diff --git a/package.json b/package.json
index 2e4ec66..6a97e31 100644
--- a/package.json
+++ b/package.json
@@ -1,6 +1,6 @@
 {
   "name": "@letta-ai/letta-code",
-  "version": "0.1.8",
+  "version": "0.1.9",
   "description": "Letta Code is a CLI tool for interacting with stateful Letta agents from the terminal.",
   "type": "module",
   "bin": {
diff --git a/src/index.ts b/src/index.ts
index 194f064..df61ecb 100755
--- a/src/index.ts
+++ b/src/index.ts
@@ -3,6 +3,7 @@ import { parseArgs } from "node:util";
 import type { Letta } from "@letta-ai/letta-client";
 import { getResumeData, type ResumeData } from "./agent/check-approval";
 import { getClient } from "./agent/client";
+import { permissionMode } from "./permissions/mode";
 import { loadSettings } from "./settings";
 import { loadTools, upsertToolsToServer } from "./tools/manager";
 
@@ -123,8 +124,6 @@ async function main() {
   const yoloMode = values.yolo as boolean | undefined;
 
   if (yoloMode || permissionModeValue) {
-    const { permissionMode } = await import("./permissions/mode");
-
     if (yoloMode) {
       // --yolo is an alias for --permission-mode bypassPermissions
       permissionMode.setMode("bypassPermissions");
diff --git a/src/permissions/mode.ts b/src/permissions/mode.ts
index 900cd62..e9fe8fd 100644
--- a/src/permissions/mode.ts
+++ b/src/permissions/mode.ts
@@ -7,12 +7,39 @@ export type PermissionMode =
   | "plan"
   | "bypassPermissions";
 
+// Use globalThis to ensure singleton across bundle
+// This prevents Bun's bundler from creating duplicate instances of the mode manager
+const MODE_KEY = Symbol.for("@letta/permissionMode");
+
+type GlobalWithMode = typeof globalThis & {
+  [key: symbol]: PermissionMode;
+};
+
+function getGlobalMode(): PermissionMode {
+  const global = globalThis as GlobalWithMode;
+  if (!global[MODE_KEY]) {
+    global[MODE_KEY] = "default";
+  }
+  return global[MODE_KEY];
+}
+
+function setGlobalMode(value: PermissionMode): void {
+  const global = globalThis as GlobalWithMode;
+  global[MODE_KEY] = value;
+}
+
 /**
  * Permission mode state for the current session.
  * Set via CLI --permission-mode flag or settings.json defaultMode.
  */
 class PermissionModeManager {
-  private currentMode: PermissionMode = "default";
+  private get currentMode(): PermissionMode {
+    return getGlobalMode();
+  }
+
+  private set currentMode(value: PermissionMode) {
+    setGlobalMode(value);
+  }
 
   /**
    * Set the permission mode for this session