Outlook Keeps Asking for Password
Continuous credential prompts, cached credential issues, and authentication token failures.
Credential cache troubleshooting and modern authentication validation.
Outlook Client Configuration & Connectivity Diagnostics
Professional diagnostics for password prompts, connectivity failures, and Autodiscover issues. User-side troubleshooting, client configuration validation, and enterprise deployment patterns with production-safe remediation.
Outlook Client Problem Categories
Outlook Not Connecting to Server
Connection timeouts, server unavailable errors, and protocol negotiation failures.
Network diagnostics, port validation, and certificate chain verification.
Autodiscover Failed
Autodiscover service resolution, DNS SRV record issues, and configuration discovery failures.
DNS validation, Autodiscover endpoint testing, and fallback configuration.
Outlook Connectivity Diagnostic Framework
- Gather context: What version of Outlook? Windows/Mac? When did the problem start?
- Identify scope: Single user, role-based, device-type, or tenant-wide?
- Test connectivity: Can the user ping Exchange Online endpoints? Are ports 443, 587, 995 accessible?
- Validate Autodiscover: Can Outlook locate the Autodiscover service? Check DNS SRV records
- Verify authentication: Is modern authentication enabled? Check app passwords if MFA required
- Check credentials: Are credentials cached? Is credential vault accessible?
- Test certificate chain: Are root CA certificates installed? Is certificate validation passing?
- Consider exclusions: May user be affected by GA policy or conditional access?
Common Outlook Connectivity Issues (By Frequency)
| Issue | Symptom | Solution |
|---|---|---|
| Modern auth token expired | Password prompt appears after period of inactivity | Clear cached credentials, sign in again with modern auth, verify MFA setup |
| Cached credential corruption | Continuous password prompts, old password doesn't work | Clear credential vault, update password, remove and re-add account |
| Autodiscover service unavailable | "Unable to establish connection" with Autodiscover error | Verify DNS SRV records, test with manual configuration, check firewall rules |
| Certificate trust failure | "Certificate problem" or "untrusted connection" error | Update CA root certificates, verify certificate chain, check system date/time |
| Conditional Access policy blocking | Sign-in succeeds in browser but fails in Outlook client | Check CA policy compliance (device, location, client app), use app password if eligible |
Ready for Professional Outlook Diagnostics?
Our principal engineers can diagnose and resolve user connectivity issues across your entire Outlook deployment.