diff --git a/Microsoft.Azure.Cosmos/src/Resource/CosmosExceptions/CosmosOperationCanceledException.cs b/Microsoft.Azure.Cosmos/src/Resource/CosmosExceptions/CosmosOperationCanceledException.cs
index 4ed0ac8fb4..72a0f41233 100644
--- a/Microsoft.Azure.Cosmos/src/Resource/CosmosExceptions/CosmosOperationCanceledException.cs
+++ b/Microsoft.Azure.Cosmos/src/Resource/CosmosExceptions/CosmosOperationCanceledException.cs
@@ -19,11 +19,13 @@ namespace Microsoft.Azure.Cosmos
     /// </summary> 
     [Serializable]
     public class CosmosOperationCanceledException : OperationCanceledException, ICloneable
-    {
+    {
+        private readonly Object thisLock = new object();
         private readonly OperationCanceledException originalException;
-        private readonly Lazy<string> lazyMessage;
-        private readonly Lazy<string> toStringMessage;
-        private readonly bool tokenCancellationRequested;
+        private readonly bool tokenCancellationRequested;
+
+        private string lazyMessage;
+        private string toStringMessage;
 
         /// <summary>
         /// Create an instance of CosmosOperationCanceledException
@@ -38,8 +40,8 @@ public CosmosOperationCanceledException(
             this.originalException = originalException ?? throw new ArgumentNullException(nameof(originalException));
             this.Diagnostics = diagnostics ?? throw new ArgumentNullException(nameof(diagnostics));
             this.tokenCancellationRequested = originalException.CancellationToken.IsCancellationRequested;
-            this.toStringMessage = this.CreateToStringMessage();
-            this.lazyMessage = this.CreateLazyMessage();
+            this.toStringMessage = null;
+            this.lazyMessage = null;
         }
 
         internal CosmosOperationCanceledException(
@@ -61,8 +63,8 @@ internal CosmosOperationCanceledException(
             }
             this.Diagnostics = new CosmosTraceDiagnostics(trace);
             this.tokenCancellationRequested = originalException.CancellationToken.IsCancellationRequested;
-            this.toStringMessage = this.CreateToStringMessage();
-            this.lazyMessage = this.CreateLazyMessage();
+            this.toStringMessage = null;
+            this.lazyMessage = null;
         }
 
         /// <summary>
@@ -75,8 +77,8 @@ protected CosmosOperationCanceledException(SerializationInfo info, StreamingCont
         {
             this.originalException = (OperationCanceledException)info.GetValue("originalException", typeof(OperationCanceledException));
             this.tokenCancellationRequested = (bool)info.GetValue("tokenCancellationRequested", typeof(bool));
-            this.lazyMessage = new Lazy<string>(() => (string)info.GetValue("lazyMessage", typeof(string)));
-            this.toStringMessage = new Lazy<string>(() => (string)info.GetValue("toStringMessage", typeof(string)));
+            this.lazyMessage = null;
+            this.toStringMessage = null;
             //Diagnostics cannot be serialized
             this.Diagnostics = new CosmosTraceDiagnostics(NoOpTrace.Singleton);
         }
@@ -89,7 +91,7 @@ public override string Source
         }
 
         /// <inheritdoc/>
-        public override string Message => this.lazyMessage.Value;
+        public override string Message => this.EnsureLazyMessage();
 
         /// <inheritdoc/>
 #pragma warning disable CDX1002 // DontUseExceptionStackTrace
@@ -120,18 +122,42 @@ public override Exception GetBaseException()
         /// <inheritdoc/>
         public override string ToString()
         {
-            return this.toStringMessage.Value;
+            return this.EnsureToStringMessage(skipDiagnostics: false);
         }
 
-        private Lazy<string> CreateLazyMessage()
-        {
-            return new Lazy<string>(() => $"{this.originalException.Message}{Environment.NewLine}Cancellation Token has expired: {this.tokenCancellationRequested}. Learn more at: https://aka.ms/cosmosdb-tsg-request-timeout{Environment.NewLine}CosmosDiagnostics: {this.Diagnostics}");
-        }
-        private Lazy<string> CreateToStringMessage()
-        {
-            return new Lazy<string>(() => $"{this.originalException}{Environment.NewLine}Cancellation Token has expired: {this.tokenCancellationRequested}. Learn more at: https://aka.ms/cosmosdb-tsg-request-timeout{Environment.NewLine}CosmosDiagnostics: {this.Diagnostics}");
-        }
-         
+        private string EnsureLazyMessage()
+        {
+            if (this.lazyMessage != null)
+            {
+                return this.lazyMessage;
+            }
+
+            lock (this.thisLock)
+            {
+                return this.lazyMessage ??=
+                     $"{this.originalException.Message}{Environment.NewLine}Cancellation Token has expired: {this.tokenCancellationRequested}. Learn more at: https://aka.ms/cosmosdb-tsg-request-timeout{Environment.NewLine}CosmosDiagnostics: {this.Diagnostics}";
+            }
+        }
+
+        internal string EnsureToStringMessage(bool skipDiagnostics)
+        {
+            if (this.toStringMessage != null)
+            {
+                return this.toStringMessage;
+            }
+
+            lock (this.thisLock)
+            {
+                if (skipDiagnostics)
+                {
+                    return this.toStringMessage ??=
+                                         $"{this.originalException}{Environment.NewLine}Cancellation Token has expired: {this.tokenCancellationRequested}. Learn more at: https://aka.ms/cosmosdb-tsg-request-timeout";
+                }
+                return this.toStringMessage ??=
+                     $"{this.originalException}{Environment.NewLine}Cancellation Token has expired: {this.tokenCancellationRequested}. Learn more at: https://aka.ms/cosmosdb-tsg-request-timeout{Environment.NewLine}CosmosDiagnostics: {this.Diagnostics}";
+            }
+        }
+
         /// <summary>
         /// RecordOtelAttributes
         /// </summary>
@@ -159,8 +185,8 @@ public override void GetObjectData(SerializationInfo info, StreamingContext cont
             info.AddValue("originalException", this.originalException);
 #pragma warning restore CDX1000 // DontConvertExceptionToObject
             info.AddValue("tokenCancellationRequested", this.tokenCancellationRequested);
-            info.AddValue("lazyMessage", this.lazyMessage.Value);
-            info.AddValue("toStringMessage", this.toStringMessage.Value);
+            info.AddValue("lazyMessage", this.EnsureLazyMessage());
+            info.AddValue("toStringMessage", this.EnsureToStringMessage(skipDiagnostics: false));
         }
 
         /// <summary>
diff --git a/Microsoft.Azure.Cosmos/src/Tracing/TraceWriter.TraceJsonWriter.cs b/Microsoft.Azure.Cosmos/src/Tracing/TraceWriter.TraceJsonWriter.cs
index f3880a517c..8a2eabc13b 100644
--- a/Microsoft.Azure.Cosmos/src/Tracing/TraceWriter.TraceJsonWriter.cs
+++ b/Microsoft.Azure.Cosmos/src/Tracing/TraceWriter.TraceJsonWriter.cs
@@ -130,9 +130,14 @@ private static void WriteTraceDatum(IJsonWriter writer, object value)
             {
                 writer.WriteStringValue(stringValue);
             }
-            else
-            {
-                writer.WriteStringValue(value.ToString());
+            else if (value is CosmosOperationCanceledException cosmosTimeoutException)
+            {
+                writer.WriteStringValue(
+                    cosmosTimeoutException.EnsureToStringMessage(skipDiagnostics: true));
+            }
+            else
+            {
+                writer.WriteStringValue(value.ToString());
             }
         }
 
diff --git a/Microsoft.Azure.Cosmos/tests/Microsoft.Azure.Cosmos.EmulatorTests/CosmosOperationCanceledExceptionTests.cs b/Microsoft.Azure.Cosmos/tests/Microsoft.Azure.Cosmos.EmulatorTests/CosmosOperationCanceledExceptionTests.cs
index 52c1aab8b0..4c8735d73b 100644
--- a/Microsoft.Azure.Cosmos/tests/Microsoft.Azure.Cosmos.EmulatorTests/CosmosOperationCanceledExceptionTests.cs
+++ b/Microsoft.Azure.Cosmos/tests/Microsoft.Azure.Cosmos.EmulatorTests/CosmosOperationCanceledExceptionTests.cs
@@ -7,6 +7,8 @@ namespace Microsoft.Azure.Cosmos.SDK.EmulatorTests
     using System;
     using System.Threading;
     using System.Threading.Tasks;
+    using Microsoft.Azure.Cosmos.Diagnostics;
+    using Microsoft.Azure.Cosmos.Tracing;
     using Microsoft.VisualStudio.TestTools.UnitTesting;
 
     [TestClass]
@@ -76,6 +78,32 @@ public async Task CheckCancellationTokenDirectTestAsync()
             await this.CheckCancellationTokenTestAsync(this.Container, cancellationTokenSource.Token);
         }
 
+        [TestMethod]
+        public void CheckToJsonStringConversion()
+        {
+            // This test is reproducing an issue that an internal customer faced after enabling
+            // cross region hedging 
+            // In their scenario they occassionally hit e2e timeouts as CosmosOperationCancelledException
+            // The JSON transformation of the CosmosOperationCancelledException in this case could run into
+            // an issue (InvalidOperationException due to Lazy<T> factory hitting a cyclic dependency
+            // when neither the diagnostics nor the exception had materialized the json string yet
+            // because the CosmosOperationCancelledException ias added as a trace datum to the ITrace of
+            // the CosmosTraceDiagnostics instance.
+            // The test below reproduced the issue - and is kept here to validate the fix and
+            // as a regression test
+            using ITrace outerTrace = Trace.GetRootTrace("cyclicDependencyReproOuter");
+            using ITrace innerTrace = outerTrace.StartChild("cyclicDependencyReproInner");
+
+            OperationCanceledException innerTimeout = new OperationCanceledException();
+            CosmosOperationCanceledException innerCosmosTimeoutException = new CosmosOperationCanceledException(
+                innerTimeout,
+                innerTrace);
+            CosmosOperationCanceledException outerCosmosTimeoutException = new CosmosOperationCanceledException(
+                innerCosmosTimeoutException,
+                outerTrace);
+
+            Console.WriteLine(outerCosmosTimeoutException.ToString());
+        }
 
         private async Task CheckCancellationTokenTestAsync(
             Container container,