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I have a lightswitch App (desktop app for windows) which authentications with AD against their logged in account, so the user doesn't need to log in again. This works great in the office but over the Watchguard SSL VPN in our office it doesn't work. Any attempt to connect just rejects with an authentication error (unable to authenticate access is denied) and the windows log shows no errors.

Is there anything I need to do to enable windows to authenticate properly over the VPN? Something like remote desktop works fine over the same link?

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Your users needs to reach the AD controller. Check your DNS from VPN clients, if can resolve this request, maybe is not resolving your domain's request.

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