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percula,
I'm interested in hearing your thoughts on using a managed VPN (not a cheap service like findnot but rather an ATT) rather than renting and building a personal server VPN? What are the downfalls? Lack of configuration? I assume nothing would change on the client end?
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Think there are a couple of possible issue that may or may not apply to a managed service.
1) You have to be sure that you are not sharing the broadcast domain. I would be very surprised if a service from ATT or any other large carrier had this issue.
2) I think IP is more of an issue than I was thinking before (ref why would stars see this responses). Any large carrier is going to show up easily on the registry of IP's and will provide exact information to a query from someone investigating assuming the investigation has enough weight behind it, and I think the poker sites, payment processors can leverage enough weight.
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Also, I'm not even sure if this is possible/feasible; but is there any client software or maybe it can be done on a hardware level with a VPN firewall to direct traffic based on the process using the port? For example, lets say I want to route all traffic from PartyPoker.exe through the VPN but I want traffic from Firefox.exe to not go through the VPN? Is this possible?
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On a per application basis no. On a per protocol/IP basis yes. But frankly it would be a royal PINTA to maintain. Keep in mind that poker sites and web sites use host names to connect, e.g.
www.twoplustwo.com, which can resolve to one or more IP addresses and those IPs can change and often do. But I have not ran across a firewall yet that is really very good at split tunneling on a per protocol basis, which this is. I would not want to try this with anything of value on the line.