Cached Credential Logon - Computer GPO not Applied after Making VPN
first of all, assuming have standard "everything open" vpn connection.
to question; gpos applied on logon , every 90 minutes (except policies require relog, folder redirection). logon scripts not applied if computer isn't on domain while logging on, vpn clients nowadays offer option log on before logging computer (usually third choice in login screen: last logged in user, other user, vpn solution). have experience watchguard , cisco doing this, if using microsoft vpn solution, might time consider directaccess (sorry if sound salesman, enjoy directaccess myself , it's made life easier).
Windows Server > Group Policy
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