diff --git a/src/Agent.Listener/Configuration/ConfigurationManager.cs b/src/Agent.Listener/Configuration/ConfigurationManager.cs
index 58c8ae43ca..45dcf280f2 100644
--- a/src/Agent.Listener/Configuration/ConfigurationManager.cs
+++ b/src/Agent.Listener/Configuration/ConfigurationManager.cs
@@ -21,6 +21,7 @@
 using System.Security.AccessControl;
 using System.Security.Principal;
 using Newtonsoft.Json;
+using Microsoft.Win32;
 using Microsoft.VisualStudio.Services.Agent.Listener.Telemetry;
 
 namespace Microsoft.VisualStudio.Services.Agent.Listener.Configuration
@@ -42,6 +43,9 @@ public sealed class ConfigurationManager : AgentService, IConfigurationManager
         private ILocationServer _locationServer;
         private ServerUtil _serverUtil;
 
+        private const string VsTelemetryRegPath = @"SOFTWARE\Microsoft\VisualStudio\Telemetry\PersistentPropertyBag\c57a9efce9b74de382d905a89852db71";
+        private const string VsTelemetryRegKey = "IsPipelineAgent";
+
         public override void Initialize(IHostContext hostContext)
         {
             ArgUtil.NotNull(hostContext, nameof(hostContext));
@@ -421,6 +425,12 @@ public async Task ConfigureAsync(CommandSettings command)
                 serviceControlManager.GenerateScripts(agentSettings);
             }
 
+            if(PlatformUtil.RunningOnWindows)
+            {
+                // add vstelemetry registrykey
+                this.AddVSTelemetryRegKey();
+            }
+
             try
             {
                 var telemetryData = new Dictionary<string, string>
@@ -577,6 +587,12 @@ public async Task UnconfigureAsync(CommandSettings command)
                     // delete agent runtime option
                     _store.DeleteAgentRuntimeOptions();
 
+                    if(PlatformUtil.RunningOnWindows)
+                    {
+                        // delete vstelemetry registrykey
+                        this.DeleteVSTelemetryRegKey();
+                    }
+
                     _store.DeleteSettings();
                     _term.WriteLine(StringUtil.Loc("Success") + currentAction);
                 }
@@ -855,6 +871,48 @@ private void WriteSection(string message)
             _term.WriteLine();
         }
 
+        [SupportedOSPlatform("windows")]
+        private void AddVSTelemetryRegKey()
+        {
+            try
+            {
+                //create the VsTelemetryRegKey under currentuser/VsTelemetryRegPath and set value to true
+                using (RegistryKey key = Registry.CurrentUser.OpenSubKey(VsTelemetryRegPath, writable: true))
+                {
+                    if (key != null && key.GetValue(VsTelemetryRegKey) == null)
+                    {
+                        key.SetValue(VsTelemetryRegKey, "s:true", RegistryValueKind.String);
+                    }
+                }
+            }
+            catch (Exception)
+            {
+                // ignore failure as this is not critical to agent functionality
+                Trace.Info("Error while adding VSTelemetry regkey");
+            }
+        }
+
+        [SupportedOSPlatform("windows")]
+        private void DeleteVSTelemetryRegKey()
+        {
+            try
+            {
+                // delete the VsTelemetryRegKey under currentuser/VsTelemetryRegPath
+                using (RegistryKey key = Registry.CurrentUser.OpenSubKey(VsTelemetryRegPath, writable: true))
+                {
+                    if (key != null && key.GetValue(VsTelemetryRegKey) != null)
+                    {
+                        key.DeleteValue(VsTelemetryRegKey);
+                    }
+                }
+            }
+            catch (Exception)
+            {
+                // ignore failure as this is not critical to agent functionality
+                Trace.Info("Error while deleting VSTelemetry regkey");
+            }
+        }
+
         [SupportedOSPlatform("windows")]
         private void CheckAgentRootDirectorySecure()
         {