> > I can say for sure this is the issue. First of all I can make this work with > two Ubuntu VMs under the same LAN which allowed me to compare the difference. > > Eliezer's observation is correct. On my VMs traffic goes through the gateway > (ie: the router) before going to the remote box. On Amazon VPC for some > reason it tries to go directly to the remote box since the mac address is > that of SQUID box (not that of the gateway). > > If I use clean.rules traffic goes through the gateway. > If I use proxy.rules (with policy based routing) it will use SQUID's mac. > > I don't know how to fix this issue. > > Thanks, that's a big step forward > > I finally found what's causing the packet drop. I needed to disable Source/Dest Check on VPC instance for SQUID (right-click client VPC instance: "Change Source/Dest. Check")! I did disable for VPN instance. I will continue the other steps and will report back. I think it will work now. Thanks,