FunctionEnvironmentReloadRequest'
+                )]),
+                1
+            )
+
+            self.assertEqual(
+                len([l for l in r.logs if l.message.startswith(
+                    'To enable debug level logging'
+                )]),
+                1
+            )
+
     async def test_dispatcher_send_worker_request(self):
         """Test if the worker status response will be sent correctly when
         a worker status request is received