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Captive Portal detection is an OS built-in and although something you mostly see/experience on WiFi connections also works for wired connections. There is no DHCP magic going on there. See for instance https://msdn.microsoft.com/en-us/library/windows/hardware/dn408681.aspx Windows 8 and Windows 8.1 supports captive portal networks by immediately ...


2

Your VPN is TAP, assuming that OpenVPN is the underlying tech, then this means you have a layer2 VPN. That means you have things setup as if they were all physically connected to the same switch. If you don't want a layer2 network, don't use TAP.



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