diff --git a/src/Runner.Listener/Configuration/ConfigurationManager.cs b/src/Runner.Listener/Configuration/ConfigurationManager.cs
index 25217f9be..392eb0e3c 100644
--- a/src/Runner.Listener/Configuration/ConfigurationManager.cs
+++ b/src/Runner.Listener/Configuration/ConfigurationManager.cs
@@ -1,10 +1,3 @@
-using GitHub.DistributedTask.WebApi;
-using GitHub.Runner.Common;
-using GitHub.Runner.Common.Util;
-using GitHub.Runner.Sdk;
-using GitHub.Services.Common;
-using GitHub.Services.Common.Internal;
-using GitHub.Services.OAuth;
 using System;
 using System.Collections.Generic;
 using System.Linq;
@@ -14,6 +7,13 @@ using System.Runtime.InteropServices;
 using System.Security.Cryptography;
 using System.Text;
 using System.Threading.Tasks;
+using GitHub.DistributedTask.WebApi;
+using GitHub.Runner.Common;
+using GitHub.Runner.Common.Util;
+using GitHub.Runner.Sdk;
+using GitHub.Services.Common;
+using GitHub.Services.Common.Internal;
+using GitHub.Services.OAuth;
 
 namespace GitHub.Runner.Listener.Configuration
 {
@@ -636,7 +636,7 @@ namespace GitHub.Runner.Listener.Configuration
             }
 
             int retryCount = 0;
-            while(retryCount < 3)
+            while (retryCount < 3)
             {
                 using (var httpClientHandler = HostContext.CreateHttpClientHandler())
                 using (var httpClient = new HttpClient(httpClientHandler))
@@ -646,28 +646,29 @@ namespace GitHub.Runner.Listener.Configuration
                     httpClient.DefaultRequestHeaders.Authorization = new AuthenticationHeaderValue("basic", base64EncodingToken);
                     httpClient.DefaultRequestHeaders.UserAgent.AddRange(HostContext.UserAgents);
                     httpClient.DefaultRequestHeaders.Accept.ParseAdd("application/vnd.github.v3+json");
-                    
+
                     var responseStatus = System.Net.HttpStatusCode.OK;
                     try
                     {
                         var response = await httpClient.PostAsync(githubApiUrl, new StringContent(string.Empty));
                         responseStatus = response.StatusCode;
+                        var githubRequestId = GetGitHubRequestId(response.Headers);
 
                         if (response.IsSuccessStatusCode)
                         {
-                            Trace.Info($"Http response code: {response.StatusCode} from 'POST {githubApiUrl}'");
+                            Trace.Info($"Http response code: {response.StatusCode} from 'POST {githubApiUrl}' ({githubRequestId})");
                             var jsonResponse = await response.Content.ReadAsStringAsync();
                             return StringUtil.ConvertFromJson<GitHubRunnerRegisterToken>(jsonResponse);
                         }
                         else
                         {
-                            _term.WriteError($"Http response code: {response.StatusCode} from 'POST {githubApiUrl}'");
+                            _term.WriteError($"Http response code: {response.StatusCode} from 'POST {githubApiUrl}' (Request Id: {githubRequestId})");
                             var errorResponse = await response.Content.ReadAsStringAsync();
                             _term.WriteError(errorResponse);
                             response.EnsureSuccessStatusCode();
                         }
                     }
-                    catch(Exception ex) when (retryCount < 2 && responseStatus != System.Net.HttpStatusCode.NotFound)
+                    catch (Exception ex) when (retryCount < 2 && responseStatus != System.Net.HttpStatusCode.NotFound)
                     {
                         retryCount++;
                         Trace.Error($"Failed to get JIT runner token -- Atempt: {retryCount}");
@@ -714,22 +715,23 @@ namespace GitHub.Runner.Listener.Configuration
                     {
                         var response = await httpClient.PostAsync(githubApiUrl, new StringContent(StringUtil.ConvertToJson(bodyObject), null, "application/json"));
                         responseStatus = response.StatusCode;
+                        var githubRequestId = GetGitHubRequestId(response.Headers);
 
-                        if(response.IsSuccessStatusCode)
+                        if (response.IsSuccessStatusCode)
                         {
-                            Trace.Info($"Http response code: {response.StatusCode} from 'POST {githubApiUrl}'");
+                            Trace.Info($"Http response code: {response.StatusCode} from 'POST {githubApiUrl}' ({githubRequestId})");
                             var jsonResponse = await response.Content.ReadAsStringAsync();
                             return StringUtil.ConvertFromJson<GitHubAuthResult>(jsonResponse);
                         }
                         else
                         {
-                            _term.WriteError($"Http response code: {response.StatusCode} from 'POST {githubApiUrl}'");
+                            _term.WriteError($"Http response code: {response.StatusCode} from 'POST {githubApiUrl}' (Request Id: {githubRequestId})");
                             var errorResponse = await response.Content.ReadAsStringAsync();
                             _term.WriteError(errorResponse);
                             response.EnsureSuccessStatusCode();
                         }
                     }
-                    catch(Exception ex) when (retryCount < 2 && responseStatus != System.Net.HttpStatusCode.NotFound)
+                    catch (Exception ex) when (retryCount < 2 && responseStatus != System.Net.HttpStatusCode.NotFound)
                     {
                         retryCount++;
                         Trace.Error($"Failed to get tenant credentials -- Atempt: {retryCount}");
@@ -742,5 +744,14 @@ namespace GitHub.Runner.Listener.Configuration
             }
             return null;
         }
+
+        private string GetGitHubRequestId(HttpResponseHeaders headers)
+        {
+            if (headers.TryGetValues("x-github-request-id", out var headerValues))
+            {
+                return headerValues.FirstOrDefault();
+            }
+            return string.Empty;
+        }
     }
 }