letta-nightly 0.11.6.dev20250902104140__py3-none-any.whl → 0.11.7.dev20250904045700__py3-none-any.whl

letta/agents/letta_agent.py

@@ -40,7 +40,7 @@ from letta.schemas.letta_message_content import OmittedReasoningContent, Reasoni
 from letta.schemas.letta_response import LettaResponse
 from letta.schemas.letta_stop_reason import LettaStopReason, StopReasonType
 from letta.schemas.llm_config import LLMConfig
-from letta.schemas.message import Message, MessageCreate
+from letta.schemas.message import Message, MessageCreateBase
 from letta.schemas.openai.chat_completion_response import ToolCall, UsageStatistics
 from letta.schemas.provider_trace import ProviderTraceCreate
 from letta.schemas.step import StepProgression
@@ -48,7 +48,7 @@ from letta.schemas.step_metrics import StepMetrics
 from letta.schemas.tool_execution_result import ToolExecutionResult
 from letta.schemas.usage import LettaUsageStatistics
 from letta.schemas.user import User
-from letta.server.rest_api.utils import create_letta_messages_from_llm_response
+from letta.server.rest_api.utils import create_approval_request_message_from_llm_response, create_letta_messages_from_llm_response
 from letta.services.agent_manager import AgentManager
 from letta.services.block_manager import BlockManager
 from letta.services.helpers.tool_parser_helper import runtime_override_tool_json_schema
@@ -164,7 +164,7 @@ class LettaAgent(BaseAgent):
     @trace_method
     async def step(
         self,
-        input_messages: list[MessageCreate],
+        input_messages: list[MessageCreateBase],
         max_steps: int = DEFAULT_MAX_STEPS,
         run_id: str | None = None,
         use_assistant_message: bool = True,
@@ -203,7 +203,7 @@ class LettaAgent(BaseAgent):
     @trace_method
     async def step_stream_no_tokens(
         self,
-        input_messages: list[MessageCreate],
+        input_messages: list[MessageCreateBase],
         max_steps: int = DEFAULT_MAX_STEPS,
         use_assistant_message: bool = True,
         request_start_timestamp_ns: int | None = None,
@@ -218,6 +218,7 @@ class LettaAgent(BaseAgent):
             input_messages, agent_state, self.message_manager, self.actor
         )
         initial_messages = new_in_context_messages
+        in_context_messages = current_in_context_messages
         tool_rules_solver = ToolRulesSolver(agent_state.tool_rules)
         llm_client = LLMClient.create(
             provider_type=agent_state.llm_config.model_endpoint_type,
@@ -233,137 +234,34 @@ class LettaAgent(BaseAgent):
         request_span.set_attributes({f"llm_config.{k}": v for k, v in agent_state.llm_config.model_dump().items() if v is not None})
 
         for i in range(max_steps):
-            # Check for job cancellation at the start of each step
-            if await self._check_run_cancellation():
-                stop_reason = LettaStopReason(stop_reason=StopReasonType.cancelled.value)
-                logger.info(f"Agent execution cancelled for run {self.current_run_id}")
-                yield f"data: {stop_reason.model_dump_json()}\n\n"
-                break
-
-            step_id = generate_step_id()
-            step_start = get_utc_timestamp_ns()
-            agent_step_span = tracer.start_span("agent_step", start_time=step_start)
-            agent_step_span.set_attributes({"step_id": step_id})
-
-            step_progression = StepProgression.START
-            should_continue = False
-            step_metrics = StepMetrics(id=step_id)  # Initialize metrics tracking
-
-            # Create step early with PENDING status
-            logged_step = await self.step_manager.log_step_async(
-                actor=self.actor,
-                agent_id=agent_state.id,
-                provider_name=agent_state.llm_config.model_endpoint_type,
-                provider_category=agent_state.llm_config.provider_category or "base",
-                model=agent_state.llm_config.model,
-                model_endpoint=agent_state.llm_config.model_endpoint,
-                context_window_limit=agent_state.llm_config.context_window,
-                usage=UsageStatistics(completion_tokens=0, prompt_tokens=0, total_tokens=0),
-                provider_id=None,
-                job_id=self.current_run_id if self.current_run_id else None,
-                step_id=step_id,
-                project_id=agent_state.project_id,
-                status=StepStatus.PENDING,
-            )
-            # Only use step_id in messages if step was actually created
-            effective_step_id = step_id if logged_step else None
-
-            try:
-                request_data, response_data, current_in_context_messages, new_in_context_messages, valid_tool_names = (
-                    await self._build_and_request_from_llm(
-                        current_in_context_messages,
-                        new_in_context_messages,
-                        agent_state,
-                        llm_client,
-                        tool_rules_solver,
-                        agent_step_span,
-                        step_metrics,
-                    )
-                )
-                in_context_messages = current_in_context_messages + new_in_context_messages
-
-                step_progression = StepProgression.RESPONSE_RECEIVED
-                log_event("agent.stream_no_tokens.llm_response.received")  # [3^]
-
-                response = llm_client.convert_response_to_chat_completion(response_data, in_context_messages, agent_state.llm_config)
-
-                # update usage
-                usage.step_count += 1
-                usage.completion_tokens += response.usage.completion_tokens
-                usage.prompt_tokens += response.usage.prompt_tokens
-                usage.total_tokens += response.usage.total_tokens
-                MetricRegistry().message_output_tokens.record(
-                    response.usage.completion_tokens, dict(get_ctx_attributes(), **{"model.name": agent_state.llm_config.model})
-                )
-
-                if not response.choices[0].message.tool_calls:
-                    stop_reason = LettaStopReason(stop_reason=StopReasonType.no_tool_call.value)
-                    raise ValueError("No tool calls found in response, model must make a tool call")
-                tool_call = response.choices[0].message.tool_calls[0]
-                if response.choices[0].message.reasoning_content:
-                    reasoning = [
-                        ReasoningContent(
-                            reasoning=response.choices[0].message.reasoning_content,
-                            is_native=True,
-                            signature=response.choices[0].message.reasoning_content_signature,
-                        )
-                    ]
-                elif response.choices[0].message.omitted_reasoning_content:
-                    reasoning = [OmittedReasoningContent()]
-                elif response.choices[0].message.content:
-                    reasoning = [TextContent(text=response.choices[0].message.content)]  # reasoning placed into content for legacy reasons
-                else:
-                    self.logger.info("No reasoning content found.")
-                    reasoning = None
-
+            if in_context_messages[-1].role == "approval":
+                approval_request_message = in_context_messages[-1]
+                step_metrics = await self.step_manager.get_step_metrics_async(step_id=approval_request_message.step_id, actor=self.actor)
                 persisted_messages, should_continue, stop_reason = await self._handle_ai_response(
-                    tool_call,
-                    valid_tool_names,
+                    approval_request_message.tool_calls[0],
+                    [],  # TODO: update this
                     agent_state,
                     tool_rules_solver,
-                    response.usage,
-                    reasoning_content=reasoning,
-                    step_id=effective_step_id,
+                    usage,
+                    reasoning_content=approval_request_message.content,
+                    step_id=approval_request_message.step_id,
                     initial_messages=initial_messages,
-                    agent_step_span=agent_step_span,
                     is_final_step=(i == max_steps - 1),
                     step_metrics=step_metrics,
+                    run_id=self.current_run_id,
+                    is_approval=input_messages[0].approve,
+                    is_denial=input_messages[0].approve == False,
+                    denial_reason=input_messages[0].reason,
                 )
-                step_progression = StepProgression.STEP_LOGGED
-
-                # Update step with actual usage now that we have it (if step was created)
-                if logged_step:
-                    await self.step_manager.update_step_success_async(self.actor, step_id, response.usage, stop_reason)
-
-                # TODO (cliandy): handle message contexts with larger refactor and dedupe logic
                 new_message_idx = len(initial_messages) if initial_messages else 0
                 self.response_messages.extend(persisted_messages[new_message_idx:])
                 new_in_context_messages.extend(persisted_messages[new_message_idx:])
                 initial_messages = None
-                log_event("agent.stream_no_tokens.llm_response.processed")  # [4^]
-
-                # log step time
-                now = get_utc_timestamp_ns()
-                step_ns = now - step_start
-                agent_step_span.add_event(name="step_ms", attributes={"duration_ms": ns_to_ms(step_ns)})
-                agent_step_span.end()
-
-                # Log LLM Trace
-                if settings.track_provider_trace:
-                    await self.telemetry_manager.create_provider_trace_async(
-                        actor=self.actor,
-                        provider_trace_create=ProviderTraceCreate(
-                            request_json=request_data,
-                            response_json=response_data,
-                            step_id=step_id,  # Use original step_id for telemetry
-                            organization_id=self.actor.organization_id,
-                        ),
-                    )
-                    step_progression = StepProgression.LOGGED_TRACE
+                in_context_messages = current_in_context_messages + new_in_context_messages
 
                 # stream step
                 # TODO: improve TTFT
-                filter_user_messages = [m for m in persisted_messages if m.role != "user"]
+                filter_user_messages = [m for m in persisted_messages if m.role != "user" and m.role != "approval"]
                 letta_messages = Message.to_letta_messages_from_list(
                     filter_user_messages, use_assistant_message=use_assistant_message, reverse=False
                 )
@@ -371,104 +269,262 @@ class LettaAgent(BaseAgent):
                 for message in letta_messages:
                     if include_return_message_types is None or message.message_type in include_return_message_types:
                         yield f"data: {message.model_dump_json()}\n\n"
+            else:
+                # Check for job cancellation at the start of each step
+                if await self._check_run_cancellation():
+                    stop_reason = LettaStopReason(stop_reason=StopReasonType.cancelled.value)
+                    logger.info(f"Agent execution cancelled for run {self.current_run_id}")
+                    yield f"data: {stop_reason.model_dump_json()}\n\n"
+                    break
+
+                step_id = generate_step_id()
+                step_start = get_utc_timestamp_ns()
+                agent_step_span = tracer.start_span("agent_step", start_time=step_start)
+                agent_step_span.set_attributes({"step_id": step_id})
+
+                step_progression = StepProgression.START
+                should_continue = False
+                step_metrics = StepMetrics(id=step_id)  # Initialize metrics tracking
+
+                # Create step early with PENDING status
+                logged_step = await self.step_manager.log_step_async(
+                    actor=self.actor,
+                    agent_id=agent_state.id,
+                    provider_name=agent_state.llm_config.model_endpoint_type,
+                    provider_category=agent_state.llm_config.provider_category or "base",
+                    model=agent_state.llm_config.model,
+                    model_endpoint=agent_state.llm_config.model_endpoint,
+                    context_window_limit=agent_state.llm_config.context_window,
+                    usage=UsageStatistics(completion_tokens=0, prompt_tokens=0, total_tokens=0),
+                    provider_id=None,
+                    job_id=self.current_run_id if self.current_run_id else None,
+                    step_id=step_id,
+                    project_id=agent_state.project_id,
+                    status=StepStatus.PENDING,
+                )
+                # Only use step_id in messages if step was actually created
+                effective_step_id = step_id if logged_step else None
+
+                try:
+                    (
+                        request_data,
+                        response_data,
+                        current_in_context_messages,
+                        new_in_context_messages,
+                        valid_tool_names,
+                    ) = await self._build_and_request_from_llm(
+                        current_in_context_messages,
+                        new_in_context_messages,
+                        agent_state,
+                        llm_client,
+                        tool_rules_solver,
+                        agent_step_span,
+                        step_metrics,
+                    )
+                    in_context_messages = current_in_context_messages + new_in_context_messages
 
-                MetricRegistry().step_execution_time_ms_histogram.record(get_utc_timestamp_ns() - step_start, get_ctx_attributes())
-                step_progression = StepProgression.FINISHED
+                    step_progression = StepProgression.RESPONSE_RECEIVED
+                    log_event("agent.stream_no_tokens.llm_response.received")  # [3^]
 
-                # Record step metrics for successful completion
-                if logged_step and step_metrics:
-                    # Set the step_ns that was already calculated
-                    step_metrics.step_ns = step_ns
-                    await self._record_step_metrics(
-                        step_id=step_id,
-                        agent_state=agent_state,
-                        step_metrics=step_metrics,
+                    try:
+                        response = llm_client.convert_response_to_chat_completion(
+                            response_data, in_context_messages, agent_state.llm_config
+                        )
+                    except ValueError as e:
+                        stop_reason = LettaStopReason(stop_reason=StopReasonType.invalid_llm_response.value)
+                        raise e
+
+                    # update usage
+                    usage.step_count += 1
+                    usage.completion_tokens += response.usage.completion_tokens
+                    usage.prompt_tokens += response.usage.prompt_tokens
+                    usage.total_tokens += response.usage.total_tokens
+                    MetricRegistry().message_output_tokens.record(
+                        response.usage.completion_tokens, dict(get_ctx_attributes(), **{"model.name": agent_state.llm_config.model})
                     )
 
-            except Exception as e:
-                # Handle any unexpected errors during step processing
-                self.logger.error(f"Error during step processing: {e}")
-                job_update_metadata = {"error": str(e)}
-
-                # This indicates we failed after we decided to stop stepping, which indicates a bug with our flow.
-                if not stop_reason:
-                    stop_reason = LettaStopReason(stop_reason=StopReasonType.error.value)
-                elif stop_reason.stop_reason in (StopReasonType.end_turn, StopReasonType.max_steps, StopReasonType.tool_rule):
-                    self.logger.error("Error occurred during step processing, with valid stop reason: %s", stop_reason.stop_reason)
-                elif stop_reason.stop_reason not in (StopReasonType.no_tool_call, StopReasonType.invalid_tool_call):
-                    raise ValueError(f"Invalid Stop Reason: {stop_reason}")
-
-                # Send error stop reason to client and re-raise
-                yield f"data: {stop_reason.model_dump_json()}\n\n", 500
-                raise
-
-            # Update step if it needs to be updated
-            finally:
-                if step_progression == StepProgression.FINISHED and should_continue:
-                    continue
-
-                self.logger.debug("Running cleanup for agent loop run: %s", self.current_run_id)
-                self.logger.info("Running final update. Step Progression: %s", step_progression)
-                try:
-                    if step_progression == StepProgression.FINISHED and not should_continue:
-                        # Successfully completed - update with final usage and stop reason
-                        if stop_reason is None:
-                            stop_reason = LettaStopReason(stop_reason=StopReasonType.end_turn.value)
-                        # Note: step already updated with success status after _handle_ai_response
-                        if logged_step:
-                            await self.step_manager.update_step_stop_reason(self.actor, step_id, stop_reason.stop_reason)
-                        break
-
-                    # Handle error cases
-                    if step_progression < StepProgression.STEP_LOGGED:
-                        # Error occurred before step was fully logged
-                        import traceback
-
-                        if logged_step:
-                            await self.step_manager.update_step_error_async(
-                                actor=self.actor,
-                                step_id=step_id,  # Use original step_id for telemetry
-                                error_type=type(e).__name__ if "e" in locals() else "Unknown",
-                                error_message=str(e) if "e" in locals() else "Unknown error",
-                                error_traceback=traceback.format_exc(),
-                                stop_reason=stop_reason,
+                    if not response.choices[0].message.tool_calls:
+                        stop_reason = LettaStopReason(stop_reason=StopReasonType.no_tool_call.value)
+                        raise ValueError("No tool calls found in response, model must make a tool call")
+                    tool_call = response.choices[0].message.tool_calls[0]
+                    if response.choices[0].message.reasoning_content:
+                        reasoning = [
+                            ReasoningContent(
+                                reasoning=response.choices[0].message.reasoning_content,
+                                is_native=True,
+                                signature=response.choices[0].message.reasoning_content_signature,
                             )
-
-                    if step_progression <= StepProgression.RESPONSE_RECEIVED:
-                        # TODO (cliandy): persist response if we get it back
-                        if settings.track_errored_messages and initial_messages:
-                            for message in initial_messages:
-                                message.is_err = True
-                                message.step_id = effective_step_id
-                            await self.message_manager.create_many_messages_async(initial_messages, actor=self.actor)
-                    elif step_progression <= StepProgression.LOGGED_TRACE:
-                        if stop_reason is None:
-                            self.logger.error("Error in step after logging step")
-                            stop_reason = LettaStopReason(stop_reason=StopReasonType.error.value)
-                        if logged_step:
-                            await self.step_manager.update_step_stop_reason(self.actor, step_id, stop_reason.stop_reason)
+                        ]
+                    elif response.choices[0].message.omitted_reasoning_content:
+                        reasoning = [OmittedReasoningContent()]
+                    elif response.choices[0].message.content:
+                        reasoning = [
+                            TextContent(text=response.choices[0].message.content)
+                        ]  # reasoning placed into content for legacy reasons
                     else:
-                        self.logger.error("Invalid StepProgression value")
+                        self.logger.info("No reasoning content found.")
+                        reasoning = None
 
-                    if settings.track_stop_reason:
-                        await self._log_request(request_start_timestamp_ns, request_span, job_update_metadata, is_error=True)
+                    persisted_messages, should_continue, stop_reason = await self._handle_ai_response(
+                        tool_call,
+                        valid_tool_names,
+                        agent_state,
+                        tool_rules_solver,
+                        response.usage,
+                        reasoning_content=reasoning,
+                        step_id=effective_step_id,
+                        initial_messages=initial_messages,
+                        agent_step_span=agent_step_span,
+                        is_final_step=(i == max_steps - 1),
+                        step_metrics=step_metrics,
+                    )
+                    step_progression = StepProgression.STEP_LOGGED
+
+                    # Update step with actual usage now that we have it (if step was created)
+                    if logged_step:
+                        await self.step_manager.update_step_success_async(self.actor, step_id, response.usage, stop_reason)
+
+                    # TODO (cliandy): handle message contexts with larger refactor and dedupe logic
+                    new_message_idx = len(initial_messages) if initial_messages else 0
+                    self.response_messages.extend(persisted_messages[new_message_idx:])
+                    new_in_context_messages.extend(persisted_messages[new_message_idx:])
+                    initial_messages = None
+                    log_event("agent.stream_no_tokens.llm_response.processed")  # [4^]
+
+                    # log step time
+                    now = get_utc_timestamp_ns()
+                    step_ns = now - step_start
+                    agent_step_span.add_event(name="step_ms", attributes={"duration_ms": ns_to_ms(step_ns)})
+                    agent_step_span.end()
+
+                    # Log LLM Trace
+                    if settings.track_provider_trace:
+                        await self.telemetry_manager.create_provider_trace_async(
+                            actor=self.actor,
+                            provider_trace_create=ProviderTraceCreate(
+                                request_json=request_data,
+                                response_json=response_data,
+                                step_id=step_id,  # Use original step_id for telemetry
+                                organization_id=self.actor.organization_id,
+                            ),
+                        )
+                        step_progression = StepProgression.LOGGED_TRACE
+
+                    # stream step
+                    # TODO: improve TTFT
+                    filter_user_messages = [m for m in persisted_messages if m.role != "user"]
+                    letta_messages = Message.to_letta_messages_from_list(
+                        filter_user_messages, use_assistant_message=use_assistant_message, reverse=False
+                    )
+                    letta_messages = [m for m in letta_messages if m.message_type != "approval_response_message"]
+
+                    for message in letta_messages:
+                        if include_return_message_types is None or message.message_type in include_return_message_types:
+                            yield f"data: {message.model_dump_json()}\n\n"
+
+                    MetricRegistry().step_execution_time_ms_histogram.record(get_utc_timestamp_ns() - step_start, get_ctx_attributes())
+                    step_progression = StepProgression.FINISHED
 
-                    # Record partial step metrics on failure (capture whatever timing data we have)
-                    if logged_step and step_metrics and step_progression < StepProgression.FINISHED:
-                        # Calculate total step time up to the failure point
-                        step_metrics.step_ns = get_utc_timestamp_ns() - step_start
+                    # Record step metrics for successful completion
+                    if logged_step and step_metrics:
+                        # Set the step_ns that was already calculated
+                        step_metrics.step_ns = step_ns
                         await self._record_step_metrics(
                             step_id=step_id,
                             agent_state=agent_state,
                             step_metrics=step_metrics,
-                            job_id=locals().get("run_id", self.current_run_id),
                         )
 
                 except Exception as e:
-                    self.logger.error("Failed to update step: %s", e)
+                    # Handle any unexpected errors during step processing
+                    self.logger.error(f"Error during step processing: {e}")
+                    job_update_metadata = {"error": str(e)}
+
+                    # This indicates we failed after we decided to stop stepping, which indicates a bug with our flow.
+                    if not stop_reason:
+                        stop_reason = LettaStopReason(stop_reason=StopReasonType.error.value)
+                    elif stop_reason.stop_reason in (StopReasonType.end_turn, StopReasonType.max_steps, StopReasonType.tool_rule):
+                        self.logger.error("Error occurred during step processing, with valid stop reason: %s", stop_reason.stop_reason)
+                    elif stop_reason.stop_reason not in (
+                        StopReasonType.no_tool_call,
+                        StopReasonType.invalid_tool_call,
+                        StopReasonType.invalid_llm_response,
+                    ):
+                        self.logger.error("Error occurred during step processing, with unexpected stop reason: %s", stop_reason.stop_reason)
+
+                    # Send error stop reason to client and re-raise
+                    yield f"data: {stop_reason.model_dump_json()}\n\n", 500
+                    raise
 
-            if not should_continue:
-                break
+                # Update step if it needs to be updated
+                finally:
+                    if step_progression == StepProgression.FINISHED and should_continue:
+                        continue
+
+                    self.logger.debug("Running cleanup for agent loop run: %s", self.current_run_id)
+                    self.logger.info("Running final update. Step Progression: %s", step_progression)
+                    try:
+                        if step_progression == StepProgression.FINISHED and not should_continue:
+                            # Successfully completed - update with final usage and stop reason
+                            if stop_reason is None:
+                                stop_reason = LettaStopReason(stop_reason=StopReasonType.end_turn.value)
+                            # Note: step already updated with success status after _handle_ai_response
+                            if logged_step:
+                                await self.step_manager.update_step_stop_reason(self.actor, step_id, stop_reason.stop_reason)
+                            break
+
+                        # Handle error cases
+                        if step_progression < StepProgression.STEP_LOGGED:
+                            # Error occurred before step was fully logged
+                            import traceback
+
+                            if logged_step:
+                                await self.step_manager.update_step_error_async(
+                                    actor=self.actor,
+                                    step_id=step_id,  # Use original step_id for telemetry
+                                    error_type=type(e).__name__ if "e" in locals() else "Unknown",
+                                    error_message=str(e) if "e" in locals() else "Unknown error",
+                                    error_traceback=traceback.format_exc(),
+                                    stop_reason=stop_reason,
+                                )
+
+                        if step_progression <= StepProgression.RESPONSE_RECEIVED:
+                            # TODO (cliandy): persist response if we get it back
+                            if settings.track_errored_messages and initial_messages:
+                                for message in initial_messages:
+                                    message.is_err = True
+                                    message.step_id = effective_step_id
+                                await self.message_manager.create_many_messages_async(
+                                    initial_messages, actor=self.actor, embedding_config=agent_state.embedding_config
+                                )
+                        elif step_progression <= StepProgression.LOGGED_TRACE:
+                            if stop_reason is None:
+                                self.logger.error("Error in step after logging step")
+                                stop_reason = LettaStopReason(stop_reason=StopReasonType.error.value)
+                            if logged_step:
+                                await self.step_manager.update_step_stop_reason(self.actor, step_id, stop_reason.stop_reason)
+                        else:
+                            self.logger.error("Invalid StepProgression value")
+
+                        if settings.track_stop_reason:
+                            await self._log_request(request_start_timestamp_ns, request_span, job_update_metadata, is_error=True)
+
+                        # Record partial step metrics on failure (capture whatever timing data we have)
+                        if logged_step and step_metrics and step_progression < StepProgression.FINISHED:
+                            # Calculate total step time up to the failure point
+                            step_metrics.step_ns = get_utc_timestamp_ns() - step_start
+                            await self._record_step_metrics(
+                                step_id=step_id,
+                                agent_state=agent_state,
+                                step_metrics=step_metrics,
+                                job_id=locals().get("run_id", self.current_run_id),
+                            )
+
+                    except Exception as e:
+                        self.logger.error("Failed to update step: %s", e)
+
+                if not should_continue:
+                    break
 
         # Extend the in context message ids
         if not agent_state.message_buffer_autoclear:
@@ -489,7 +545,7 @@ class LettaAgent(BaseAgent):
     async def _step(
         self,
         agent_state: AgentState,
-        input_messages: list[MessageCreate],
+        input_messages: list[MessageCreateBase],
         max_steps: int = DEFAULT_MAX_STEPS,
         run_id: str | None = None,
         request_start_timestamp_ns: int | None = None,
@@ -506,6 +562,7 @@ class LettaAgent(BaseAgent):
             input_messages, agent_state, self.message_manager, self.actor
         )
         initial_messages = new_in_context_messages
+        in_context_messages = current_in_context_messages
         tool_rules_solver = ToolRulesSolver(agent_state.tool_rules)
         llm_client = LLMClient.create(
             provider_type=agent_state.llm_config.model_endpoint_type,
@@ -521,53 +578,83 @@ class LettaAgent(BaseAgent):
         job_update_metadata = None
         usage = LettaUsageStatistics()
         for i in range(max_steps):
-            # If dry run, build request data and return it without making LLM call
-            if dry_run:
-                request_data, valid_tool_names = await self._create_llm_request_data_async(
-                    llm_client=llm_client,
-                    in_context_messages=current_in_context_messages + new_in_context_messages,
-                    agent_state=agent_state,
-                    tool_rules_solver=tool_rules_solver,
+            if in_context_messages[-1].role == "approval":
+                approval_request_message = in_context_messages[-1]
+                step_metrics = await self.step_manager.get_step_metrics_async(step_id=approval_request_message.step_id, actor=self.actor)
+                persisted_messages, should_continue, stop_reason = await self._handle_ai_response(
+                    approval_request_message.tool_calls[0],
+                    [],  # TODO: update this
+                    agent_state,
+                    tool_rules_solver,
+                    usage,
+                    reasoning_content=approval_request_message.content,
+                    step_id=approval_request_message.step_id,
+                    initial_messages=initial_messages,
+                    is_final_step=(i == max_steps - 1),
+                    step_metrics=step_metrics,
+                    run_id=run_id or self.current_run_id,
+                    is_approval=input_messages[0].approve,
+                    is_denial=input_messages[0].approve == False,
+                    denial_reason=input_messages[0].reason,
                 )
-                return request_data
+                new_message_idx = len(initial_messages) if initial_messages else 0
+                self.response_messages.extend(persisted_messages[new_message_idx:])
+                new_in_context_messages.extend(persisted_messages[new_message_idx:])
+                initial_messages = None
+                in_context_messages = current_in_context_messages + new_in_context_messages
+            else:
+                # If dry run, build request data and return it without making LLM call
+                if dry_run:
+                    request_data, valid_tool_names = await self._create_llm_request_data_async(
+                        llm_client=llm_client,
+                        in_context_messages=current_in_context_messages + new_in_context_messages,
+                        agent_state=agent_state,
+                        tool_rules_solver=tool_rules_solver,
+                    )
+                    return request_data
 
-            # Check for job cancellation at the start of each step
-            if await self._check_run_cancellation():
-                stop_reason = LettaStopReason(stop_reason=StopReasonType.cancelled.value)
-                logger.info(f"Agent execution cancelled for run {self.current_run_id}")
-                break
+                # Check for job cancellation at the start of each step
+                if await self._check_run_cancellation():
+                    stop_reason = LettaStopReason(stop_reason=StopReasonType.cancelled.value)
+                    logger.info(f"Agent execution cancelled for run {self.current_run_id}")
+                    break
 
-            step_id = generate_step_id()
-            step_start = get_utc_timestamp_ns()
-            agent_step_span = tracer.start_span("agent_step", start_time=step_start)
-            agent_step_span.set_attributes({"step_id": step_id})
+                step_id = generate_step_id()
+                step_start = get_utc_timestamp_ns()
+                agent_step_span = tracer.start_span("agent_step", start_time=step_start)
+                agent_step_span.set_attributes({"step_id": step_id})
 
-            step_progression = StepProgression.START
-            should_continue = False
-            step_metrics = StepMetrics(id=step_id)  # Initialize metrics tracking
+                step_progression = StepProgression.START
+                should_continue = False
+                step_metrics = StepMetrics(id=step_id)  # Initialize metrics tracking
 
-            # Create step early with PENDING status
-            logged_step = await self.step_manager.log_step_async(
-                actor=self.actor,
-                agent_id=agent_state.id,
-                provider_name=agent_state.llm_config.model_endpoint_type,
-                provider_category=agent_state.llm_config.provider_category or "base",
-                model=agent_state.llm_config.model,
-                model_endpoint=agent_state.llm_config.model_endpoint,
-                context_window_limit=agent_state.llm_config.context_window,
-                usage=UsageStatistics(completion_tokens=0, prompt_tokens=0, total_tokens=0),
-                provider_id=None,
-                job_id=run_id if run_id else self.current_run_id,
-                step_id=step_id,
-                project_id=agent_state.project_id,
-                status=StepStatus.PENDING,
-            )
-            # Only use step_id in messages if step was actually created
-            effective_step_id = step_id if logged_step else None
+                # Create step early with PENDING status
+                logged_step = await self.step_manager.log_step_async(
+                    actor=self.actor,
+                    agent_id=agent_state.id,
+                    provider_name=agent_state.llm_config.model_endpoint_type,
+                    provider_category=agent_state.llm_config.provider_category or "base",
+                    model=agent_state.llm_config.model,
+                    model_endpoint=agent_state.llm_config.model_endpoint,
+                    context_window_limit=agent_state.llm_config.context_window,
+                    usage=UsageStatistics(completion_tokens=0, prompt_tokens=0, total_tokens=0),
+                    provider_id=None,
+                    job_id=run_id if run_id else self.current_run_id,
+                    step_id=step_id,
+                    project_id=agent_state.project_id,
+                    status=StepStatus.PENDING,
+                )
+                # Only use step_id in messages if step was actually created
+                effective_step_id = step_id if logged_step else None
 
-            try:
-                request_data, response_data, current_in_context_messages, new_in_context_messages, valid_tool_names = (
-                    await self._build_and_request_from_llm(
+                try:
+                    (
+                        request_data,
+                        response_data,
+                        current_in_context_messages,
+                        new_in_context_messages,
+                        valid_tool_names,
+                    ) = await self._build_and_request_from_llm(
                         current_in_context_messages,
                         new_in_context_messages,
                         agent_state,
@@ -576,180 +663,193 @@ class LettaAgent(BaseAgent):
                         agent_step_span,
                         step_metrics,
                     )
-                )
-                in_context_messages = current_in_context_messages + new_in_context_messages
-
-                step_progression = StepProgression.RESPONSE_RECEIVED
-                log_event("agent.step.llm_response.received")  # [3^]
-
-                response = llm_client.convert_response_to_chat_completion(response_data, in_context_messages, agent_state.llm_config)
+                    in_context_messages = current_in_context_messages + new_in_context_messages
 
-                usage.step_count += 1
-                usage.completion_tokens += response.usage.completion_tokens
-                usage.prompt_tokens += response.usage.prompt_tokens
-                usage.total_tokens += response.usage.total_tokens
-                usage.run_ids = [run_id] if run_id else None
-                MetricRegistry().message_output_tokens.record(
-                    response.usage.completion_tokens, dict(get_ctx_attributes(), **{"model.name": agent_state.llm_config.model})
-                )
+                    step_progression = StepProgression.RESPONSE_RECEIVED
+                    log_event("agent.step.llm_response.received")  # [3^]
 
-                if not response.choices[0].message.tool_calls:
-                    stop_reason = LettaStopReason(stop_reason=StopReasonType.no_tool_call.value)
-                    raise ValueError("No tool calls found in response, model must make a tool call")
-                tool_call = response.choices[0].message.tool_calls[0]
-                if response.choices[0].message.reasoning_content:
-                    reasoning = [
-                        ReasoningContent(
-                            reasoning=response.choices[0].message.reasoning_content,
-                            is_native=True,
-                            signature=response.choices[0].message.reasoning_content_signature,
+                    try:
+                        response = llm_client.convert_response_to_chat_completion(
+                            response_data, in_context_messages, agent_state.llm_config
                         )
-                    ]
-                elif response.choices[0].message.content:
-                    reasoning = [TextContent(text=response.choices[0].message.content)]  # reasoning placed into content for legacy reasons
-                elif response.choices[0].message.omitted_reasoning_content:
-                    reasoning = [OmittedReasoningContent()]
-                else:
-                    self.logger.info("No reasoning content found.")
-                    reasoning = None
-
-                persisted_messages, should_continue, stop_reason = await self._handle_ai_response(
-                    tool_call,
-                    valid_tool_names,
-                    agent_state,
-                    tool_rules_solver,
-                    response.usage,
-                    reasoning_content=reasoning,
-                    step_id=effective_step_id,
-                    initial_messages=initial_messages,
-                    agent_step_span=agent_step_span,
-                    is_final_step=(i == max_steps - 1),
-                    run_id=run_id,
-                    step_metrics=step_metrics,
-                )
-                step_progression = StepProgression.STEP_LOGGED
-
-                # Update step with actual usage now that we have it (if step was created)
-                if logged_step:
-                    await self.step_manager.update_step_success_async(self.actor, step_id, response.usage, stop_reason)
-
-                new_message_idx = len(initial_messages) if initial_messages else 0
-                self.response_messages.extend(persisted_messages[new_message_idx:])
-                new_in_context_messages.extend(persisted_messages[new_message_idx:])
-
-                initial_messages = None
-                log_event("agent.step.llm_response.processed")  # [4^]
-
-                # log step time
-                now = get_utc_timestamp_ns()
-                step_ns = now - step_start
-                agent_step_span.add_event(name="step_ms", attributes={"duration_ms": ns_to_ms(step_ns)})
-                agent_step_span.end()
-
-                # Log LLM Trace
-                if settings.track_provider_trace:
-                    await self.telemetry_manager.create_provider_trace_async(
-                        actor=self.actor,
-                        provider_trace_create=ProviderTraceCreate(
-                            request_json=request_data,
-                            response_json=response_data,
-                            step_id=step_id,  # Use original step_id for telemetry
-                            organization_id=self.actor.organization_id,
-                        ),
+                    except ValueError as e:
+                        stop_reason = LettaStopReason(stop_reason=StopReasonType.invalid_llm_response.value)
+                        raise e
+
+                    usage.step_count += 1
+                    usage.completion_tokens += response.usage.completion_tokens
+                    usage.prompt_tokens += response.usage.prompt_tokens
+                    usage.total_tokens += response.usage.total_tokens
+                    usage.run_ids = [run_id] if run_id else None
+                    MetricRegistry().message_output_tokens.record(
+                        response.usage.completion_tokens, dict(get_ctx_attributes(), **{"model.name": agent_state.llm_config.model})
                     )
-                    step_progression = StepProgression.LOGGED_TRACE
 
-                MetricRegistry().step_execution_time_ms_histogram.record(get_utc_timestamp_ns() - step_start, get_ctx_attributes())
-                step_progression = StepProgression.FINISHED
+                    if not response.choices[0].message.tool_calls:
+                        stop_reason = LettaStopReason(stop_reason=StopReasonType.no_tool_call.value)
+                        raise ValueError("No tool calls found in response, model must make a tool call")
+                    tool_call = response.choices[0].message.tool_calls[0]
+                    if response.choices[0].message.reasoning_content:
+                        reasoning = [
+                            ReasoningContent(
+                                reasoning=response.choices[0].message.reasoning_content,
+                                is_native=True,
+                                signature=response.choices[0].message.reasoning_content_signature,
+                            )
+                        ]
+                    elif response.choices[0].message.content:
+                        reasoning = [
+                            TextContent(text=response.choices[0].message.content)
+                        ]  # reasoning placed into content for legacy reasons
+                    elif response.choices[0].message.omitted_reasoning_content:
+                        reasoning = [OmittedReasoningContent()]
+                    else:
+                        self.logger.info("No reasoning content found.")
+                        reasoning = None
 
-                # Record step metrics for successful completion
-                if logged_step and step_metrics:
-                    # Set the step_ns that was already calculated
-                    step_metrics.step_ns = step_ns
-                    await self._record_step_metrics(
-                        step_id=step_id,
-                        agent_state=agent_state,
+                    persisted_messages, should_continue, stop_reason = await self._handle_ai_response(
+                        tool_call,
+                        valid_tool_names,
+                        agent_state,
+                        tool_rules_solver,
+                        response.usage,
+                        reasoning_content=reasoning,
+                        step_id=effective_step_id,
+                        initial_messages=initial_messages,
+                        agent_step_span=agent_step_span,
+                        is_final_step=(i == max_steps - 1),
+                        run_id=run_id,
                         step_metrics=step_metrics,
-                        job_id=run_id if run_id else self.current_run_id,
                     )
-
-            except Exception as e:
-                # Handle any unexpected errors during step processing
-                self.logger.error(f"Error during step processing: {e}")
-                job_update_metadata = {"error": str(e)}
-
-                # This indicates we failed after we decided to stop stepping, which indicates a bug with our flow.
-                if not stop_reason:
-                    stop_reason = LettaStopReason(stop_reason=StopReasonType.error.value)
-                elif stop_reason.stop_reason in (StopReasonType.end_turn, StopReasonType.max_steps, StopReasonType.tool_rule):
-                    self.logger.error("Error occurred during step processing, with valid stop reason: %s", stop_reason.stop_reason)
-                elif stop_reason.stop_reason not in (StopReasonType.no_tool_call, StopReasonType.invalid_tool_call):
-                    raise ValueError(f"Invalid Stop Reason: {stop_reason}")
-                raise
-
-                # Update step if it needs to be updated
-            finally:
-                if step_progression == StepProgression.FINISHED and should_continue:
-                    continue
-
-                self.logger.debug("Running cleanup for agent loop run: %s", self.current_run_id)
-                self.logger.info("Running final update. Step Progression: %s", step_progression)
-                try:
-                    if step_progression == StepProgression.FINISHED and not should_continue:
-                        # Successfully completed - update with final usage and stop reason
-                        if stop_reason is None:
-                            stop_reason = LettaStopReason(stop_reason=StopReasonType.end_turn.value)
-                        if logged_step:
-                            await self.step_manager.update_step_success_async(self.actor, step_id, usage, stop_reason)
-                        break
-
-                    # Handle error cases
-                    if step_progression < StepProgression.STEP_LOGGED:
-                        # Error occurred before step was fully logged
-                        import traceback
-
-                        if logged_step:
-                            await self.step_manager.update_step_error_async(
-                                actor=self.actor,
+                    step_progression = StepProgression.STEP_LOGGED
+
+                    # Update step with actual usage now that we have it (if step was created)
+                    if logged_step:
+                        await self.step_manager.update_step_success_async(self.actor, step_id, response.usage, stop_reason)
+
+                    new_message_idx = len(initial_messages) if initial_messages else 0
+                    self.response_messages.extend(persisted_messages[new_message_idx:])
+                    new_in_context_messages.extend(persisted_messages[new_message_idx:])
+
+                    initial_messages = None
+                    log_event("agent.step.llm_response.processed")  # [4^]
+
+                    # log step time
+                    now = get_utc_timestamp_ns()
+                    step_ns = now - step_start
+                    agent_step_span.add_event(name="step_ms", attributes={"duration_ms": ns_to_ms(step_ns)})
+                    agent_step_span.end()
+
+                    # Log LLM Trace
+                    if settings.track_provider_trace:
+                        await self.telemetry_manager.create_provider_trace_async(
+                            actor=self.actor,
+                            provider_trace_create=ProviderTraceCreate(
+                                request_json=request_data,
+                                response_json=response_data,
                                 step_id=step_id,  # Use original step_id for telemetry
-                                error_type=type(e).__name__ if "e" in locals() else "Unknown",
-                                error_message=str(e) if "e" in locals() else "Unknown error",
-                                error_traceback=traceback.format_exc(),
-                                stop_reason=stop_reason,
-                            )
-
-                    if step_progression <= StepProgression.RESPONSE_RECEIVED:
-                        # TODO (cliandy): persist response if we get it back
-                        if settings.track_errored_messages and initial_messages:
-                            for message in initial_messages:
-                                message.is_err = True
-                                message.step_id = effective_step_id
-                            await self.message_manager.create_many_messages_async(initial_messages, actor=self.actor)
-                    elif step_progression <= StepProgression.LOGGED_TRACE:
-                        if stop_reason is None:
-                            self.logger.error("Error in step after logging step")
-                            stop_reason = LettaStopReason(stop_reason=StopReasonType.error.value)
-                        if logged_step:
-                            await self.step_manager.update_step_stop_reason(self.actor, step_id, stop_reason.stop_reason)
-                    else:
-                        self.logger.error("Invalid StepProgression value")
+                                organization_id=self.actor.organization_id,
+                            ),
+                        )
+                        step_progression = StepProgression.LOGGED_TRACE
 
-                    if settings.track_stop_reason:
-                        await self._log_request(request_start_timestamp_ns, request_span, job_update_metadata, is_error=True)
+                    MetricRegistry().step_execution_time_ms_histogram.record(get_utc_timestamp_ns() - step_start, get_ctx_attributes())
+                    step_progression = StepProgression.FINISHED
 
-                    # Record partial step metrics on failure (capture whatever timing data we have)
-                    if logged_step and step_metrics and step_progression < StepProgression.FINISHED:
-                        # Calculate total step time up to the failure point
-                        step_metrics.step_ns = get_utc_timestamp_ns() - step_start
+                    # Record step metrics for successful completion
+                    if logged_step and step_metrics:
+                        # Set the step_ns that was already calculated
+                        step_metrics.step_ns = step_ns
                         await self._record_step_metrics(
                             step_id=step_id,
                             agent_state=agent_state,
                             step_metrics=step_metrics,
-                            job_id=locals().get("run_id", self.current_run_id),
+                            job_id=run_id if run_id else self.current_run_id,
                         )
 
                 except Exception as e:
-                    self.logger.error("Failed to update step: %s", e)
+                    # Handle any unexpected errors during step processing
+                    self.logger.error(f"Error during step processing: {e}")
+                    job_update_metadata = {"error": str(e)}
+
+                    # This indicates we failed after we decided to stop stepping, which indicates a bug with our flow.
+                    if not stop_reason:
+                        stop_reason = LettaStopReason(stop_reason=StopReasonType.error.value)
+                    elif stop_reason.stop_reason in (StopReasonType.end_turn, StopReasonType.max_steps, StopReasonType.tool_rule):
+                        self.logger.error("Error occurred during step processing, with valid stop reason: %s", stop_reason.stop_reason)
+                    elif stop_reason.stop_reason not in (
+                        StopReasonType.no_tool_call,
+                        StopReasonType.invalid_tool_call,
+                        StopReasonType.invalid_llm_response,
+                    ):
+                        self.logger.error("Error occurred during step processing, with unexpected stop reason: %s", stop_reason.stop_reason)
+                    raise
+
+                    # Update step if it needs to be updated
+                finally:
+                    if step_progression == StepProgression.FINISHED and should_continue:
+                        continue
+
+                    self.logger.debug("Running cleanup for agent loop run: %s", self.current_run_id)
+                    self.logger.info("Running final update. Step Progression: %s", step_progression)
+                    try:
+                        if step_progression == StepProgression.FINISHED and not should_continue:
+                            # Successfully completed - update with final usage and stop reason
+                            if stop_reason is None:
+                                stop_reason = LettaStopReason(stop_reason=StopReasonType.end_turn.value)
+                            if logged_step:
+                                await self.step_manager.update_step_success_async(self.actor, step_id, usage, stop_reason)
+                            break
+
+                        # Handle error cases
+                        if step_progression < StepProgression.STEP_LOGGED:
+                            # Error occurred before step was fully logged
+                            import traceback
+
+                            if logged_step:
+                                await self.step_manager.update_step_error_async(
+                                    actor=self.actor,
+                                    step_id=step_id,  # Use original step_id for telemetry
+                                    error_type=type(e).__name__ if "e" in locals() else "Unknown",
+                                    error_message=str(e) if "e" in locals() else "Unknown error",
+                                    error_traceback=traceback.format_exc(),
+                                    stop_reason=stop_reason,
+                                )
+
+                        if step_progression <= StepProgression.RESPONSE_RECEIVED:
+                            # TODO (cliandy): persist response if we get it back
+                            if settings.track_errored_messages and initial_messages:
+                                for message in initial_messages:
+                                    message.is_err = True
+                                    message.step_id = effective_step_id
+                                await self.message_manager.create_many_messages_async(
+                                    initial_messages, actor=self.actor, embedding_config=agent_state.embedding_config
+                                )
+                        elif step_progression <= StepProgression.LOGGED_TRACE:
+                            if stop_reason is None:
+                                self.logger.error("Error in step after logging step")
+                                stop_reason = LettaStopReason(stop_reason=StopReasonType.error.value)
+                            if logged_step:
+                                await self.step_manager.update_step_stop_reason(self.actor, step_id, stop_reason.stop_reason)
+                        else:
+                            self.logger.error("Invalid StepProgression value")
+
+                        if settings.track_stop_reason:
+                            await self._log_request(request_start_timestamp_ns, request_span, job_update_metadata, is_error=True)
+
+                        # Record partial step metrics on failure (capture whatever timing data we have)
+                        if logged_step and step_metrics and step_progression < StepProgression.FINISHED:
+                            # Calculate total step time up to the failure point
+                            step_metrics.step_ns = get_utc_timestamp_ns() - step_start
+                            await self._record_step_metrics(
+                                step_id=step_id,
+                                agent_state=agent_state,
+                                step_metrics=step_metrics,
+                                job_id=locals().get("run_id", self.current_run_id),
+                            )
+
+                    except Exception as e:
+                        self.logger.error("Failed to update step: %s", e)
 
             if not should_continue:
                 break
@@ -783,7 +883,7 @@ class LettaAgent(BaseAgent):
     @trace_method
     async def step_stream(
         self,
-        input_messages: list[MessageCreate],
+        input_messages: list[MessageCreateBase],
         max_steps: int = DEFAULT_MAX_STEPS,
         use_assistant_message: bool = True,
         request_start_timestamp_ns: int | None = None,
@@ -806,6 +906,7 @@ class LettaAgent(BaseAgent):
             input_messages, agent_state, self.message_manager, self.actor
         )
         initial_messages = new_in_context_messages
+        in_context_messages = current_in_context_messages
 
         tool_rules_solver = ToolRulesSolver(agent_state.tool_rules)
         llm_client = LLMClient.create(
@@ -822,219 +923,30 @@ class LettaAgent(BaseAgent):
             request_span.set_attributes({f"llm_config.{k}": v for k, v in agent_state.llm_config.model_dump().items() if v is not None})
 
         for i in range(max_steps):
-            step_id = generate_step_id()
-            # Check for job cancellation at the start of each step
-            if await self._check_run_cancellation():
-                stop_reason = LettaStopReason(stop_reason=StopReasonType.cancelled.value)
-                logger.info(f"Agent execution cancelled for run {self.current_run_id}")
-                yield f"data: {stop_reason.model_dump_json()}\n\n"
-                break
-
-            step_start = get_utc_timestamp_ns()
-            agent_step_span = tracer.start_span("agent_step", start_time=step_start)
-            agent_step_span.set_attributes({"step_id": step_id})
-
-            step_progression = StepProgression.START
-            should_continue = False
-            step_metrics = StepMetrics(id=step_id)  # Initialize metrics tracking
-
-            # Create step early with PENDING status
-            logged_step = await self.step_manager.log_step_async(
-                actor=self.actor,
-                agent_id=agent_state.id,
-                provider_name=agent_state.llm_config.model_endpoint_type,
-                provider_category=agent_state.llm_config.provider_category or "base",
-                model=agent_state.llm_config.model,
-                model_endpoint=agent_state.llm_config.model_endpoint,
-                context_window_limit=agent_state.llm_config.context_window,
-                usage=UsageStatistics(completion_tokens=0, prompt_tokens=0, total_tokens=0),
-                provider_id=None,
-                job_id=self.current_run_id if self.current_run_id else None,
-                step_id=step_id,
-                project_id=agent_state.project_id,
-                status=StepStatus.PENDING,
-            )
-            # Only use step_id in messages if step was actually created
-            effective_step_id = step_id if logged_step else None
-
-            try:
-                (
-                    request_data,
-                    stream,
-                    current_in_context_messages,
-                    new_in_context_messages,
-                    valid_tool_names,
-                    provider_request_start_timestamp_ns,
-                ) = await self._build_and_request_from_llm_streaming(
-                    first_chunk,
-                    agent_step_span,
-                    request_start_timestamp_ns,
-                    current_in_context_messages,
-                    new_in_context_messages,
-                    agent_state,
-                    llm_client,
-                    tool_rules_solver,
-                )
-
-                step_progression = StepProgression.STREAM_RECEIVED
-                log_event("agent.stream.llm_response.received")  # [3^]
-
-                # TODO: THIS IS INCREDIBLY UGLY
-                # TODO: THERE ARE MULTIPLE COPIES OF THE LLM_CONFIG EVERYWHERE THAT ARE GETTING MANIPULATED
-                if agent_state.llm_config.model_endpoint_type in [ProviderType.anthropic, ProviderType.bedrock]:
-                    interface = AnthropicStreamingInterface(
-                        use_assistant_message=use_assistant_message,
-                        put_inner_thoughts_in_kwarg=agent_state.llm_config.put_inner_thoughts_in_kwargs,
-                    )
-                elif agent_state.llm_config.model_endpoint_type == ProviderType.openai:
-                    interface = OpenAIStreamingInterface(
-                        use_assistant_message=use_assistant_message,
-                        is_openai_proxy=agent_state.llm_config.provider_name == "lmstudio_openai",
-                        messages=current_in_context_messages + new_in_context_messages,
-                        tools=request_data.get("tools", []),
-                    )
-                else:
-                    raise ValueError(f"Streaming not supported for {agent_state.llm_config}")
-
-                async for chunk in interface.process(
-                    stream,
-                    ttft_span=request_span,
-                ):
-                    # Measure TTFT (trace, metric, and db). This should be consolidated.
-                    if first_chunk and request_span is not None:
-                        now = get_utc_timestamp_ns()
-                        ttft_ns = now - request_start_timestamp_ns
-
-                        request_span.add_event(name="time_to_first_token_ms", attributes={"ttft_ms": ns_to_ms(ttft_ns)})
-                        metric_attributes = get_ctx_attributes()
-                        metric_attributes["model.name"] = agent_state.llm_config.model
-                        MetricRegistry().ttft_ms_histogram.record(ns_to_ms(ttft_ns), metric_attributes)
-
-                        if self.current_run_id and self.job_manager:
-                            await self.job_manager.record_ttft(self.current_run_id, ttft_ns, self.actor)
-
-                        first_chunk = False
-
-                    if include_return_message_types is None or chunk.message_type in include_return_message_types:
-                        # filter down returned data
-                        yield f"data: {chunk.model_dump_json()}\n\n"
-
-                stream_end_time_ns = get_utc_timestamp_ns()
-
-                # Some providers that rely on the OpenAI client currently e.g. LMStudio don't get usage metrics back on the last streaming chunk, fall back to manual values
-                if isinstance(interface, OpenAIStreamingInterface) and not interface.input_tokens and not interface.output_tokens:
-                    logger.warning(
-                        f"No token usage metrics received from OpenAI streaming interface for {agent_state.llm_config.model}, falling back to estimated values. Input tokens: {interface.fallback_input_tokens}, Output tokens: {interface.fallback_output_tokens}"
-                    )
-                    interface.input_tokens = interface.fallback_input_tokens
-                    interface.output_tokens = interface.fallback_output_tokens
-
-                usage.step_count += 1
-                usage.completion_tokens += interface.output_tokens
-                usage.prompt_tokens += interface.input_tokens
-                usage.total_tokens += interface.input_tokens + interface.output_tokens
-                MetricRegistry().message_output_tokens.record(
-                    usage.completion_tokens, dict(get_ctx_attributes(), **{"model.name": agent_state.llm_config.model})
-                )
-
-                # log LLM request time
-                llm_request_ns = stream_end_time_ns - provider_request_start_timestamp_ns
-                step_metrics.llm_request_ns = llm_request_ns
-
-                llm_request_ms = ns_to_ms(llm_request_ns)
-                agent_step_span.add_event(name="llm_request_ms", attributes={"duration_ms": llm_request_ms})
-                MetricRegistry().llm_execution_time_ms_histogram.record(
-                    llm_request_ms,
-                    dict(get_ctx_attributes(), **{"model.name": agent_state.llm_config.model}),
-                )
-
-                # Process resulting stream content
-                try:
-                    tool_call = interface.get_tool_call_object()
-                except ValueError as e:
-                    stop_reason = LettaStopReason(stop_reason=StopReasonType.no_tool_call.value)
-                    raise e
-                except Exception as e:
-                    stop_reason = LettaStopReason(stop_reason=StopReasonType.invalid_tool_call.value)
-                    raise e
-                reasoning_content = interface.get_reasoning_content()
+            if in_context_messages[-1].role == "approval":
+                approval_request_message = in_context_messages[-1]
+                step_metrics = await self.step_manager.get_step_metrics_async(step_id=approval_request_message.step_id, actor=self.actor)
                 persisted_messages, should_continue, stop_reason = await self._handle_ai_response(
-                    tool_call,
-                    valid_tool_names,
+                    approval_request_message.tool_calls[0],
+                    [],  # TODO: update this
                     agent_state,
                     tool_rules_solver,
-                    UsageStatistics(
-                        completion_tokens=usage.completion_tokens,
-                        prompt_tokens=usage.prompt_tokens,
-                        total_tokens=usage.total_tokens,
-                    ),
-                    reasoning_content=reasoning_content,
-                    pre_computed_assistant_message_id=interface.letta_message_id,
-                    step_id=effective_step_id,
-                    initial_messages=initial_messages,
-                    agent_step_span=agent_step_span,
+                    usage,
+                    reasoning_content=approval_request_message.content,
+                    step_id=approval_request_message.step_id,
+                    initial_messages=new_in_context_messages,
                     is_final_step=(i == max_steps - 1),
                     step_metrics=step_metrics,
+                    run_id=self.current_run_id,
+                    is_approval=input_messages[0].approve,
+                    is_denial=input_messages[0].approve == False,
+                    denial_reason=input_messages[0].reason,
                 )
-                step_progression = StepProgression.STEP_LOGGED
-
-                # Update step with actual usage now that we have it (if step was created)
-                if logged_step:
-                    await self.step_manager.update_step_success_async(
-                        self.actor,
-                        step_id,
-                        UsageStatistics(
-                            completion_tokens=usage.completion_tokens,
-                            prompt_tokens=usage.prompt_tokens,
-                            total_tokens=usage.total_tokens,
-                        ),
-                        stop_reason,
-                    )
-
                 new_message_idx = len(initial_messages) if initial_messages else 0
                 self.response_messages.extend(persisted_messages[new_message_idx:])
                 new_in_context_messages.extend(persisted_messages[new_message_idx:])
-
                 initial_messages = None
-
-                # log total step time
-                now = get_utc_timestamp_ns()
-                step_ns = now - step_start
-                agent_step_span.add_event(name="step_ms", attributes={"duration_ms": ns_to_ms(step_ns)})
-                agent_step_span.end()
-
-                # TODO (cliandy): the stream POST request span has ended at this point, we should tie this to the stream
-                # log_event("agent.stream.llm_response.processed") # [4^]
-
-                # Log LLM Trace
-                # We are piecing together the streamed response here.
-                # Content here does not match the actual response schema as streams come in chunks.
-                if settings.track_provider_trace:
-                    await self.telemetry_manager.create_provider_trace_async(
-                        actor=self.actor,
-                        provider_trace_create=ProviderTraceCreate(
-                            request_json=request_data,
-                            response_json={
-                                "content": {
-                                    "tool_call": tool_call.model_dump_json(),
-                                    "reasoning": [content.model_dump_json() for content in reasoning_content],
-                                },
-                                "id": interface.message_id,
-                                "model": interface.model,
-                                "role": "assistant",
-                                # "stop_reason": "",
-                                # "stop_sequence": None,
-                                "type": "message",
-                                "usage": {
-                                    "input_tokens": usage.prompt_tokens,
-                                    "output_tokens": usage.completion_tokens,
-                                },
-                            },
-                            step_id=step_id,  # Use original step_id for telemetry
-                            organization_id=self.actor.organization_id,
-                        ),
-                    )
-                    step_progression = StepProgression.LOGGED_TRACE
+                in_context_messages = current_in_context_messages + new_in_context_messages
 
                 # yields tool response as this is handled from Letta and not the response from the LLM provider
                 tool_return = [msg for msg in persisted_messages if msg.role == "tool"][-1].to_letta_messages()[0]
@@ -1042,103 +954,238 @@ class LettaAgent(BaseAgent):
                     # Apply message type filtering if specified
                     if include_return_message_types is None or tool_return.message_type in include_return_message_types:
                         yield f"data: {tool_return.model_dump_json()}\n\n"
+            else:
+                step_id = generate_step_id()
+                # Check for job cancellation at the start of each step
+                if await self._check_run_cancellation():
+                    stop_reason = LettaStopReason(stop_reason=StopReasonType.cancelled.value)
+                    logger.info(f"Agent execution cancelled for run {self.current_run_id}")
+                    yield f"data: {stop_reason.model_dump_json()}\n\n"
+                    break
+
+                step_start = get_utc_timestamp_ns()
+                agent_step_span = tracer.start_span("agent_step", start_time=step_start)
+                agent_step_span.set_attributes({"step_id": step_id})
+
+                step_progression = StepProgression.START
+                should_continue = False
+                step_metrics = StepMetrics(id=step_id)  # Initialize metrics tracking
+
+                # Create step early with PENDING status
+                logged_step = await self.step_manager.log_step_async(
+                    actor=self.actor,
+                    agent_id=agent_state.id,
+                    provider_name=agent_state.llm_config.model_endpoint_type,
+                    provider_category=agent_state.llm_config.provider_category or "base",
+                    model=agent_state.llm_config.model,
+                    model_endpoint=agent_state.llm_config.model_endpoint,
+                    context_window_limit=agent_state.llm_config.context_window,
+                    usage=UsageStatistics(completion_tokens=0, prompt_tokens=0, total_tokens=0),
+                    provider_id=None,
+                    job_id=self.current_run_id if self.current_run_id else None,
+                    step_id=step_id,
+                    project_id=agent_state.project_id,
+                    status=StepStatus.PENDING,
+                )
+                # Only use step_id in messages if step was actually created
+                effective_step_id = step_id if logged_step else None
 
-                # TODO (cliandy): consolidate and expand with trace
-                MetricRegistry().step_execution_time_ms_histogram.record(get_utc_timestamp_ns() - step_start, get_ctx_attributes())
-                step_progression = StepProgression.FINISHED
+                try:
+                    (
+                        request_data,
+                        stream,
+                        current_in_context_messages,
+                        new_in_context_messages,
+                        valid_tool_names,
+                        provider_request_start_timestamp_ns,
+                    ) = await self._build_and_request_from_llm_streaming(
+                        first_chunk,
+                        agent_step_span,
+                        request_start_timestamp_ns,
+                        current_in_context_messages,
+                        new_in_context_messages,
+                        agent_state,
+                        llm_client,
+                        tool_rules_solver,
+                    )
 
-                # Record step metrics for successful completion
-                if logged_step and step_metrics:
-                    try:
-                        # Set the step_ns that was already calculated
-                        step_metrics.step_ns = step_ns
+                    step_progression = StepProgression.STREAM_RECEIVED
+                    log_event("agent.stream.llm_response.received")  # [3^]
+
+                    # TODO: THIS IS INCREDIBLY UGLY
+                    # TODO: THERE ARE MULTIPLE COPIES OF THE LLM_CONFIG EVERYWHERE THAT ARE GETTING MANIPULATED
+                    if agent_state.llm_config.model_endpoint_type in [ProviderType.anthropic, ProviderType.bedrock]:
+                        interface = AnthropicStreamingInterface(
+                            use_assistant_message=use_assistant_message,
+                            put_inner_thoughts_in_kwarg=agent_state.llm_config.put_inner_thoughts_in_kwargs,
+                        )
+                    elif agent_state.llm_config.model_endpoint_type == ProviderType.openai:
+                        interface = OpenAIStreamingInterface(
+                            use_assistant_message=use_assistant_message,
+                            is_openai_proxy=agent_state.llm_config.provider_name == "lmstudio_openai",
+                            messages=current_in_context_messages + new_in_context_messages,
+                            tools=request_data.get("tools", []),
+                            put_inner_thoughts_in_kwarg=agent_state.llm_config.put_inner_thoughts_in_kwargs,
+                        )
+                    else:
+                        raise ValueError(f"Streaming not supported for {agent_state.llm_config}")
 
-                        # Get context attributes for project and template IDs
-                        ctx_attrs = get_ctx_attributes()
+                    async for chunk in interface.process(
+                        stream,
+                        ttft_span=request_span,
+                    ):
+                        # Measure TTFT (trace, metric, and db). This should be consolidated.
+                        if first_chunk and request_span is not None:
+                            now = get_utc_timestamp_ns()
+                            ttft_ns = now - request_start_timestamp_ns
 
-                        await self._record_step_metrics(
-                            step_id=step_id,
-                            agent_state=agent_state,
-                            step_metrics=step_metrics,
-                            ctx_attrs=ctx_attrs,
-                            job_id=self.current_run_id,
+                            request_span.add_event(name="time_to_first_token_ms", attributes={"ttft_ms": ns_to_ms(ttft_ns)})
+                            metric_attributes = get_ctx_attributes()
+                            metric_attributes["model.name"] = agent_state.llm_config.model
+                            MetricRegistry().ttft_ms_histogram.record(ns_to_ms(ttft_ns), metric_attributes)
+
+                            if self.current_run_id and self.job_manager:
+                                await self.job_manager.record_ttft(self.current_run_id, ttft_ns, self.actor)
+
+                            first_chunk = False
+
+                        if include_return_message_types is None or chunk.message_type in include_return_message_types:
+                            # filter down returned data
+                            yield f"data: {chunk.model_dump_json()}\n\n"
+
+                    stream_end_time_ns = get_utc_timestamp_ns()
+
+                    # Some providers that rely on the OpenAI client currently e.g. LMStudio don't get usage metrics back on the last streaming chunk, fall back to manual values
+                    if isinstance(interface, OpenAIStreamingInterface) and not interface.input_tokens and not interface.output_tokens:
+                        logger.warning(
+                            f"No token usage metrics received from OpenAI streaming interface for {agent_state.llm_config.model}, falling back to estimated values. Input tokens: {interface.fallback_input_tokens}, Output tokens: {interface.fallback_output_tokens}"
                         )
-                    except Exception as metrics_error:
-                        self.logger.warning(f"Failed to record step metrics: {metrics_error}")
+                        interface.input_tokens = interface.fallback_input_tokens
+                        interface.output_tokens = interface.fallback_output_tokens
+
+                    usage.step_count += 1
+                    usage.completion_tokens += interface.output_tokens
+                    usage.prompt_tokens += interface.input_tokens
+                    usage.total_tokens += interface.input_tokens + interface.output_tokens
+                    MetricRegistry().message_output_tokens.record(
+                        usage.completion_tokens, dict(get_ctx_attributes(), **{"model.name": agent_state.llm_config.model})
+                    )
 
-            except Exception as e:
-                # Handle any unexpected errors during step processing
-                self.logger.error(f"Error during step processing: {e}")
-                job_update_metadata = {"error": str(e)}
-
-                # This indicates we failed after we decided to stop stepping, which indicates a bug with our flow.
-                if not stop_reason:
-                    stop_reason = LettaStopReason(stop_reason=StopReasonType.error.value)
-                elif stop_reason.stop_reason in (StopReasonType.end_turn, StopReasonType.max_steps, StopReasonType.tool_rule):
-                    self.logger.error("Error occurred during step processing, with valid stop reason: %s", stop_reason.stop_reason)
-                elif stop_reason.stop_reason not in (StopReasonType.no_tool_call, StopReasonType.invalid_tool_call):
-                    raise ValueError(f"Invalid Stop Reason: {stop_reason}")
-
-                # Send error stop reason to client and re-raise with expected response code
-                yield f"data: {stop_reason.model_dump_json()}\n\n", 500
-                raise
-
-            # Update step if it needs to be updated
-            finally:
-                if step_progression == StepProgression.FINISHED and should_continue:
-                    continue
-
-                self.logger.debug("Running cleanup for agent loop run: %s", self.current_run_id)
-                self.logger.info("Running final update. Step Progression: %s", step_progression)
-                try:
-                    if step_progression == StepProgression.FINISHED and not should_continue:
-                        # Successfully completed - update with final usage and stop reason
-                        if stop_reason is None:
-                            stop_reason = LettaStopReason(stop_reason=StopReasonType.end_turn.value)
-                        # Note: step already updated with success status after _handle_ai_response
-                        if logged_step:
-                            await self.step_manager.update_step_stop_reason(self.actor, step_id, stop_reason.stop_reason)
-                        break
-
-                    # Handle error cases
-                    if step_progression < StepProgression.STEP_LOGGED:
-                        # Error occurred before step was fully logged
-                        import traceback
-
-                        if logged_step:
-                            await self.step_manager.update_step_error_async(
-                                actor=self.actor,
+                    # log LLM request time
+                    llm_request_ns = stream_end_time_ns - provider_request_start_timestamp_ns
+                    step_metrics.llm_request_ns = llm_request_ns
+
+                    llm_request_ms = ns_to_ms(llm_request_ns)
+                    agent_step_span.add_event(name="llm_request_ms", attributes={"duration_ms": llm_request_ms})
+                    MetricRegistry().llm_execution_time_ms_histogram.record(
+                        llm_request_ms,
+                        dict(get_ctx_attributes(), **{"model.name": agent_state.llm_config.model}),
+                    )
+
+                    # Process resulting stream content
+                    try:
+                        tool_call = interface.get_tool_call_object()
+                    except ValueError as e:
+                        stop_reason = LettaStopReason(stop_reason=StopReasonType.no_tool_call.value)
+                        raise e
+                    except Exception as e:
+                        stop_reason = LettaStopReason(stop_reason=StopReasonType.invalid_tool_call.value)
+                        raise e
+                    reasoning_content = interface.get_reasoning_content()
+                    persisted_messages, should_continue, stop_reason = await self._handle_ai_response(
+                        tool_call,
+                        valid_tool_names,
+                        agent_state,
+                        tool_rules_solver,
+                        UsageStatistics(
+                            completion_tokens=usage.completion_tokens,
+                            prompt_tokens=usage.prompt_tokens,
+                            total_tokens=usage.total_tokens,
+                        ),
+                        reasoning_content=reasoning_content,
+                        pre_computed_assistant_message_id=interface.letta_message_id,
+                        step_id=effective_step_id,
+                        initial_messages=initial_messages,
+                        agent_step_span=agent_step_span,
+                        is_final_step=(i == max_steps - 1),
+                        step_metrics=step_metrics,
+                    )
+                    step_progression = StepProgression.STEP_LOGGED
+
+                    # Update step with actual usage now that we have it (if step was created)
+                    if logged_step:
+                        await self.step_manager.update_step_success_async(
+                            self.actor,
+                            step_id,
+                            UsageStatistics(
+                                completion_tokens=usage.completion_tokens,
+                                prompt_tokens=usage.prompt_tokens,
+                                total_tokens=usage.total_tokens,
+                            ),
+                            stop_reason,
+                        )
+
+                    new_message_idx = len(initial_messages) if initial_messages else 0
+                    self.response_messages.extend(persisted_messages[new_message_idx:])
+                    new_in_context_messages.extend(persisted_messages[new_message_idx:])
+
+                    initial_messages = None
+
+                    # log total step time
+                    now = get_utc_timestamp_ns()
+                    step_ns = now - step_start
+                    agent_step_span.add_event(name="step_ms", attributes={"duration_ms": ns_to_ms(step_ns)})
+                    agent_step_span.end()
+
+                    # TODO (cliandy): the stream POST request span has ended at this point, we should tie this to the stream
+                    # log_event("agent.stream.llm_response.processed") # [4^]
+
+                    # Log LLM Trace
+                    # We are piecing together the streamed response here.
+                    # Content here does not match the actual response schema as streams come in chunks.
+                    if settings.track_provider_trace:
+                        await self.telemetry_manager.create_provider_trace_async(
+                            actor=self.actor,
+                            provider_trace_create=ProviderTraceCreate(
+                                request_json=request_data,
+                                response_json={
+                                    "content": {
+                                        "tool_call": tool_call.model_dump_json(),
+                                        "reasoning": [content.model_dump_json() for content in reasoning_content],
+                                    },
+                                    "id": interface.message_id,
+                                    "model": interface.model,
+                                    "role": "assistant",
+                                    # "stop_reason": "",
+                                    # "stop_sequence": None,
+                                    "type": "message",
+                                    "usage": {
+                                        "input_tokens": usage.prompt_tokens,
+                                        "output_tokens": usage.completion_tokens,
+                                    },
+                                },
                                 step_id=step_id,  # Use original step_id for telemetry
-                                error_type=type(e).__name__ if "e" in locals() else "Unknown",
-                                error_message=str(e) if "e" in locals() else "Unknown error",
-                                error_traceback=traceback.format_exc(),
-                                stop_reason=stop_reason,
-                            )
+                                organization_id=self.actor.organization_id,
+                            ),
+                        )
+                        step_progression = StepProgression.LOGGED_TRACE
 
-                    if step_progression <= StepProgression.STREAM_RECEIVED:
-                        if first_chunk and settings.track_errored_messages and initial_messages:
-                            for message in initial_messages:
-                                message.is_err = True
-                                message.step_id = effective_step_id
-                            await self.message_manager.create_many_messages_async(initial_messages, actor=self.actor)
-                    elif step_progression <= StepProgression.LOGGED_TRACE:
-                        if stop_reason is None:
-                            self.logger.error("Error in step after logging step")
-                            stop_reason = LettaStopReason(stop_reason=StopReasonType.error.value)
-                        if logged_step:
-                            await self.step_manager.update_step_stop_reason(self.actor, step_id, stop_reason.stop_reason)
-                    else:
-                        self.logger.error("Invalid StepProgression value")
+                    # yields tool response as this is handled from Letta and not the response from the LLM provider
+                    tool_return = [msg for msg in persisted_messages if msg.role == "tool"][-1].to_letta_messages()[0]
+                    if not (use_assistant_message and tool_return.name == "send_message"):
+                        # Apply message type filtering if specified
+                        if include_return_message_types is None or tool_return.message_type in include_return_message_types:
+                            yield f"data: {tool_return.model_dump_json()}\n\n"
 
-                    # Do tracking for failure cases. Can consolidate with success conditions later.
-                    if settings.track_stop_reason:
-                        await self._log_request(request_start_timestamp_ns, request_span, job_update_metadata, is_error=True)
+                    # TODO (cliandy): consolidate and expand with trace
+                    MetricRegistry().step_execution_time_ms_histogram.record(get_utc_timestamp_ns() - step_start, get_ctx_attributes())
+                    step_progression = StepProgression.FINISHED
 
-                    # Record partial step metrics on failure (capture whatever timing data we have)
-                    if logged_step and step_metrics and step_progression < StepProgression.FINISHED:
+                    # Record step metrics for successful completion
+                    if logged_step and step_metrics:
                         try:
-                            # Calculate total step time up to the failure point
-                            step_metrics.step_ns = get_utc_timestamp_ns() - step_start
+                            # Set the step_ns that was already calculated
+                            step_metrics.step_ns = step_ns
 
                             # Get context attributes for project and template IDs
                             ctx_attrs = get_ctx_attributes()
@@ -1148,16 +1195,109 @@ class LettaAgent(BaseAgent):
                                 agent_state=agent_state,
                                 step_metrics=step_metrics,
                                 ctx_attrs=ctx_attrs,
-                                job_id=locals().get("run_id", self.current_run_id),
+                                job_id=self.current_run_id,
                             )
                         except Exception as metrics_error:
                             self.logger.warning(f"Failed to record step metrics: {metrics_error}")
 
                 except Exception as e:
-                    self.logger.error("Failed to update step: %s", e)
+                    # Handle any unexpected errors during step processing
+                    self.logger.error(f"Error during step processing: {e}")
+                    job_update_metadata = {"error": str(e)}
+
+                    # This indicates we failed after we decided to stop stepping, which indicates a bug with our flow.
+                    if not stop_reason:
+                        stop_reason = LettaStopReason(stop_reason=StopReasonType.error.value)
+                    elif stop_reason.stop_reason in (StopReasonType.end_turn, StopReasonType.max_steps, StopReasonType.tool_rule):
+                        self.logger.error("Error occurred during step processing, with valid stop reason: %s", stop_reason.stop_reason)
+                    elif stop_reason.stop_reason not in (
+                        StopReasonType.no_tool_call,
+                        StopReasonType.invalid_tool_call,
+                        StopReasonType.invalid_llm_response,
+                    ):
+                        self.logger.error("Error occurred during step processing, with unexpected stop reason: %s", stop_reason.stop_reason)
+
+                    # Send error stop reason to client and re-raise with expected response code
+                    yield f"data: {stop_reason.model_dump_json()}\n\n", 500
+                    raise
 
-            if not should_continue:
-                break
+                # Update step if it needs to be updated
+                finally:
+                    if step_progression == StepProgression.FINISHED and should_continue:
+                        continue
+
+                    self.logger.debug("Running cleanup for agent loop run: %s", self.current_run_id)
+                    self.logger.info("Running final update. Step Progression: %s", step_progression)
+                    try:
+                        if step_progression == StepProgression.FINISHED and not should_continue:
+                            # Successfully completed - update with final usage and stop reason
+                            if stop_reason is None:
+                                stop_reason = LettaStopReason(stop_reason=StopReasonType.end_turn.value)
+                            # Note: step already updated with success status after _handle_ai_response
+                            if logged_step:
+                                await self.step_manager.update_step_stop_reason(self.actor, step_id, stop_reason.stop_reason)
+                            break
+
+                        # Handle error cases
+                        if step_progression < StepProgression.STEP_LOGGED:
+                            # Error occurred before step was fully logged
+                            import traceback
+
+                            if logged_step:
+                                await self.step_manager.update_step_error_async(
+                                    actor=self.actor,
+                                    step_id=step_id,  # Use original step_id for telemetry
+                                    error_type=type(e).__name__ if "e" in locals() else "Unknown",
+                                    error_message=str(e) if "e" in locals() else "Unknown error",
+                                    error_traceback=traceback.format_exc(),
+                                    stop_reason=stop_reason,
+                                )
+
+                        if step_progression <= StepProgression.STREAM_RECEIVED:
+                            if first_chunk and settings.track_errored_messages and initial_messages:
+                                for message in initial_messages:
+                                    message.is_err = True
+                                    message.step_id = effective_step_id
+                                await self.message_manager.create_many_messages_async(
+                                    initial_messages, actor=self.actor, embedding_config=agent_state.embedding_config
+                                )
+                        elif step_progression <= StepProgression.LOGGED_TRACE:
+                            if stop_reason is None:
+                                self.logger.error("Error in step after logging step")
+                                stop_reason = LettaStopReason(stop_reason=StopReasonType.error.value)
+                            if logged_step:
+                                await self.step_manager.update_step_stop_reason(self.actor, step_id, stop_reason.stop_reason)
+                        else:
+                            self.logger.error("Invalid StepProgression value")
+
+                        # Do tracking for failure cases. Can consolidate with success conditions later.
+                        if settings.track_stop_reason:
+                            await self._log_request(request_start_timestamp_ns, request_span, job_update_metadata, is_error=True)
+
+                        # Record partial step metrics on failure (capture whatever timing data we have)
+                        if logged_step and step_metrics and step_progression < StepProgression.FINISHED:
+                            try:
+                                # Calculate total step time up to the failure point
+                                step_metrics.step_ns = get_utc_timestamp_ns() - step_start
+
+                                # Get context attributes for project and template IDs
+                                ctx_attrs = get_ctx_attributes()
+
+                                await self._record_step_metrics(
+                                    step_id=step_id,
+                                    agent_state=agent_state,
+                                    step_metrics=step_metrics,
+                                    ctx_attrs=ctx_attrs,
+                                    job_id=locals().get("run_id", self.current_run_id),
+                                )
+                            except Exception as metrics_error:
+                                self.logger.warning(f"Failed to record step metrics: {metrics_error}")
+
+                    except Exception as e:
+                        self.logger.error("Failed to update step: %s", e)
+
+                if not should_continue:
+                    break
         # Extend the in context message ids
         if not agent_state.message_buffer_autoclear:
             await self._rebuild_context_window(
@@ -1494,14 +1634,46 @@ class LettaAgent(BaseAgent):
         is_final_step: bool | None = None,
         run_id: str | None = None,
         step_metrics: StepMetrics = None,
+        is_approval: bool | None = None,
+        is_denial: bool | None = None,
+        denial_reason: str | None = None,
     ) -> tuple[list[Message], bool, LettaStopReason | None]:
         """
         Handle the final AI response once streaming completes, execute / validate the
         tool call, decide whether we should keep stepping, and persist state.
         """
+        tool_call_id: str = tool_call.id or f"call_{uuid.uuid4().hex[:8]}"
+
+        if is_denial:
+            continue_stepping = True
+            stop_reason = None
+            tool_call_messages = create_letta_messages_from_llm_response(
+                agent_id=agent_state.id,
+                model=agent_state.llm_config.model,
+                function_name="",
+                function_arguments={},
+                tool_execution_result=ToolExecutionResult(status="error"),
+                tool_call_id=tool_call_id,
+                function_call_success=False,
+                function_response=f"Error: request to call tool denied. User reason: {denial_reason}",
+                timezone=agent_state.timezone,
+                actor=self.actor,
+                continue_stepping=continue_stepping,
+                heartbeat_reason=f"{NON_USER_MSG_PREFIX}Continuing: user denied request to call tool.",
+                reasoning_content=None,
+                pre_computed_assistant_message_id=None,
+                step_id=step_id,
+                is_approval_response=True,
+            )
+            messages_to_persist = (initial_messages or []) + tool_call_messages
+            persisted_messages = await self.message_manager.create_many_messages_async(
+                messages_to_persist, actor=self.actor, embedding_config=agent_state.embedding_config
+            )
+            return persisted_messages, continue_stepping, stop_reason
+
         # 1.  Parse and validate the tool-call envelope
         tool_call_name: str = tool_call.function.name
-        tool_call_id: str = tool_call.id or f"call_{uuid.uuid4().hex[:8]}"
+
         tool_args = _safe_load_tool_call_str(tool_call.function.arguments)
         request_heartbeat: bool = _pop_heartbeat(tool_args)
         tool_args.pop(INNER_THOUGHTS_KWARG, None)
@@ -1515,77 +1687,99 @@ class LettaAgent(BaseAgent):
             request_heartbeat=request_heartbeat,
         )
 
-        # 2.  Execute the tool (or synthesize an error result if disallowed)
-        tool_rule_violated = tool_call_name not in valid_tool_names
-        if tool_rule_violated:
-            tool_execution_result = _build_rule_violation_result(tool_call_name, valid_tool_names, tool_rules_solver)
-        else:
-            # Track tool execution time
-            tool_start_time = get_utc_timestamp_ns()
-            tool_execution_result = await self._execute_tool(
-                tool_name=tool_call_name,
-                tool_args=tool_args,
-                agent_state=agent_state,
-                agent_step_span=agent_step_span,
+        if not is_approval and tool_rules_solver.is_requires_approval_tool(tool_call_name):
+            approval_message = create_approval_request_message_from_llm_response(
+                agent_id=agent_state.id,
+                model=agent_state.llm_config.model,
+                function_name=tool_call_name,
+                function_arguments=tool_args,
+                tool_call_id=tool_call_id,
+                actor=self.actor,
+                continue_stepping=request_heartbeat,
+                reasoning_content=reasoning_content,
+                pre_computed_assistant_message_id=pre_computed_assistant_message_id,
                 step_id=step_id,
             )
-            tool_end_time = get_utc_timestamp_ns()
+            messages_to_persist = (initial_messages or []) + [approval_message]
+            continue_stepping = False
+            stop_reason = LettaStopReason(stop_reason=StopReasonType.requires_approval.value)
+        else:
+            # 2.  Execute the tool (or synthesize an error result if disallowed)
+            tool_rule_violated = tool_call_name not in valid_tool_names and not is_approval
+            if tool_rule_violated:
+                tool_execution_result = _build_rule_violation_result(tool_call_name, valid_tool_names, tool_rules_solver)
+            else:
+                # Track tool execution time
+                tool_start_time = get_utc_timestamp_ns()
+                tool_execution_result = await self._execute_tool(
+                    tool_name=tool_call_name,
+                    tool_args=tool_args,
+                    agent_state=agent_state,
+                    agent_step_span=agent_step_span,
+                    step_id=step_id,
+                )
+                tool_end_time = get_utc_timestamp_ns()
 
-            # Store tool execution time in metrics
-            step_metrics.tool_execution_ns = tool_end_time - tool_start_time
+                # Store tool execution time in metrics
+                step_metrics.tool_execution_ns = tool_end_time - tool_start_time
 
-        log_telemetry(
-            self.logger, "_handle_ai_response execute tool finish", tool_execution_result=tool_execution_result, tool_call_id=tool_call_id
-        )
+            log_telemetry(
+                self.logger,
+                "_handle_ai_response execute tool finish",
+                tool_execution_result=tool_execution_result,
+                tool_call_id=tool_call_id,
+            )
 
-        # 3.  Prepare the function-response payload
-        truncate = tool_call_name not in {"conversation_search", "conversation_search_date", "archival_memory_search"}
-        return_char_limit = next(
-            (t.return_char_limit for t in agent_state.tools if t.name == tool_call_name),
-            None,
-        )
-        function_response_string = validate_function_response(
-            tool_execution_result.func_return,
-            return_char_limit=return_char_limit,
-            truncate=truncate,
-        )
-        self.last_function_response = package_function_response(
-            was_success=tool_execution_result.success_flag,
-            response_string=function_response_string,
-            timezone=agent_state.timezone,
-        )
+            # 3.  Prepare the function-response payload
+            truncate = tool_call_name not in {"conversation_search", "conversation_search_date", "archival_memory_search"}
+            return_char_limit = next(
+                (t.return_char_limit for t in agent_state.tools if t.name == tool_call_name),
+                None,
+            )
+            function_response_string = validate_function_response(
+                tool_execution_result.func_return,
+                return_char_limit=return_char_limit,
+                truncate=truncate,
+            )
+            self.last_function_response = package_function_response(
+                was_success=tool_execution_result.success_flag,
+                response_string=function_response_string,
+                timezone=agent_state.timezone,
+            )
 
-        # 4.  Decide whether to keep stepping  (<<< focal section simplified)
-        continue_stepping, heartbeat_reason, stop_reason = self._decide_continuation(
-            agent_state=agent_state,
-            request_heartbeat=request_heartbeat,
-            tool_call_name=tool_call_name,
-            tool_rule_violated=tool_rule_violated,
-            tool_rules_solver=tool_rules_solver,
-            is_final_step=is_final_step,
-        )
+            # 4.  Decide whether to keep stepping  (focal section simplified)
+            continue_stepping, heartbeat_reason, stop_reason = self._decide_continuation(
+                agent_state=agent_state,
+                request_heartbeat=request_heartbeat,
+                tool_call_name=tool_call_name,
+                tool_rule_violated=tool_rule_violated,
+                tool_rules_solver=tool_rules_solver,
+                is_final_step=is_final_step,
+            )
 
-        # 5.  Create messages (step was already created at the beginning)
-        tool_call_messages = create_letta_messages_from_llm_response(
-            agent_id=agent_state.id,
-            model=agent_state.llm_config.model,
-            function_name=tool_call_name,
-            function_arguments=tool_args,
-            tool_execution_result=tool_execution_result,
-            tool_call_id=tool_call_id,
-            function_call_success=tool_execution_result.success_flag,
-            function_response=function_response_string,
-            timezone=agent_state.timezone,
-            actor=self.actor,
-            continue_stepping=continue_stepping,
-            heartbeat_reason=heartbeat_reason,
-            reasoning_content=reasoning_content,
-            pre_computed_assistant_message_id=pre_computed_assistant_message_id,
-            step_id=step_id,
-        )
+            # 5.  Create messages (step was already created at the beginning)
+            tool_call_messages = create_letta_messages_from_llm_response(
+                agent_id=agent_state.id,
+                model=agent_state.llm_config.model,
+                function_name=tool_call_name,
+                function_arguments=tool_args,
+                tool_execution_result=tool_execution_result,
+                tool_call_id=tool_call_id,
+                function_call_success=tool_execution_result.success_flag,
+                function_response=function_response_string,
+                timezone=agent_state.timezone,
+                actor=self.actor,
+                continue_stepping=continue_stepping,
+                heartbeat_reason=heartbeat_reason,
+                reasoning_content=reasoning_content,
+                pre_computed_assistant_message_id=pre_computed_assistant_message_id,
+                step_id=step_id,
+                is_approval_response=is_approval or is_denial,
+            )
+            messages_to_persist = (initial_messages or []) + tool_call_messages
 
         persisted_messages = await self.message_manager.create_many_messages_async(
-            (initial_messages or []) + tool_call_messages, actor=self.actor
+            messages_to_persist, actor=self.actor, embedding_config=agent_state.embedding_config
         )
 
         if run_id:
@@ -1606,7 +1800,6 @@ class LettaAgent(BaseAgent):
         tool_rules_solver: ToolRulesSolver,
         is_final_step: bool | None,
     ) -> tuple[bool, str | None, LettaStopReason | None]:
-
         continue_stepping = request_heartbeat
         heartbeat_reason: str | None = None
         stop_reason: LettaStopReason | None = None
@@ -1638,9 +1831,7 @@ class LettaAgent(BaseAgent):
             uncalled = tool_rules_solver.get_uncalled_required_tools(available_tools=set([t.name for t in agent_state.tools]))
             if not continue_stepping and uncalled:
                 continue_stepping = True
-                heartbeat_reason = (
-                    f"{NON_USER_MSG_PREFIX}Continuing, user expects these tools: [" f"{', '.join(uncalled)}] to be called still."
-                )
+                heartbeat_reason = f"{NON_USER_MSG_PREFIX}Continuing, user expects these tools: [{', '.join(uncalled)}] to be called still."
 
                 stop_reason = None  # reset – we’re still going