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Fix AutoDiscoverFailedConfigurationErrorException in Microsoft 365 Cutover Migration
Question details
The migration service throws an AutoDiscoverFailedConfigurationErrorException for certain mailboxes during an Exchange 2019 to Microsoft 365 cutover migration.
- Product
- Microsoft 365 / Exchange 2019
- Device & OS
- not provided
- Scenario
- Executing a cutover migration to move mailboxes from an on-premises Exchange 2019 server to Microsoft 365.
- Observed behavior
- The migration fails for specific mailboxes because the service cannot automatically detect the migration endpoint through Autodiscover, despite other mailboxes migrating successfully.
Ensure you have global administrator privileges in the Microsoft 365 admin center and administrative access to your on-premises Exchange server to modify endpoints and run connectivity tests.
Verify and Test Autodiscover Configuration
Use Microsoft's diagnostic tools to check the DNS records, SSL certificates, and firewall rules for the affected mailboxes.
In many cases, an AutoDiscoverFailedConfigurationErrorException occurs when specific mailboxes have mismatched configurations, missing routing addresses, or backend external connectivity issues that prevent the migration service from discovering them.
Navigate to the Microsoft Remote Connectivity Analyzer website. Select 'Exchange Server' and run the 'Outlook Autodiscover' test using the credentials of one of the affected mailboxes.
Check that your Autodiscover CNAME or A records correctly point to your on-premises Exchange server and that the SSL certificate is valid and trusted by a public Certificate Authority.
Log into your Exchange Admin Center and compare the properties (such as primary SMTP address and User Principal Name) of the affected mailboxes with those that migrated successfully to identify discrepancies.
Configure the Migration Endpoint Manually
Bypass the Autodiscover process by manually creating and defining the migration endpoint in Microsoft 365.
Open a Microsoft 365 Support Request
Contact Microsoft support if the endpoint is perfectly valid but the migration batch continues to fail for specific users.
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Frequently Asked Questions
What causes the AutoDiscoverFailedConfigurationErrorException during a cutover migration?
This error occurs when the Microsoft 365 migration service cannot automatically discover the on-premises Exchange server settings for specific mailboxes. It is often caused by missing DNS records, mismatched UPNs, firewall blocks, or untrusted SSL certificates on the source server.
How do I use the Microsoft Remote Connectivity Analyzer for migration issues?
Go to the Microsoft Remote Connectivity Analyzer website, choose the 'Exchange Server' tab, and select the 'Outlook Autodiscover' test. Enter the email address and credentials of a mailbox that failed to migrate to see where the connection breaks down.
Can I perform an Exchange cutover migration without relying on Autodiscover?
Yes. If Autodiscover fails to locate the endpoint automatically, you can manually define the migration endpoint in the Exchange admin center by entering the exact FQDN of your on-premises Exchange server during the migration batch setup.
Why do only some mailboxes fail with this error while others migrate successfully?
This usually indicates that the affected mailboxes have incorrect primary SMTP addresses, mismatched User Principal Names (UPNs), or are hidden from the Exchange Global Address List (GAL). Ensure their properties match those of the successfully migrated users.
