diff --git a/src/Runner.Listener/JobDispatcher.cs b/src/Runner.Listener/JobDispatcher.cs
index 6d003d026..7b75c72ef 100644
--- a/src/Runner.Listener/JobDispatcher.cs
+++ b/src/Runner.Listener/JobDispatcher.cs
@@ -2,17 +2,19 @@ using System;
 using System.Collections.Concurrent;
 using System.Collections.Generic;
 using System.IO;
+using System.Linq;
+using System.Text;
+using System.Text.RegularExpressions;
 using System.Threading;
 using System.Threading.Tasks;
 using GitHub.DistributedTask.WebApi;
-using GitHub.Runner.Common.Util;
-using GitHub.Services.WebApi;
-using Pipelines = GitHub.DistributedTask.Pipelines;
-using System.Linq;
-using GitHub.Services.Common;
 using GitHub.Runner.Common;
+using GitHub.Runner.Common.Util;
 using GitHub.Runner.Sdk;
+using GitHub.Services.Common;
+using GitHub.Services.WebApi;
 using GitHub.Services.WebApi.Jwt;
+using Pipelines = GitHub.DistributedTask.Pipelines;
 
 namespace GitHub.Runner.Listener
 {
@@ -34,6 +36,7 @@ namespace GitHub.Runner.Listener
     // and the server will not send another job while this one is still running.
     public sealed class JobDispatcher : RunnerService, IJobDispatcher
     {
+        private static Regex _invalidJsonRegex = new Regex(@"invalid\ Json\ at\ position\ '(\d+)':", RegexOptions.Compiled | RegexOptions.IgnoreCase);
         private readonly Lazy<Dictionary<long, TaskResult>> _localRunJobResult = new Lazy<Dictionary<long, TaskResult>>();
         private int _poolId;
 
@@ -964,6 +967,30 @@ namespace GitHub.Runner.Listener
                 TimelineRecord jobRecord = timeline.Records.FirstOrDefault(x => x.Id == message.JobId && x.RecordType == "Job");
                 ArgUtil.NotNull(jobRecord, nameof(jobRecord));
 
+                try
+                {
+                    if (!string.IsNullOrEmpty(errorMessage) &&
+                        message.Variables.TryGetValue("DistributedTask.EnableRunnerIPCDebug", out var enableRunnerIPCDebug) &&
+                        StringUtil.ConvertToBoolean(enableRunnerIPCDebug.Value))
+                    {
+                        // the trace should be best effort and not affect any job result
+                        var match = _invalidJsonRegex.Match(errorMessage);
+                        if (match.Success &&
+                            match.Groups.Count == 2)
+                        {
+                            var jsonPosition = int.Parse(match.Groups[1].Value);
+                            var serializedJobMessage = JsonUtility.ToString(message);
+                            var originalJson = serializedJobMessage.Substring(jsonPosition - 10, 20);
+                            errorMessage = $"Runner sent Json at position '{jsonPosition}': {originalJson} ({Convert.ToBase64String(Encoding.UTF8.GetBytes(originalJson))})\n{errorMessage}";
+                        }
+                    }
+                }
+                catch (Exception ex)
+                {
+                    Trace.Error(ex);
+                    errorMessage = $"Fail to check json IPC error: {ex.Message}\n{errorMessage}";
+                }
+
                 var unhandledExceptionIssue = new Issue() { Type = IssueType.Error, Message = errorMessage };
                 unhandledExceptionIssue.Data[Constants.Runner.InternalTelemetryIssueDataKey] = Constants.Runner.WorkerCrash;
                 jobRecord.ErrorCount++;
diff --git a/src/Runner.Listener/Runner.cs b/src/Runner.Listener/Runner.cs
index f9fb8ab45..89dcbb94a 100644
--- a/src/Runner.Listener/Runner.cs
+++ b/src/Runner.Listener/Runner.cs
@@ -318,7 +318,7 @@ namespace GitHub.Runner.Listener
 
                 IJobDispatcher jobDispatcher = null;
                 CancellationTokenSource messageQueueLoopTokenSource = CancellationTokenSource.CreateLinkedTokenSource(HostContext.RunnerShutdownToken);
-                
+
                 // Should we try to cleanup ephemeral runners
                 bool runOnceJobCompleted = false;
                 try
@@ -425,6 +425,7 @@ namespace GitHub.Runner.Listener
                                 }
                                 else
                                 {
+                                    Trace.Info($"Received job message of length {message.Body.Length} from service, with hash '{IOUtil.GetSha256Hash(message.Body)}'");
                                     var jobMessage = StringUtil.ConvertFromJson<Pipelines.AgentJobRequestMessage>(message.Body);
                                     jobDispatcher.Run(jobMessage, runOnce);
                                     if (runOnce)
@@ -546,7 +547,7 @@ Config Options:
     _term.WriteLine($@" --windowslogonaccount string   Account to run the service as. Requires runasservice");
     _term.WriteLine($@" --windowslogonpassword string  Password for the service account. Requires runasservice");
 #endif
-    _term.WriteLine($@"
+            _term.WriteLine($@"
 Examples:
  Check GitHub server network connectivity:
   .{separator}run.{ext} --check --url <url> --pat <pat>
diff --git a/src/Runner.Worker/Worker.cs b/src/Runner.Worker/Worker.cs
index 115789c4f..b26ae9451 100644
--- a/src/Runner.Worker/Worker.cs
+++ b/src/Runner.Worker/Worker.cs
@@ -9,6 +9,7 @@ using System.Threading.Tasks;
 using GitHub.Services.WebApi;
 using GitHub.Runner.Common;
 using GitHub.Runner.Sdk;
+using System.Text;
 
 namespace GitHub.Runner.Worker
 {
@@ -43,6 +44,7 @@ namespace GitHub.Runner.Worker
                 ArgUtil.NotNullOrEmpty(pipeOut, nameof(pipeOut));
                 VssUtil.InitializeVssClientSettings(HostContext.UserAgents, HostContext.WebProxy);
                 var jobRunner = HostContext.CreateService<IJobRunner>();
+                var terminal = HostContext.GetService<ITerminal>();
 
                 using (var channel = HostContext.CreateService<IProcessChannel>())
                 using (var jobRequestCancellationToken = CancellationTokenSource.CreateLinkedTokenSource(HostContext.RunnerShutdownToken))
@@ -64,7 +66,22 @@ namespace GitHub.Runner.Worker
                     Trace.Info("Message received.");
                     ArgUtil.Equal(MessageType.NewJobRequest, channelMessage.MessageType, nameof(channelMessage.MessageType));
                     ArgUtil.NotNullOrEmpty(channelMessage.Body, nameof(channelMessage.Body));
-                    var jobMessage = StringUtil.ConvertFromJson<Pipelines.AgentJobRequestMessage>(channelMessage.Body);
+                    Pipelines.AgentJobRequestMessage jobMessage = null;
+                    try
+                    {
+                        jobMessage = StringUtil.ConvertFromJson<Pipelines.AgentJobRequestMessage>(channelMessage.Body);
+                    }
+                    catch (JsonReaderException ex)
+                    {
+                        if (channelMessage.Body.Length > ex.LinePosition + 10)
+                        {
+                            var errorChunk = channelMessage.Body.Substring(ex.LinePosition - 10, 20);
+                            terminal.WriteError($"Worker received invalid Json at position '{ex.LinePosition}': {errorChunk} ({Convert.ToBase64String(Encoding.UTF8.GetBytes(errorChunk))})");
+                        }
+
+                        throw;
+                    }
+
                     ArgUtil.NotNull(jobMessage, nameof(jobMessage));
                     HostContext.WritePerfCounter($"WorkerJobMessageReceived_{jobMessage.RequestId.ToString()}");