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RDS Remoteapp SSO issues when out of the office

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We are running 2008 R2 w/SP1 as a Session Host/Gateway/Webapp/Remoteapp server, everything works fine with external Webapp SSO and internal RemoteApp SSO. There must be something I am missing though since when a laptop leaves the office and they launch a RemoteApp they get a credential prompt which they can connect if they type there password in but they will not get a prompt if they have a VPN connection running. I would imagine this has to do with SSO to the RG Gateway but I have read about this until my eyes are bleeding.

Workstations are all XP/Vista/Windows 7

All have the latest updated RDC clients

Private RDS FQDN:       rds01.domain.local

Public RDS A Record:  remoteapp.domain.com

The A Record matches my certs Common Name

The Certificate meets the correct requirements

Server Authentication (1.3.6.1.5.5.7.3.1)

Client Authentication (1.3.6.1.5.5.7.3.2)

Can anyone help?

Thank,

Chris Harvey


Thanks, Chris Harvey


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