diff --git a/fern/openapi.json b/fern/openapi.json
index 9ef69f2c..d20c3629 100644
--- a/fern/openapi.json
+++ b/fern/openapi.json
@@ -29731,7 +29731,7 @@
             "anyOf": [
               {
                 "items": {
-                  "$ref": "#/components/schemas/ToolReturn"
+                  "$ref": "#/components/schemas/letta__schemas__message__ToolReturn"
                 },
                 "type": "array"
               },
@@ -34073,7 +34073,7 @@
         "required": ["name", "description", "parameters"],
         "title": "ToolJSONSchema"
       },
-      "ToolReturn": {
+      "ToolReturn-Input": {
         "properties": {
           "tool_call_id": {
             "anyOf": [
@@ -34264,16 +34264,19 @@
           },
           "tool_return": {
             "type": "string",
-            "title": "Tool Return"
+            "title": "Tool Return",
+            "deprecated": true
           },
           "status": {
             "type": "string",
             "enum": ["success", "error"],
-            "title": "Status"
+            "title": "Status",
+            "deprecated": true
           },
           "tool_call_id": {
             "type": "string",
-            "title": "Tool Call Id"
+            "title": "Tool Call Id",
+            "deprecated": true
           },
           "stdout": {
             "anyOf": [
@@ -34287,7 +34290,8 @@
                 "type": "null"
               }
             ],
-            "title": "Stdout"
+            "title": "Stdout",
+            "deprecated": true
           },
           "stderr": {
             "anyOf": [
@@ -34301,13 +34305,28 @@
                 "type": "null"
               }
             ],
-            "title": "Stderr"
+            "title": "Stderr",
+            "deprecated": true
+          },
+          "tool_returns": {
+            "anyOf": [
+              {
+                "items": {
+                  "$ref": "#/components/schemas/letta__schemas__letta_message__ToolReturn"
+                },
+                "type": "array"
+              },
+              {
+                "type": "null"
+              }
+            ],
+            "title": "Tool Returns"
           }
         },
         "type": "object",
         "required": ["id", "date", "tool_return", "status", "tool_call_id"],
         "title": "ToolReturnMessage",
-        "description": "A message representing the return value of a tool call (generated by Letta executing the requested tool).\n\nArgs:\n    id (str): The ID of the message\n    date (datetime): The date the message was created in ISO format\n    name (Optional[str]): The name of the sender of the message\n    tool_return (str): The return value of the tool\n    status (Literal[\"success\", \"error\"]): The status of the tool call\n    tool_call_id (str): A unique identifier for the tool call that generated this message\n    stdout (Optional[List(str)]): Captured stdout (e.g. prints, logs) from the tool invocation\n    stderr (Optional[List(str)]): Captured stderr from the tool invocation"
+        "description": "A message representing the return value of a tool call (generated by Letta executing the requested tool).\n\nArgs:\n    id (str): The ID of the message\n    date (datetime): The date the message was created in ISO format\n    name (Optional[str]): The name of the sender of the message\n    tool_return (str): The return value of the tool (deprecated, use tool_returns)\n    status (Literal[\"success\", \"error\"]): The status of the tool call (deprecated, use tool_returns)\n    tool_call_id (str): A unique identifier for the tool call that generated this message (deprecated, use tool_returns)\n    stdout (Optional[List(str)]): Captured stdout (e.g. prints, logs) from the tool invocation (deprecated, use tool_returns)\n    stderr (Optional[List(str)]): Captured stderr from the tool invocation (deprecated, use tool_returns)\n    tool_returns (Optional[List[ToolReturn]]): List of tool returns for multi-tool support"
       },
       "ToolRunFromSource": {
         "properties": {
@@ -36449,7 +36468,7 @@
             "anyOf": [
               {
                 "items": {
-                  "$ref": "#/components/schemas/ToolReturn"
+                  "$ref": "#/components/schemas/ToolReturn-Input"
                 },
                 "type": "array"
               },
@@ -36695,6 +36714,119 @@
         "title": "ToolSchema",
         "description": "Tool with human-readable ID for agent file"
       },
+      "letta__schemas__letta_message__ToolReturn": {
+        "properties": {
+          "tool_return": {
+            "type": "string",
+            "title": "Tool Return"
+          },
+          "status": {
+            "type": "string",
+            "enum": ["success", "error"],
+            "title": "Status"
+          },
+          "tool_call_id": {
+            "type": "string",
+            "title": "Tool Call Id"
+          },
+          "stdout": {
+            "anyOf": [
+              {
+                "items": {
+                  "type": "string"
+                },
+                "type": "array"
+              },
+              {
+                "type": "null"
+              }
+            ],
+            "title": "Stdout"
+          },
+          "stderr": {
+            "anyOf": [
+              {
+                "items": {
+                  "type": "string"
+                },
+                "type": "array"
+              },
+              {
+                "type": "null"
+              }
+            ],
+            "title": "Stderr"
+          }
+        },
+        "type": "object",
+        "required": ["tool_return", "status", "tool_call_id"],
+        "title": "ToolReturn"
+      },
+      "letta__schemas__message__ToolReturn": {
+        "properties": {
+          "tool_call_id": {
+            "anyOf": [
+              {},
+              {
+                "type": "null"
+              }
+            ],
+            "title": "Tool Call Id",
+            "description": "The ID for the tool call"
+          },
+          "status": {
+            "type": "string",
+            "enum": ["success", "error"],
+            "title": "Status",
+            "description": "The status of the tool call"
+          },
+          "stdout": {
+            "anyOf": [
+              {
+                "items": {
+                  "type": "string"
+                },
+                "type": "array"
+              },
+              {
+                "type": "null"
+              }
+            ],
+            "title": "Stdout",
+            "description": "Captured stdout (e.g. prints, logs) from the tool invocation"
+          },
+          "stderr": {
+            "anyOf": [
+              {
+                "items": {
+                  "type": "string"
+                },
+                "type": "array"
+              },
+              {
+                "type": "null"
+              }
+            ],
+            "title": "Stderr",
+            "description": "Captured stderr from the tool invocation"
+          },
+          "func_response": {
+            "anyOf": [
+              {
+                "type": "string"
+              },
+              {
+                "type": "null"
+              }
+            ],
+            "title": "Func Response",
+            "description": "The function response string"
+          }
+        },
+        "type": "object",
+        "required": ["status"],
+        "title": "ToolReturn"
+      },
       "letta__serialize_schemas__pydantic_agent_schema__AgentSchema": {
         "properties": {
           "agent_type": {
diff --git a/letta/schemas/letta_message.py b/letta/schemas/letta_message.py
index 1d1904e0..2c436b41 100644
--- a/letta/schemas/letta_message.py
+++ b/letta/schemas/letta_message.py
@@ -226,6 +226,14 @@ class ToolCallMessage(LettaMessage):
         return v
 
 
+class ToolReturn(BaseModel):
+    tool_return: str
+    status: Literal["success", "error"]
+    tool_call_id: str
+    stdout: Optional[List[str]] = None
+    stderr: Optional[List[str]] = None
+
+
 class ToolReturnMessage(LettaMessage):
     """
     A message representing the return value of a tool call (generated by Letta executing the requested tool).
@@ -234,21 +242,23 @@ class ToolReturnMessage(LettaMessage):
         id (str): The ID of the message
         date (datetime): The date the message was created in ISO format
         name (Optional[str]): The name of the sender of the message
-        tool_return (str): The return value of the tool
-        status (Literal["success", "error"]): The status of the tool call
-        tool_call_id (str): A unique identifier for the tool call that generated this message
-        stdout (Optional[List(str)]): Captured stdout (e.g. prints, logs) from the tool invocation
-        stderr (Optional[List(str)]): Captured stderr from the tool invocation
+        tool_return (str): The return value of the tool (deprecated, use tool_returns)
+        status (Literal["success", "error"]): The status of the tool call (deprecated, use tool_returns)
+        tool_call_id (str): A unique identifier for the tool call that generated this message (deprecated, use tool_returns)
+        stdout (Optional[List(str)]): Captured stdout (e.g. prints, logs) from the tool invocation (deprecated, use tool_returns)
+        stderr (Optional[List(str)]): Captured stderr from the tool invocation (deprecated, use tool_returns)
+        tool_returns (Optional[List[ToolReturn]]): List of tool returns for multi-tool support
     """
 
     message_type: Literal[MessageType.tool_return_message] = Field(
         default=MessageType.tool_return_message, description="The type of the message."
     )
-    tool_return: str
-    status: Literal["success", "error"]
-    tool_call_id: str
-    stdout: Optional[List[str]] = None
-    stderr: Optional[List[str]] = None
+    tool_return: str = Field(..., deprecated=True)
+    status: Literal["success", "error"] = Field(..., deprecated=True)
+    tool_call_id: str = Field(..., deprecated=True)
+    stdout: Optional[List[str]] = Field(None, deprecated=True)
+    stderr: Optional[List[str]] = Field(None, deprecated=True)
+    tool_returns: Optional[List[ToolReturn]] = None
 
 
 class ApprovalRequestMessage(LettaMessage):