diff --git a/channels/webui.py b/channels/webui.py
index e4c806e6..7fe5d471 100644
--- a/channels/webui.py
+++ b/channels/webui.py
@@ -49,6 +49,7 @@
     "upload",
     "theming",
     "modal_settings",
+    "new_menu_options",
     "storage_editor",
     "responsive",
     "init"
diff --git a/channels/webui/static/js/new_menu_options.js b/channels/webui/static/js/new_menu_options.js
new file mode 100644
index 00000000..6c9a6cbb
--- /dev/null
+++ b/channels/webui/static/js/new_menu_options.js
@@ -0,0 +1,22 @@
+// =============================================================================
+// Agent Menu Options
+// =============================================================================
+
+// Defines metadata for agent-related configuration options.
+// Loaded after modal_settings.js to extend FIELD_DESCRIPTIONS.
+const AGENT_MENU_OPTIONS = [
+    {
+        key: 'model.agent_replan_on_error',
+        label: 'Replan on error',
+        description: 'When enabled, the agent will restart its planning loop when a tool call returns an error, prompting it to try a different strategy instead of continuing with a failed result.',
+        type: 'boolean',
+        default: false
+    }
+];
+
+// Extend field descriptions for agent options so they appear in the settings UI
+for (const option of AGENT_MENU_OPTIONS) {
+    if (option.description) {
+        FIELD_DESCRIPTIONS[option.key] = option.description;
+    }
+}
diff --git a/core/config.py b/core/config.py
index 5e680387..0d49a273 100644
--- a/core/config.py
+++ b/core/config.py
@@ -16,7 +16,8 @@
     "model": {
         "name": "MODEL_HERE",
         "temperature": 0.2,
-        "use_tools": True
+        "use_tools": True,
+        "agent_replan_on_error": False
     },
     "channels": {
         "enabled": ["cli", "webui"],
diff --git a/core/toolcalls.py b/core/toolcalls.py
index de7f95ab..1eb6e72d 100644
--- a/core/toolcalls.py
+++ b/core/toolcalls.py
@@ -55,6 +55,8 @@ async def process(self, tool_calls, initial_content=""):
         await self.channel.context.chat.add(assistant_message)
 
         # Execute each tool and add their responses
+        had_tool_error = False
+
         for tool_call_dict in repaired_tool_calls:
             tool_name = tool_call_dict['function']['name']
             tool_args = json_repair.loads(tool_call_dict['function']['arguments'])
@@ -97,6 +99,7 @@ async def process(self, tool_calls, initial_content=""):
                     }
                 except Exception as e:
                     core.log("toolcall", f"error: {str(e)}")
+                    had_tool_error = True
                     tool_response = {
                         "role": "tool",
                         "tool_call_id": tool_call_dict['id'],
@@ -116,13 +119,23 @@ async def process(self, tool_calls, initial_content=""):
 
         # Build context and stream response
         context = await self.channel.context.get(system_prompt=False)
+
+        replan_on_error = core.config.get("model", {}).get("agent_replan_on_error", False)
+        if had_tool_error and replan_on_error:
+            system_content = (
+                "One or more tool calls returned an error. "
+                "Please replan your approach and try a different strategy to achieve the goal."
+            )
+        else:
+            system_content = (
+                "If the tool response provides sufficient answers, "
+                "explain the results to the user. If not, call another tool."
+            )
+
         prompt = [
             {
                 "role": "system",
-                "content": (
-                    "If the tool response provides sufficient answers, "
-                    "explain the results to the user. If not, call another tool."
-                )
+                "content": system_content
             }
         ] + context