diff --git a/aikido_zen/background_process/commands/sync_data_test.py b/aikido_zen/background_process/commands/sync_data_test.py
index 1f1899ea..ad89f1ff 100644
--- a/aikido_zen/background_process/commands/sync_data_test.py
+++ b/aikido_zen/background_process/commands/sync_data_test.py
@@ -16,6 +16,7 @@ def setup_connection_manager():
     connection_manager.conf.blocked_uids = ["user1", "user2"]
     connection_manager.conf.last_updated_at = 200
     connection_manager.statistics.requests = {"total": 0}  # Initialize total requests
+    connection_manager.middleware_installed = False
     return connection_manager
 
 
@@ -38,6 +39,7 @@ def test_process_sync_data_initialization(setup_connection_manager):
             },
         },
         "reqs": 10,  # Total requests to be added
+        "middleware_installed": False,
     }
 
     result = process_sync_data(connection_manager, data, None)
@@ -63,6 +65,7 @@ def test_process_sync_data_initialization(setup_connection_manager):
     # Check that the return value is correct
     assert result["routes"] == dict(connection_manager.routes.routes)
     assert result["config"] == connection_manager.conf
+    assert connection_manager.middleware_installed == False
 
 
 def test_process_sync_data_with_last_updated_at_below_zero(setup_connection_manager):
@@ -85,6 +88,7 @@ def test_process_sync_data_with_last_updated_at_below_zero(setup_connection_mana
             },
         },
         "reqs": 10,  # Total requests to be added
+        "middleware_installed": True,
     }
 
     result = process_sync_data(connection_manager, data, None)
@@ -106,7 +110,7 @@ def test_process_sync_data_with_last_updated_at_below_zero(setup_connection_mana
 
     # Check that the total requests were updated
     assert connection_manager.statistics.requests["total"] == 10
-
+    assert connection_manager.middleware_installed == True
     # Check that the return value is correct
     assert result == {}
 
@@ -154,6 +158,7 @@ def test_process_sync_data_existing_route(setup_connection_manager):
 
     # Check that the total requests were updated
     assert connection_manager.statistics.requests["total"] == 20  # 5 + 15
+    assert connection_manager.middleware_installed == False
 
     # Check that the return value is correct
     assert result["routes"] == dict(connection_manager.routes.routes)
diff --git a/aikido_zen/middleware/init_test.py b/aikido_zen/middleware/init_test.py
index 5a30e9ec..dea1e69a 100644
--- a/aikido_zen/middleware/init_test.py
+++ b/aikido_zen/middleware/init_test.py
@@ -56,12 +56,14 @@ def test_with_context_with_cache():
 
     thread_cache.config.blocked_uids = ["123"]
     assert get_current_context().executed_middleware == False
+    assert thread_cache.middleware_installed == False
     assert should_block_request() == {
         "block": True,
         "trigger": "user",
         "type": "blocked",
     }
     assert get_current_context().executed_middleware == True
+    assert thread_cache.middleware_installed == True
 
     thread_cache.config.blocked_uids = []
     assert should_block_request() == {"block": False}
@@ -69,6 +71,7 @@ def test_with_context_with_cache():
     thread_cache.config.blocked_uids = ["23", "234", "456"]
     assert should_block_request() == {"block": False}
     assert get_current_context().executed_middleware == True
+    assert thread_cache.middleware_installed == True
 
 
 def test_cache_comms_with_endpoints():
@@ -88,11 +91,13 @@ def test_cache_comms_with_endpoints():
         }
     ]
     assert get_current_context().executed_middleware == False
+    assert thread_cache.middleware_installed == False
 
     with patch("aikido_zen.background_process.comms.get_comms") as mock_get_comms:
         mock_get_comms.return_value = None  # Set the return value of get_comms
         assert should_block_request() == {"block": False}
     assert get_current_context().executed_middleware == True
+    assert thread_cache.middleware_installed == True
 
     with patch("aikido_zen.background_process.comms.get_comms") as mock_get_comms:
         mock_comms = MagicMock()