diff --git a/letta/server/server.py b/letta/server/server.py
index e532d467..ee0fb45c 100644
--- a/letta/server/server.py
+++ b/letta/server/server.py
@@ -83,6 +83,7 @@ from letta.server.rest_api.utils import sse_async_generator
 from letta.services.agent_manager import AgentManager
 from letta.services.block_manager import BlockManager
 from letta.services.group_manager import GroupManager
+from letta.services.helpers.tool_execution_helper import prepare_local_sandbox
 from letta.services.identity_manager import IdentityManager
 from letta.services.job_manager import JobManager
 from letta.services.llm_batch_manager import LLMBatchManager
@@ -259,6 +260,13 @@ class SyncServer(Server):
                 )
                 logger.info(f"Successfully created default local sandbox config:\n{sandbox_config.get_local_config().model_dump()}")
 
+                if use_venv and tool_settings.tool_exec_autoreload_venv:
+                    prepare_local_sandbox(
+                        sandbox_config.get_local_config(),
+                        env=os.environ.copy(),
+                        force_recreate=True,
+                    )
+
         # collect providers (always has Letta as a default)
         self._enabled_providers: List[Provider] = [LettaProvider()]
         if model_settings.openai_api_key:
diff --git a/letta/services/helpers/tool_execution_helper.py b/letta/services/helpers/tool_execution_helper.py
index ac86f480..043594cc 100644
--- a/letta/services/helpers/tool_execution_helper.py
+++ b/letta/services/helpers/tool_execution_helper.py
@@ -171,3 +171,30 @@ def add_imports_and_pydantic_schemas_for_args(args_json_schema: dict) -> str:
     )
     result = parser.parse()
     return result
+
+
+def prepare_local_sandbox(
+    local_cfg: LocalSandboxConfig,
+    env: Dict[str, str],
+    force_recreate: bool = False,
+) -> None:
+    """
+    Ensure the sandbox virtual-env is freshly created and that
+    requirements are installed.  Uses your existing helpers.
+    """
+    sandbox_dir = os.path.expanduser(local_cfg.sandbox_dir)
+    venv_path = os.path.join(sandbox_dir, local_cfg.venv_name)
+
+    create_venv_for_local_sandbox(
+        sandbox_dir_path=sandbox_dir,
+        venv_path=venv_path,
+        env=env,
+        force_recreate=force_recreate,
+    )
+
+    install_pip_requirements_for_sandbox(
+        local_cfg,
+        upgrade=True,
+        user_install_if_no_venv=False,
+        env=env,
+    )
diff --git a/letta/settings.py b/letta/settings.py
index 59a4cd7c..7adea271 100644
--- a/letta/settings.py
+++ b/letta/settings.py
@@ -19,6 +19,7 @@ class ToolSettings(BaseSettings):
     tool_exec_dir: Optional[str] = None
     tool_sandbox_timeout: float = 180
     tool_exec_venv_name: Optional[str] = None
+    tool_exec_autoreload_venv: bool = True
 
     # MCP settings
     mcp_connect_to_server_timeout: float = 30.0