diff --git a/backend/open_webui/models/messages.py b/backend/open_webui/models/messages.py
index 98be21463d..5b068b6449 100644
--- a/backend/open_webui/models/messages.py
+++ b/backend/open_webui/models/messages.py
@@ -9,7 +9,7 @@ from open_webui.models.users import Users, User, UserNameResponse
 from open_webui.models.channels import Channels, ChannelMember
 
 
-from pydantic import BaseModel, ConfigDict
+from pydantic import BaseModel, ConfigDict, field_validator
 from sqlalchemy import BigInteger, Boolean, Column, String, Text, JSON
 from sqlalchemy import or_, func, select, and_, text
 from sqlalchemy.sql import exists
@@ -108,11 +108,24 @@ class MessageUserResponse(MessageModel):
     user: Optional[UserNameResponse] = None
 
 
+class MessageUserSlimResponse(MessageUserResponse):
+    data: bool | None = None
+
+    @field_validator("data", mode="before")
+    def convert_data_to_bool(cls, v):
+        # No data or not a dict → False
+        if not isinstance(v, dict):
+            return False
+
+        # True if ANY value in the dict is non-empty
+        return any(bool(val) for val in v.values())
+
+
 class MessageReplyToResponse(MessageUserResponse):
-    reply_to_message: Optional[MessageUserResponse] = None
+    reply_to_message: Optional[MessageUserSlimResponse] = None
 
 
-class MessageWithReactionsResponse(MessageUserResponse):
+class MessageWithReactionsResponse(MessageUserSlimResponse):
     reactions: list[Reactions]