Outlook is one of the most used Email application does face error sometimes. If you are wondering, why your Outlook won’t start? It can be resolved by simple troubleshooting. Try another Email client. You can create a new profile. Make sure that Outlook is not running in compatibility mode. Try removing VPN software from your computer. For Mac users, ensure that your Mac OS and Outlook are updated. You can clear the browsing data in chrome. If you see, “Outlook disconnected” message. Restart your computer.