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Connecting to VPN and Exchange and Skype for Business - Credentials

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Hello all,

When I am at work and I VPN into a different network and I use a proxy ) my Outlook and Skype for business will re-ask me to enter in my credentials  and when I re-enter in my credentials it keeps prompting me for my credentials even though they are correct.

Since I am using O365 and its based in the cloud, shouldn't I be able to access this from anywhere?

Any advice would be appreciated.

Where would one start troubleshooting this?


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