diff --git a/.github/workflows/build.yml b/.github/workflows/build.yml
index 7eabfb9cfe2..c041cf336a7 100644
--- a/.github/workflows/build.yml
+++ b/.github/workflows/build.yml
@@ -75,7 +75,7 @@ jobs:
     # Upload runner package tar.gz/zip as artifact
     - name: Publish Artifact
       if: github.event_name != 'pull_request'
-      uses: actions/upload-artifact@v2
+      uses: actions/upload-artifact@v4
       with:
         name: runner-package-${{ matrix.runtime }}
         path: |
diff --git a/.github/workflows/release.yml b/.github/workflows/release.yml
index de94bcc4b26..73dc6477759 100644
--- a/.github/workflows/release.yml
+++ b/.github/workflows/release.yml
@@ -120,7 +120,7 @@ jobs:
     # Since each package name is unique, so we don't need to put ${{matrix}} info into artifact name
     - name: Publish Artifact
       if: github.event_name != 'pull_request'
-      uses: actions/upload-artifact@v2
+      uses: actions/upload-artifact@v4
       with:
         name: runner-packages
         path: |
@@ -135,7 +135,7 @@ jobs:
 
     # Download runner package tar.gz/zip produced by 'build' job
     - name: Download Artifact
-      uses: actions/download-artifact@v1
+      uses: actions/download-artifact@v4
       with:
         name: runner-packages
         path: ./
diff --git a/src/Runner.Common/HostContext.cs b/src/Runner.Common/HostContext.cs
index 46ea7042d8b..0b2ae0ae979 100644
--- a/src/Runner.Common/HostContext.cs
+++ b/src/Runner.Common/HostContext.cs
@@ -36,6 +36,7 @@ public interface IHostContext : IDisposable
         event EventHandler Unloading;
         void ShutdownRunner(ShutdownReason reason);
         void WritePerfCounter(string counter);
+        void LoadDefaultUserAgents();
     }
 
     public enum StartupType
@@ -67,6 +68,7 @@ public sealed class HostContext : EventListener, IObserver<DiagnosticListener>,
         private StartupType _startupType;
         private string _perfFile;
         private RunnerWebProxy _webProxy = new();
+        private string _hostType = string.Empty;
 
         public event EventHandler Unloading;
         public CancellationToken RunnerShutdownToken => _runnerShutdownTokenSource.Token;
@@ -78,6 +80,7 @@ public HostContext(string hostType, string logFile = null)
         {
             // Validate args.
             ArgUtil.NotNullOrEmpty(hostType, nameof(hostType));
+            _hostType = hostType;
 
             _loadContext = AssemblyLoadContext.GetLoadContext(typeof(HostContext).GetTypeInfo().Assembly);
             _loadContext.Unloading += LoadContext_Unloading;
@@ -196,6 +199,16 @@ public HostContext(string hostType, string logFile = null)
                 }
             }
 
+            if (StringUtil.ConvertToBoolean(Environment.GetEnvironmentVariable("GITHUB_ACTIONS_RUNNER_TLS_NO_VERIFY")))
+            {
+                _trace.Warning($"Runner is running under insecure mode: HTTPS server certificate validation has been turned off by GITHUB_ACTIONS_RUNNER_TLS_NO_VERIFY environment variable.");
+            }
+
+            LoadDefaultUserAgents();
+        }
+
+        public void LoadDefaultUserAgents()
+        {
             if (string.IsNullOrEmpty(WebProxy.HttpProxyAddress) && string.IsNullOrEmpty(WebProxy.HttpsProxyAddress))
             {
                 _trace.Info($"No proxy settings were found based on environmental variables (http_proxy/https_proxy/HTTP_PROXY/HTTPS_PROXY)");
@@ -205,11 +218,6 @@ public HostContext(string hostType, string logFile = null)
                 _userAgents.Add(new ProductInfoHeaderValue("HttpProxyConfigured", bool.TrueString));
             }
 
-            if (StringUtil.ConvertToBoolean(Environment.GetEnvironmentVariable("GITHUB_ACTIONS_RUNNER_TLS_NO_VERIFY")))
-            {
-                _trace.Warning($"Runner is running under insecure mode: HTTPS server certificate validation has been turned off by GITHUB_ACTIONS_RUNNER_TLS_NO_VERIFY environment variable.");
-            }
-
             var credFile = GetConfigFile(WellKnownConfigFile.Credentials);
             if (File.Exists(credFile))
             {
@@ -248,7 +256,7 @@ public HostContext(string hostType, string logFile = null)
             var currentProcess = Process.GetCurrentProcess();
             _userAgents.Add(new ProductInfoHeaderValue("Pid", currentProcess.Id.ToString()));
             _userAgents.Add(new ProductInfoHeaderValue("CreationTime", Uri.EscapeDataString(DateTime.UtcNow.ToString("O"))));
-            _userAgents.Add(new ProductInfoHeaderValue($"({hostType})"));
+            _userAgents.Add(new ProductInfoHeaderValue($"({_hostType})"));
         }
 
         public string GetDirectory(WellKnownDirectory directory)
diff --git a/src/Runner.Listener/Runner.cs b/src/Runner.Listener/Runner.cs
index e2f638522b8..8649af7354f 100644
--- a/src/Runner.Listener/Runner.cs
+++ b/src/Runner.Listener/Runner.cs
@@ -237,6 +237,10 @@ public async Task<int> ExecuteCommand(CommandSettings command)
                             File.SetAttributes(configFile, File.GetAttributes(configFile) | FileAttributes.Hidden);
                             Trace.Info($"Saved {configContent.Length} bytes to '{configFile}'.");
                         }
+
+                        // make sure we have the right user agent data added from the jitconfig
+                        HostContext.LoadDefaultUserAgents();
+                        VssUtil.InitializeVssClientSettings(HostContext.UserAgents, HostContext.WebProxy);
                     }
                     catch (Exception ex)
                     {
diff --git a/src/Test/L0/TestHostContext.cs b/src/Test/L0/TestHostContext.cs
index c44f13f1c4a..124bcd5bd06 100644
--- a/src/Test/L0/TestHostContext.cs
+++ b/src/Test/L0/TestHostContext.cs
@@ -370,6 +370,11 @@ private void LoadContext_Unloading(AssemblyLoadContext obj)
                 Unloading(this, null);
             }
         }
+
+        public void LoadDefaultUserAgents()
+        {
+            return;
+        }
     }
 
     public class DelayEventArgs : EventArgs