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Exchange Connection Problems

How to Fix Autodiscover Security Alerts in Microsoft 365 Apps

Aamir Naveed AkramAamir Naveed Akram Oct 10, 2026 869 views

Question details

Users are experiencing repeated Autodiscover security alerts and long loading delays across Microsoft 365 applications.

How to Fix Autodiscover Security Alerts in Microsoft 365 Apps
Product
Microsoft 365 Apps (Outlook, Word, Excel, PowerPoint)
Device & OS
not provided
Scenario
Connecting to Exchange servers or launching Microsoft 365 applications with Autodiscover configurations.
Observed behavior
The system repeatedly prompts Autodiscover security alerts and causes significant delays in application performance.
Before you start

Before troubleshooting, ensure you have administrative access to your domain's DNS settings and Microsoft 365 admin center, as resolving Autodiscover issues often requires advanced permissions.

Solution 1Recommended

Verify Autodiscover DNS Records and SSL Certificates

Ensure your domain's Autodiscover records point to the correct server and the SSL certificate is valid.

Incorrect DNS records or expired SSL certificates are the most common causes of Autodiscover mismatch warnings.

1
Access DNS Settings

Log in to your domain registrar or DNS hosting provider's administrative dashboard.

2
Check CNAME Record

Locate the CNAME record for 'autodiscover' and ensure it correctly points to your Exchange or Microsoft 365 server.

3
Validate SSL Certificate

Check your Exchange server's SSL certificate to confirm it is valid, not expired, and exactly matches the domain name.

4
Run Remote Connectivity Analyzer

Visit the Microsoft Remote Connectivity Analyzer online tool to test your Autodiscover configuration and identify any specific failure points.

Verify Autodiscover DNS Records and SSL Certificates
DNS Propagation Time: If you make changes to your DNS records, please allow up to 24-48 hours for the changes to propagate fully across the internet.
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Frequently Asked Questions

Why do I keep getting Autodiscover security alerts in Microsoft Outlook?

These alerts typically occur when Outlook tries to connect to an Exchange server but encounters a DNS mismatch, an expired SSL certificate, or a redirection to an untrusted server. It is a built-in protection mechanism to prevent connections to potentially malicious servers.

Can a third-party add-in cause Autodiscover issues in Microsoft 365 apps?

Yes, outdated or incompatible COM add-ins in Outlook can interfere with network requests and authentication processes. You can test this by launching Outlook in Safe Mode or temporarily disabling add-ins via File > Options > Add-ins.

How do I suppress the Autodiscover mismatch warning?

If you have verified that the server is safe but the domain name naturally mismatches, you can suppress the warning by editing the Windows Registry. However, this is generally only recommended for advanced administrators. Refer to Microsoft's official documentation on suppressing Autodiscover mismatch warnings for the exact registry keys.

What is the Microsoft Support and Recovery Assistant (SaRA)?

SaRA is a free diagnostic tool provided by Microsoft. It runs tests on your local machine to figure out what is wrong with your Office apps or Outlook profile, and offers automated solutions for identified problems, including Autodiscover connection failures.