If you are not set up with a Winning VPN, please see info in link
https://winninggroup.freshdesk.com/a/solutions/articles/22000211114
Open the window on the bottom right of the Chromebook.
And click on the VPN key logo.
Select the Winning VPN you have set up on the chromebook.
(If you dont have one set up contact helpdesk to set you up)
Sign in using your credentials.
PW should be your normal general password.
The VPN key will now be blue as shown and you will be on the Winning VPN.
(Remember to use only when needed)