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I would like the following setup: Tails -> Tor -> VPN.

My limited knowledge on the matter tells me that this would render me "anonymous" to the VPN and provide me with some privacy with regards to bad apples on the Tor-network.

So how would I go about áchieving this? I'll be using one of the well-known VPN providers (TorGuard, PIA, or the like), if that makes a difference.

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    The VPN providers you stated require a paid account. Hiding behind Tor is of no use if you login to your VPN using an account, which can identify you.
    – Nasrus
    Commented May 12, 2014 at 12:04

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The Tor Browser Bundle has a built in proxy, if you want to tunnel a software through Tor (In this case your VPN Client), you need to tell that software to use the Tor proxy. The flow goes like this: VPN Client > Tor (Via localhost proxy) > VPN Server

This guide is about setting up a proxy for a browser. I don't know what VPN software you use, so I cannot give you specific instructions regarding that. You should be able to adapt that guide to your VPN client, if not, feel free to ask about a specific VPN client.

You should note that Tails recommends against this setup.

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