Running multiple VPNs without VM

Hi guys,

Utter noob here that started browsing a few days ago (great resource here by the way).

Anyways, I might be embarking on a sensitive project in the future, for which I'll need a pretty high level of anonymity and minimal traceability. From what I've gathered here so far coupled with suggestions from colleagues, my proposed setup would be two chained VPNs that don't keep logs (or so they say) --> Tails/Tor --> PGP for all text. I was wondering whether there's a way to chain two VPNs without a VM (as, according to the Tails website, running Tails in a VM isn't as secure as running it on the host).

Also, how anonymous would I be with that setup? I've also read suggestions to exclusively use a computer that isn't used for any personal tasks, as well as exclusively use Starbucks wifi. With two VPNs and Tails/Tor already in place, would it make a huge difference whether I use open wifi or my personal ISP?

Much thanks in advance for any help/suggestions.

 

I believe it possible to tunnel one VPN through another in Linux using iptables rules. But I don't know iptables well enough for that.

Also, using Tails it'd be necessary to redo the entire setup after each boot. Perhaps one could write scripts for installing VPNs and configuring iptables. But

With two nested/chained VPNs and Tails, it's unlikely (but not impossible) that you'd be traced back to your real IP.

That is, unless you mess up.

Using the library computer didn't protect DPR

 

Regarding DPR, true. Just shows that anonymity can't be fully guaranteed, although I wonder whether they would've gotten him if it weren't for that minor slip-up way back when.

Mirimir, anything you would add to that basic setup? I recall reading some of your posts suggesting the use of certain firewalls/rules to make sure all activity routes through Tor and/or a VPN. Would that be needed here (that is, in addition to checking off "Send all traffic over VPN connection" on your VPN client preferences)?

Thanks, mate. Just saw the link to your privacy guides. Definitely will check them out tomorrow. Maybe after studying them, I'll be a little less of a noob.

 

To add two VPNs to Tails, and have one (VPN2) connect through the other (VPN1), and then have Tor connect through VPN2, you'd need advanced iptables (Linux "firewall") rules to specify that routing, and prevent leaks.

Maybe someone who knows iptables well could say more.