diff --git a/packages/genesys-web-messaging-tester/src/genesys/message-delayer/MessageDelayer.ts b/packages/genesys-web-messaging-tester/src/genesys/message-delayer/MessageDelayer.ts
index df25c9a..b6d36b8 100644
--- a/packages/genesys-web-messaging-tester/src/genesys/message-delayer/MessageDelayer.ts
+++ b/packages/genesys-web-messaging-tester/src/genesys/message-delayer/MessageDelayer.ts
@@ -1,6 +1,7 @@
 import { EventEmitter } from 'events';
 import { Response } from '../Response';
 import { orderByTimestamp } from './orderByTimestamp';
+import debug from 'debug';
 
 /**
  * Provides the ability to delay messages for the purpose of re-ordering them.
@@ -16,6 +17,8 @@ export interface MessageDelayer extends EventEmitter {
  * timestamps.
  */
 export class ReorderedMessageDelayer extends EventEmitter implements MessageDelayer {
+  private static readonly debugger = debug('ReorderedMessageDelayer');
+
   private static readonly DELAY_IN_MS = 2000;
   private messages: Response<unknown>[] = [];
 
@@ -58,7 +61,13 @@ export class ReorderedMessageDelayer extends EventEmitter implements MessageDela
 
   private releaseOldestMessage(): void {
     if (this.messages.length > 0) {
-      this.messages = orderByTimestamp(this.messages);
+      const result = orderByTimestamp(this.messages);
+      if (result.wasRearranged) {
+        ReorderedMessageDelayer.debugger('Messages out of order: %O', this.messages);
+      }
+
+      this.messages = result.responses;
+
       this.emit('message', this.messages.shift());
     }
   }
diff --git a/packages/genesys-web-messaging-tester/src/genesys/message-delayer/orderByTimestamp.spec.ts b/packages/genesys-web-messaging-tester/src/genesys/message-delayer/orderByTimestamp.spec.ts
index 3eeed13..78c0b2d 100644
--- a/packages/genesys-web-messaging-tester/src/genesys/message-delayer/orderByTimestamp.spec.ts
+++ b/packages/genesys-web-messaging-tester/src/genesys/message-delayer/orderByTimestamp.spec.ts
@@ -1,4 +1,4 @@
-import { orderByTimestamp } from './orderByTimestamp';
+import { orderByTimestamp, orderByTimestampResult } from './orderByTimestamp';
 import { Response } from '../Response';
 import { StructuredMessage } from '../StructuredMessage';
 import { SessionResponse, SessionResponseSuccessBody } from '../SessionResponse';
@@ -45,29 +45,35 @@ describe('orderWithTimestamps', () => {
       createStructuredMessage('6', '2023-07-22T21:19:25.256Z'),
     ];
 
-    expect(orderByTimestamp(unordered)).toEqual([
-      createStructuredMessage('7', '2023-07-22T20:13:55.256Z'),
-      createSessionResponse({ connected: true, newSession: false, readOnly: false }),
-      createStructuredMessage('6', '2023-07-22T21:19:25.256Z'),
-      createStructuredMessage('1', '2023-07-22T21:19:41.256Z'),
-      createSessionResponse({ connected: false, newSession: true, readOnly: false }),
-      createSessionResponse({ connected: false, newSession: false, readOnly: true }),
-      createStructuredMessage('3', '2023-07-22T21:19:55.256Z'),
-    ]);
+    expect(orderByTimestamp(unordered)).toStrictEqual<orderByTimestampResult>({
+      wasRearranged: true,
+      responses: [
+        createStructuredMessage('7', '2023-07-22T20:13:55.256Z'),
+        createSessionResponse({ connected: true, newSession: false, readOnly: false }),
+        createStructuredMessage('6', '2023-07-22T21:19:25.256Z'),
+        createStructuredMessage('1', '2023-07-22T21:19:41.256Z'),
+        createSessionResponse({ connected: false, newSession: true, readOnly: false }),
+        createSessionResponse({ connected: false, newSession: false, readOnly: true }),
+        createStructuredMessage('3', '2023-07-22T21:19:55.256Z'),
+      ],
+    });
   });
 
   test('Does not change the order of non-timestamped elements', () => {
     const input: Response<unknown>[] = [
       createSessionResponse({ connected: true, newSession: false, readOnly: false }),
-      createSessionResponse({ connected: false, newSession: true, readOnly: false }),
-      createSessionResponse({ connected: false, newSession: false, readOnly: true }),
+      createSessionResponse({ connected: true, newSession: true, readOnly: false }),
+      createSessionResponse({ connected: true, newSession: true, readOnly: true }),
     ];
 
-    expect(orderByTimestamp(input)).toEqual([
-      createSessionResponse({ connected: true, newSession: false, readOnly: false }),
-      createSessionResponse({ connected: true, newSession: true, readOnly: false }),
-      createSessionResponse({ connected: false, newSession: false, readOnly: true }),
-    ]);
+    expect(orderByTimestamp(input)).toStrictEqual<orderByTimestampResult>({
+      wasRearranged: false,
+      responses: [
+        createSessionResponse({ connected: true, newSession: false, readOnly: false }),
+        createSessionResponse({ connected: true, newSession: true, readOnly: false }),
+        createSessionResponse({ connected: true, newSession: true, readOnly: true }),
+      ],
+    });
   });
 
   test('Correctly sorts an array with only timestamped elements', () => {
@@ -77,10 +83,13 @@ describe('orderWithTimestamps', () => {
       createStructuredMessage('3', '2023-07-22T21:19:25.256Z'),
     ];
 
-    expect(orderByTimestamp(unordered)).toStrictEqual([
-      createStructuredMessage('3', '2023-07-22T21:19:25.256Z'),
-      createStructuredMessage('1', '2023-07-22T21:19:41.256Z'),
-      createStructuredMessage('2', '2023-07-22T21:19:55.256Z'),
-    ]);
+    expect(orderByTimestamp(unordered)).toStrictEqual<orderByTimestampResult>({
+      wasRearranged: true,
+      responses: [
+        createStructuredMessage('3', '2023-07-22T21:19:25.256Z'),
+        createStructuredMessage('1', '2023-07-22T21:19:41.256Z'),
+        createStructuredMessage('2', '2023-07-22T21:19:55.256Z'),
+      ],
+    });
   });
 });
diff --git a/packages/genesys-web-messaging-tester/src/genesys/message-delayer/orderByTimestamp.ts b/packages/genesys-web-messaging-tester/src/genesys/message-delayer/orderByTimestamp.ts
index 9353274..0a6bc00 100644
--- a/packages/genesys-web-messaging-tester/src/genesys/message-delayer/orderByTimestamp.ts
+++ b/packages/genesys-web-messaging-tester/src/genesys/message-delayer/orderByTimestamp.ts
@@ -2,7 +2,12 @@ import { Response } from '../Response';
 import { StructuredMessage } from '../StructuredMessage';
 import { isStructuredMessage } from '../WebMessengerGuestSession';
 
-export function orderByTimestamp(array: Response<unknown>[]): Response<unknown>[] {
+export interface orderByTimestampResult {
+  wasRearranged: boolean;
+  responses: Response<unknown>[];
+}
+
+export function orderByTimestamp(array: Response<unknown>[]): orderByTimestampResult {
   const withTimestamps: StructuredMessage[] = [];
   const withoutTimestamps: Response<unknown>[] = [];
 
@@ -32,5 +37,13 @@ export function orderByTimestamp(array: Response<unknown>[]): Response<unknown>[
     }
   }
 
-  return result;
+  let wasRearranged = false;
+  for (let i = 0; i < array.length; i++) {
+    if (!Object.is(result[i], array[i])) {
+      wasRearranged = true;
+      break;
+    }
+  }
+
+  return { wasRearranged, responses: result };
 }