On the client-side, i have a loopback adapter at 192.168.1.1, with a 255.255.255.0 mask. I also have a wireless connection that does not work when the loopback adapter is enabled. Would it make sense for the operating system to give me a warning when I am connecting to a network that is on the same subnet over a different adapter?

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No. Having multiple network adapters on the same subnet is a totally valid configuration assuming that both the adapters connect to the same network. That's why we have subnets, after all.

So, as far as the operating system is concerned, you just have two NICs on the same network. There's no reason for it to complain about that.

You'll need to take one of your networks and change its subnet (I suggest the loopback adapter, probably easier).

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