What kind of hardware does the pfSense 2.1 run on (specifically the lan controller)? Although not the same problem as you're describing, I have a Windows 7 machine that occasionally drops out of the network due to not being able to renew its DHCP lease. I could see the DISCOVER/OFFER sequence (but not the ACK) when it happened in the DHCP logs on the pfSense unit. Since I haven't had this problem with my previous router (Netgear), I suspected that it might have something to do with the pfSense box I am running on. In my case, the pfSense box has Realtek 8111 chip (and so does the Windows 7 box). At some point, I need to track it down and figure out why it can renew DHCP lease. Not that I think it might be relevant, however, there are a couple of settings in the Advanced Networking tab (System->Advanced->Networking) such as LRO, TSO, and hardware checksum. You could try if enabling/disabling any would make a difference (might need to reboot after modifying the settings). Good luck.