diff --git a/src/Runner.Sdk/Util/VssUtil.cs b/src/Runner.Sdk/Util/VssUtil.cs
index f35b0c21d..012d27f73 100644
--- a/src/Runner.Sdk/Util/VssUtil.cs
+++ b/src/Runner.Sdk/Util/VssUtil.cs
@@ -38,6 +38,7 @@ namespace GitHub.Runner.Sdk
             if (StringUtil.ConvertToBoolean(Environment.GetEnvironmentVariable("GITHUB_ACTIONS_RUNNER_TLS_NO_VERIFY")))
             {
                 VssClientHttpRequestSettings.Default.ServerCertificateValidationCallback = HttpClientHandler.DangerousAcceptAnyServerCertificateValidator;
+                RawClientHttpRequestSettings.Default.ServerCertificateValidationCallback = HttpClientHandler.DangerousAcceptAnyServerCertificateValidator;
             }
 
             var rawHeaderValues = new List<ProductInfoHeaderValue>();
diff --git a/src/Sdk/Common/Common/RawHttpMessageHandler.cs b/src/Sdk/Common/Common/RawHttpMessageHandler.cs
index 316bcd576..e80e6a747 100644
--- a/src/Sdk/Common/Common/RawHttpMessageHandler.cs
+++ b/src/Sdk/Common/Common/RawHttpMessageHandler.cs
@@ -106,6 +106,18 @@ namespace GitHub.Services.Common
         {
             VssTraceActivity traceActivity = VssTraceActivity.Current;
 
+            if (!m_appliedServerCertificateValidationCallbackToTransportHandler &&
+                            request.RequestUri.Scheme == "https")
+            {
+                HttpClientHandler httpClientHandler = m_transportHandler as HttpClientHandler;
+                if (httpClientHandler != null &&
+                    this.Settings.ServerCertificateValidationCallback != null)
+                {
+                    httpClientHandler.ServerCertificateCustomValidationCallback = this.Settings.ServerCertificateValidationCallback;
+                }
+                m_appliedServerCertificateValidationCallbackToTransportHandler = true;
+            }
+
             lock (m_thisLock)
             {
                 // Ensure that we attempt to use the most appropriate authentication mechanism by default.
@@ -291,6 +303,7 @@ namespace GitHub.Services.Common
             }
         }
 
+        private bool m_appliedServerCertificateValidationCallbackToTransportHandler;
         private readonly HttpMessageHandler m_transportHandler;
         private HttpMessageInvoker m_messageInvoker;
         private CredentialWrapper m_credentialWrapper;