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".

Namaste.

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