diff --git a/letta/agents/letta_agent_v2.py b/letta/agents/letta_agent_v2.py
index acccc530..09a02be3 100644
--- a/letta/agents/letta_agent_v2.py
+++ b/letta/agents/letta_agent_v2.py
@@ -306,7 +306,7 @@ class LettaAgentV2(BaseAgentV2):
                 )
 
         except:
-            if self.stop_reason:
+            if self.stop_reason and not first_chunk:
                 yield f"data: {self.stop_reason.model_dump_json()}\n\n"
             raise
 
diff --git a/letta/server/rest_api/app.py b/letta/server/rest_api/app.py
index 853b8096..25f6a886 100644
--- a/letta/server/rest_api/app.py
+++ b/letta/server/rest_api/app.py
@@ -17,7 +17,15 @@ from starlette.middleware.cors import CORSMiddleware
 from letta.__init__ import __version__ as letta_version
 from letta.agents.exceptions import IncompatibleAgentType
 from letta.constants import ADMIN_PREFIX, API_PREFIX, OPENAI_API_PREFIX
-from letta.errors import BedrockPermissionError, LettaAgentNotFoundError, LettaUserNotFoundError
+from letta.errors import (
+    BedrockPermissionError,
+    LettaAgentNotFoundError,
+    LettaUserNotFoundError,
+    LLMAuthenticationError,
+    LLMError,
+    LLMRateLimitError,
+    LLMTimeoutError,
+)
 from letta.helpers.pinecone_utils import get_pinecone_indices, should_use_pinecone, upsert_pinecone_indices
 from letta.jobs.scheduler import start_scheduler_with_leader_election
 from letta.log import get_logger
@@ -276,6 +284,58 @@ def create_application() -> "FastAPI":
             },
         )
 
+    @app.exception_handler(LLMTimeoutError)
+    async def llm_timeout_error_handler(request: Request, exc: LLMTimeoutError):
+        return JSONResponse(
+            status_code=504,
+            content={
+                "error": {
+                    "type": "llm_timeout",
+                    "message": "The LLM request timed out. Please try again.",
+                    "detail": str(exc),
+                }
+            },
+        )
+
+    @app.exception_handler(LLMRateLimitError)
+    async def llm_rate_limit_error_handler(request: Request, exc: LLMRateLimitError):
+        return JSONResponse(
+            status_code=429,
+            content={
+                "error": {
+                    "type": "llm_rate_limit",
+                    "message": "Rate limit exceeded for LLM model provider. Please wait before making another request.",
+                    "detail": str(exc),
+                }
+            },
+        )
+
+    @app.exception_handler(LLMAuthenticationError)
+    async def llm_auth_error_handler(request: Request, exc: LLMAuthenticationError):
+        return JSONResponse(
+            status_code=401,
+            content={
+                "error": {
+                    "type": "llm_authentication",
+                    "message": "Authentication failed with the LLM model provider.",
+                    "detail": str(exc),
+                }
+            },
+        )
+
+    @app.exception_handler(LLMError)
+    async def llm_error_handler(request: Request, exc: LLMError):
+        return JSONResponse(
+            status_code=502,
+            content={
+                "error": {
+                    "type": "llm_error",
+                    "message": "An error occurred with the LLM request.",
+                    "detail": str(exc),
+                }
+            },
+        )
+
     settings.cors_origins.append("https://app.letta.com")
 
     if (os.getenv("LETTA_SERVER_SECURE") == "true") or "--secure" in sys.argv:
diff --git a/letta/server/rest_api/routers/v1/agents.py b/letta/server/rest_api/routers/v1/agents.py
index bccd68e8..8bda580d 100644
--- a/letta/server/rest_api/routers/v1/agents.py
+++ b/letta/server/rest_api/routers/v1/agents.py
@@ -1316,15 +1316,52 @@ async def send_message_streaming(
     try:
         if agent_eligible and model_compatible:
             agent_loop = AgentLoop.load(agent_state=agent, actor=actor)
-            raw_stream = agent_loop.stream(
-                input_messages=request.messages,
-                max_steps=request.max_steps,
-                stream_tokens=request.stream_tokens and model_compatible_token_streaming,
-                run_id=run.id if run else None,
-                use_assistant_message=request.use_assistant_message,
-                request_start_timestamp_ns=request_start_timestamp_ns,
-                include_return_message_types=request.include_return_message_types,
-            )
+
+            async def error_aware_stream():
+                """Stream that handles early LLM errors gracefully in streaming format."""
+                from letta.errors import LLMAuthenticationError, LLMError, LLMRateLimitError, LLMTimeoutError
+
+                try:
+                    stream = agent_loop.stream(
+                        input_messages=request.messages,
+                        max_steps=request.max_steps,
+                        stream_tokens=request.stream_tokens and model_compatible_token_streaming,
+                        run_id=run.id if run else None,
+                        use_assistant_message=request.use_assistant_message,
+                        request_start_timestamp_ns=request_start_timestamp_ns,
+                        include_return_message_types=request.include_return_message_types,
+                    )
+                    async for chunk in stream:
+                        yield chunk
+
+                except LLMTimeoutError as e:
+                    error_data = {
+                        "error": {"type": "llm_timeout", "message": "The LLM request timed out. Please try again.", "detail": str(e)}
+                    }
+                    yield (f"data: {json.dumps(error_data)}\n\n", 504)
+                except LLMRateLimitError as e:
+                    error_data = {
+                        "error": {
+                            "type": "llm_rate_limit",
+                            "message": "Rate limit exceeded for LLM model provider. Please wait before making another request.",
+                            "detail": str(e),
+                        }
+                    }
+                    yield (f"data: {json.dumps(error_data)}\n\n", 429)
+                except LLMAuthenticationError as e:
+                    error_data = {
+                        "error": {
+                            "type": "llm_authentication",
+                            "message": "Authentication failed with the LLM model provider.",
+                            "detail": str(e),
+                        }
+                    }
+                    yield (f"data: {json.dumps(error_data)}\n\n", 401)
+                except LLMError as e:
+                    error_data = {"error": {"type": "llm_error", "message": "An error occurred with the LLM request.", "detail": str(e)}}
+                    yield (f"data: {json.dumps(error_data)}\n\n", 502)
+
+            raw_stream = error_aware_stream()
 
             from letta.server.rest_api.streaming_response import StreamingResponseWithStatusCode, add_keepalive_to_stream