diff --git a/.circleci/config.yml b/.circleci/config.yml
index 0a6327bb3..e7005b5d1 100644
--- a/.circleci/config.yml
+++ b/.circleci/config.yml
@@ -1039,6 +1039,47 @@ jobs:
             ls
             python -m pytest -vv tests/otel_tests -x --junitxml=test-results/junit.xml --durations=5
           no_output_timeout: 120m
+           # Clean up first container
+      - run:
+          name: Stop and remove first container
+          command: |
+            docker stop my-app
+            docker rm my-app
+
+      # Second Docker Container Run with Different Config
+      - run:
+          name: Run Second Docker container
+          command: |
+            docker run -d \
+              -p 4000:4000 \
+              -e DATABASE_URL=$PROXY_DATABASE_URL \
+              -e REDIS_HOST=$REDIS_HOST \
+              -e REDIS_PASSWORD=$REDIS_PASSWORD \
+              -e REDIS_PORT=$REDIS_PORT \
+              -e LITELLM_MASTER_KEY="sk-1234" \
+              -e OPENAI_API_KEY=$OPENAI_API_KEY \
+              -e LITELLM_LICENSE="bad-license" \
+              --name my-app-3 \
+              -v $(pwd)/litellm/proxy/example_config_yaml/enterprise_config.yaml:/app/config.yaml \
+              my-app:latest \
+              --config /app/config.yaml \
+              --port 4000 \
+              --detailed_debug
+
+      - run:
+          name: Start outputting logs for second container
+          command: docker logs -f my-app-2
+          background: true
+
+      - run:
+          name: Wait for second app to be ready
+          command: dockerize -wait http://localhost:4000 -timeout 5m
+
+      - run:
+          name: Run second round of tests
+          command: |
+            python -m pytest -vv tests/basic_proxy_startup_tests -x --junitxml=test-results/junit-2.xml --durations=5
+          no_output_timeout: 120m
 
       # Store test results
       - store_test_results:
diff --git a/litellm/proxy/example_config_yaml/enterprise_config.yaml b/litellm/proxy/example_config_yaml/enterprise_config.yaml
new file mode 100644
index 000000000..337e85177
--- /dev/null
+++ b/litellm/proxy/example_config_yaml/enterprise_config.yaml
@@ -0,0 +1,17 @@
+model_list:
+ - model_name: gpt-4
+   litellm_params:
+     model: openai/fake
+     api_key: fake-key
+     api_base: https://exampleopenaiendpoint-production.up.railway.app/
+     tags: ["teamA"]
+   model_info:
+     id: "team-a-model"
+
+litellm_settings:
+  cache: true
+  callbacks: ["prometheus"]
+
+router_settings:
+  enable_tag_filtering: True # 👈 Key Change
+
diff --git a/tests/basic_proxy_startup_tests/test_basic_proxy_startup.py b/tests/basic_proxy_startup_tests/test_basic_proxy_startup.py
new file mode 100644
index 000000000..e49a01413
--- /dev/null
+++ b/tests/basic_proxy_startup_tests/test_basic_proxy_startup.py
@@ -0,0 +1,44 @@
+import pytest
+import aiohttp
+from typing import Optional
+
+
+@pytest.mark.asyncio
+async def test_health_and_chat_completion():
+    """
+    Test health endpoints and chat completion:
+    1. Check /health/readiness
+    2. Check /health/liveness
+    3. Make a chat completion call
+    """
+    async with aiohttp.ClientSession() as session:
+        # Test readiness endpoint
+        async with session.get("http://0.0.0.0:4000/health/readiness") as response:
+            assert response.status == 200
+            readiness_response = await response.json()
+            assert readiness_response["status"] == "OK"
+
+        # Test liveness endpoint
+        async with session.get("http://0.0.0.0:4000/health/liveness") as response:
+            assert response.status == 200
+            liveness_response = await response.json()
+            assert liveness_response["status"] == "OK"
+
+        # Make a chat completion call
+        url = "http://0.0.0.0:4000/chat/completions"
+        headers = {
+            "Authorization": "Bearer sk-1234",
+            "Content-Type": "application/json",
+        }
+        data = {
+            "model": "gpt-4",
+            "messages": [
+                {"role": "system", "content": "You are a helpful assistant."},
+                {"role": "user", "content": "Hello!"},
+            ],
+        }
+
+        async with session.post(url, headers=headers, json=data) as response:
+            assert response.status == 200
+            completion_response = await response.json()
+            assert "choices" in completion_response
diff --git a/tests/local_testing/test_configs/test_enterprise_config.yaml b/tests/local_testing/test_configs/test_enterprise_config.yaml
deleted file mode 100644
index def055fdc..000000000
--- a/tests/local_testing/test_configs/test_enterprise_config.yaml
+++ /dev/null
@@ -1,26 +0,0 @@
-model_list: 
-  - model_name: Azure OpenAI GPT-4 Canada
-    litellm_params:
-      model: azure/chatgpt-v-2
-      api_base: os.environ/AZURE_API_BASE
-      api_key: os.environ/AZURE_API_KEY
-      api_version: "2023-07-01-preview"
-    model_info:
-      mode: chat
-      input_cost_per_token: 0.0002
-      id: gm
-  - model_name: azure-embedding-model
-    litellm_params:
-      model: azure/azure-embedding-model
-      api_base: os.environ/AZURE_API_BASE
-      api_key: os.environ/AZURE_API_KEY
-      api_version: "2023-07-01-preview"
-    model_info:
-      mode: embedding
-      input_cost_per_token: 0.002
-      id: hello
-
-litellm_settings:
-  drop_params: True
-  set_verbose: True
-  callbacks: ["prometheus", "gcs_bucket"]
\ No newline at end of file