diff --git a/litellm/proxy/proxy_server.py b/litellm/proxy/proxy_server.py
index 0503d2aad..471e26d3d 100644
--- a/litellm/proxy/proxy_server.py
+++ b/litellm/proxy/proxy_server.py
@@ -370,7 +370,7 @@ async def user_api_key_auth(
                     # Token exists but is expired.
                     raise HTTPException(
                         status_code=status.HTTP_403_FORBIDDEN,
-                        detail="expired user key",
+                        detail=f"Authentication Error - Expired Key. Key Expiry time {expiry_time} and current time {current_time}",
                     )
 
             # Token passed all checks
diff --git a/litellm/proxy/utils.py b/litellm/proxy/utils.py
index 80c05e78d..ae4aebad5 100644
--- a/litellm/proxy/utils.py
+++ b/litellm/proxy/utils.py
@@ -7,10 +7,12 @@ from litellm.proxy.hooks.parallel_request_limiter import MaxParallelRequestsHand
 from litellm.proxy.hooks.max_budget_limiter import MaxBudgetLimiter
 from litellm.integrations.custom_logger import CustomLogger
 from litellm.proxy.db.base_client import CustomDB
+from litellm._logging import verbose_proxy_logger
 from fastapi import HTTPException, status
 import smtplib
 from email.mime.text import MIMEText
 from email.mime.multipart import MIMEMultipart
+from datetime import datetime
 
 
 def print_verbose(print_statement):
@@ -375,13 +377,14 @@ class PrismaClient:
                 print_verbose(f"PrismaClient: response={response}")
                 if response is not None:
                     # for prisma we need to cast the expires time to str
-                    response.expires = response.expires.isoformat()
+                    if isinstance(response.expires, datetime):
+                        response.expires = response.expires.isoformat()
                     return response
                 else:
                     # Token does not exist.
                     raise HTTPException(
                         status_code=status.HTTP_401_UNAUTHORIZED,
-                        detail="invalid user key",
+                        detail="Authentication Error: invalid user key - token does not exist",
                     )
             elif user_id is not None:
                 response = await self.db.litellm_usertable.find_unique(  # type: ignore
@@ -559,7 +562,13 @@ class PrismaClient:
     )
     async def connect(self):
         try:
+            verbose_proxy_logger.debug(
+                "PrismaClient: connect() called Attempting to Connect to DB"
+            )
             if self.db.is_connected() == False:
+                verbose_proxy_logger.debug(
+                    "PrismaClient: DB not connected, Attempting to Connect to DB"
+                )
                 await self.db.connect()
         except Exception as e:
             asyncio.create_task(
diff --git a/litellm/tests/test_key_generate_dynamodb.py b/litellm/tests/test_key_generate_dynamodb.py
index 207c8835a..09f699af7 100644
--- a/litellm/tests/test_key_generate_dynamodb.py
+++ b/litellm/tests/test_key_generate_dynamodb.py
@@ -32,16 +32,6 @@ from litellm.proxy.utils import DBClient
 from starlette.datastructures import URL
 
 
-db_args = {
-    "ssl_verify": False,
-    "billing_mode": "PAY_PER_REQUEST",
-    "region_name": "us-west-2",
-}
-custom_db_client = DBClient(
-    custom_db_type="dynamo_db",
-    custom_db_args=db_args,
-)
-
 request_data = {
     "model": "azure-gpt-3.5",
     "messages": [
@@ -50,7 +40,25 @@ request_data = {
 }
 
 
-def test_generate_and_call_with_valid_key():
+@pytest.fixture
+def custom_db_client():
+    # Assuming DBClient is a class that needs to be instantiated
+    db_args = {
+        "ssl_verify": False,
+        "billing_mode": "PAY_PER_REQUEST",
+        "region_name": "us-west-2",
+    }
+    custom_db_client = DBClient(
+        custom_db_type="dynamo_db",
+        custom_db_args=db_args,
+    )
+    # Reset litellm.proxy.proxy_server.prisma_client to None
+    litellm.proxy.proxy_server.prisma_client = None
+
+    return custom_db_client
+
+
+def test_generate_and_call_with_valid_key(custom_db_client):
     # 1. Generate a Key, and use it to make a call
     setattr(litellm.proxy.proxy_server, "custom_db_client", custom_db_client)
     setattr(litellm.proxy.proxy_server, "master_key", "sk-1234")
@@ -76,7 +84,7 @@ def test_generate_and_call_with_valid_key():
         pytest.fail(f"An exception occurred - {str(e)}")
 
 
-def test_call_with_invalid_key():
+def test_call_with_invalid_key(custom_db_client):
     # 2. Make a call with invalid key, expect it to fail
     setattr(litellm.proxy.proxy_server, "custom_db_client", custom_db_client)
     setattr(litellm.proxy.proxy_server, "master_key", "sk-1234")
@@ -101,7 +109,7 @@ def test_call_with_invalid_key():
         pass
 
 
-def test_call_with_invalid_model():
+def test_call_with_invalid_model(custom_db_client):
     # 3. Make a call to a key with an invalid model - expect to fail
     setattr(litellm.proxy.proxy_server, "custom_db_client", custom_db_client)
     setattr(litellm.proxy.proxy_server, "master_key", "sk-1234")
@@ -136,7 +144,7 @@ def test_call_with_invalid_model():
         pass
 
 
-def test_call_with_valid_model():
+def test_call_with_valid_model(custom_db_client):
     # 4. Make a call to a key with a valid model - expect to pass
     setattr(litellm.proxy.proxy_server, "custom_db_client", custom_db_client)
     setattr(litellm.proxy.proxy_server, "master_key", "sk-1234")
@@ -167,7 +175,7 @@ def test_call_with_valid_model():
         pytest.fail(f"An exception occurred - {str(e)}")
 
 
-def test_call_with_key_over_budget():
+def test_call_with_key_over_budget(custom_db_client):
     # 5. Make a call with a key over budget, expect to fail
     setattr(litellm.proxy.proxy_server, "custom_db_client", custom_db_client)
     setattr(litellm.proxy.proxy_server, "master_key", "sk-1234")
@@ -233,7 +241,7 @@ def test_call_with_key_over_budget():
         print(vars(e))
 
 
-def test_call_with_key_over_budget_stream():
+def test_call_with_key_over_budget_stream(custom_db_client):
     # 6. Make a call with a key over budget, expect to fail
     setattr(litellm.proxy.proxy_server, "custom_db_client", custom_db_client)
     setattr(litellm.proxy.proxy_server, "master_key", "sk-1234")
diff --git a/litellm/tests/test_key_generate_prisma.py b/litellm/tests/test_key_generate_prisma.py
new file mode 100644
index 000000000..7a9e2bddc
--- /dev/null
+++ b/litellm/tests/test_key_generate_prisma.py
@@ -0,0 +1,391 @@
+# Test the following scenarios:
+# 1. Generate a Key, and use it to make a call
+# 2. Make a call with invalid key, expect it to fail
+# 3. Make a call to a key with invalid model - expect to fail
+# 4. Make a call to a key with valid model - expect to pass
+# 5. Make a call with key over budget, expect to fail
+# 6. Make a streaming chat/completions call with key over budget, expect to fail
+# 7. Make a call with an key that never expires, expect to pass
+# 8. Make a call with an expired key, expect to fail
+
+
+# function to call to generate key - async def new_user(data: NewUserRequest):
+# function to validate a request - async def user_auth(request: Request):
+
+import sys, os
+import traceback
+from dotenv import load_dotenv
+from fastapi import Request
+
+load_dotenv()
+import os, io
+
+# this file is to test litellm/proxy
+
+sys.path.insert(
+    0, os.path.abspath("../..")
+)  # Adds the parent directory to the system path
+import pytest, logging, asyncio
+import litellm, asyncio
+from litellm.proxy.proxy_server import new_user, user_api_key_auth, user_update
+from litellm.proxy.utils import PrismaClient, ProxyLogging
+from litellm._logging import verbose_proxy_logger
+
+verbose_proxy_logger.setLevel(level=logging.DEBUG)
+
+from litellm.proxy._types import NewUserRequest, DynamoDBArgs
+from litellm.proxy.utils import DBClient
+from starlette.datastructures import URL
+from litellm.caching import DualCache
+
+proxy_logging_obj = ProxyLogging(user_api_key_cache=DualCache())
+
+
+request_data = {
+    "model": "azure-gpt-3.5",
+    "messages": [
+        {"role": "user", "content": "this is my new test. respond in 50 lines"}
+    ],
+}
+
+
+@pytest.fixture
+def prisma_client():
+    # Assuming DBClient is a class that needs to be instantiated
+    prisma_client = PrismaClient(
+        database_url=os.environ["DATABASE_URL"], proxy_logging_obj=proxy_logging_obj
+    )
+
+    # Reset litellm.proxy.proxy_server.prisma_client to None
+    litellm.proxy.proxy_server.custom_db_client = None
+
+    return prisma_client
+
+
+def test_generate_and_call_with_valid_key(prisma_client):
+    # 1. Generate a Key, and use it to make a call
+
+    print("prisma client=", prisma_client)
+
+    setattr(litellm.proxy.proxy_server, "prisma_client", prisma_client)
+    setattr(litellm.proxy.proxy_server, "master_key", "sk-1234")
+    try:
+
+        async def test():
+            await litellm.proxy.proxy_server.prisma_client.connect()
+            request = NewUserRequest()
+            key = await new_user(request)
+            print(key)
+
+            generated_key = key.key
+            bearer_token = "Bearer " + generated_key
+
+            request = Request(scope={"type": "http"})
+            request._url = URL(url="/chat/completions")
+
+            # use generated key to auth in
+            result = await user_api_key_auth(request=request, api_key=bearer_token)
+            print("result from user auth with new key", result)
+
+        asyncio.run(test())
+    except Exception as e:
+        pytest.fail(f"An exception occurred - {str(e)}")
+
+
+def test_call_with_invalid_key(prisma_client):
+    # 2. Make a call with invalid key, expect it to fail
+    setattr(litellm.proxy.proxy_server, "prisma_client", prisma_client)
+    setattr(litellm.proxy.proxy_server, "master_key", "sk-1234")
+    try:
+
+        async def test():
+            await litellm.proxy.proxy_server.prisma_client.connect()
+            generated_key = "bad-key"
+            bearer_token = "Bearer " + generated_key
+
+            request = Request(scope={"type": "http"}, receive=None)
+            request._url = URL(url="/chat/completions")
+
+            # use generated key to auth in
+            result = await user_api_key_auth(request=request, api_key=bearer_token)
+            print("got result", result)
+            pytest.fail(f"This should have failed!. IT's an invalid key")
+
+        asyncio.run(test())
+    except Exception as e:
+        print("Got Exception", e)
+        print(e.detail)
+        assert "Authentication Error" in e.detail
+        pass
+
+
+def test_call_with_invalid_model(prisma_client):
+    # 3. Make a call to a key with an invalid model - expect to fail
+    setattr(litellm.proxy.proxy_server, "prisma_client", prisma_client)
+    setattr(litellm.proxy.proxy_server, "master_key", "sk-1234")
+    try:
+
+        async def test():
+            await litellm.proxy.proxy_server.prisma_client.connect()
+            request = NewUserRequest(models=["mistral"])
+            key = await new_user(request)
+            print(key)
+
+            generated_key = key.key
+            bearer_token = "Bearer " + generated_key
+
+            request = Request(scope={"type": "http"})
+            request._url = URL(url="/chat/completions")
+
+            async def return_body():
+                return b'{"model": "gemini-pro-vision"}'
+
+            request.body = return_body
+
+            # use generated key to auth in
+            result = await user_api_key_auth(request=request, api_key=bearer_token)
+            pytest.fail(f"This should have failed!. IT's an invalid model")
+
+        asyncio.run(test())
+    except Exception as e:
+        assert (
+            e.detail
+            == "Authentication Error, API Key not allowed to access model. This token can only access models=['mistral']. Tried to access gemini-pro-vision"
+        )
+        pass
+
+
+def test_call_with_valid_model(prisma_client):
+    # 4. Make a call to a key with a valid model - expect to pass
+    setattr(litellm.proxy.proxy_server, "prisma_client", prisma_client)
+    setattr(litellm.proxy.proxy_server, "master_key", "sk-1234")
+    try:
+
+        async def test():
+            await litellm.proxy.proxy_server.prisma_client.connect()
+            request = NewUserRequest(models=["mistral"])
+            key = await new_user(request)
+            print(key)
+
+            generated_key = key.key
+            bearer_token = "Bearer " + generated_key
+
+            request = Request(scope={"type": "http"})
+            request._url = URL(url="/chat/completions")
+
+            async def return_body():
+                return b'{"model": "mistral"}'
+
+            request.body = return_body
+
+            # use generated key to auth in
+            result = await user_api_key_auth(request=request, api_key=bearer_token)
+            print("result from user auth with new key", result)
+
+        asyncio.run(test())
+    except Exception as e:
+        pytest.fail(f"An exception occurred - {str(e)}")
+
+
+def test_call_with_key_over_budget(prisma_client):
+    # 5. Make a call with a key over budget, expect to fail
+    setattr(litellm.proxy.proxy_server, "prisma_client", prisma_client)
+    setattr(litellm.proxy.proxy_server, "master_key", "sk-1234")
+    try:
+
+        async def test():
+            await litellm.proxy.proxy_server.prisma_client.connect()
+            request = NewUserRequest(max_budget=0.00001)
+            key = await new_user(request)
+            print(key)
+
+            generated_key = key.key
+            user_id = key.user_id
+            bearer_token = "Bearer " + generated_key
+
+            request = Request(scope={"type": "http"})
+            request._url = URL(url="/chat/completions")
+
+            # use generated key to auth in
+            result = await user_api_key_auth(request=request, api_key=bearer_token)
+            print("result from user auth with new key", result)
+
+            # update spend using track_cost callback, make 2nd request, it should fail
+            from litellm.proxy.proxy_server import track_cost_callback
+            from litellm import ModelResponse, Choices, Message, Usage
+
+            resp = ModelResponse(
+                id="chatcmpl-e41836bb-bb8b-4df2-8e70-8f3e160155ac",
+                choices=[
+                    Choices(
+                        finish_reason=None,
+                        index=0,
+                        message=Message(
+                            content=" Sure! Here is a short poem about the sky:\n\nA canvas of blue, a",
+                            role="assistant",
+                        ),
+                    )
+                ],
+                model="gpt-35-turbo",  # azure always has model written like this
+                usage=Usage(prompt_tokens=210, completion_tokens=200, total_tokens=410),
+            )
+            await track_cost_callback(
+                kwargs={
+                    "stream": False,
+                    "litellm_params": {
+                        "metadata": {
+                            "user_api_key": generated_key,
+                            "user_api_key_user_id": user_id,
+                        }
+                    },
+                },
+                completion_response=resp,
+            )
+
+            # use generated key to auth in
+            result = await user_api_key_auth(request=request, api_key=bearer_token)
+            print("result from user auth with new key", result)
+            pytest.fail(f"This should have failed!. They key crossed it's budget")
+
+        asyncio.run(test())
+    except Exception as e:
+        error_detail = e.detail
+        assert "Authentication Error, ExceededBudget:" in error_detail
+        print(vars(e))
+
+
+def test_call_with_key_over_budget_stream(prisma_client):
+    # 6. Make a call with a key over budget, expect to fail
+    setattr(litellm.proxy.proxy_server, "prisma_client", prisma_client)
+    setattr(litellm.proxy.proxy_server, "master_key", "sk-1234")
+    from litellm._logging import verbose_proxy_logger
+    import logging
+
+    litellm.set_verbose = True
+    verbose_proxy_logger.setLevel(logging.DEBUG)
+    try:
+
+        async def test():
+            await litellm.proxy.proxy_server.prisma_client.connect()
+            request = NewUserRequest(max_budget=0.00001)
+            key = await new_user(request)
+            print(key)
+
+            generated_key = key.key
+            user_id = key.user_id
+            bearer_token = "Bearer " + generated_key
+
+            request = Request(scope={"type": "http"})
+            request._url = URL(url="/chat/completions")
+
+            # use generated key to auth in
+            result = await user_api_key_auth(request=request, api_key=bearer_token)
+            print("result from user auth with new key", result)
+
+            # update spend using track_cost callback, make 2nd request, it should fail
+            from litellm.proxy.proxy_server import track_cost_callback
+            from litellm import ModelResponse, Choices, Message, Usage
+
+            resp = ModelResponse(
+                id="chatcmpl-e41836bb-bb8b-4df2-8e70-8f3e160155ac",
+                choices=[
+                    Choices(
+                        finish_reason=None,
+                        index=0,
+                        message=Message(
+                            content=" Sure! Here is a short poem about the sky:\n\nA canvas of blue, a",
+                            role="assistant",
+                        ),
+                    )
+                ],
+                model="gpt-35-turbo",  # azure always has model written like this
+                usage=Usage(prompt_tokens=210, completion_tokens=200, total_tokens=410),
+            )
+            await track_cost_callback(
+                kwargs={
+                    "stream": True,
+                    "complete_streaming_response": resp,
+                    "litellm_params": {
+                        "metadata": {
+                            "user_api_key": generated_key,
+                            "user_api_key_user_id": user_id,
+                        }
+                    },
+                },
+                completion_response=ModelResponse(),
+            )
+
+            # use generated key to auth in
+            result = await user_api_key_auth(request=request, api_key=bearer_token)
+            print("result from user auth with new key", result)
+            pytest.fail(f"This should have failed!. They key crossed it's budget")
+
+        asyncio.run(test())
+    except Exception as e:
+        error_detail = e.detail
+        assert "Authentication Error, ExceededBudget:" in error_detail
+        print(vars(e))
+
+
+def test_generate_and_call_with_valid_key_never_expires(prisma_client):
+    # 7. Make a call with an key that never expires, expect to pass
+
+    print("prisma client=", prisma_client)
+
+    setattr(litellm.proxy.proxy_server, "prisma_client", prisma_client)
+    setattr(litellm.proxy.proxy_server, "master_key", "sk-1234")
+    try:
+
+        async def test():
+            await litellm.proxy.proxy_server.prisma_client.connect()
+            request = NewUserRequest(duration=None)
+            key = await new_user(request)
+            print(key)
+
+            generated_key = key.key
+            bearer_token = "Bearer " + generated_key
+
+            request = Request(scope={"type": "http"})
+            request._url = URL(url="/chat/completions")
+
+            # use generated key to auth in
+            result = await user_api_key_auth(request=request, api_key=bearer_token)
+            print("result from user auth with new key", result)
+
+        asyncio.run(test())
+    except Exception as e:
+        pytest.fail(f"An exception occurred - {str(e)}")
+
+
+def test_generate_and_call_with_expired_key(prisma_client):
+    # 8. Make a call with an expired key, expect to fail
+
+    print("prisma client=", prisma_client)
+
+    setattr(litellm.proxy.proxy_server, "prisma_client", prisma_client)
+    setattr(litellm.proxy.proxy_server, "master_key", "sk-1234")
+    try:
+
+        async def test():
+            await litellm.proxy.proxy_server.prisma_client.connect()
+            request = NewUserRequest(duration="0s")
+            key = await new_user(request)
+            print(key)
+
+            generated_key = key.key
+            bearer_token = "Bearer " + generated_key
+
+            request = Request(scope={"type": "http"})
+            request._url = URL(url="/chat/completions")
+
+            # use generated key to auth in
+            result = await user_api_key_auth(request=request, api_key=bearer_token)
+            print("result from user auth with new key", result)
+            pytest.fail(f"This should have failed!. IT's an expired key")
+
+        asyncio.run(test())
+    except Exception as e:
+        print("Got Exception", e)
+        print(e.detail)
+        assert "Authentication Error" in e.detail
+        pass