Troubleshooting issues with cached mode not working properly in Outlook for Exchange? Here are some helpful steps to follow:

1. Verify Outlook is configured to use Cached Mode: Automatic Configuration should be checked, or if using manual setup the box for ‘Use Cached Exchange Mode’ should be checked
2. Check for connectivity issues: Test an outlook profile with Test E-mail AutoConfiguration and Exchange Remote Connectivity Analyzer
3. Enable Outlook Diagnostics logging: Diagnostic logging will help pinpoint any errors that could be preventing a connection
4. Review recent changes: Review any recent changes such as installation of service packs, recent profile changes, or installation of add-ins
5. Check Event Viewer: Look for errors in the Application log that can help identify misconfigurations or other issues
6. Reinstall Outlook: If all else fails, try uninstalling and reinstalling Outlook