diff --git a/docs/azrepos-misp.md b/docs/azrepos-misp.md
index 60a3c3e..9d11dbf 100644
--- a/docs/azrepos-misp.md
+++ b/docs/azrepos-misp.md
@@ -108,6 +108,7 @@ Type|Git Configuration|Environment Variable
 -|-|-
 Client Secret|[`credential.azreposServicePrincipalSecret`][gcm-sp-secret-config]|[`GCM_AZREPOS_SP_SECRET`][gcm-sp-secret-env]
 Certificate|[`credential.azreposServicePrincipalCertificateThumbprint`][gcm-sp-cert-config]|[`GCM_AZREPOS_SP_CERT_THUMBPRINT`][gcm-sp-cert-env]
+Send X5C|[`credential.azreposServicePrincipalCertificateSendX5C`][gcm-sp-cert-x5c-config]|[`GCM_AZREPOS_SP_CERT_SEND_X5C`][gcm-sp-cert-x5c-env]
 
 The value for these options should be the client secret or the thumbrint of the
 certificate that is associated with the Service Principal.
@@ -126,4 +127,6 @@ current user or the local machine.
 [gcm-sp-secret-config]: https://gh.io/gcm/config#credentialazreposserviceprincipalsecret
 [gcm-sp-secret-env]: https://gh.io/gcm/env#GCM_AZREPOS_SP_SECRET
 [gcm-sp-cert-config]: https://gh.io/gcm/config#credentialazreposserviceprincipalcertificatethumbprint
+[gcm-sp-cert-x5c-config]: https://gh.io/gcm/config#credentialazreposserviceprincipalcertificatesendx5c
 [gcm-sp-cert-env]: https://gh.io/gcm/env#GCM_AZREPOS_SP_CERT_THUMBPRINT
+[gcm-sp-cert-x5c-env]: https://gh.io/gcm/env#GCM_AZREPOS_SP_CERT_SEND_X5C
diff --git a/docs/configuration.md b/docs/configuration.md
index 2439c92..f6993df 100644
--- a/docs/configuration.md
+++ b/docs/configuration.md
@@ -858,6 +858,7 @@ You must also set at least one authentication mechanism if you set this value:
 
 - [credential.azreposServicePrincipalSecret][credential-azrepos-sp-secret]
 - [credential.azreposServicePrincipalCertificateThumbprint][credential-azrepos-sp-cert-thumbprint]
+- [credential.azreposServicePrincipalCertificateSendX5C][credential-azrepos-sp-cert-x5c]
 
 For more information about service principals, see the Azure DevOps
 [documentation][azrepos-sp-mid].
@@ -904,6 +905,25 @@ git config --global credential.azreposServicePrincipalCertificateThumbprint "9b6
 
 ---
 
+### credential.azreposServicePrincipalCertificateSendX5C
+
+When using a certificate for [service principal][service-principal] authentication, this configuration
+specifies whether the X5C claim should be should be sent to the STS. Sending the x5c
+enables application developers to achieve easy certificate rollover in Azure AD:
+this method will send the public certificate to Azure AD along with the token request,
+so that Azure AD can use it to validate the subject name based on a trusted issuer
+policy. This saves the application admin from the need to explicitly manage the
+certificate rollover. For details see [https://aka.ms/msal-net-sni](https://aka.ms/msal-net-sni).
+
+#### Example
+
+```shell
+git config --global credential.azreposServicePrincipalCertificateSendX5C true
+```
+**Also see: [GCM_AZREPOS_SP_CERT_SEND_X5C][gcm-azrepos-sp-cert-x5c]**
+
+---
+
 ### trace2.normalTarget
 
 Turns on Trace2 Normal Format tracing - see [Git's Trace2 Normal Format
@@ -1034,6 +1054,8 @@ Defaults to disabled.
 [credential-azrepos-sp]: #credentialazreposserviceprincipal
 [credential-azrepos-sp-secret]: #credentialazreposserviceprincipalsecret
 [credential-azrepos-sp-cert-thumbprint]: #credentialazreposserviceprincipalcertificatethumbprint
+[credential-azrepos-sp-cert-x5c]: #credentialazreposserviceprincipalcertificatesendx5c
 [gcm-azrepos-service-principal]: environment.md#GCM_AZREPOS_SERVICE_PRINCIPAL
 [gcm-azrepos-sp-secret]: environment.md#GCM_AZREPOS_SP_SECRET
 [gcm-azrepos-sp-cert-thumbprint]: environment.md#GCM_AZREPOS_SP_CERT_THUMBPRINT
+[gcm-azrepos-sp-cert-x5c]: environment.md#GCM_AZREPOS_SP_CERT_SEND_X5C
diff --git a/docs/environment.md b/docs/environment.md
index 18f3f05..edda0d7 100644
--- a/docs/environment.md
+++ b/docs/environment.md
@@ -1039,6 +1039,32 @@ export GCM_AZREPOS_SP_CERT_THUMBPRINT="9b6555292e4ea21cbc2ebd23e66e2f91ebbe92dc"
 
 ---
 
+### GCM_AZREPOS_SP_CERT_SEND_X5C
+
+When using a certificate for service principal authentication, this configuration
+specifies whether the X5C claim should be should be sent to the STS. Sending the x5c
+enables application developers to achieve easy certificate rollover in Azure AD:
+this method will send the public certificate to Azure AD along with the token request,
+so that Azure AD can use it to validate the subject name based on a trusted issuer
+policy. This saves the application admin from the need to explicitly manage the
+certificate rollover. For details see [https://aka.ms/msal-net-sni](https://aka.ms/msal-net-sni).
+
+#### Windows
+
+```batch
+SET GCM_AZREPOS_SP_CERT_SEND_X5C="true"
+```
+
+#### macOS/Linux
+
+```bash
+export GCM_AZREPOS_SP_CERT_SEND_X5C="true"
+```
+
+**Also see: [credential.azreposServicePrincipalCertificateSendX5C][credential-azrepos-sp-cert-x5c]**
+
+---
+
 ### GIT_TRACE2
 
 Turns on Trace2 Normal Format tracing - see [Git's Trace2 Normal Format
@@ -1184,6 +1210,8 @@ Defaults to disabled.
 [gcm-azrepos-sp]: #gcm_azrepos_service_principal
 [gcm-azrepos-sp-secret]: #gcm_azrepos_sp_secret
 [gcm-azrepos-sp-cert-thumbprint]: #gcm_azrepos_sp_cert_thumbprint
+[gcm-azrepos-sp-cert-x5c]: #gcm_azrepos_sp_cert_send_x5c
 [credential-azrepos-sp]: configuration.md#credentialazreposserviceprincipal
 [credential-azrepos-sp-secret]: configuration.md#credentialazreposserviceprincipalsecret
 [credential-azrepos-sp-cert-thumbprint]: configuration.md#credentialazreposserviceprincipalcertificatethumbprint
+[credential-azrepos-sp-cert-x5c]: configuration.md#credentialazreposserviceprincipalcertificatesendx5c
diff --git a/src/shared/Core/Authentication/MicrosoftAuthentication.cs b/src/shared/Core/Authentication/MicrosoftAuthentication.cs
index b39cc1a..12bccf5 100644
--- a/src/shared/Core/Authentication/MicrosoftAuthentication.cs
+++ b/src/shared/Core/Authentication/MicrosoftAuthentication.cs
@@ -92,6 +92,11 @@ namespace GitCredentialManager.Authentication
         /// If both <see cref="Certificate"/> and <see cref="ClientSecret"/> are set, the certificate will be used.
         /// </remarks>
         public string ClientSecret { get; set; }
+
+        /// <summary>
+        /// Whether the authentication should send X5C
+        /// </summary>
+        public bool SendX5C { get; set; }
     }
 
     public interface IMicrosoftAuthenticationResult
@@ -269,12 +274,14 @@ namespace GitCredentialManager.Authentication
 
             try
             {
-                AuthenticationResult result = await app.AcquireTokenForClient(scopes).ExecuteAsync();
+                Context.Trace.WriteLine($"Sending with X5C: '{sp.SendX5C}'.");
+                AuthenticationResult result = await app.AcquireTokenForClient(scopes).WithSendX5C(sp.SendX5C).ExecuteAsync();;
+
                 return new MsalResult(result);
             }
             catch (Exception ex)
             {
-                Context.Trace.WriteLine($"Failed to acquire token for service principal '{sp.TenantId}/{sp.TenantId}'.");
+                Context.Trace.WriteLine($"Failed to acquire token for service principal '{sp.TenantId}/{sp.Id}'.");
                 Context.Trace.WriteException(ex);
                 throw;
             }
diff --git a/src/shared/Microsoft.AzureRepos/AzureDevOpsConstants.cs b/src/shared/Microsoft.AzureRepos/AzureDevOpsConstants.cs
index c46f08c..a282d4e 100644
--- a/src/shared/Microsoft.AzureRepos/AzureDevOpsConstants.cs
+++ b/src/shared/Microsoft.AzureRepos/AzureDevOpsConstants.cs
@@ -44,6 +44,7 @@ namespace Microsoft.AzureRepos
             public const string ServicePrincipalId = "GCM_AZREPOS_SERVICE_PRINCIPAL";
             public const string ServicePrincipalSecret = "GCM_AZREPOS_SP_SECRET";
             public const string ServicePrincipalCertificateThumbprint = "GCM_AZREPOS_SP_CERT_THUMBPRINT";
+            public const string ServicePrincipalCertificateSendX5C = "GCM_AZREPOS_SP_CERT_SEND_X5C";
             public const string ManagedIdentity = "GCM_AZREPOS_MANAGEDIDENTITY";
         }
 
@@ -59,6 +60,7 @@ namespace Microsoft.AzureRepos
                 public const string ServicePrincipal = "azreposServicePrincipal";
                 public const string ServicePrincipalSecret = "azreposServicePrincipalSecret";
                 public const string ServicePrincipalCertificateThumbprint = "azreposServicePrincipalCertificateThumbprint";
+                public const string ServicePrincipalCertificateSendX5C = "azreposServicePrincipalCertificateSendX5C";
                 public const string ManagedIdentity = "azreposManagedIdentity";
             }
         }
diff --git a/src/shared/Microsoft.AzureRepos/AzureReposHostProvider.cs b/src/shared/Microsoft.AzureRepos/AzureReposHostProvider.cs
index 55b1449..1d5c649 100644
--- a/src/shared/Microsoft.AzureRepos/AzureReposHostProvider.cs
+++ b/src/shared/Microsoft.AzureRepos/AzureReposHostProvider.cs
@@ -549,6 +549,12 @@ namespace Microsoft.AzureRepos
 
             if (hasCertThumbprint)
             {
+                sp.SendX5C = _context.Settings.TryGetSetting(
+                    AzureDevOpsConstants.EnvironmentVariables.ServicePrincipalCertificateSendX5C,
+                    Constants.GitConfiguration.Credential.SectionName,
+                    AzureDevOpsConstants.GitConfiguration.Credential.ServicePrincipalCertificateSendX5C,
+                    out string certHasX5CStr) && certHasX5CStr.ToBooleanyOrDefault(false);
+
                 X509Certificate2 cert = X509Utils.GetCertificateByThumbprint(certThumbprint);
                 if (cert is null)
                 {