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All HttpListenerRequest.IsLocal does now is to check whether the remote endpoint IP address is the loopback device (https://github.com/mono/mono/blob/master/mcs/class/System/System.Net/HttpListenerRequest.cs#L406), which is not the documented behavior of the property (https://msdn.microsoft.com/en-us/library/system.net.httplistenerrequest.islocal%28v=vs.110%29.aspx). The property should determine whether the remote endpoint IP address is assigned to one of the network interfaces on the machine instead.
Thanks for the bug report.
This issue should be fixed by the pull request below.
Fixed in master c7683d0cbd7c18becca400390a28714a0f84f9a1