outlook requiring password after exchange reboot

Solution 1:

This is because the Outlook account settings were configured with "Outlook Anywhere" turned on. You can turn it off, if you do not want it.

So that when exchange is rebooted, it will loose connection and restore it once it is back online, and it will not try to connect via https - Outlook Anywhere.

I normally advice my user to restart outlook. If they enter their credential, it will change their connection to exchange from native connection via lan to HTTPS.