diff --git a/letta/schemas/message.py b/letta/schemas/message.py
index bc5869f6c..5a5bd17ac 100644
--- a/letta/schemas/message.py
+++ b/letta/schemas/message.py
@@ -25,6 +25,7 @@ from letta.schemas.letta_message import (
     ToolReturnMessage,
     UserMessage,
 )
+from letta.system import unpack_message
 from letta.utils import get_utc_time, is_utc_datetime, json_dumps
 
 
@@ -264,11 +265,12 @@ class Message(BaseMessage):
         elif self.role == MessageRole.user:
             # This is type UserMessage
             assert self.text is not None, self
+            message_str = unpack_message(self.text)
             messages.append(
                 UserMessage(
                     id=self.id,
                     date=self.created_at,
-                    content=self.text,
+                    content=message_str or self.text,
                 )
             )
         elif self.role == MessageRole.system:
diff --git a/letta/system.py b/letta/system.py
index 9c795704c..a13e36f1e 100644
--- a/letta/system.py
+++ b/letta/system.py
@@ -1,5 +1,6 @@
 import json
 import uuid
+import warnings
 from typing import Optional
 
 from .constants import (
@@ -205,3 +206,22 @@ def get_token_limit_warning():
     }
 
     return json_dumps(packaged_message)
+
+
+def unpack_message(packed_message) -> str:
+    """Take a packed message string and attempt to extract the inner message content"""
+
+    try:
+        message_json = json.loads(packed_message)
+    except:
+        warnings.warn(f"Was unable to load message as JSON to unpack: ''{packed_message}")
+        return packed_message
+
+    if "message" not in message_json:
+        if "type" in message_json and message_json["type"] in ["login", "heartbeat"]:
+            # This is a valid user message that the ADE expects, so don't print warning
+            return packed_message
+        warnings.warn(f"Was unable to find 'message' field in packed message object: '{packed_message}'")
+        return packed_message
+    else:
+        return message_json.get("message")
diff --git a/tests/test_server.py b/tests/test_server.py
index 8f7e1e3c8..aef057368 100644
--- a/tests/test_server.py
+++ b/tests/test_server.py
@@ -26,6 +26,7 @@ from letta.schemas.job import Job as PydanticJob
 from letta.schemas.message import Message
 from letta.schemas.source import Source as PydanticSource
 from letta.server.server import SyncServer
+from letta.system import unpack_message
 
 from .utils import DummyDataConnector
 
@@ -711,7 +712,7 @@ def _test_get_messages_letta_format(
 
             elif message.role == MessageRole.user:
                 assert isinstance(letta_message, UserMessage)
-                assert message.text == letta_message.content
+                assert unpack_message(message.text) == letta_message.content
                 letta_message_index += 1
 
             elif message.role == MessageRole.system:
@@ -734,8 +735,7 @@ def _test_get_messages_letta_format(
 
 
 def test_get_messages_letta_format(server, user, agent_id):
-    # for reverse in [False, True]:
-    for reverse in [False]:
+    for reverse in [False, True]:
         _test_get_messages_letta_format(server, user, agent_id, reverse=reverse)