diff --git a/holmes/core/robusta_ai.py b/holmes/core/robusta_ai.py
index dd53315f..eb4883e2 100644
--- a/holmes/core/robusta_ai.py
+++ b/holmes/core/robusta_ai.py
@@ -1,14 +1,16 @@
-# TODO finish refactor
 import logging
 
 import requests
-from fastapi import HTTPException
 
 from holmes.core.runbooks import RunbookManager
-from holmes.core.tool_calling_llm import BaseIssueInvestigator, BaseToolCallingLLM, LLMResult
+from holmes.core.tool_calling_llm import BaseIssueInvestigator, BaseToolCallingLLM, LLMError, LLMResult
 from holmes.utils.auth import SessionManager
 
 
+class RobustaAICallError(LLMError):
+    pass
+
+
 class RobustaAIToolCallingLLM(BaseToolCallingLLM):
     def __init__(self):
         raise NotImplementedError("Robusta AI tool calling LLM is not supported yet")
@@ -27,12 +29,18 @@ def call(self, system_prompt: str, user_prompt: str) -> LLMResult:
 
         payload = {
             "auth": {"account_id": auth_token.account_id, "token": auth_token.token},
-            "system_message": system_prompt,
-            "user_message": user_prompt,
-# TODO
-#            "model": request.model,
+            "body": {
+                "system_message": system_prompt,
+                "user_message": user_prompt,
+# TODO?
+#                "model": request.model,
+            },
         }
-        resp = requests.post(self.base_url + "/api/ai", json=payload)
+        try:
+            resp = requests.post(f"{self.base_url}/api/ai", json=payload)
+        except:
+            logging.exception("Robusta AI API call failed")
+            raise RobustaAICallError("Robusta AI API call failed")
         if resp.status_code == 401:
             self.session_manager.invalidate_token(auth_token)
             # Attempt auth again using a fresh token
@@ -44,6 +52,8 @@ def call(self, system_prompt: str, user_prompt: str) -> LLMResult:
                 logging.error(
                     f"Failed to reauth with Robusta AI. Response status {resp.status_code}, content: {resp.text}"
                 )
-                raise HTTPException(status_code=400, detail="Unable to auth with Robusta AI")
-        # TODO LLMResult
-        return resp.json()
+                raise RobustaAICallError("Unable to auth with Robusta AI")
+        resp_data = resp.json()
+        if not resp_data["success"]:
+            raise RobustaAICallError("Robusta AI API call failed")
+        return LLMResult(result=resp_data["msg"], prompt=user_prompt)
diff --git a/holmes/core/tool_calling_llm.py b/holmes/core/tool_calling_llm.py
index cb64c06e..09c2f8db 100644
--- a/holmes/core/tool_calling_llm.py
+++ b/holmes/core/tool_calling_llm.py
@@ -15,6 +15,10 @@
 from holmes.core.tools import YAMLToolExecutor
 
 
+class LLMError(Exception):
+    pass
+
+
 class ToolCallResult(BaseModel):
     tool_name: str
     description: str
diff --git a/server.py b/server.py
index f254bb1f..70259586 100644
--- a/server.py
+++ b/server.py
@@ -15,7 +15,7 @@
 
 import colorlog
 import uvicorn
-from fastapi import FastAPI
+from fastapi import FastAPI, HTTPException
 from rich.console import Console
 
 from holmes.common.env_vars import ALLOWED_TOOLSETS, HOLMES_HOST, HOLMES_PORT
@@ -24,6 +24,7 @@
 from holmes.core.provider import LLMProviderFactory
 from holmes.core.server_models import InvestigateContext, InvestigateRequest
 from holmes.core.supabase_dal import SupabaseDal
+from holmes.core.tool_calling_llm import LLMError
 from holmes.plugins.prompts import load_prompt
 from holmes.utils.auth import SessionManager
 
@@ -54,7 +55,7 @@ def init_logging():
 if not dal.initialized and config.llm_provider == LLMProviderType.ROBUSTA:
     logging.error("Holmes cannot run without store configuration when the LLM provider is Robusta AI")
     sys.exit(1)
-session_manager = SessionManager(dal, "RelayHolmes")
+session_manager = SessionManager(dal, "AIRelay")
 provider_factory = LLMProviderFactory(config, session_manager)
 app = FastAPI()
 
@@ -88,12 +89,16 @@ def investigate_issue(request: InvestigateRequest):
     investigator = provider_factory.create_issue_investigator(
         console, allowed_toolsets=ALLOWED_TOOLSETS
     )
-    return {
-        "analysis": investigator.investigate(
+    try:
+        result = investigator.investigate(
             issue,
             prompt=load_prompt(request.system_prompt),
             console=console,
         ).result
+    except LLMError as exc:
+        raise HTTPException(status_code=500, detail=f"Error calling the LLM provider: {str(exc)}")
+    return {
+        "analysis": result
     }