diff --git a/nanobot/cli/commands.py b/nanobot/cli/commands.py
index 1c20b50..fc4c261 100644
--- a/nanobot/cli/commands.py
+++ b/nanobot/cli/commands.py
@@ -20,6 +20,7 @@ from prompt_toolkit.patch_stdout import patch_stdout
 
 from nanobot import __version__, __logo__
 from nanobot.config.schema import Config
+from nanobot.utils.helpers import sync_workspace_templates
 
 app = typer.Typer(
     name="nanobot",
@@ -185,8 +186,7 @@ def onboard():
         workspace.mkdir(parents=True, exist_ok=True)
         console.print(f"[green]✓[/green] Created workspace at {workspace}")
     
-    # Create default bootstrap files
-    _create_workspace_templates(workspace)
+    sync_workspace_templates(workspace)
     
     console.print(f"\n{__logo__} nanobot is ready!")
     console.print("\nNext steps:")
@@ -198,36 +198,6 @@ def onboard():
 
 
 
-def _create_workspace_templates(workspace: Path):
-    """Create default workspace template files from bundled templates."""
-    from importlib.resources import files as pkg_files
-
-    templates_dir = pkg_files("nanobot") / "templates"
-
-    for item in templates_dir.iterdir():
-        if not item.name.endswith(".md"):
-            continue
-        dest = workspace / item.name
-        if not dest.exists():
-            dest.write_text(item.read_text(encoding="utf-8"), encoding="utf-8")
-            console.print(f"  [dim]Created {item.name}[/dim]")
-
-    memory_dir = workspace / "memory"
-    memory_dir.mkdir(exist_ok=True)
-
-    memory_template = templates_dir / "memory" / "MEMORY.md"
-    memory_file = memory_dir / "MEMORY.md"
-    if not memory_file.exists():
-        memory_file.write_text(memory_template.read_text(encoding="utf-8"), encoding="utf-8")
-        console.print("  [dim]Created memory/MEMORY.md[/dim]")
-
-    history_file = memory_dir / "HISTORY.md"
-    if not history_file.exists():
-        history_file.write_text("", encoding="utf-8")
-        console.print("  [dim]Created memory/HISTORY.md[/dim]")
-
-    (workspace / "skills").mkdir(exist_ok=True)
-
 
 def _make_provider(config: Config):
     """Create the appropriate LLM provider from config."""
@@ -294,6 +264,7 @@ def gateway(
     console.print(f"{__logo__} Starting nanobot gateway on port {port}...")
     
     config = load_config()
+    sync_workspace_templates(config.workspace_path)
     bus = MessageBus()
     provider = _make_provider(config)
     session_manager = SessionManager(config.workspace_path)
@@ -447,6 +418,7 @@ def agent(
     from loguru import logger
     
     config = load_config()
+    sync_workspace_templates(config.workspace_path)
     
     bus = MessageBus()
     provider = _make_provider(config)
diff --git a/nanobot/utils/helpers.py b/nanobot/utils/helpers.py
index 06d8fd5..8963138 100644
--- a/nanobot/utils/helpers.py
+++ b/nanobot/utils/helpers.py
@@ -76,4 +76,37 @@ def parse_session_key(key: str) -> tuple[str, str]:
     parts = key.split(":", 1)
     if len(parts) != 2:
         raise ValueError(f"Invalid session key: {key}")
-    return parts[0], parts[1]
\ No newline at end of file
+    return parts[0], parts[1]
+
+def sync_workspace_templates(workspace: Path, silent: bool = False) -> list[str]:
+    """Sync bundled templates to workspace. Only creates missing files."""
+    from importlib.resources import files as pkg_files
+    try:
+        tpl = pkg_files("nanobot") / "templates"
+    except Exception:
+        return []
+    if not tpl.is_dir():
+        return []
+
+    added: list[str] = []
+
+    def _write(src, dest: Path):
+        """Write src content (or empty string if None) to dest if missing."""
+        if dest.exists():
+            return
+        dest.parent.mkdir(parents=True, exist_ok=True)
+        dest.write_text(src.read_text(encoding="utf-8") if src else "", encoding="utf-8")
+        added.append(str(dest.relative_to(workspace)))
+
+    for item in tpl.iterdir():
+        if item.name.endswith(".md"):
+            _write(item, workspace / item.name)
+    _write(tpl / "memory" / "MEMORY.md", workspace / "memory" / "MEMORY.md")
+    _write(None, workspace / "memory" / "HISTORY.md")
+    (workspace / "skills").mkdir(exist_ok=True)
+
+    if added and not silent:
+        from rich.console import Console
+        for name in added:
+            Console().print(f"  [dim]Created {name}[/dim]")
+    return added