diff --git a/lib/internal/bootstrap/node.js b/lib/internal/bootstrap/node.js
index 2b5d2ee3f41ee8..be8512bb93511b 100644
--- a/lib/internal/bootstrap/node.js
+++ b/lib/internal/bootstrap/node.js
@@ -157,17 +157,6 @@ if (isMainThread) {
 const { nativeHooks } = require('internal/async_hooks');
 internalBinding('async_wrap').setupHooks(nativeHooks);
 
-// XXX(joyeecheung): this has to be done after the initial load of
-// `internal/async_hooks` otherwise `async_hooks` cannot require
-// `internal/async_hooks`. Investigate why.
-if (config.hasInspector) {
-  const {
-    enable,
-    disable
-  } = require('internal/inspector_async_hook');
-  internalBinding('inspector').registerAsyncHook(enable, disable);
-}
-
 const {
   setupTaskQueue,
   queueMicrotask
diff --git a/lib/internal/bootstrap/pre_execution.js b/lib/internal/bootstrap/pre_execution.js
index f10397df79c870..719b6c8de0e497 100644
--- a/lib/internal/bootstrap/pre_execution.js
+++ b/lib/internal/bootstrap/pre_execution.js
@@ -6,7 +6,7 @@ function prepareMainThreadExecution() {
   // Patch the process object with legacy properties and normalizations
   patchProcessObject();
   setupTraceCategoryState();
-
+  setupInspectorHooks();
   setupWarningHandler();
 
   // Resolve the coverage directory to an absolute path, and
@@ -181,6 +181,21 @@ function setupTraceCategoryState() {
   toggleTraceCategoryState(isTraceCategoryEnabled('node.async_hooks'));
 }
 
+function setupInspectorHooks() {
+  // If Debugger.setAsyncCallStackDepth is sent during bootstrap,
+  // we cannot immediately call into JS to enable the hooks, which could
+  // interrupt the JS execution of bootstrap. So instead we save the
+  // notification in the inspector agent if it's sent in the middle of
+  // bootstrap, and process the notification later here.
+  if (internalBinding('config').hasInspector) {
+    const {
+      enable,
+      disable
+    } = require('internal/inspector_async_hook');
+    internalBinding('inspector').registerAsyncHook(enable, disable);
+  }
+}
+
 // In general deprecations are intialized wherever the APIs are implemented,
 // this is used to deprecate APIs implemented in C++ where the deprecation
 // utitlities are not easily accessible.
@@ -360,5 +375,6 @@ module.exports = {
   initializeFrozenIntrinsics,
   loadPreloadModules,
   setupTraceCategoryState,
+  setupInspectorHooks,
   initializeReport
 };
diff --git a/lib/internal/main/worker_thread.js b/lib/internal/main/worker_thread.js
index fd3502e0784a1a..71babafd0e867e 100644
--- a/lib/internal/main/worker_thread.js
+++ b/lib/internal/main/worker_thread.js
@@ -6,6 +6,7 @@
 const {
   patchProcessObject,
   setupCoverageHooks,
+  setupInspectorHooks,
   setupWarningHandler,
   setupDebugEnv,
   initializeDeprecations,
@@ -43,6 +44,7 @@ const {
 const publicWorker = require('worker_threads');
 
 patchProcessObject();
+setupInspectorHooks();
 setupDebugEnv();
 
 const debug = require('internal/util/debuglog').debuglog('worker');
diff --git a/src/inspector_agent.cc b/src/inspector_agent.cc
index 90ed2857815e60..91a57b9944ec4c 100644
--- a/src/inspector_agent.cc
+++ b/src/inspector_agent.cc
@@ -835,6 +835,7 @@ void Agent::DisableAsyncHook() {
 
 void Agent::ToggleAsyncHook(Isolate* isolate,
                             const node::Persistent<Function>& fn) {
+  CHECK(parent_env_->has_run_bootstrapping_code());
   HandleScope handle_scope(isolate);
   CHECK(!fn.IsEmpty());
   auto context = parent_env_->context();