diff --git a/memgpt/agent.py b/memgpt/agent.py
index 86295e92..4db48180 100644
--- a/memgpt/agent.py
+++ b/memgpt/agent.py
@@ -430,9 +430,6 @@ class Agent(object):
                 response_message.tool_calls = [response_message.tool_calls[0]]
             assert response_message.tool_calls is not None and len(response_message.tool_calls) > 0
 
-            # The content if then internal monologue, not chat
-            self.interface.internal_monologue(response_message.content)
-
             # generate UUID for tool call
             if override_tool_call_id or response_message.function_call:
                 tool_call_id = get_tool_call_id()  # needs to be a string for JSON
@@ -456,6 +453,9 @@ class Agent(object):
             )  # extend conversation with assistant's reply
             printd(f"Function call message: {messages[-1]}")
 
+            # The content if then internal monologue, not chat
+            self.interface.internal_monologue(response_message.content, msg_obj=messages[-1])
+
             # Step 3: call the function
             # Note: the JSON response may not always be valid; be sure to handle errors
 
@@ -483,7 +483,7 @@ class Agent(object):
                         },
                     )
                 )  # extend conversation with function response
-                self.interface.function_message(f"Error: {error_msg}")
+                self.interface.function_message(f"Error: {error_msg}", msg_obj=messages[-1])
                 return messages, False, True  # force a heartbeat to allow agent to handle error
 
             # Failure case 2: function name is OK, but function args are bad JSON
@@ -506,7 +506,7 @@ class Agent(object):
                         },
                     )
                 )  # extend conversation with function response
-                self.interface.function_message(f"Error: {error_msg}")
+                self.interface.function_message(f"Error: {error_msg}", msg_obj=messages[-1])
                 return messages, False, True  # force a heartbeat to allow agent to handle error
 
             # (Still parsing function args)
@@ -519,7 +519,9 @@ class Agent(object):
                 heartbeat_request = False
 
             # Failure case 3: function failed during execution
-            self.interface.function_message(f"Running {function_name}({function_args})")
+            # NOTE: the msg_obj associated with the "Running " message is the prior assistant message, not the function/tool role message
+            #       this is because the function/tool role message is only created once the function/tool has executed/returned
+            self.interface.function_message(f"Running {function_name}({function_args})", msg_obj=messages[-1])
             try:
                 spec = inspect.getfullargspec(function_to_call).annotations
 
@@ -562,12 +564,12 @@ class Agent(object):
                         },
                     )
                 )  # extend conversation with function response
-                self.interface.function_message(f"Error: {error_msg}")
+                self.interface.function_message(f"Ran {function_name}({function_args})", msg_obj=messages[-1])
+                self.interface.function_message(f"Error: {error_msg}", msg_obj=messages[-1])
                 return messages, False, True  # force a heartbeat to allow agent to handle error
 
             # If no failures happened along the way: ...
             # Step 4: send the info on the function call and function response to GPT
-            self.interface.function_message(f"Success: {function_response_string}")
             messages.append(
                 Message.dict_to_message(
                     agent_id=self.agent_state.id,
@@ -581,10 +583,11 @@ class Agent(object):
                     },
                 )
             )  # extend conversation with function response
+            self.interface.function_message(f"Ran {function_name}({function_args})", msg_obj=messages[-1])
+            self.interface.function_message(f"Success: {function_response_string}", msg_obj=messages[-1])
 
         else:
             # Standard non-function reply
-            self.interface.internal_monologue(response_message.content)
             messages.append(
                 Message.dict_to_message(
                     agent_id=self.agent_state.id,
@@ -593,6 +596,7 @@ class Agent(object):
                     openai_message_dict=response_message.model_dump(),
                 )
             )  # extend conversation with assistant's reply
+            self.interface.internal_monologue(response_message.content, msg_obj=messages[-1])
             heartbeat_request = False
             function_failed = False
 
@@ -604,7 +608,8 @@ class Agent(object):
         first_message: bool = False,
         first_message_retry_limit: int = FIRST_MESSAGE_ATTEMPTS,
         skip_verify: bool = False,
-    ) -> Tuple[List[dict], bool, bool, bool]:
+        return_dicts: bool = True,  # if True, return dicts, if False, return Message objects
+    ) -> Tuple[List[Union[dict, Message]], bool, bool, bool]:
         """Top-level event message handler for the MemGPT agent"""
 
         try:
@@ -617,7 +622,6 @@ class Agent(object):
                 else:
                     raise ValueError(f"Bad type for user_message: {type(user_message)}")
 
-                self.interface.user_message(user_message_text)
                 packed_user_message = {"role": "user", "content": user_message_text}
                 # Special handling for AutoGen messages with 'name' field
                 try:
@@ -639,6 +643,7 @@ class Agent(object):
                     model=self.model,
                     openai_message_dict=packed_user_message,
                 )
+                self.interface.user_message(user_message_text, msg_obj=packed_user_message_obj)
 
                 input_message_sequence = self.messages + [packed_user_message]
             # Alternatively, the requestor can send an empty user message
@@ -729,8 +734,8 @@ class Agent(object):
                 )
 
             self._append_to_messages(all_new_messages)
-            all_new_messages_dicts = [msg.to_openai_dict() for msg in all_new_messages]
-            return all_new_messages_dicts, heartbeat_request, function_failed, active_memory_warning, response.usage.completion_tokens
+            messages_to_return = [msg.to_openai_dict() for msg in all_new_messages] if return_dicts else all_new_messages
+            return messages_to_return, heartbeat_request, function_failed, active_memory_warning, response.usage.completion_tokens
 
         except Exception as e:
             printd(f"step() failed\nuser_message = {user_message}\nerror = {e}")
@@ -741,7 +746,7 @@ class Agent(object):
                 self.summarize_messages_inplace()
 
                 # Try step again
-                return self.step(user_message, first_message=first_message)
+                return self.step(user_message, first_message=first_message, return_dicts=return_dicts)
             else:
                 printd(f"step() failed with an unrecognized exception: '{str(e)}'")
                 raise e
diff --git a/memgpt/autogen/interface.py b/memgpt/autogen/interface.py
index 2b1b8706..504df9c8 100644
--- a/memgpt/autogen/interface.py
+++ b/memgpt/autogen/interface.py
@@ -1,8 +1,10 @@
 import json
 import re
+from typing import Optional
 
 from colorama import Fore, Style, init
 
+from memgpt.data_types import Message
 from memgpt.constants import CLI_WARNING_PREFIX, JSON_LOADS_STRICT
 
 init(autoreset=True)
@@ -64,7 +66,7 @@ class AutoGenInterface(object):
         """Clears the buffer. Call before every agent.step() when using MemGPT+AutoGen"""
         self.message_list = []
 
-    def internal_monologue(self, msg):
+    def internal_monologue(self, msg: str, msg_obj: Optional[Message]):
         # NOTE: never gets appended
         if self.debug:
             print(f"inner thoughts :: {msg}")
@@ -74,14 +76,14 @@ class AutoGenInterface(object):
         message = f"\x1B[3m{Fore.LIGHTBLACK_EX}💭 {msg}{Style.RESET_ALL}" if self.fancy else f"[MemGPT agent's inner thoughts] {msg}"
         print(message)
 
-    def assistant_message(self, msg):
+    def assistant_message(self, msg: str, msg_obj: Optional[Message]):
         # NOTE: gets appended
         if self.debug:
             print(f"assistant :: {msg}")
         # message = f"{Fore.YELLOW}{Style.BRIGHT}🤖 {Fore.YELLOW}{msg}{Style.RESET_ALL}" if self.fancy else msg
         self.message_list.append(msg)
 
-    def memory_message(self, msg):
+    def memory_message(self, msg: str):
         # NOTE: never gets appended
         if self.debug:
             print(f"memory :: {msg}")
@@ -90,7 +92,7 @@ class AutoGenInterface(object):
         )
         print(message)
 
-    def system_message(self, msg):
+    def system_message(self, msg: str):
         # NOTE: gets appended
         if self.debug:
             print(f"system :: {msg}")
@@ -98,7 +100,7 @@ class AutoGenInterface(object):
         print(message)
         self.message_list.append(msg)
 
-    def user_message(self, msg, raw=False):
+    def user_message(self, msg: str, msg_obj: Optional[Message], raw=False):
         if self.debug:
             print(f"user :: {msg}")
         if not self.show_user_message:
@@ -136,7 +138,7 @@ class AutoGenInterface(object):
         # TODO should we ever be appending this?
         self.message_list.append(message)
 
-    def function_message(self, msg):
+    def function_message(self, msg: str, msg_obj: Optional[Message]):
         if self.debug:
             print(f"function :: {msg}")
         if not self.show_function_outputs:
diff --git a/memgpt/functions/function_sets/base.py b/memgpt/functions/function_sets/base.py
index a5974f88..a3df806d 100644
--- a/memgpt/functions/function_sets/base.py
+++ b/memgpt/functions/function_sets/base.py
@@ -4,13 +4,14 @@ import json
 import math
 
 from memgpt.constants import MAX_PAUSE_HEARTBEATS, RETRIEVAL_QUERY_DEFAULT_PAGE_SIZE, JSON_ENSURE_ASCII
+from memgpt.agent import Agent
 
 ### Functions / tools the agent can use
 # All functions should return a response string (or None)
 # If the function fails, throw an exception
 
 
-def send_message(self, message: str) -> Optional[str]:
+def send_message(self: Agent, message: str) -> Optional[str]:
     """
     Sends a message to the human user.
 
@@ -20,7 +21,8 @@ def send_message(self, message: str) -> Optional[str]:
     Returns:
         Optional[str]: None is always returned as this function does not produce a response.
     """
-    self.interface.assistant_message(message)
+    # FIXME passing of msg_obj here is a hack, unclear if guaranteed to be the correct reference
+    self.interface.assistant_message(message, msg_obj=self._messages[-1])
     return None
 
 
@@ -36,7 +38,7 @@ Returns:
 """
 
 
-def pause_heartbeats(self, minutes: int) -> Optional[str]:
+def pause_heartbeats(self: Agent, minutes: int) -> Optional[str]:
     minutes = min(MAX_PAUSE_HEARTBEATS, minutes)
 
     # Record the current time
@@ -50,7 +52,7 @@ def pause_heartbeats(self, minutes: int) -> Optional[str]:
 pause_heartbeats.__doc__ = pause_heartbeats_docstring
 
 
-def core_memory_append(self, name: str, content: str) -> Optional[str]:
+def core_memory_append(self: Agent, name: str, content: str) -> Optional[str]:
     """
     Append to the contents of core memory.
 
@@ -66,7 +68,7 @@ def core_memory_append(self, name: str, content: str) -> Optional[str]:
     return None
 
 
-def core_memory_replace(self, name: str, old_content: str, new_content: str) -> Optional[str]:
+def core_memory_replace(self: Agent, name: str, old_content: str, new_content: str) -> Optional[str]:
     """
     Replace the contents of core memory. To delete memories, use an empty string for new_content.
 
@@ -83,7 +85,7 @@ def core_memory_replace(self, name: str, old_content: str, new_content: str) ->
     return None
 
 
-def conversation_search(self, query: str, page: Optional[int] = 0) -> Optional[str]:
+def conversation_search(self: Agent, query: str, page: Optional[int] = 0) -> Optional[str]:
     """
     Search prior conversation history using case-insensitive string matching.
 
@@ -112,7 +114,7 @@ def conversation_search(self, query: str, page: Optional[int] = 0) -> Optional[s
     return results_str
 
 
-def conversation_search_date(self, start_date: str, end_date: str, page: Optional[int] = 0) -> Optional[str]:
+def conversation_search_date(self: Agent, start_date: str, end_date: str, page: Optional[int] = 0) -> Optional[str]:
     """
     Search prior conversation history using a date range.
 
@@ -142,7 +144,7 @@ def conversation_search_date(self, start_date: str, end_date: str, page: Optiona
     return results_str
 
 
-def archival_memory_insert(self, content: str) -> Optional[str]:
+def archival_memory_insert(self: Agent, content: str) -> Optional[str]:
     """
     Add to archival memory. Make sure to phrase the memory contents such that it can be easily queried later.
 
@@ -156,7 +158,7 @@ def archival_memory_insert(self, content: str) -> Optional[str]:
     return None
 
 
-def archival_memory_search(self, query: str, page: Optional[int] = 0) -> Optional[str]:
+def archival_memory_search(self: Agent, query: str, page: Optional[int] = 0) -> Optional[str]:
     """
     Search archival memory using semantic (embedding-based) search.
 
diff --git a/memgpt/interface.py b/memgpt/interface.py
index cbaec27a..edfd86a2 100644
--- a/memgpt/interface.py
+++ b/memgpt/interface.py
@@ -1,11 +1,13 @@
 from abc import ABC, abstractmethod
 import json
 import re
+from typing import List, Optional
 
 from colorama import Fore, Style, init
 
 from memgpt.utils import printd
 from memgpt.constants import CLI_WARNING_PREFIX, JSON_LOADS_STRICT
+from memgpt.data_types import Message
 
 init(autoreset=True)
 
@@ -16,25 +18,28 @@ STRIP_UI = False
 
 
 class AgentInterface(ABC):
-    """Interfaces handle MemGPT-related events (observer pattern)"""
+    """Interfaces handle MemGPT-related events (observer pattern)
+
+    The 'msg' args provides the scoped message, and the optional Message arg can provide additional metadata.
+    """
 
     @abstractmethod
-    def user_message(self, msg):
+    def user_message(self, msg: str, msg_obj: Optional[Message] = None):
         """MemGPT receives a user message"""
         raise NotImplementedError
 
     @abstractmethod
-    def internal_monologue(self, msg):
+    def internal_monologue(self, msg: str, msg_obj: Optional[Message] = None):
         """MemGPT generates some internal monologue"""
         raise NotImplementedError
 
     @abstractmethod
-    def assistant_message(self, msg):
+    def assistant_message(self, msg: str, msg_obj: Optional[Message] = None):
         """MemGPT uses send_message"""
         raise NotImplementedError
 
     @abstractmethod
-    def function_message(self, msg):
+    def function_message(self, msg: str, msg_obj: Optional[Message] = None):
         """MemGPT calls a function"""
         raise NotImplementedError
 
@@ -58,14 +63,14 @@ class CLIInterface(AgentInterface):
     """Basic interface for dumping agent events to the command-line"""
 
     @staticmethod
-    def important_message(msg):
+    def important_message(msg: str):
         fstr = f"{Fore.MAGENTA}{Style.BRIGHT}{{msg}}{Style.RESET_ALL}"
         if STRIP_UI:
             fstr = "{msg}"
         print(fstr.format(msg=msg))
 
     @staticmethod
-    def warning_message(msg):
+    def warning_message(msg: str):
         fstr = f"{Fore.RED}{Style.BRIGHT}{{msg}}{Style.RESET_ALL}"
         if STRIP_UI:
             fstr = "{msg}"
@@ -73,7 +78,7 @@ class CLIInterface(AgentInterface):
             print(fstr.format(msg=msg))
 
     @staticmethod
-    def internal_monologue(msg):
+    def internal_monologue(msg: str, msg_obj: Optional[Message] = None):
         # ANSI escape code for italic is '\x1B[3m'
         fstr = f"\x1B[3m{Fore.LIGHTBLACK_EX}💭 {{msg}}{Style.RESET_ALL}"
         if STRIP_UI:
@@ -81,28 +86,28 @@ class CLIInterface(AgentInterface):
         print(fstr.format(msg=msg))
 
     @staticmethod
-    def assistant_message(msg):
+    def assistant_message(msg: str, msg_obj: Optional[Message] = None):
         fstr = f"{Fore.YELLOW}{Style.BRIGHT}🤖 {Fore.YELLOW}{{msg}}{Style.RESET_ALL}"
         if STRIP_UI:
             fstr = "{msg}"
         print(fstr.format(msg=msg))
 
     @staticmethod
-    def memory_message(msg):
+    def memory_message(msg: str, msg_obj: Optional[Message] = None):
         fstr = f"{Fore.LIGHTMAGENTA_EX}{Style.BRIGHT}🧠 {Fore.LIGHTMAGENTA_EX}{{msg}}{Style.RESET_ALL}"
         if STRIP_UI:
             fstr = "{msg}"
         print(fstr.format(msg=msg))
 
     @staticmethod
-    def system_message(msg):
+    def system_message(msg: str, msg_obj: Optional[Message] = None):
         fstr = f"{Fore.MAGENTA}{Style.BRIGHT}🖥️ [system] {Fore.MAGENTA}{msg}{Style.RESET_ALL}"
         if STRIP_UI:
             fstr = "{msg}"
         print(fstr.format(msg=msg))
 
     @staticmethod
-    def user_message(msg, raw=False, dump=False, debug=DEBUG):
+    def user_message(msg: str, msg_obj: Optional[Message] = None, raw: bool = False, dump: bool = False, debug: bool = DEBUG):
         def print_user_message(icon, msg, printf=print):
             if STRIP_UI:
                 printf(f"{icon} {msg}")
@@ -148,7 +153,8 @@ class CLIInterface(AgentInterface):
             printd_user_message("🧑", msg_json)
 
     @staticmethod
-    def function_message(msg, debug=DEBUG):
+    def function_message(msg: str, msg_obj: Optional[Message] = None, debug: bool = DEBUG):
+
         def print_function_message(icon, msg, color=Fore.RED, printf=print):
             if STRIP_UI:
                 printf(f"⚡{icon} [function] {msg}")
@@ -166,6 +172,9 @@ class CLIInterface(AgentInterface):
             printd_function_message("🟢", msg)
         elif msg.startswith("Error: "):
             printd_function_message("🔴", msg)
+        elif msg.startswith("Ran "):
+            # NOTE: ignore 'ran' messages that come post-execution
+            return
         elif msg.startswith("Running "):
             if debug:
                 printd_function_message("", msg)
@@ -230,7 +239,10 @@ class CLIInterface(AgentInterface):
                 printd_function_message("", msg)
 
     @staticmethod
-    def print_messages(message_sequence, dump=False):
+    def print_messages(message_sequence: List[Message], dump=False):
+        # rewrite to dict format
+        message_sequence = [msg.to_openai_dict() for msg in message_sequence]
+
         idx = len(message_sequence)
         for msg in message_sequence:
             if dump:
@@ -270,7 +282,10 @@ class CLIInterface(AgentInterface):
                 print(f"Unknown role: {content}")
 
     @staticmethod
-    def print_messages_simple(message_sequence):
+    def print_messages_simple(message_sequence: List[Message]):
+        # rewrite to dict format
+        message_sequence = [msg.to_openai_dict() for msg in message_sequence]
+
         for msg in message_sequence:
             role = msg["role"]
             content = msg["content"]
@@ -285,7 +300,10 @@ class CLIInterface(AgentInterface):
                 print(f"Unknown role: {content}")
 
     @staticmethod
-    def print_messages_raw(message_sequence):
+    def print_messages_raw(message_sequence: List[Message]):
+        # rewrite to dict format
+        message_sequence = [msg.to_openai_dict() for msg in message_sequence]
+
         for msg in message_sequence:
             print(msg)
 
diff --git a/memgpt/main.py b/memgpt/main.py
index 010af6af..54253185 100644
--- a/memgpt/main.py
+++ b/memgpt/main.py
@@ -155,13 +155,13 @@ def run_agent_loop(memgpt_agent, config: MemGPTConfig, first, ms: MetadataStore,
                     command = user_input.strip().split()
                     amount = int(command[1]) if len(command) > 1 and command[1].isdigit() else 0
                     if amount == 0:
-                        interface.print_messages(memgpt_agent.messages, dump=True)
+                        interface.print_messages(memgpt_agent._messages, dump=True)
                     else:
-                        interface.print_messages(memgpt_agent.messages[-min(amount, len(memgpt_agent.messages)) :], dump=True)
+                        interface.print_messages(memgpt_agent._messages[-min(amount, len(memgpt_agent.messages)) :], dump=True)
                     continue
 
                 elif user_input.lower() == "/dumpraw":
-                    interface.print_messages_raw(memgpt_agent.messages)
+                    interface.print_messages_raw(memgpt_agent._messages)
                     continue
 
                 elif user_input.lower() == "/memory":
diff --git a/memgpt/server/rest_api/interface.py b/memgpt/server/rest_api/interface.py
index c9abfa28..eb8f635a 100644
--- a/memgpt/server/rest_api/interface.py
+++ b/memgpt/server/rest_api/interface.py
@@ -1,10 +1,12 @@
 import asyncio
 import queue
 from datetime import datetime
+from typing import Optional
 
 import pytz
 
 from memgpt.interface import AgentInterface
+from memgpt.data_types import Message
 
 
 class QueuingInterface(AgentInterface):
@@ -38,7 +40,8 @@ class QueuingInterface(AgentInterface):
                 message = self.buffer.get()
                 if message == "STOP":
                     break
-                yield message | {"date": datetime.now(tz=pytz.utc).isoformat()}
+                # yield message | {"date": datetime.now(tz=pytz.utc).isoformat()}
+                yield message
             else:
                 await asyncio.sleep(0.1)  # Small sleep to prevent a busy loop
 
@@ -51,38 +54,73 @@ class QueuingInterface(AgentInterface):
         self.buffer.put({"internal_error": error})
         self.buffer.put("STOP")
 
-    def user_message(self, msg: str):
+    def user_message(self, msg: str, msg_obj: Optional[Message] = None):
         """Handle reception of a user message"""
+        assert msg_obj is not None, "QueuingInterface requires msg_obj references for metadata"
 
-    def internal_monologue(self, msg: str) -> None:
+    def internal_monologue(self, msg: str, msg_obj: Optional[Message] = None) -> None:
         """Handle the agent's internal monologue"""
+        assert msg_obj is not None, "QueuingInterface requires msg_obj references for metadata"
         if self.debug:
             print(msg)
-        self.buffer.put({"internal_monologue": msg})
 
-    def assistant_message(self, msg: str) -> None:
+        new_message = {"internal_monologue": msg}
+
+        # add extra metadata
+        if msg_obj is not None:
+            new_message["id"] = str(msg_obj.id)
+            new_message["date"] = msg_obj.created_at.isoformat()
+
+        self.buffer.put(new_message)
+
+    def assistant_message(self, msg: str, msg_obj: Optional[Message] = None) -> None:
         """Handle the agent sending a message"""
+        assert msg_obj is not None, "QueuingInterface requires msg_obj references for metadata"
         if self.debug:
             print(msg)
-        self.buffer.put({"assistant_message": msg})
 
-    def function_message(self, msg: str) -> None:
+        new_message = {"assistant_message": msg}
+
+        # add extra metadata
+        if msg_obj is not None:
+            new_message["id"] = str(msg_obj.id)
+            new_message["date"] = msg_obj.created_at.isoformat()
+
+        self.buffer.put(new_message)
+
+    def function_message(self, msg: str, msg_obj: Optional[Message] = None, include_ran_messages: bool = False) -> None:
         """Handle the agent calling a function"""
+        # TODO handle 'function' messages that indicate the start of a function call
+        assert msg_obj is not None, "QueuingInterface requires msg_obj references for metadata"
+
         if self.debug:
             print(msg)
 
         if msg.startswith("Running "):
             msg = msg.replace("Running ", "")
-            self.buffer.put({"function_call": msg})
+            new_message = {"function_call": msg}
+
+        elif msg.startswith("Ran "):
+            if not include_ran_messages:
+                return
+            msg = msg.replace("Ran ", "Function call returned: ")
+            new_message = {"function_call": msg}
 
         elif msg.startswith("Success: "):
             msg = msg.replace("Success: ", "")
-            self.buffer.put({"function_return": msg, "status": "success"})
+            new_message = {"function_return": msg, "status": "success"}
 
         elif msg.startswith("Error: "):
             msg = msg.replace("Error: ", "")
-            self.buffer.put({"function_return": msg, "status": "error"})
+            new_message = {"function_return": msg, "status": "error"}
 
         else:
             # NOTE: generic, should not happen
-            self.buffer.put({"function_message": msg})
+            new_message = {"function_message": msg}
+
+        # add extra metadata
+        if msg_obj is not None:
+            new_message["id"] = str(msg_obj.id)
+            new_message["date"] = msg_obj.created_at.isoformat()
+
+        self.buffer.put(new_message)
diff --git a/memgpt/server/server.py b/memgpt/server/server.py
index bf739208..13c0c965 100644
--- a/memgpt/server/server.py
+++ b/memgpt/server/server.py
@@ -336,7 +336,10 @@ class SyncServer(LockingServer):
         counter = 0
         while True:
             new_messages, heartbeat_request, function_failed, token_warning, tokens_accumulated = memgpt_agent.step(
-                next_input_message, first_message=False, skip_verify=no_verify
+                next_input_message,
+                first_message=False,
+                skip_verify=no_verify,
+                return_dicts=False,
             )
             counter += 1