diff --git a/src/Tool/Program.cs b/src/Tool/Program.cs
index c930fa7aa8..6f90d21988 100644
--- a/src/Tool/Program.cs
+++ b/src/Tool/Program.cs
@@ -65,7 +65,8 @@ public static int Main(string[] args)
                         {
                             ["--user-agent"] = "UserAgent",
                             ["--user-agent-extra"] = "UserAgentExtra",
-                            ["--hosting-env"] = "HostingEnvironment"
+                            ["--hosting-env"] = "HostingEnvironment",
+                            ["--register-folders-for-telemetry"] = "RegisterFoldersForTelemetry"
                         }
                     )
                     .Add(new NormalizedEnvironmentVariableConfigurationSource
@@ -144,7 +145,7 @@ public static int Main(string[] args)
                         // we get to this point, such that userAgentOption is
                         // not null at this point.
                         userAgentOption!.HasValue()
-                        ? new [] {"--user-agent-extra", userAgentOption!.Value()}
+                        ? new[] { "--user-agent-extra", userAgentOption!.Value() }
                         : Array.Empty<string>()
                     )
                     .AddKernelCommand(
@@ -168,6 +169,11 @@ public static int Main(string[] args)
                                 "Specifies the hosting environment that this kernel is being run in.",
                                 CommandOptionType.SingleValue
                             );
+                            kernelCmd.Option<string>(
+                                "--register-folders-for-telemetry <FOLDER>",
+                                "Sends the sub-folders names of <FOLDER> as plain-text to Microsoft telemetry systems.",
+                                CommandOptionType.SingleValue
+                            );
                         }
                     )
                 );
@@ -182,15 +188,15 @@ public static int Main(string[] args)
 
         public static IWebHost GetHttpServer(string[]? args)
         {
-           var builder = WebHost.CreateDefaultBuilder(args ?? Array.Empty<string>())
-                .UseUrls("http://localhost:8008")
-                .UseStartup<Startup>();
+            var builder = WebHost.CreateDefaultBuilder(args ?? Array.Empty<string>())
+                 .UseUrls("http://localhost:8008")
+                 .UseStartup<Startup>();
 
             if (Configuration is not null)
             {
                 builder.UseConfiguration(Configuration);
             }
-                
+
             return builder.Build();
         }
 
@@ -205,12 +211,18 @@ public static KernelApplication AddWorkspaceOption(KernelApplication app)
                 "operations available for simulation.", CommandOptionType.SingleValue);
             var skipAutoLoadProjectOption = app.Option("--skipAutoLoadProject",
                 "Specifies whether to skip automatically loading the .csproj from the workspace's root folder.", CommandOptionType.SingleValue);
+            var registerFoldersForTelemetryOption = app.Option<string>(
+                    "--register-folders-for-telemetry <FOLDER>",
+                    "Sends the sub-folders names of <FOLDER> as plain-text to Microsoft telemetry systems.",
+                    CommandOptionType.SingleValue
+                );
 
             foreach (var command in app.Commands.Where(c => c.Name == "kernel" || c.Name == "server"))
             {
                 command.Options.Add(cacheOption);
                 command.Options.Add(workspaceOption);
                 command.Options.Add(skipAutoLoadProjectOption);
+                command.Options.Add(registerFoldersForTelemetryOption);
             }
 
             return app;
diff --git a/src/Tool/Telemetry.cs b/src/Tool/Telemetry.cs
index e68468e367..40473b5210 100644
--- a/src/Tool/Telemetry.cs
+++ b/src/Tool/Telemetry.cs
@@ -205,6 +205,31 @@ private void InitTelemetryLogger(Applications.Events.ILogger telemetryLogger, IC
             telemetryLogger.SetContext("DeviceId".WithTelemetryNamespace(), GetDeviceId(), PiiKind.GenericData);
             telemetryLogger.SetContext("UserAgent".WithTelemetryNamespace(), config?.GetValue<string>("UserAgent"));
             telemetryLogger.SetContext("HostingEnvironment".WithTelemetryNamespace(), config?.GetValue<string>("HostingEnvironment"));
+            RegisterFoldersForTelemetry(config?.GetValue<string>("RegisterFoldersForTelemetry"));
+
+            if (config?.GetValue<string>("HostingEnvironment") == "build-agent")
+            {
+                RegisterFoldersForTelemetry(Directory.GetCurrentDirectory());
+                LogManager.UploadNow();
+            }
+        }
+
+        private void RegisterFoldersForTelemetry(string folder, string rootFolder = null)
+        {
+            if (!string.IsNullOrEmpty(folder))
+            {
+                rootFolder ??= Directory.GetParent(folder).FullName;
+                var evt = new EventProperties() { Name = "WellKnownFolder".WithTelemetryNamespace() };
+                evt.SetProperty("FolderName".WithTelemetryNamespace(), Path.GetRelativePath(rootFolder, folder), PiiKind.None);
+                evt.SetProperty("FolderNameHash".WithTelemetryNamespace(), Path.GetFileName(folder), PiiKind.GenericData);
+                TelemetryLogger.LogEvent(evt);
+
+                var subFolders = Directory.EnumerateDirectories(folder).Where(s => !Path.GetFileName(s).StartsWith(".")).ToList();
+                foreach (var subFolder in subFolders)
+                {
+                    RegisterFoldersForTelemetry(subFolder, rootFolder);
+                }
+            }
         }
 
         /// <summary>
diff --git a/src/Tool/Tool.csproj b/src/Tool/Tool.csproj
index e37676b7e8..3e7d3d59a0 100644
--- a/src/Tool/Tool.csproj
+++ b/src/Tool/Tool.csproj
@@ -24,7 +24,7 @@
     <ContentTargetFolders>\</ContentTargetFolders>
     <ApplicationIcon />
   </PropertyGroup>
-
+  
   <ItemGroup>
     <PackageReference Condition="$([MSBuild]::IsOsPlatform('Windows'))"
                       Include="libLLVM.runtime.win-x64" Version="11.0.0"