diff --git a/letta/agents/letta_agent.py b/letta/agents/letta_agent.py
index c8c5284d..619d0902 100644
--- a/letta/agents/letta_agent.py
+++ b/letta/agents/letta_agent.py
@@ -940,7 +940,10 @@ class LettaAgent(BaseAgent):
             tool_call_id=tool_call_id,
             request_heartbeat=request_heartbeat,
         )
-        if tool_call_name not in valid_tool_names:
+        # Check if tool rule is violated - if so, we'll force continuation
+        tool_rule_violated = tool_call_name not in valid_tool_names
+
+        if tool_rule_violated:
             base_error_message = f"[ToolConstraintError] Cannot call {tool_call_name}, valid tools to call include: {valid_tool_names}."
             violated_rule_messages = tool_rules_solver.guess_rule_violation(tool_call_name)
             if violated_rule_messages:
@@ -969,7 +972,7 @@ class LettaAgent(BaseAgent):
 
         # get the function response limit
         target_tool = next((x for x in agent_state.tools if x.name == tool_call_name), None)
-        return_char_limit = target_tool.return_char_limit
+        return_char_limit = target_tool.return_char_limit if target_tool else None
         function_response_string = validate_function_response(
             tool_execution_result.func_return, return_char_limit=return_char_limit, truncate=truncate
         )
@@ -981,15 +984,20 @@ class LettaAgent(BaseAgent):
         # 4. Register tool call with tool rule solver
         # Resolve whether or not to continue stepping
         continue_stepping = request_heartbeat
-        tool_rules_solver.register_tool_call(tool_name=tool_call_name)
-        if tool_rules_solver.is_terminal_tool(tool_name=tool_call_name):
-            if continue_stepping:
-                stop_reason = LettaStopReason(stop_reason=StopReasonType.tool_rule.value)
-            continue_stepping = False
-        elif tool_rules_solver.has_children_tools(tool_name=tool_call_name):
-            continue_stepping = True
-        elif tool_rules_solver.is_continue_tool(tool_name=tool_call_name):
+
+        # Force continuation if tool rule was violated to give the model another chance
+        if tool_rule_violated:
             continue_stepping = True
+        else:
+            tool_rules_solver.register_tool_call(tool_name=tool_call_name)
+            if tool_rules_solver.is_terminal_tool(tool_name=tool_call_name):
+                if continue_stepping:
+                    stop_reason = LettaStopReason(stop_reason=StopReasonType.tool_rule.value)
+                continue_stepping = False
+            elif tool_rules_solver.has_children_tools(tool_name=tool_call_name):
+                continue_stepping = True
+            elif tool_rules_solver.is_continue_tool(tool_name=tool_call_name):
+                continue_stepping = True
 
         # 5a. Persist Steps to DB
         # Following agent loop to persist this before messages