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Troubleshooting Entra ID Connect Sync Issue Authentication Failure with Entra ID

Troubleshooting Entra ID Connect Sync Issue Authentication Failure with Entra ID

Written By Anoop C Nair
Last Updated February 26, 2025
Posted In Entra
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Hi, Let’s Discuss Troubleshooting the Entra Connect Sync Issue. Many of you may be experiencing problems with autologon.microsoftazuread-sso.com when connecting to Microsoft Entra ID. A recent report revealed some issues with Entra Connect.

Microsoft Entra Connect is usually used to integrate and synchronize with Azure Active Directory. Handling user identities can be difficult because organizations use both on-premises and cloud-based services. In this case, Entra Connect is the best way to resolve this issue.

This is only possible by syncing on-premises directories with Entra ID to ensure users have the same identity across both environments. So Recently, some users have been facing an issue with Entra Connect Sync Issue, and they got an alert that Entra Connect Sync couldn’t authenticate to Entra.

The autologon.microsoftazuread-sso.com is used on the Entra IDs SSO (Seamless Single Sign-on), so we understand the issue with the SSO. In this post, we can look into this issue and understand the workaround for it.

Patch My PC

Troubleshooting Entra ID Connect Sync Issue Authentication Failure with Entra ID

We have explored various aspects of troubleshooting the Entra Connect Sync issue and SSO. Now, let’s dive into the root cause of this issue and the possible workarounds. The URL autologon.microsoftazuread-sso.com plays a key role in SSO, which is crucial to understanding the problem.

  • So we can assume that this issues happend because of DNS resolution problem.
Troubleshooting Entra ID Connect Sync Issue Authentication Failure with Entra ID - Fig.1
Troubleshooting Entra ID Connect Sync Issue Authentication Failure with Entra ID – Fig.1

Main Causes for this Issue

There may be some causes for these issues, but mainly, they happen with the DNS change. This may be a DNS resolution Failure, and it may also happen because of a Network issue. Sometimes, a network issue is the main problem for Connect Sync.

  • The problem with autologon.microsoftazuread-sso.com might be due to the Seamless Single Sign-On (SSO) feature.
  • If Seamless SSO is not enabled or has configuration issues, it can cause DNS resolution problems for autologon.microsoftazuread-sso.com, leading to authentication failures.
How to Check SSO is Enabled
Identity > Hybrid management > Microsoft Entra Connect > Connect Sync. Here you can verify the Seamless Single Sign-On is set to Enabled or Not.
Troubleshooting Entra ID Connect Sync Issue Authentication Failure with Entra ID – Table 1
Troubleshooting Entra ID Connect Sync Issue Authentication Failure with Entra ID - Fig.2 - Creds to MS
Troubleshooting Entra ID Connect Sync Issue Authentication Failure with Entra ID – Fig.2 – Creds to MS

Workaround For the Issue

Microsoft recently fixed the issue but when it happens again you can resolve the issue with these workarounds. Make sure your network’s DNS servers can resolve the domain autologon.microsoftazuread-sso.com. First, check your DNS settings to ensure they are set up correctly. You can do this by login into your DNS management console.

  • Also you can check the Seamless SSO feature is still Enabled on your tenant. If its not it will affect your autologon.microsoftazuread-sso.com issue.
  • Also you can resolve the DNS issue, manually add a record to the hosts file on the sync server, pointing it to the last known IP address of autologon.microsoftazuread-sso.com.
Troubleshooting Entra ID Connect Sync Issue Authentication Failure with Entra ID - Fig.3
Troubleshooting Entra ID Connect Sync Issue Authentication Failure with Entra ID – Fig.3

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Author

Anoop C Nair has been Microsoft MVP from 2015 onwards for 10 consecutive years! He is a Workplace Solution Architect with more than 22+ years of experience in Workplace technologies. He is also a Blogger, Speaker, and Local User Group Community leader. His primary focus is on Device Management technologies like SCCM and Intune. He writes about technologies like Intune, SCCM, Windows, Cloud PC, Windows, Entra, Microsoft Security, Career, etc.

Written by

Anoop C Nair is Workplace Technology solution architect with 25+ years of experience in global enterprise organizations such as JP Morgan, Capgemini, etc. Microsoft Certified Trainer. Microsoft MVP from 2015 onwards for consecutive 11+ years! He also conducts Intune and modern workplace tech training for enterprise organizations. He is Blogger, Speaker, and Founder of HTMD Community and HTMD Conference. His main focus is on Device Management technologies like Intune, Windows, Cloud PC. He writes about technologies like Intune, SCCM, Windows, Cloud PC, Windows, Entra, Microsoft Security.

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