diff --git a/src/Runner.Common/JobServerQueue.cs b/src/Runner.Common/JobServerQueue.cs
index 6234b4bdd..e6a00f1c8 100644
--- a/src/Runner.Common/JobServerQueue.cs
+++ b/src/Runner.Common/JobServerQueue.cs
@@ -1,6 +1,7 @@
 using System;
 using System.Collections.Concurrent;
 using System.Collections.Generic;
+using System.Diagnostics;
 using System.IO;
 using System.Linq;
 using System.Threading;
@@ -14,10 +15,11 @@ namespace GitHub.Runner.Common
     [ServiceLocator(Default = typeof(JobServerQueue))]
     public interface IJobServerQueue : IRunnerService, IThrottlingReporter
     {
+        IList<JobTelemetry> JobTelemetries { get; }
         TaskCompletionSource<int> JobRecordUpdated { get; }
         event EventHandler<ThrottlingEventArgs> JobServerQueueThrottling;
         Task ShutdownAsync();
-        void Start(Pipelines.AgentJobRequestMessage jobRequest, bool resultsServiceOnly = false);
+        void Start(Pipelines.AgentJobRequestMessage jobRequest, bool resultsServiceOnly = false, bool enableTelemetry = false);
         void QueueWebConsoleLine(Guid stepRecordId, string line, long? lineNumber = null);
         void QueueFileUpload(Guid timelineId, Guid timelineRecordId, string type, string name, string path, bool deleteSource);
         void QueueResultsUpload(Guid timelineRecordId, string name, string path, string type, bool deleteSource, bool finalize, bool firstBlock, long totalLines);
@@ -69,13 +71,18 @@ namespace GitHub.Runner.Common
         private Task[] _allDequeueTasks;
         private readonly TaskCompletionSource<int> _jobCompletionSource = new();
         private readonly TaskCompletionSource<int> _jobRecordUpdated = new();
+        private readonly List<JobTelemetry> _jobTelemetries = new();
         private bool _queueInProcess = false;
         private bool _resultsServiceOnly = false;
+        private Stopwatch _resultsUploadTimer = new();
+        private Stopwatch _actionsUploadTimer = new();
 
         public TaskCompletionSource<int> JobRecordUpdated => _jobRecordUpdated;
 
         public event EventHandler<ThrottlingEventArgs> JobServerQueueThrottling;
 
+        public IList<JobTelemetry> JobTelemetries => _jobTelemetries;
+
         // Web console dequeue will start with process queue every 250ms for the first 60*4 times (~60 seconds).
         // Then the dequeue will happen every 500ms.
         // In this way, customer still can get instance live console output on job start,
@@ -87,6 +94,7 @@ namespace GitHub.Runner.Common
         private bool _firstConsoleOutputs = true;
 
         private bool _resultsClientInitiated = false;
+        private bool _enableTelemetry = false;
         private delegate Task ResultsFileUploadHandler(ResultsUploadFileInfo file);
 
         public override void Initialize(IHostContext hostContext)
@@ -96,10 +104,11 @@ namespace GitHub.Runner.Common
             _resultsServer = hostContext.GetService<IResultsServer>();
         }
 
-        public void Start(Pipelines.AgentJobRequestMessage jobRequest, bool resultsServiceOnly = false)
+        public void Start(Pipelines.AgentJobRequestMessage jobRequest, bool resultsServiceOnly = false, bool enableTelemetry = false)
         {
             Trace.Entering();
             _resultsServiceOnly = resultsServiceOnly;
+            _enableTelemetry = enableTelemetry;
 
             var serviceEndPoint = jobRequest.Resources.Endpoints.Single(x => string.Equals(x.Name, WellKnownServiceEndpointNames.SystemVssConnection, StringComparison.OrdinalIgnoreCase));
 
@@ -211,6 +220,12 @@ namespace GitHub.Runner.Common
             await _resultsServer.DisposeAsync();
 
             Trace.Info("All queue process tasks have been stopped, and all queues are drained.");
+            if (_enableTelemetry)
+            {
+                var uploadTimeComparison = $"Actions upload time: {_actionsUploadTimer.ElapsedMilliseconds} ms, Result upload time: {_resultsUploadTimer.ElapsedMilliseconds} ms";
+                Trace.Info(uploadTimeComparison);
+                _jobTelemetries.Add(new JobTelemetry() { Type = JobTelemetryType.General, Message = uploadTimeComparison });
+            }
         }
 
         public void QueueWebConsoleLine(Guid stepRecordId, string line, long? lineNumber)
@@ -456,6 +471,10 @@ namespace GitHub.Runner.Common
                     {
                         try
                         {
+                            if (_enableTelemetry)
+                            {
+                                _actionsUploadTimer.Start();
+                            }
                             await UploadFile(file);
                         }
                         catch (Exception ex)
@@ -471,6 +490,13 @@ namespace GitHub.Runner.Common
                             //    _fileUploadQueue.Enqueue(file);
                             //}
                         }
+                        finally
+                        {
+                            if (_enableTelemetry)
+                            {
+                                _actionsUploadTimer.Stop();
+                            }
+                        }
                     }
 
                     Trace.Info("Try to upload {0} log files or attachments, success rate: {1}/{0}.", filesToUpload.Count, filesToUpload.Count - errorCount);
@@ -517,6 +543,10 @@ namespace GitHub.Runner.Common
                     {
                         try
                         {
+                            if (_enableTelemetry)
+                            {
+                                _resultsUploadTimer.Start();
+                            }
                             if (String.Equals(file.Type, ChecksAttachmentType.StepSummary, StringComparison.OrdinalIgnoreCase))
                             {
                                 await UploadSummaryFile(file);
@@ -548,6 +578,13 @@ namespace GitHub.Runner.Common
                                 SendResultsTelemetry(ex);
                             }
                         }
+                        finally
+                        {
+                            if (_enableTelemetry)
+                            {
+                                _resultsUploadTimer.Stop();
+                            }
+                        }
                     }
 
                     Trace.Info("Tried to upload {0} file(s) to results, success rate: {1}/{0}.", filesToUpload.Count, filesToUpload.Count - errorCount);
diff --git a/src/Runner.Worker/JobRunner.cs b/src/Runner.Worker/JobRunner.cs
index aa6580402..4e2c4e95a 100644
--- a/src/Runner.Worker/JobRunner.cs
+++ b/src/Runner.Worker/JobRunner.cs
@@ -51,6 +51,13 @@ namespace GitHub.Runner.Worker
                 HostContext.UserAgents.Add(new ProductInfoHeaderValue("OrchestrationId", orchestrationId.Value));
             }
 
+            var jobServerQueueTelemetry = false;
+            if (message.Variables.TryGetValue("DistributedTask.EnableJobServerQueueTelemetry", out VariableValue enableJobServerQueueTelemetry) &&
+                !string.IsNullOrEmpty(enableJobServerQueueTelemetry?.Value))
+            {
+                jobServerQueueTelemetry = StringUtil.ConvertToBoolean(enableJobServerQueueTelemetry.Value);
+            }
+
             ServiceEndpoint systemConnection = message.Resources.Endpoints.Single(x => string.Equals(x.Name, WellKnownServiceEndpointNames.SystemVssConnection, StringComparison.OrdinalIgnoreCase));
             if (MessageUtil.IsRunServiceJob(message.MessageType))
             {
@@ -72,7 +79,7 @@ namespace GitHub.Runner.Worker
                     launchServer.InitializeLaunchClient(new Uri(launchReceiverEndpoint), accessToken);
                 }
                 _jobServerQueue = HostContext.GetService<IJobServerQueue>();
-                _jobServerQueue.Start(message, resultsServiceOnly: true);
+                _jobServerQueue.Start(message, resultsServiceOnly: true, enableTelemetry: jobServerQueueTelemetry);
             }
             else
             {
@@ -94,7 +101,7 @@ namespace GitHub.Runner.Worker
                 VssConnection jobConnection = VssUtil.CreateConnection(jobServerUrl, jobServerCredential, delegatingHandlers);
                 await jobServer.ConnectAsync(jobConnection);
 
-                _jobServerQueue.Start(message);
+                _jobServerQueue.Start(message, enableTelemetry: jobServerQueueTelemetry);
                 server = jobServer;
             }
 
@@ -405,6 +412,13 @@ namespace GitHub.Runner.Worker
                 result = TaskResultUtil.MergeTaskResults(result, TaskResult.Failed);
             }
 
+            // include any job telemetry from the background upload process.
+            if (_jobServerQueue != null &&
+                _jobServerQueue.JobTelemetries.Count > 0)
+            {
+                jobContext.Global.JobTelemetry.AddRange(_jobServerQueue.JobTelemetries);
+            }
+
             // Clean TEMP after finish process jobserverqueue, since there might be a pending fileupload still use the TEMP dir.
             _tempDirectoryManager?.CleanupTempDirectory();
 
diff --git a/src/Sdk/DTWebApi/WebApi/JobTelemetryType.cs b/src/Sdk/DTWebApi/WebApi/JobTelemetryType.cs
index 88c14c695..2228a9e5e 100644
--- a/src/Sdk/DTWebApi/WebApi/JobTelemetryType.cs
+++ b/src/Sdk/DTWebApi/WebApi/JobTelemetryType.cs
@@ -2,6 +2,7 @@
 
 namespace GitHub.DistributedTask.WebApi
 {
+    // do NOT add new enum since it will break backward compatibility with GHES
     public enum JobTelemetryType
     {
         [EnumMember]