Outlook Keeps Asking Password
Repeated password prompts.
Check MFA, clear creds, update client.
Outlook Troubleshooting: Prevent $200–$400 per user per day in downtime
Rapid diagnosis for authentication, connectivity, and Autodiscover failures. Each guide includes business impact assessment and 12–20 minute resolution timeframes to minimize user productivity loss.
Covers modern authentication failures (MFA loops, CA blocks), connection timeouts, profile corruption, Autodiscover misconfigurations, and hybrid routing issues. Includes safe rollback procedures and validation steps. Prevents help desk ticket avalanches (10–20+ tickets per widespread issue).
Outlook Problem Categories
Select the category that best matches your symptoms. Each guide walks through diagnostics, common causes, and remediation steps with safe rollback procedures. Start with connection issues if Outlook cannot reach the server, authentication issues if credentials are repeatedly rejected, or autodiscover issues if profile autoconfiguration fails.
Outlook Not Connecting to Server
Connection failures or timeouts.
Check Autodiscover, DNS, firewall, routing.
Autodiscover Failed
Auto setup fails or wrong settings.
Verify DNS, routing, hybrid, SSL/TLS.
When to Use This Section
Use these guides when users report connection failures, repeated password prompts, or Outlook failing to connect to Exchange Online. Common scenarios include modern auth enforcement breaking legacy Outlook versions, conditional access policies blocking clients, autodiscover misconfigurations in hybrid environments, or credential caching issues after password resets. These diagnostics cover both Outlook desktop clients and Outlook Web Access authentication flows.
Related Guides
Full diagnostic procedures and escalation criteria.