What I really want is a tool which lets me masquerade (to nmap, etc.) as whatever kind of machine I want. Pick MAC addresses out of the correct range, but also change how the network stack, etc. respond to various passive and active attempts at fingerprinting.
It's eventually going to throw up alarms if your macbook pro osx 10.8.2 with an valid apple or intel MAC is on a network segment, then drops off, then a machine reappears with a DECstation MAC address.
> but also change how the network stack, etc. respond to various passive and active attempts at fingerprinting.
I can't see how you could do this without swapping out part of the OS, which is where the network stack lives these days. A simpler way might be to swap out the whole OS, by using virtual machines that communicate on an internal virtual LAN: The Windows XP virtual machine sends the packets under control of the Linux virtual machine that's hosting the analysis software.
> It's eventually going to throw up alarms if your macbook pro osx 10.8.2 with an valid apple or intel MAC is on a network segment, then drops off, then a machine reappears with a DECstation MAC address.
It's an eternal game of cat and mouse anyway; if it isn't detailed MAC address analysis, it's subtle timing quirks, or hooking AM radio receivers to computers listening for the sounds of CPUs grinding through AES, or something else.
It's eventually going to throw up alarms if your macbook pro osx 10.8.2 with an valid apple or intel MAC is on a network segment, then drops off, then a machine reappears with a DECstation MAC address.