diff --git a/compose.tracing.yaml b/compose.tracing.yaml
new file mode 100644
index 00000000..80d6a3c1
--- /dev/null
+++ b/compose.tracing.yaml
@@ -0,0 +1,18 @@
+services:
+  letta_server:
+    environment:
+      - OTEL_EXPORTER_OTLP_ENDPOINT=http://otel-collector:4317
+
+  otel-collector:
+    image: otel/opentelemetry-collector-contrib:0.92.0
+    command: ["--config=/etc/otel-collector-config.yaml"]
+    volumes:
+      - ./otel-collector-config.yaml:/etc/otel-collector-config.yaml
+    environment:
+      - CLICKHOUSE_ENDPOINT=${CLICKHOUSE_ENDPOINT}
+      - CLICKHOUSE_DATABASE=${CLICKHOUSE_DATABASE}
+      - CLICKHOUSE_USER=${CLICKHOUSE_USER}
+      - CLICKHOUSE_PASSWORD=${CLICKHOUSE_PASSWORD}
+    ports:
+      - "4317:4317"
+      - "4318:4318"
diff --git a/compose.yaml b/compose.yaml
index 0ecdadb1..f6d13abc 100644
--- a/compose.yaml
+++ b/compose.yaml
@@ -49,9 +49,12 @@ services:
       - VLLM_API_BASE=${VLLM_API_BASE}
       - OPENLLM_AUTH_TYPE=${OPENLLM_AUTH_TYPE}
       - OPENLLM_API_KEY=${OPENLLM_API_KEY}
-    #volumes:
-    #- ./configs/server_config.yaml:/root/.letta/config # config file
-    #- ~/.letta/credentials:/root/.letta/credentials # credentials file
+    # volumes:
+    # - ./configs/server_config.yaml:/root/.letta/config # config file
+    # - ~/.letta/credentials:/root/.letta/credentials # credentials file
+    # Uncomment this line to mount a local directory for tool execution, and specify the mount path
+    # before running docker compose: `export LETTA_SANDBOX_MOUNT_PATH=$PWD/directory`
+    # - ${LETTA_SANDBOX_MOUNT_PATH:?}:/root/.letta/tool_execution_dir # mounted volume for tool execution
   letta_nginx:
     hostname: letta-nginx
     image: nginx:stable-alpine3.17-slim
diff --git a/letta/__init__.py b/letta/__init__.py
index e4e33377..e871e65e 100644
--- a/letta/__init__.py
+++ b/letta/__init__.py
@@ -1,4 +1,4 @@
-__version__ = "0.6.35"
+__version__ = "0.6.36"
 
 # import clients
 from letta.client.client import LocalClient, RESTClient, create_client
diff --git a/letta/client/client.py b/letta/client/client.py
index 58f680c9..e26ffa0a 100644
--- a/letta/client/client.py
+++ b/letta/client/client.py
@@ -1,4 +1,5 @@
 import logging
+import sys
 import time
 from typing import Callable, Dict, Generator, List, Optional, Union
 
@@ -40,6 +41,16 @@ from letta.schemas.tool_rule import BaseToolRule
 from letta.server.rest_api.interface import QueuingInterface
 from letta.utils import get_human_text, get_persona_text
 
+# Print deprecation notice in yellow when module is imported
+print(
+    "\n\n\033[93m"
+    + "DEPRECATION WARNING: This legacy Python client has been deprecated and will be removed in a future release.\n"
+    + "Please migrate to the new official python SDK by running: pip install letta-client\n"
+    + "For further documentation, visit: https://docs.letta.com/api-reference/overview#python-sdk"
+    + "\033[0m\n\n",
+    file=sys.stderr,
+)
+
 
 def create_client(base_url: Optional[str] = None, token: Optional[str] = None):
     if base_url is None:
diff --git a/letta/constants.py b/letta/constants.py
index 95db4282..e06984a3 100644
--- a/letta/constants.py
+++ b/letta/constants.py
@@ -2,7 +2,7 @@ import os
 from logging import CRITICAL, DEBUG, ERROR, INFO, NOTSET, WARN, WARNING
 
 LETTA_DIR = os.path.join(os.path.expanduser("~"), ".letta")
-LETTA_DIR_TOOL_SANDBOX = os.path.join(LETTA_DIR, "tool_sandbox_dir")
+LETTA_TOOL_EXECUTION_DIR = os.path.join(LETTA_DIR, "tool_execution_dir")
 
 ADMIN_PREFIX = "/v1/admin"
 API_PREFIX = "/v1"
@@ -146,6 +146,9 @@ MESSAGE_SUMMARY_WARNING_STR = " ".join(
         # "Remember to pass request_heartbeat = true if you would like to send a message immediately after.",
     ]
 )
+DATA_SOURCE_ATTACH_ALERT = (
+    "[ALERT] New data was just uploaded to archival memory. You can view this data by calling the archival_memory_search tool."
+)
 
 # The ackknowledgement message used in the summarize sequence
 MESSAGE_SUMMARY_REQUEST_ACK = "Understood, I will respond with a summary of the message (and only the summary, nothing else) once I receive the conversation history. I'm ready."
diff --git a/letta/log.py b/letta/log.py
index 0d4ad8e1..8a2506ac 100644
--- a/letta/log.py
+++ b/letta/log.py
@@ -54,7 +54,7 @@ DEVELOPMENT_LOGGING = {
             "propagate": True,  # Let logs bubble up to root
         },
         "uvicorn": {
-            "level": "DEBUG",
+            "level": "INFO",
             "handlers": ["console"],
             "propagate": True,
         },
diff --git a/letta/schemas/letta_base.py b/letta/schemas/letta_base.py
index d6850933..5d2a3da3 100644
--- a/letta/schemas/letta_base.py
+++ b/letta/schemas/letta_base.py
@@ -38,15 +38,15 @@ class LettaBase(BaseModel):
             description=cls._id_description(prefix),
             pattern=cls._id_regex_pattern(prefix),
             examples=[cls._id_example(prefix)],
-            default_factory=cls._generate_id,
+            default_factory=cls.generate_id,
         )
 
     @classmethod
-    def _generate_id(cls, prefix: Optional[str] = None) -> str:
+    def generate_id(cls, prefix: Optional[str] = None) -> str:
         prefix = prefix or cls.__id_prefix__
         return f"{prefix}-{uuid.uuid4()}"
 
-    # def _generate_id(self) -> str:
+    # def generate_id(self) -> str:
     #    return f"{self.__id_prefix__}-{uuid.uuid4()}"
 
     @classmethod
diff --git a/letta/schemas/providers.py b/letta/schemas/providers.py
index b7917038..9084c729 100644
--- a/letta/schemas/providers.py
+++ b/letta/schemas/providers.py
@@ -27,7 +27,7 @@ class Provider(ProviderBase):
 
     def resolve_identifier(self):
         if not self.id:
-            self.id = ProviderBase._generate_id(prefix=ProviderBase.__id_prefix__)
+            self.id = ProviderBase.generate_id(prefix=ProviderBase.__id_prefix__)
 
     def list_llm_models(self) -> List[LLMConfig]:
         return []
diff --git a/letta/schemas/sandbox_config.py b/letta/schemas/sandbox_config.py
index 51f13919..80e93c11 100644
--- a/letta/schemas/sandbox_config.py
+++ b/letta/schemas/sandbox_config.py
@@ -6,6 +6,7 @@ from typing import Any, Dict, List, Literal, Optional, Union
 
 from pydantic import BaseModel, Field, model_validator
 
+from letta.constants import LETTA_TOOL_EXECUTION_DIR
 from letta.schemas.agent import AgentState
 from letta.schemas.letta_base import LettaBase, OrmMetadataBase
 from letta.settings import tool_settings
@@ -71,7 +72,7 @@ class LocalSandboxConfig(BaseModel):
             if tool_settings.local_sandbox_dir:
                 data["sandbox_dir"] = tool_settings.local_sandbox_dir
             else:
-                data["sandbox_dir"] = "~/.letta"
+                data["sandbox_dir"] = LETTA_TOOL_EXECUTION_DIR
 
         return data
 
diff --git a/letta/serialize_schemas/agent.py b/letta/serialize_schemas/agent.py
index 036adf44..dfb3ff0e 100644
--- a/letta/serialize_schemas/agent.py
+++ b/letta/serialize_schemas/agent.py
@@ -1,9 +1,16 @@
-from marshmallow import fields
+from typing import Dict
+
+from marshmallow import fields, post_dump
 
 from letta.orm import Agent
+from letta.schemas.agent import AgentState as PydanticAgentState
+from letta.schemas.user import User
 from letta.serialize_schemas.base import BaseSchema
+from letta.serialize_schemas.block import SerializedBlockSchema
 from letta.serialize_schemas.custom_fields import EmbeddingConfigField, LLMConfigField, ToolRulesField
 from letta.serialize_schemas.message import SerializedMessageSchema
+from letta.serialize_schemas.tool import SerializedToolSchema
+from letta.server.db import SessionLocal
 
 
 class SerializedAgentSchema(BaseSchema):
@@ -12,25 +19,51 @@ class SerializedAgentSchema(BaseSchema):
     Excludes relational fields.
     """
 
+    __pydantic_model__ = PydanticAgentState
+
     llm_config = LLMConfigField()
     embedding_config = EmbeddingConfigField()
     tool_rules = ToolRulesField()
 
     messages = fields.List(fields.Nested(SerializedMessageSchema))
+    core_memory = fields.List(fields.Nested(SerializedBlockSchema))
+    tools = fields.List(fields.Nested(SerializedToolSchema))
 
-    def __init__(self, *args, session=None, **kwargs):
-        super().__init__(*args, **kwargs)
-        if session:
-            self.session = session
+    def __init__(self, *args, session: SessionLocal, actor: User, **kwargs):
+        super().__init__(*args, actor=actor, **kwargs)
+        self.session = session
 
-            # propagate session to nested schemas
-            for field_name, field_obj in self.fields.items():
-                if isinstance(field_obj, fields.List) and hasattr(field_obj.inner, "schema"):
-                    field_obj.inner.schema.session = session
-                elif hasattr(field_obj, "schema"):
-                    field_obj.schema.session = session
+        # Propagate session and actor to nested schemas automatically
+        for field in self.fields.values():
+            if isinstance(field, fields.List) and isinstance(field.inner, fields.Nested):
+                field.inner.schema.session = session
+                field.inner.schema.actor = actor
+            elif isinstance(field, fields.Nested):
+                field.schema.session = session
+                field.schema.actor = actor
+
+    @post_dump
+    def sanitize_ids(self, data: Dict, **kwargs):
+        data = super().sanitize_ids(data, **kwargs)
+
+        # Remap IDs of messages
+        # Need to do this in post, so we can correctly map the in-context message IDs
+        # TODO: Remap message_ids to reference objects, not just be a list
+        id_remapping = dict()
+        for message in data.get("messages"):
+            message_id = message.get("id")
+            if message_id not in id_remapping:
+                id_remapping[message_id] = SerializedMessageSchema.__pydantic_model__.generate_id()
+                message["id"] = id_remapping[message_id]
+            else:
+                raise ValueError(f"Duplicate message IDs in agent.messages: {message_id}")
+
+        # Remap in context message ids
+        data["message_ids"] = [id_remapping[message_id] for message_id in data.get("message_ids")]
+
+        return data
 
     class Meta(BaseSchema.Meta):
         model = Agent
         # TODO: Serialize these as well...
-        exclude = ("tools", "sources", "core_memory", "tags", "source_passages", "agent_passages", "organization")
+        exclude = BaseSchema.Meta.exclude + ("sources", "tags", "source_passages", "agent_passages")
diff --git a/letta/serialize_schemas/base.py b/letta/serialize_schemas/base.py
index b64e76e2..e4051408 100644
--- a/letta/serialize_schemas/base.py
+++ b/letta/serialize_schemas/base.py
@@ -1,4 +1,10 @@
+from typing import Dict, Optional
+
+from marshmallow import post_dump, pre_load
 from marshmallow_sqlalchemy import SQLAlchemyAutoSchema
+from sqlalchemy.inspection import inspect
+
+from letta.schemas.user import User
 
 
 class BaseSchema(SQLAlchemyAutoSchema):
@@ -7,6 +13,41 @@ class BaseSchema(SQLAlchemyAutoSchema):
     This ensures all schemas share the same session.
     """
 
+    __pydantic_model__ = None
+    sensitive_ids = {"_created_by_id", "_last_updated_by_id"}
+    sensitive_relationships = {"organization"}
+    id_scramble_placeholder = "xxx"
+
+    def __init__(self, *args, actor: Optional[User] = None, **kwargs):
+        super().__init__(*args, **kwargs)
+        self.actor = actor
+
+    @post_dump
+    def sanitize_ids(self, data: Dict, **kwargs):
+        data["id"] = self.__pydantic_model__.generate_id()
+
+        for sensitive_id in BaseSchema.sensitive_ids.union(BaseSchema.sensitive_relationships):
+            if sensitive_id in data:
+                data[sensitive_id] = BaseSchema.id_scramble_placeholder
+
+        return data
+
+    @pre_load
+    def regenerate_ids(self, data: Dict, **kwargs):
+        if self.Meta.model:
+            mapper = inspect(self.Meta.model)
+            for sensitive_id in BaseSchema.sensitive_ids:
+                if sensitive_id in mapper.columns:
+                    data[sensitive_id] = self.actor.id
+
+            for relationship in BaseSchema.sensitive_relationships:
+                if relationship in mapper.relationships:
+                    data[relationship] = self.actor.organization_id
+
+        return data
+
     class Meta:
+        model = None
         include_relationships = True
         load_instance = True
+        exclude = ()
diff --git a/letta/serialize_schemas/block.py b/letta/serialize_schemas/block.py
new file mode 100644
index 00000000..41139121
--- /dev/null
+++ b/letta/serialize_schemas/block.py
@@ -0,0 +1,15 @@
+from letta.orm.block import Block
+from letta.schemas.block import Block as PydanticBlock
+from letta.serialize_schemas.base import BaseSchema
+
+
+class SerializedBlockSchema(BaseSchema):
+    """
+    Marshmallow schema for serializing/deserializing Block objects.
+    """
+
+    __pydantic_model__ = PydanticBlock
+
+    class Meta(BaseSchema.Meta):
+        model = Block
+        exclude = BaseSchema.Meta.exclude + ("agents",)
diff --git a/letta/serialize_schemas/message.py b/letta/serialize_schemas/message.py
index 58d055d6..f1300d24 100644
--- a/letta/serialize_schemas/message.py
+++ b/letta/serialize_schemas/message.py
@@ -1,4 +1,9 @@
+from typing import Dict
+
+from marshmallow import post_dump
+
 from letta.orm.message import Message
+from letta.schemas.message import Message as PydanticMessage
 from letta.serialize_schemas.base import BaseSchema
 from letta.serialize_schemas.custom_fields import ToolCallField
 
@@ -8,8 +13,17 @@ class SerializedMessageSchema(BaseSchema):
     Marshmallow schema for serializing/deserializing Message objects.
     """
 
+    __pydantic_model__ = PydanticMessage
+
     tool_calls = ToolCallField()
 
+    @post_dump
+    def sanitize_ids(self, data: Dict, **kwargs):
+        # We don't want to remap here
+        # Because of the way that message_ids is just a JSON field on agents
+        # We need to wait for the agent dumps, and then keep track of all the message IDs we remapped
+        return data
+
     class Meta(BaseSchema.Meta):
         model = Message
-        exclude = ("step", "job_message")
+        exclude = BaseSchema.Meta.exclude + ("step", "job_message", "agent")
diff --git a/letta/serialize_schemas/tool.py b/letta/serialize_schemas/tool.py
new file mode 100644
index 00000000..fe2debe8
--- /dev/null
+++ b/letta/serialize_schemas/tool.py
@@ -0,0 +1,15 @@
+from letta.orm import Tool
+from letta.schemas.tool import Tool as PydanticTool
+from letta.serialize_schemas.base import BaseSchema
+
+
+class SerializedToolSchema(BaseSchema):
+    """
+    Marshmallow schema for serializing/deserializing Tool objects.
+    """
+
+    __pydantic_model__ = PydanticTool
+
+    class Meta(BaseSchema.Meta):
+        model = Tool
+        exclude = BaseSchema.Meta.exclude
diff --git a/letta/server/rest_api/routers/v1/identities.py b/letta/server/rest_api/routers/v1/identities.py
index a8a9ad27..b22d355a 100644
--- a/letta/server/rest_api/routers/v1/identities.py
+++ b/letta/server/rest_api/routers/v1/identities.py
@@ -42,6 +42,8 @@ def list_identities(
         )
     except HTTPException:
         raise
+    except NoResultFound as e:
+        raise HTTPException(status_code=404, detail=str(e))
     except Exception as e:
         raise HTTPException(status_code=500, detail=f"{e}")
     return identities
@@ -75,11 +77,11 @@ def create_identity(
     except UniqueConstraintViolationError:
         if identity.project_id:
             raise HTTPException(
-                status_code=400,
+                status_code=409,
                 detail=f"An identity with identifier key {identity.identifier_key} already exists for project {identity.project_id}",
             )
         else:
-            raise HTTPException(status_code=400, detail=f"An identity with identifier key {identity.identifier_key} already exists")
+            raise HTTPException(status_code=409, detail=f"An identity with identifier key {identity.identifier_key} already exists")
     except Exception as e:
         raise HTTPException(status_code=500, detail=f"{e}")
 
@@ -96,6 +98,8 @@ def upsert_identity(
         return server.identity_manager.upsert_identity(identity=identity, actor=actor)
     except HTTPException:
         raise
+    except NoResultFound as e:
+        raise HTTPException(status_code=404, detail=str(e))
     except Exception as e:
         raise HTTPException(status_code=500, detail=f"{e}")
 
@@ -112,6 +116,8 @@ def modify_identity(
         return server.identity_manager.update_identity(identity_id=identity_id, identity=identity, actor=actor)
     except HTTPException:
         raise
+    except NoResultFound as e:
+        raise HTTPException(status_code=404, detail=str(e))
     except Exception as e:
         raise HTTPException(status_code=500, detail=f"{e}")
 
@@ -125,5 +131,12 @@ def delete_identity(
     """
     Delete an identity by its identifier key
     """
-    actor = server.user_manager.get_user_or_default(user_id=actor_id)
-    server.identity_manager.delete_identity(identity_id=identity_id, actor=actor)
+    try:
+        actor = server.user_manager.get_user_or_default(user_id=actor_id)
+        server.identity_manager.delete_identity(identity_id=identity_id, actor=actor)
+    except HTTPException:
+        raise
+    except NoResultFound as e:
+        raise HTTPException(status_code=404, detail=str(e))
+    except Exception as e:
+        raise HTTPException(status_code=500, detail=f"{e}")
diff --git a/letta/server/startup.sh b/letta/server/startup.sh
index d4523cce..44b790f1 100755
--- a/letta/server/startup.sh
+++ b/letta/server/startup.sh
@@ -38,6 +38,15 @@ if ! alembic upgrade head; then
 fi
 echo "Database migration completed successfully."
 
+# Set permissions for tool execution directory if configured
+if [ -n "$LETTA_SANDBOX_MOUNT_PATH" ]; then
+    if ! chmod 777 "$LETTA_SANDBOX_MOUNT_PATH"; then
+        echo "ERROR: Failed to set permissions for tool execution directory at: $LETTA_SANDBOX_MOUNT_PATH"
+        echo "Please check that the directory exists and is accessible"
+        exit 1
+    fi
+fi
+
 # If ADE is enabled, add the --ade flag to the command
 CMD="letta server --host $HOST --port $PORT"
 if [ "${SECURE:-false}" = "true" ]; then
diff --git a/letta/services/agent_manager.py b/letta/services/agent_manager.py
index d57ab21c..06e0ef22 100644
--- a/letta/services/agent_manager.py
+++ b/letta/services/agent_manager.py
@@ -4,7 +4,7 @@ from typing import Dict, List, Optional
 import numpy as np
 from sqlalchemy import Select, and_, func, literal, or_, select, union_all
 
-from letta.constants import BASE_MEMORY_TOOLS, BASE_TOOLS, MAX_EMBEDDING_DIM, MULTI_AGENT_TOOLS
+from letta.constants import BASE_MEMORY_TOOLS, BASE_TOOLS, DATA_SOURCE_ATTACH_ALERT, MAX_EMBEDDING_DIM, MULTI_AGENT_TOOLS
 from letta.embeddings import embedding_model
 from letta.helpers.datetime_helpers import get_utc_time
 from letta.log import get_logger
@@ -35,6 +35,7 @@ from letta.schemas.tool_rule import TerminalToolRule as PydanticTerminalToolRule
 from letta.schemas.tool_rule import ToolRule as PydanticToolRule
 from letta.schemas.user import User as PydanticUser
 from letta.serialize_schemas import SerializedAgentSchema
+from letta.serialize_schemas.tool import SerializedToolSchema
 from letta.services.block_manager import BlockManager
 from letta.services.helpers.agent_manager_helper import (
     _process_relationship,
@@ -394,18 +395,28 @@ class AgentManager:
         with self.session_maker() as session:
             # Retrieve the agent
             agent = AgentModel.read(db_session=session, identifier=agent_id, actor=actor)
-            schema = SerializedAgentSchema(session=session)
+            schema = SerializedAgentSchema(session=session, actor=actor)
             return schema.dump(agent)
 
     @enforce_types
-    def deserialize(self, serialized_agent: dict, actor: PydanticUser) -> PydanticAgentState:
-        # TODO: Use actor to override fields
+    def deserialize(self, serialized_agent: dict, actor: PydanticUser, mark_as_copy: bool = True) -> PydanticAgentState:
+        tool_data_list = serialized_agent.pop("tools", [])
+
         with self.session_maker() as session:
-            schema = SerializedAgentSchema(session=session)
+            schema = SerializedAgentSchema(session=session, actor=actor)
             agent = schema.load(serialized_agent, session=session)
-            agent.organization_id = actor.organization_id
-            agent = agent.create(session, actor=actor)
-            return agent.to_pydantic()
+            if mark_as_copy:
+                agent.name += "_copy"
+            agent.create(session, actor=actor)
+            pydantic_agent = agent.to_pydantic()
+
+        # Need to do this separately as there's some fancy upsert logic that SqlAlchemy cannot handle
+        for tool_data in tool_data_list:
+            pydantic_tool = SerializedToolSchema(actor=actor).load(tool_data, transient=True).to_pydantic()
+            pydantic_tool = self.tool_manager.create_or_update_tool(pydantic_tool, actor=actor)
+            pydantic_agent = self.attach_tool(agent_id=pydantic_agent.id, tool_id=pydantic_tool.id, actor=actor)
+
+        return pydantic_agent
 
     # ======================================================================================================================
     # Per Agent Environment Variable Management
@@ -670,6 +681,7 @@ class AgentManager:
             ValueError: If either agent or source doesn't exist
             IntegrityError: If the source is already attached to the agent
         """
+
         with self.session_maker() as session:
             # Verify both agent and source exist and user has permission to access them
             agent = AgentModel.read(db_session=session, identifier=agent_id, actor=actor)
@@ -687,7 +699,27 @@ class AgentManager:
 
             # Commit the changes
             agent.update(session, actor=actor)
-            return agent.to_pydantic()
+
+        # Add system messsage alert to agent
+        self.append_system_message(
+            agent_id=agent_id,
+            content=DATA_SOURCE_ATTACH_ALERT,
+            actor=actor,
+        )
+
+        return agent.to_pydantic()
+
+    @enforce_types
+    def append_system_message(self, agent_id: str, content: str, actor: PydanticUser):
+
+        # get the agent
+        agent = self.get_agent_by_id(agent_id=agent_id, actor=actor)
+        message = PydanticMessage.dict_to_message(
+            agent_id=agent.id, user_id=actor.id, model=agent.llm_config.model, openai_message_dict={"role": "system", "content": content}
+        )
+
+        # update agent in-context message IDs
+        self.append_to_in_context_messages(messages=[message], agent_id=agent_id, actor=actor)
 
     @enforce_types
     def list_attached_sources(self, agent_id: str, actor: PydanticUser) -> List[PydanticSource]:
diff --git a/letta/services/message_manager.py b/letta/services/message_manager.py
index 26f0bee5..26f7c27b 100644
--- a/letta/services/message_manager.py
+++ b/letta/services/message_manager.py
@@ -46,7 +46,7 @@ class MessageManager:
 
             # Sort results directly based on message_ids
             result_dict = {msg.id: msg.to_pydantic() for msg in results}
-            return [result_dict[msg_id] for msg_id in message_ids]
+            return list(filter(lambda x: x is not None, [result_dict.get(msg_id, None) for msg_id in message_ids]))
 
     @enforce_types
     def create_message(self, pydantic_msg: PydanticMessage, actor: PydanticUser) -> PydanticMessage:
diff --git a/letta/services/sandbox_config_manager.py b/letta/services/sandbox_config_manager.py
index e4e01111..9feaf2a0 100644
--- a/letta/services/sandbox_config_manager.py
+++ b/letta/services/sandbox_config_manager.py
@@ -1,6 +1,6 @@
 from typing import Dict, List, Optional
 
-from letta.constants import LETTA_DIR_TOOL_SANDBOX
+from letta.constants import LETTA_TOOL_EXECUTION_DIR
 from letta.log import get_logger
 from letta.orm.errors import NoResultFound
 from letta.orm.sandbox_config import SandboxConfig as SandboxConfigModel
@@ -35,7 +35,7 @@ class SandboxConfigManager:
                 default_config = {}  # Empty
             else:
                 # TODO: May want to move this to environment variables v.s. persisting in database
-                default_local_sandbox_path = LETTA_DIR_TOOL_SANDBOX
+                default_local_sandbox_path = LETTA_TOOL_EXECUTION_DIR
                 default_config = LocalSandboxConfig(sandbox_dir=default_local_sandbox_path).model_dump(exclude_none=True)
 
             sandbox_config = self.create_or_update_sandbox_config(SandboxConfigCreate(config=default_config), actor=actor)
diff --git a/otel-collector-config.yaml b/otel-collector-config.yaml
new file mode 100644
index 00000000..d13164ea
--- /dev/null
+++ b/otel-collector-config.yaml
@@ -0,0 +1,32 @@
+receivers:
+  otlp:
+    protocols:
+      grpc:
+        endpoint: 0.0.0.0:4317
+      http:
+        endpoint: 0.0.0.0:4318
+
+processors:
+  batch:
+    timeout: 1s
+    send_batch_size: 1024
+
+exporters:
+  clickhouse:
+    endpoint: ${CLICKHOUSE_ENDPOINT}
+    username: ${CLICKHOUSE_USER}
+    password: ${CLICKHOUSE_PASSWORD}
+    database: ${CLICKHOUSE_DATABASE}
+    timeout: 10s
+    retry_on_failure:
+      enabled: true
+      initial_interval: 5s
+      max_interval: 30s
+      max_elapsed_time: 300s
+
+service:
+  pipelines:
+    traces:
+      receivers: [otlp]
+      processors: [batch]
+      exporters: [clickhouse]
diff --git a/poetry.lock b/poetry.lock
index dbf1d59c..32158702 100644
--- a/poetry.lock
+++ b/poetry.lock
@@ -2,13 +2,13 @@
 
 [[package]]
 name = "aiohappyeyeballs"
-version = "2.4.6"
+version = "2.4.8"
 description = "Happy Eyeballs for asyncio"
 optional = false
 python-versions = ">=3.9"
 files = [
-    {file = "aiohappyeyeballs-2.4.6-py3-none-any.whl", hash = "sha256:147ec992cf873d74f5062644332c539fcd42956dc69453fe5204195e560517e1"},
-    {file = "aiohappyeyeballs-2.4.6.tar.gz", hash = "sha256:9b05052f9042985d32ecbe4b59a77ae19c006a78f1344d7fdad69d28ded3d0b0"},
+    {file = "aiohappyeyeballs-2.4.8-py3-none-any.whl", hash = "sha256:6cac4f5dd6e34a9644e69cf9021ef679e4394f54e58a183056d12009e42ea9e3"},
+    {file = "aiohappyeyeballs-2.4.8.tar.gz", hash = "sha256:19728772cb12263077982d2f55453babd8bec6a052a926cd5c0c42796da8bf62"},
 ]
 
 [[package]]
@@ -130,22 +130,22 @@ frozenlist = ">=1.1.0"
 
 [[package]]
 name = "alembic"
-version = "1.14.1"
+version = "1.15.1"
 description = "A database migration tool for SQLAlchemy."
 optional = false
-python-versions = ">=3.8"
+python-versions = ">=3.9"
 files = [
-    {file = "alembic-1.14.1-py3-none-any.whl", hash = "sha256:1acdd7a3a478e208b0503cd73614d5e4c6efafa4e73518bb60e4f2846a37b1c5"},
-    {file = "alembic-1.14.1.tar.gz", hash = "sha256:496e888245a53adf1498fcab31713a469c65836f8de76e01399aa1c3e90dd213"},
+    {file = "alembic-1.15.1-py3-none-any.whl", hash = "sha256:197de710da4b3e91cf66a826a5b31b5d59a127ab41bd0fc42863e2902ce2bbbe"},
+    {file = "alembic-1.15.1.tar.gz", hash = "sha256:e1a1c738577bca1f27e68728c910cd389b9a92152ff91d902da649c192e30c49"},
 ]
 
 [package.dependencies]
 Mako = "*"
-SQLAlchemy = ">=1.3.0"
-typing-extensions = ">=4"
+SQLAlchemy = ">=1.4.0"
+typing-extensions = ">=4.12"
 
 [package.extras]
-tz = ["backports.zoneinfo", "tzdata"]
+tz = ["tzdata"]
 
 [[package]]
 name = "annotated-types"
@@ -447,17 +447,17 @@ files = [
 
 [[package]]
 name = "boto3"
-version = "1.37.5"
+version = "1.37.6"
 description = "The AWS SDK for Python"
 optional = true
 python-versions = ">=3.8"
 files = [
-    {file = "boto3-1.37.5-py3-none-any.whl", hash = "sha256:12166353519aca0cc8d9dcfbbb0d38f8915955a5912b8cb241b2b2314f0dbc14"},
-    {file = "boto3-1.37.5.tar.gz", hash = "sha256:ae6e7048beeaa4478368e554a4b290e3928beb0ae8d8767d108d72381a81af30"},
+    {file = "boto3-1.37.6-py3-none-any.whl", hash = "sha256:4c661389e68437a3fbc1f63decea24b88f7175e022c68622848d47fdf6e0144f"},
+    {file = "boto3-1.37.6.tar.gz", hash = "sha256:e2f4a1edb7e6dbd541c2962117e1c6fea8d5a42788c441a958700a43a3ca7c47"},
 ]
 
 [package.dependencies]
-botocore = ">=1.37.5,<1.38.0"
+botocore = ">=1.37.6,<1.38.0"
 jmespath = ">=0.7.1,<2.0.0"
 s3transfer = ">=0.11.0,<0.12.0"
 
@@ -466,13 +466,13 @@ crt = ["botocore[crt] (>=1.21.0,<2.0a0)"]
 
 [[package]]
 name = "botocore"
-version = "1.37.5"
+version = "1.37.6"
 description = "Low-level, data-driven core of boto 3."
 optional = true
 python-versions = ">=3.8"
 files = [
-    {file = "botocore-1.37.5-py3-none-any.whl", hash = "sha256:e5cfbb8026d5b4fadd9b3a18b61d238a41a8b8f620ab75873dc1467d456150d6"},
-    {file = "botocore-1.37.5.tar.gz", hash = "sha256:f8f526d33ae74d242c577e0440b57b9ec7d53edd41db211155ec8087fe7a5a21"},
+    {file = "botocore-1.37.6-py3-none-any.whl", hash = "sha256:cd282fe9c8adbb55a08c7290982a98ac6cc4507fa1c493f48bc43fd6c8376a57"},
+    {file = "botocore-1.37.6.tar.gz", hash = "sha256:2cb121a403cbec047d76e2401a402a6b2efd3309169037fbac588e8f7125aec4"},
 ]
 
 [package.dependencies]
@@ -2670,30 +2670,24 @@ test = ["ipykernel", "pre-commit", "pytest (<8)", "pytest-cov", "pytest-timeout"
 
 [[package]]
 name = "langchain"
-version = "0.3.19"
+version = "0.3.20"
 description = "Building applications with LLMs through composability"
 optional = false
 python-versions = "<4.0,>=3.9"
 files = [
-    {file = "langchain-0.3.19-py3-none-any.whl", hash = "sha256:1e16d97db9106640b7de4c69f8f5ed22eeda56b45b9241279e83f111640eff16"},
-    {file = "langchain-0.3.19.tar.gz", hash = "sha256:b96f8a445f01d15d522129ffe77cc89c8468dbd65830d153a676de8f6b899e7b"},
+    {file = "langchain-0.3.20-py3-none-any.whl", hash = "sha256:273287f8e61ffdf7e811cf8799e6a71e9381325b8625fd6618900faba79cfdd0"},
+    {file = "langchain-0.3.20.tar.gz", hash = "sha256:edcc3241703e1f6557ef5a5c35cd56f9ccc25ff12e38b4829c66d94971737a93"},
 ]
 
 [package.dependencies]
-aiohttp = ">=3.8.3,<4.0.0"
 async-timeout = {version = ">=4.0.0,<5.0.0", markers = "python_version < \"3.11\""}
-langchain-core = ">=0.3.35,<1.0.0"
+langchain-core = ">=0.3.41,<1.0.0"
 langchain-text-splitters = ">=0.3.6,<1.0.0"
 langsmith = ">=0.1.17,<0.4"
-numpy = [
-    {version = ">=1.26.4,<2", markers = "python_version < \"3.12\""},
-    {version = ">=1.26.2,<3", markers = "python_version >= \"3.12\""},
-]
 pydantic = ">=2.7.4,<3.0.0"
 PyYAML = ">=5.3"
 requests = ">=2,<3"
 SQLAlchemy = ">=1.4,<3"
-tenacity = ">=8.1.0,<8.4.0 || >8.4.0,<10"
 
 [package.extras]
 anthropic = ["langchain-anthropic"]
@@ -2714,26 +2708,23 @@ xai = ["langchain-xai"]
 
 [[package]]
 name = "langchain-community"
-version = "0.3.18"
+version = "0.3.19"
 description = "Community contributed LangChain integrations."
 optional = true
 python-versions = "<4.0,>=3.9"
 files = [
-    {file = "langchain_community-0.3.18-py3-none-any.whl", hash = "sha256:0d4a70144a1750045c4f726f9a43379ed2484178f76e4b8295bcef3a7fdf41d5"},
-    {file = "langchain_community-0.3.18.tar.gz", hash = "sha256:fa2889a8f0b2d22b5c306fd1b070c0970e1f11b604bf55fad2f4a1d0bf68a077"},
+    {file = "langchain_community-0.3.19-py3-none-any.whl", hash = "sha256:268ce7b322c0d1961d7bab1a9419d6ff30c99ad09487dca48d47389b69875b16"},
+    {file = "langchain_community-0.3.19.tar.gz", hash = "sha256:fc100b6d4d6523566a957cdc306b0500e4982d5b221b98f67432da18ba5b2bf5"},
 ]
 
 [package.dependencies]
 aiohttp = ">=3.8.3,<4.0.0"
 dataclasses-json = ">=0.5.7,<0.7"
 httpx-sse = ">=0.4.0,<1.0.0"
-langchain = ">=0.3.19,<1.0.0"
-langchain-core = ">=0.3.37,<1.0.0"
+langchain = ">=0.3.20,<1.0.0"
+langchain-core = ">=0.3.41,<1.0.0"
 langsmith = ">=0.1.125,<0.4"
-numpy = [
-    {version = ">=1.26.4,<2", markers = "python_version < \"3.12\""},
-    {version = ">=1.26.2,<3", markers = "python_version >= \"3.12\""},
-]
+numpy = ">=1.26.2,<3"
 pydantic-settings = ">=2.4.0,<3.0.0"
 PyYAML = ">=5.3"
 requests = ">=2,<3"
@@ -2742,13 +2733,13 @@ tenacity = ">=8.1.0,<8.4.0 || >8.4.0,<10"
 
 [[package]]
 name = "langchain-core"
-version = "0.3.40"
+version = "0.3.41"
 description = "Building applications with LLMs through composability"
 optional = false
 python-versions = "<4.0,>=3.9"
 files = [
-    {file = "langchain_core-0.3.40-py3-none-any.whl", hash = "sha256:9f31358741f10a13db8531e8288b8a5ae91904018c5c2e6f739d6645a98fca03"},
-    {file = "langchain_core-0.3.40.tar.gz", hash = "sha256:893a238b38491967c804662c1ec7c3e6ebaf223d1125331249c3cf3862ff2746"},
+    {file = "langchain_core-0.3.41-py3-none-any.whl", hash = "sha256:1a27cca5333bae7597de4004fb634b5f3e71667a3da6493b94ce83bcf15a23bd"},
+    {file = "langchain_core-0.3.41.tar.gz", hash = "sha256:d3ee9f3616ebbe7943470ade23d4a04e1729b1512c0ec55a4a07bd2ac64dedb4"},
 ]
 
 [package.dependencies]
@@ -3074,13 +3065,13 @@ llama-index-program-openai = ">=0.3.0,<0.4.0"
 
 [[package]]
 name = "llama-index-readers-file"
-version = "0.4.5"
+version = "0.4.6"
 description = "llama-index readers file integration"
 optional = false
 python-versions = "<4.0,>=3.9"
 files = [
-    {file = "llama_index_readers_file-0.4.5-py3-none-any.whl", hash = "sha256:704ac6b549f0ec59c0bd796007fceced2fff89a44b03d7ee36bce2d26b39e526"},
-    {file = "llama_index_readers_file-0.4.5.tar.gz", hash = "sha256:3ce5c8ad7f285bb7ff828c5b2e20088856ac65cf96640287eca770b69a21df88"},
+    {file = "llama_index_readers_file-0.4.6-py3-none-any.whl", hash = "sha256:5b5589a528bd3bdf41798406ad0b3ad1a55f28085ff9078a00b61567ff29acba"},
+    {file = "llama_index_readers_file-0.4.6.tar.gz", hash = "sha256:50119fdffb7f5aa4638dda2227c79ad6a5f326b9c55a7e46054df99f46a709e0"},
 ]
 
 [package.dependencies]
@@ -3655,13 +3646,13 @@ files = [
 
 [[package]]
 name = "openai"
-version = "1.65.2"
+version = "1.65.3"
 description = "The official Python library for the openai API"
 optional = false
 python-versions = ">=3.8"
 files = [
-    {file = "openai-1.65.2-py3-none-any.whl", hash = "sha256:27d9fe8de876e31394c2553c4e6226378b6ed85e480f586ccfe25b7193fb1750"},
-    {file = "openai-1.65.2.tar.gz", hash = "sha256:729623efc3fd91c956f35dd387fa5c718edd528c4bed9f00b40ef290200fb2ce"},
+    {file = "openai-1.65.3-py3-none-any.whl", hash = "sha256:a155fa5d60eccda516384d3d60d923e083909cc126f383fe4a350f79185c232a"},
+    {file = "openai-1.65.3.tar.gz", hash = "sha256:9b7cd8f79140d03d77f4ed8aeec6009be5dcd79bbc02f03b0e8cd83356004f71"},
 ]
 
 [package.dependencies]
@@ -5696,20 +5687,20 @@ pyasn1 = ">=0.1.3"
 
 [[package]]
 name = "s3transfer"
-version = "0.11.3"
+version = "0.11.4"
 description = "An Amazon S3 Transfer Manager"
 optional = true
 python-versions = ">=3.8"
 files = [
-    {file = "s3transfer-0.11.3-py3-none-any.whl", hash = "sha256:ca855bdeb885174b5ffa95b9913622459d4ad8e331fc98eb01e6d5eb6a30655d"},
-    {file = "s3transfer-0.11.3.tar.gz", hash = "sha256:edae4977e3a122445660c7c114bba949f9d191bae3b34a096f18a1c8c354527a"},
+    {file = "s3transfer-0.11.4-py3-none-any.whl", hash = "sha256:ac265fa68318763a03bf2dc4f39d5cbd6a9e178d81cc9483ad27da33637e320d"},
+    {file = "s3transfer-0.11.4.tar.gz", hash = "sha256:559f161658e1cf0a911f45940552c696735f5c74e64362e515f333ebed87d679"},
 ]
 
 [package.dependencies]
-botocore = ">=1.36.0,<2.0a.0"
+botocore = ">=1.37.4,<2.0a.0"
 
 [package.extras]
-crt = ["botocore[crt] (>=1.36.0,<2.0a.0)"]
+crt = ["botocore[crt] (>=1.37.4,<2.0a.0)"]
 
 [[package]]
 name = "scramp"
diff --git a/pyproject.toml b/pyproject.toml
index 72f2b4b7..29a79b34 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -1,6 +1,6 @@
 [tool.poetry]
 name = "letta"
-version = "0.6.35"
+version = "0.6.36"
 packages = [
     {include = "letta"},
 ]
diff --git a/tests/test_agent_serialization.py b/tests/test_agent_serialization.py
index ade9f2f4..2651c08c 100644
--- a/tests/test_agent_serialization.py
+++ b/tests/test_agent_serialization.py
@@ -1,15 +1,27 @@
+import difflib
 import json
+from datetime import datetime, timezone
+from typing import Any, Dict, List, Mapping
 
 import pytest
+from rich.console import Console
+from rich.syntax import Syntax
 
 from letta import create_client
 from letta.config import LettaConfig
 from letta.orm import Base
-from letta.schemas.agent import CreateAgent
+from letta.schemas.agent import AgentState, CreateAgent
+from letta.schemas.block import CreateBlock
 from letta.schemas.embedding_config import EmbeddingConfig
+from letta.schemas.enums import MessageRole
 from letta.schemas.llm_config import LLMConfig
+from letta.schemas.message import MessageCreate
+from letta.schemas.organization import Organization
+from letta.schemas.user import User
 from letta.server.server import SyncServer
 
+console = Console()
+
 
 def _clear_tables():
     from letta.server.db import db_context
@@ -58,80 +70,291 @@ def default_user(server: SyncServer, default_organization):
 
 
 @pytest.fixture
-def sarah_agent(server: SyncServer, default_user, default_organization):
+def other_organization(server: SyncServer):
+    """Fixture to create and return the default organization."""
+    org = server.organization_manager.create_organization(pydantic_org=Organization(name="letta"))
+    yield org
+
+
+@pytest.fixture
+def other_user(server: SyncServer, other_organization):
+    """Fixture to create and return the default user within the default organization."""
+    user = server.user_manager.create_user(pydantic_user=User(organization_id=other_organization.id, name="sarah"))
+    yield user
+
+
+@pytest.fixture
+def serialize_test_agent(server: SyncServer, default_user, default_organization):
     """Fixture to create and return a sample agent within the default organization."""
+    timestamp = datetime.now().strftime("%Y%m%d_%H%M%S")
+    agent_name = f"serialize_test_agent_{timestamp}"
+
+    server.tool_manager.upsert_base_tools(actor=default_user)
+
     agent_state = server.agent_manager.create_agent(
         agent_create=CreateAgent(
-            name="sarah_agent",
-            memory_blocks=[],
+            name=agent_name,
+            memory_blocks=[
+                CreateBlock(
+                    value="Name: Caren",
+                    label="human",
+                ),
+            ],
             llm_config=LLMConfig.default_config("gpt-4o-mini"),
             embedding_config=EmbeddingConfig.default_config(provider="openai"),
+            include_base_tools=True,
         ),
         actor=default_user,
     )
     yield agent_state
 
 
-def test_agent_serialization(server, sarah_agent, default_user):
-    """Test serializing an Agent instance to JSON."""
-    result = server.agent_manager.serialize(agent_id=sarah_agent.id, actor=default_user)
-
-    # Assert that the result is a dictionary (JSON object)
-    assert isinstance(result, dict), "Expected a dictionary result"
-
-    # Assert that the 'id' field is present and matches the agent's ID
-    assert "id" in result, "Agent 'id' is missing in the serialized result"
-    assert result["id"] == sarah_agent.id, f"Expected agent 'id' to be {sarah_agent.id}, but got {result['id']}"
-
-    # Assert that the 'llm_config' and 'embedding_config' fields exist
-    assert "llm_config" in result, "'llm_config' is missing in the serialized result"
-    assert "embedding_config" in result, "'embedding_config' is missing in the serialized result"
-
-    # Assert that 'messages' is a list
-    assert isinstance(result.get("messages", []), list), "'messages' should be a list"
-
-    # Assert that the 'tool_exec_environment_variables' field is a list (empty or populated)
-    assert isinstance(result.get("tool_exec_environment_variables", []), list), "'tool_exec_environment_variables' should be a list"
-
-    # Assert that the 'agent_type' is a valid string
-    assert isinstance(result.get("agent_type"), str), "'agent_type' should be a string"
-
-    # Assert that the 'tool_rules' field is a list (even if empty)
-    assert isinstance(result.get("tool_rules", []), list), "'tool_rules' should be a list"
-
-    # Check that all necessary fields are present in the 'messages' section, focusing on core elements
-    if "messages" in result:
-        for message in result["messages"]:
-            assert "id" in message, "Message 'id' is missing"
-            assert "text" in message, "Message 'text' is missing"
-            assert "role" in message, "Message 'role' is missing"
-            assert "created_at" in message, "Message 'created_at' is missing"
-            assert "updated_at" in message, "Message 'updated_at' is missing"
-
-    # Optionally check that 'created_at' and 'updated_at' are in ISO 8601 format
-    assert isinstance(result["created_at"], str), "Expected 'created_at' to be a string"
-    assert isinstance(result["updated_at"], str), "Expected 'updated_at' to be a string"
-
-    # Optionally check for presence of any required metadata or ensure it is null if expected
-    assert "metadata_" in result, "'metadata_' field is missing"
-    assert result["metadata_"] is None, "'metadata_' should be null"
-
-    # Assert that the agent name is as expected (if defined)
-    assert result.get("name") == sarah_agent.name, "Expected agent 'name' to not be None, but found something else"
-
-    print(json.dumps(result, indent=4))
+# Helper functions below
 
 
-def test_agent_deserialization_basic(local_client, server, sarah_agent, default_user):
+def dict_to_pretty_json(d: Dict[str, Any]) -> str:
+    """Convert a dictionary to a pretty JSON string with sorted keys, handling datetime objects."""
+    return json.dumps(d, indent=2, sort_keys=True, default=_json_serializable)
+
+
+def _json_serializable(obj: Any) -> Any:
+    """Convert non-serializable objects (like datetime) to a JSON-friendly format."""
+    if isinstance(obj, datetime):
+        return obj.isoformat()  # Convert datetime to ISO 8601 format
+    raise TypeError(f"Object of type {obj.__class__.__name__} is not JSON serializable")
+
+
+def print_dict_diff(dict1: Dict[str, Any], dict2: Dict[str, Any]) -> None:
+    """Prints a detailed colorized diff between two dictionaries."""
+    json1 = dict_to_pretty_json(dict1).splitlines()
+    json2 = dict_to_pretty_json(dict2).splitlines()
+
+    diff = list(difflib.unified_diff(json1, json2, fromfile="Expected", tofile="Actual", lineterm=""))
+
+    if diff:
+        console.print("\n🔍 [bold red]Dictionary Diff:[/bold red]")
+        diff_text = "\n".join(diff)
+        syntax = Syntax(diff_text, "diff", theme="monokai", line_numbers=False)
+        console.print(syntax)
+    else:
+        console.print("\n✅ [bold green]No differences found in dictionaries.[/bold green]")
+
+
+def has_same_prefix(value1: Any, value2: Any) -> bool:
+    """Check if two string values have the same major prefix (before the second hyphen)."""
+    if not isinstance(value1, str) or not isinstance(value2, str):
+        return False
+
+    prefix1 = value1.split("-")[0]
+    prefix2 = value2.split("-")[0]
+
+    return prefix1 == prefix2
+
+
+def compare_lists(list1: List[Any], list2: List[Any]) -> bool:
+    """Compare lists while handling unordered dictionaries inside."""
+    if len(list1) != len(list2):
+        return False
+
+    if all(isinstance(item, Mapping) for item in list1) and all(isinstance(item, Mapping) for item in list2):
+        return all(any(_compare_agent_state_model_dump(i1, i2, log=False) for i2 in list2) for i1 in list1)
+
+    return sorted(list1) == sorted(list2)
+
+
+def strip_datetime_fields(d: Dict[str, Any]) -> Dict[str, Any]:
+    """Remove datetime fields from a dictionary before comparison."""
+    return {k: v for k, v in d.items() if not isinstance(v, datetime)}
+
+
+def _log_mismatch(key: str, expected: Any, actual: Any, log: bool) -> None:
+    """Log detailed information about a mismatch."""
+    if log:
+        print(f"\n🔴 Mismatch Found in Key: '{key}'")
+        print(f"Expected: {expected}")
+        print(f"Actual:   {actual}")
+
+        if isinstance(expected, str) and isinstance(actual, str):
+            print("\n🔍 String Diff:")
+            diff = difflib.ndiff(expected.splitlines(), actual.splitlines())
+            print("\n".join(diff))
+
+
+def _compare_agent_state_model_dump(d1: Dict[str, Any], d2: Dict[str, Any], log: bool = True) -> bool:
+    """
+    Compare two dictionaries with special handling:
+    - Keys in `ignore_prefix_fields` should match only by prefix.
+    - 'message_ids' lists should match in length only.
+    - Datetime fields are ignored.
+    - Order-independent comparison for lists of dicts.
+    """
+    ignore_prefix_fields = {"id", "last_updated_by_id", "organization_id", "created_by_id"}
+
+    # Remove datetime fields upfront
+    d1 = strip_datetime_fields(d1)
+    d2 = strip_datetime_fields(d2)
+
+    if d1.keys() != d2.keys():
+        _log_mismatch("dict_keys", set(d1.keys()), set(d2.keys()))
+        return False
+
+    for key, v1 in d1.items():
+        v2 = d2[key]
+
+        if key in ignore_prefix_fields:
+            if v1 and v2 and not has_same_prefix(v1, v2):
+                _log_mismatch(key, v1, v2, log)
+                return False
+        elif key == "message_ids":
+            if not isinstance(v1, list) or not isinstance(v2, list) or len(v1) != len(v2):
+                _log_mismatch(key, v1, v2, log)
+                return False
+        elif isinstance(v1, Dict) and isinstance(v2, Dict):
+            if not _compare_agent_state_model_dump(v1, v2):
+                _log_mismatch(key, v1, v2, log)
+                return False
+        elif isinstance(v1, list) and isinstance(v2, list):
+            if not compare_lists(v1, v2):
+                _log_mismatch(key, v1, v2, log)
+                return False
+        elif v1 != v2:
+            _log_mismatch(key, v1, v2, log)
+            return False
+
+    return True
+
+
+def compare_agent_state(original: AgentState, copy: AgentState, mark_as_copy: bool) -> bool:
+    """Wrapper function that provides a default set of ignored prefix fields."""
+    if not mark_as_copy:
+        assert original.name == copy.name
+
+    return _compare_agent_state_model_dump(original.model_dump(exclude="name"), copy.model_dump(exclude="name"))
+
+
+# Sanity tests for our agent model_dump verifier helpers
+
+
+def test_sanity_identical_dicts():
+    d1 = {"name": "Alice", "age": 30, "details": {"city": "New York"}}
+    d2 = {"name": "Alice", "age": 30, "details": {"city": "New York"}}
+    assert _compare_agent_state_model_dump(d1, d2)
+
+
+def test_sanity_different_dicts():
+    d1 = {"name": "Alice", "age": 30}
+    d2 = {"name": "Bob", "age": 30}
+    assert not _compare_agent_state_model_dump(d1, d2)
+
+
+def test_sanity_ignored_id_fields():
+    d1 = {"id": "user-abc123", "name": "Alice"}
+    d2 = {"id": "user-xyz789", "name": "Alice"}  # Different ID, same prefix
+    assert _compare_agent_state_model_dump(d1, d2)
+
+
+def test_sanity_different_id_prefix_fails():
+    d1 = {"id": "user-abc123"}
+    d2 = {"id": "admin-xyz789"}  # Different prefix
+    assert not _compare_agent_state_model_dump(d1, d2)
+
+
+def test_sanity_nested_dicts():
+    d1 = {"user": {"id": "user-123", "name": "Alice"}}
+    d2 = {"user": {"id": "user-456", "name": "Alice"}}  # ID changes, but prefix matches
+    assert _compare_agent_state_model_dump(d1, d2)
+
+
+def test_sanity_list_handling():
+    d1 = {"items": [1, 2, 3]}
+    d2 = {"items": [1, 2, 3]}
+    assert _compare_agent_state_model_dump(d1, d2)
+
+
+def test_sanity_list_mismatch():
+    d1 = {"items": [1, 2, 3]}
+    d2 = {"items": [1, 2, 4]}
+    assert not _compare_agent_state_model_dump(d1, d2)
+
+
+def test_sanity_message_ids_length_check():
+    d1 = {"message_ids": ["msg-123", "msg-456", "msg-789"]}
+    d2 = {"message_ids": ["msg-abc", "msg-def", "msg-ghi"]}  # Same length, different values
+    assert _compare_agent_state_model_dump(d1, d2)
+
+
+def test_sanity_message_ids_different_length():
+    d1 = {"message_ids": ["msg-123", "msg-456"]}
+    d2 = {"message_ids": ["msg-123"]}
+    assert not _compare_agent_state_model_dump(d1, d2)
+
+
+def test_sanity_datetime_fields():
+    d1 = {"created_at": datetime(2025, 3, 4, 18, 25, 37, tzinfo=timezone.utc)}
+    d2 = {"created_at": datetime(2025, 3, 4, 18, 25, 37, tzinfo=timezone.utc)}
+    assert _compare_agent_state_model_dump(d1, d2)
+
+
+def test_sanity_datetime_mismatch():
+    d1 = {"created_at": datetime(2025, 3, 4, 18, 25, 37, tzinfo=timezone.utc)}
+    d2 = {"created_at": datetime(2025, 3, 4, 18, 25, 38, tzinfo=timezone.utc)}  # One second difference
+    assert _compare_agent_state_model_dump(d1, d2)  # Should ignore
+
+
+# Agent serialize/deserialize tests
+
+
+@pytest.mark.parametrize("mark_as_copy", [True, False])
+def test_mark_as_copy_simple(local_client, server, serialize_test_agent, default_user, other_user, mark_as_copy):
     """Test deserializing JSON into an Agent instance."""
-    # Send a message first
-    sarah_agent = server.agent_manager.get_agent_by_id(agent_id=sarah_agent.id, actor=default_user)
-    result = server.agent_manager.serialize(agent_id=sarah_agent.id, actor=default_user)
+    result = server.agent_manager.serialize(agent_id=serialize_test_agent.id, actor=default_user)
 
-    # Delete the agent
-    server.agent_manager.delete_agent(sarah_agent.id, actor=default_user)
+    # Deserialize the agent
+    agent_copy = server.agent_manager.deserialize(serialized_agent=result, actor=other_user, mark_as_copy=mark_as_copy)
 
-    agent_state = server.agent_manager.deserialize(serialized_agent=result, actor=default_user)
+    # Compare serialized representations to check for exact match
+    print_dict_diff(json.loads(serialize_test_agent.model_dump_json()), json.loads(agent_copy.model_dump_json()))
+    assert compare_agent_state(agent_copy, serialize_test_agent, mark_as_copy=mark_as_copy)
 
-    assert agent_state.name == sarah_agent.name
-    assert len(agent_state.message_ids) == len(sarah_agent.message_ids)
+
+def test_in_context_message_id_remapping(local_client, server, serialize_test_agent, default_user, other_user):
+    """Test deserializing JSON into an Agent instance."""
+    result = server.agent_manager.serialize(agent_id=serialize_test_agent.id, actor=default_user)
+
+    # Check remapping on message_ids and messages is consistent
+    assert sorted([m["id"] for m in result["messages"]]) == sorted(result["message_ids"])
+
+    # Deserialize the agent
+    agent_copy = server.agent_manager.deserialize(serialized_agent=result, actor=other_user)
+
+    # Make sure all the messages are able to be retrieved
+    in_context_messages = server.agent_manager.get_in_context_messages(agent_id=agent_copy.id, actor=other_user)
+    assert len(in_context_messages) == len(result["message_ids"])
+    assert sorted([m.id for m in in_context_messages]) == sorted(result["message_ids"])
+
+
+def test_agent_serialize_with_user_messages(local_client, server, serialize_test_agent, default_user, other_user):
+    """Test deserializing JSON into an Agent instance."""
+    mark_as_copy = False
+    server.send_messages(
+        actor=default_user, agent_id=serialize_test_agent.id, messages=[MessageCreate(role=MessageRole.user, content="hello")]
+    )
+    result = server.agent_manager.serialize(agent_id=serialize_test_agent.id, actor=default_user)
+
+    # Deserialize the agent
+    agent_copy = server.agent_manager.deserialize(serialized_agent=result, actor=other_user, mark_as_copy=mark_as_copy)
+
+    # Get most recent original agent instance
+    serialize_test_agent = server.agent_manager.get_agent_by_id(agent_id=serialize_test_agent.id, actor=default_user)
+
+    # Compare serialized representations to check for exact match
+    print_dict_diff(json.loads(serialize_test_agent.model_dump_json()), json.loads(agent_copy.model_dump_json()))
+    assert compare_agent_state(agent_copy, serialize_test_agent, mark_as_copy=mark_as_copy)
+
+    # Make sure both agents can receive messages after
+    server.send_messages(
+        actor=default_user, agent_id=serialize_test_agent.id, messages=[MessageCreate(role=MessageRole.user, content="and hello again")]
+    )
+    server.send_messages(
+        actor=other_user, agent_id=agent_copy.id, messages=[MessageCreate(role=MessageRole.user, content="and hello again")]
+    )
diff --git a/tests/test_managers.py b/tests/test_managers.py
index 52206d72..334e72ed 100644
--- a/tests/test_managers.py
+++ b/tests/test_managers.py
@@ -8,7 +8,7 @@ from openai.types.chat.chat_completion_message_tool_call import Function as Open
 from sqlalchemy.exc import IntegrityError
 
 from letta.config import LettaConfig
-from letta.constants import BASE_MEMORY_TOOLS, BASE_TOOLS, MULTI_AGENT_TOOLS
+from letta.constants import BASE_MEMORY_TOOLS, BASE_TOOLS, LETTA_TOOL_EXECUTION_DIR, MULTI_AGENT_TOOLS
 from letta.embeddings import embedding_model
 from letta.functions.functions import derive_openai_json_schema, parse_source_code
 from letta.orm import Base
@@ -2340,7 +2340,7 @@ def test_create_local_sandbox_config_defaults(server: SyncServer, default_user):
     # Assertions
     assert created_config.type == SandboxType.LOCAL
     assert created_config.get_local_config() == sandbox_config_create.config
-    assert created_config.get_local_config().sandbox_dir in {"~/.letta", tool_settings.local_sandbox_dir}
+    assert created_config.get_local_config().sandbox_dir in {LETTA_TOOL_EXECUTION_DIR, tool_settings.local_sandbox_dir}
     assert created_config.organization_id == default_user.organization_id