diff --git a/test/parallel/test-vm-global-property-enumerator.js b/test/parallel/test-vm-global-property-enumerator.js
index 7443c2c27d6c89..140baf692c3dd4 100644
--- a/test/parallel/test-vm-global-property-enumerator.js
+++ b/test/parallel/test-vm-global-property-enumerator.js
@@ -8,6 +8,9 @@ const assert = require('assert');
 
 const cases = [
   {
+    get 1() {
+      return 'value';
+    },
     get key() {
       return 'value';
     },
@@ -16,15 +19,21 @@ const cases = [
     // Intentionally single setter.
     // eslint-disable-next-line accessor-pairs
     set key(value) {},
+    // eslint-disable-next-line accessor-pairs
+    set 1(value) {},
   },
   {},
   {
     key: 'value',
+    1: 'value',
   },
   (new class GetterObject {
     get key() {
       return 'value';
     }
+    get 1() {
+      return 'value';
+    }
   }()),
   (new class SetterObject {
     // Intentionally single setter.
@@ -32,12 +41,17 @@ const cases = [
     set key(value) {
       // noop
     }
+    // eslint-disable-next-line accessor-pairs
+    set 1(value) {
+      // noop
+    }
   }()),
   [],
   [['key', 'value']],
   {
     __proto__: {
       key: 'value',
+      1: 'value',
     },
   },
   (() => {
diff --git a/test/parallel/test-vm-global-property-prototype.js b/test/parallel/test-vm-global-property-prototype.js
index fe8abc8be45ee2..0a854c43a8d184 100644
--- a/test/parallel/test-vm-global-property-prototype.js
+++ b/test/parallel/test-vm-global-property-prototype.js
@@ -3,48 +3,110 @@ require('../common');
 const assert = require('assert');
 const vm = require('vm');
 
+const outerProto = {
+  onOuterProto: 'onOuterProto',
+  bothProto: 'onOuterProto',
+};
+function onOuterProtoGetter() {
+  return 'onOuterProtoGetter';
+}
+Object.defineProperties(outerProto, {
+  onOuterProtoGetter: {
+    get: onOuterProtoGetter,
+  },
+  bothProtoGetter: {
+    get: onOuterProtoGetter,
+  },
+  // outer proto indexed
+  0: {
+    value: 'onOuterProtoIndexed',
+    writable: false,
+    enumerable: false,
+    configurable: true,
+  },
+  // both proto indexed
+  3: {
+    value: 'onOuterProtoIndexed',
+    writable: false,
+    enumerable: false,
+    configurable: true,
+  },
+});
+
+// Creating a new intermediate proto to mimic the
+// window -> Window.prototype -> EventTarget.prototype chain in JSDom.
+const sandboxProto = {
+  __proto__: outerProto,
+};
+
 const sandbox = {
+  __proto__: sandboxProto,
   onSelf: 'onSelf',
 };
 
 function onSelfGetter() {
   return 'onSelfGetter';
 }
-
-Object.defineProperty(sandbox, 'onSelfGetter', {
-  get: onSelfGetter,
-});
-
-Object.defineProperty(sandbox, 1, {
-  value: 'onSelfIndexed',
-  writable: false,
-  enumerable: false,
-  configurable: true,
+Object.defineProperties(sandbox, {
+  onSelfGetter: {
+    get: onSelfGetter,
+  },
+  1: {
+    value: 'onSelfIndexed',
+    writable: false,
+    enumerable: false,
+    configurable: true,
+  }
 });
 
 const ctx = vm.createContext(sandbox);
 
 const result = vm.runInContext(`
-Object.prototype.onProto = 'onProto';
-Object.defineProperty(Object.prototype, 'onProtoGetter', {
-  get() {
-    return 'onProtoGetter';
+Object.prototype.onInnerProto = 'onInnerProto';
+Object.defineProperties(Object.prototype, {
+  onInnerProtoGetter: {
+    get() {
+      return 'onInnerProtoGetter';
+    },
+  },
+  2: {
+    value: 'onInnerProtoIndexed',
+    writable: false,
+    enumerable: false,
+    configurable: true,
   },
 });
-Object.defineProperty(Object.prototype, 2, {
-  value: 'onProtoIndexed',
-  writable: false,
-  enumerable: false,
-  configurable: true,
+
+// Override outer proto properties
+Object.prototype.bothProto = 'onInnerProto';
+Object.defineProperties(Object.prototype, {
+  bothProtoGetter: {
+    get() {
+      return 'onInnerProtoGetter';
+    },
+  },
+  // outer proto indexed
+  3: {
+    value: 'onInnerProtoIndexed',
+    writable: false,
+    enumerable: false,
+    configurable: true,
+  },
 });
 
 const resultHasOwn = {
   onSelf: Object.hasOwn(this, 'onSelf'),
   onSelfGetter: Object.hasOwn(this, 'onSelfGetter'),
   onSelfIndexed: Object.hasOwn(this, 1),
-  onProto: Object.hasOwn(this, 'onProto'),
-  onProtoGetter: Object.hasOwn(this, 'onProtoGetter'),
-  onProtoIndexed: Object.hasOwn(this, 2),
+  onOuterProto: Object.hasOwn(this, 'onOuterProto'),
+  onOuterProtoGetter: Object.hasOwn(this, 'onOuterProtoGetter'),
+  onOuterProtoIndexed: Object.hasOwn(this, 0),
+  onInnerProto: Object.hasOwn(this, 'onInnerProto'),
+  onInnerProtoGetter: Object.hasOwn(this, 'onInnerProtoGetter'),
+  onInnerProtoIndexed: Object.hasOwn(this, 2),
+  bothProto: Object.hasOwn(this, 'bothProto'),
+  bothProtoGetter: Object.hasOwn(this, 'bothProtoGetter'),
+  bothProtoIndexed: Object.hasOwn(this, 3),
 };
 
 const getDesc = (prop) => Object.getOwnPropertyDescriptor(this, prop);
@@ -52,13 +114,49 @@ const resultDesc = {
   onSelf: getDesc('onSelf'),
   onSelfGetter: getDesc('onSelfGetter'),
   onSelfIndexed: getDesc(1),
-  onProto: getDesc('onProto'),
-  onProtoGetter: getDesc('onProtoGetter'),
-  onProtoIndexed: getDesc(2),
+  onOuterProto: getDesc('onOuterProto'),
+  onOuterProtoGetter: getDesc('onOuterProtoGetter'),
+  onOuterProtoIndexed: getDesc(0),
+  onInnerProto: getDesc('onInnerProto'),
+  onInnerProtoGetter: getDesc('onInnerProtoGetter'),
+  onInnerProtoIndexed: getDesc(2),
+  bothProto: getDesc('bothProto'),
+  bothProtoGetter: getDesc('bothProtoGetter'),
+  bothProtoIndexed: getDesc(3),
+};
+const resultIn = {
+  onSelf: 'onSelf' in this,
+  onSelfGetter: 'onSelfGetter' in this,
+  onSelfIndexed: 1 in this,
+  onOuterProto: 'onOuterProto' in this,
+  onOuterProtoGetter: 'onOuterProtoGetter' in this,
+  onOuterProtoIndexed: 0 in this,
+  onInnerProto: 'onInnerProto' in this,
+  onInnerProtoGetter: 'onInnerProtoGetter' in this,
+  onInnerProtoIndexed: 2 in this,
+  bothProto: 'bothProto' in this,
+  bothProtoGetter: 'bothProtoGetter' in this,
+  bothProtoIndexed: 3 in this,
+};
+const resultValue = {
+  onSelf: this.onSelf,
+  onSelfGetter: this.onSelfGetter,
+  onSelfIndexed: this[1],
+  onOuterProto: this.onOuterProto,
+  onOuterProtoGetter: this.onOuterProtoGetter,
+  onOuterProtoIndexed: this[0],
+  onInnerProto: this.onInnerProto,
+  onInnerProtoGetter: this.onInnerProtoGetter,
+  onInnerProtoIndexed: this[2],
+  bothProto: this.bothProto,
+  bothProtoGetter: this.bothProtoGetter,
+  bothProtoIndexed: this[3],
 };
 ({
   resultHasOwn,
   resultDesc,
+  resultIn,
+  resultValue,
 });
 `, ctx);
 
@@ -68,16 +166,80 @@ assert.deepEqual(result, {
     onSelf: true,
     onSelfGetter: true,
     onSelfIndexed: true,
-    onProto: false,
-    onProtoGetter: false,
-    onProtoIndexed: false,
+
+    // All prototype properties are not own properties.
+    onOuterProto: false,
+    onOuterProtoGetter: false,
+    onOuterProtoIndexed: false,
+    onInnerProto: false,
+    onInnerProtoGetter: false,
+    onInnerProtoIndexed: false,
+    bothProto: false,
+    bothProtoGetter: false,
+    bothProtoIndexed: false,
   },
   resultDesc: {
     onSelf: { value: 'onSelf', writable: true, enumerable: true, configurable: true },
     onSelfGetter: { get: onSelfGetter, set: undefined, enumerable: false, configurable: false },
     onSelfIndexed: { value: 'onSelfIndexed', writable: false, enumerable: false, configurable: true },
-    onProto: undefined,
-    onProtoGetter: undefined,
-    onProtoIndexed: undefined,
+
+    // All prototype properties are not own properties.
+    onOuterProto: undefined,
+    onOuterProtoGetter: undefined,
+    onOuterProtoIndexed: undefined,
+    onInnerProto: undefined,
+    onInnerProtoGetter: undefined,
+    onInnerProtoIndexed: undefined,
+    bothProto: undefined,
+    bothProtoGetter: undefined,
+    bothProtoIndexed: undefined,
+  },
+  resultIn: {
+    onSelf: true,
+    onSelfGetter: true,
+    onSelfIndexed: true,
+
+    // Only properties exist on inner prototype chain will be looked up
+    // on `in` operator. In the VM Context, the prototype chain will be like:
+    // ```
+    // Object
+    // ^
+    // | prototype
+    // InnerPrototype
+    // ^
+    // | prototype
+    // globalThis
+    // ```
+    // Outer prototype is not in the inner global object prototype chain and it
+    // will not be looked up on `in` operator.
+    onOuterProto: false,
+    onOuterProtoGetter: false,
+    onOuterProtoIndexed: false,
+    onInnerProto: true,
+    onInnerProtoGetter: true,
+    onInnerProtoIndexed: true,
+    bothProto: true,
+    bothProtoGetter: true,
+    bothProtoIndexed: true,
+  },
+  resultValue: {
+    onSelf: 'onSelf',
+    onSelfGetter: 'onSelfGetter',
+    onSelfIndexed: 'onSelfIndexed',
+
+    // FIXME(legendecas): The outer prototype is not observable from the inner
+    // vm. Allowing property getter on the outer prototype can be confusing
+    // comparing to the normal JavaScript objects.
+    // Additionally, this may expose unexpected properties on the outer
+    // prototype chain, like polyfills, to the vm context.
+    onOuterProto: 'onOuterProto',
+    onOuterProtoGetter: 'onOuterProtoGetter',
+    onOuterProtoIndexed: 'onOuterProtoIndexed',
+    onInnerProto: 'onInnerProto',
+    onInnerProtoGetter: 'onInnerProtoGetter',
+    onInnerProtoIndexed: 'onInnerProtoIndexed',
+    bothProto: 'onOuterProto',
+    bothProtoGetter: 'onOuterProtoGetter',
+    bothProtoIndexed: 'onOuterProtoIndexed',
   },
 });