Sometimes when Outlook changes network contexts (i.e. from wired to wireless), it triggers an annoying authentication popup. There’s a way around:
- Open Outlook.
- Go to “Tools” > “Account Settings”.
- Double click on your account.
- At the bottom right, click on “More Settings…”.
- Click on the “Connection” tab.
- Under “Outlook Anywhere”, click on “Exchange Proxy Settings”.
- Uncheck the “On slow networks, connect using HTTP first, then connect using TCP/IP”.
Just a useful tip from the top of my head. If you want to migrate Outlook settings without having to reconfigure accounts, delivery options and PST locations, here is the registry key you need to export: