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I wonder if I understand well VPN. I connected to SecurityKiss, they provide a list of TunnelBlick configs. In order you to connect their VPN. (TUnnelBlick is OpenVPN based).

Am I right : your IP is masked. OK. Masked more again if you - farrer - connect an anonymous proxy. myMachine -> VPN SecurityKiss -> Anonymous Proxy in HongKong.

But at each "node" (->), the server owner can listen to your data , right ?

(just a question, no real needs).

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Am I right : your IP is masked.

Slightly masked. For something like a basic HTTP or FTP request, it will appear to come from the VPN server address, but with things like full email headers, Javascript and iFrames on websites, depending on the configuration it might be possible for some servers to see or work out your IP.

The VPN company could leak your IP if they were malicious (e.g. inserting it into every HTTP header).

But at each "node" (->), the server owner can listen to your data , right ?

Yes. You are making the VPN people act as your internet service provider. They have complete access to everything that happens over the connection, unless it's end-to-end encrypted, e.g. by HTTPS or SSH.

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  • It is a bonus if you can trust your VPN provider, but they are probably more trustworthy than the local Internet or their provider. Even if your VPN provider is compromised you should have other security, such as the HTTPS and SSH, mentioned in the answer.
    – chicks
    Jun 24, 2015 at 19:49
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    they are probably more trustworthy than the local Internet or their provider - why would they be more trustworthy? They are less regulated, they are distant and less accountable because of it, they offer a product which is hard to validate (ok the VPN works, but is it actually protecting you? Exactly how much? From who/what?), and their business model encourages customers with valuable or interesting information to hide. They could be anyone. I won't claim they are inherently untrustworthy, but neither are they automatically more trustworthy than any other company.
    – TessellatingHeckler
    Jun 24, 2015 at 19:58
  • ISPs are much more likely to have direct government influence through regulations or protected incumbent deals. In most cases you don't have any choice of your ISP in an immediate sense so you're basically going to use whatever you can get. Your VPN provider allows for much more reflection, competition, and auditing. If you document your VPN provider leaking information I'm sure there would be a lot of folks that would like to hear about it.
    – chicks
    Jun 24, 2015 at 21:59
  • @TessellatingHeckler : I think you re precisely right. That's it. You dont connect your provider, but you dont know what you connect. Proxies locations are sometimes frightening. "and their business model encourages customers with valuable or interesting information to hide." Absolutely. If I were a N54 guy, I'd provide super anonymousity services, ovpn conf, etc, and I d wait for the birds landing in...
    – ArchiT3K
    Jun 25, 2015 at 7:20
  • @ArchiT3K indeed - remember it.slashdot.org/story/07/09/11/1730258/… and how a security researcher setup a Tor exit node in ~2007 so he could sniff traffic, and found plaintext POP3 passwords for high level people.
    – TessellatingHeckler
    Jun 25, 2015 at 12:25
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Assuming a full-tunnel configuration, your data is protected between your computer and the VPN service, and from a web site's perspective your traffic will appear to originate with the VPN provider.

However, you are now placing a lot of trust in the VPN service. They do have un-encrypted access to all of your traffic. Additionally, anyone upstream to the internet from the VPN service will have access to your traffic (ie, this won't help you hide from the NSA).

A trusted, reputable VPN service is useful for places like coffee shops, where you're stuck with un-encrypted wifi and anyone else in the shop could trivially listen to your traffic. Here, the VPN would encrypt that traffic while in transit over the wifi network, all the way to VPN provider.

I also need to mention that OpenVPN also supports split-tunnel connections. A split-tunnel connection means the VPN link is only used to access resources on the VPN network itself. Split tunnel is useful for things like access to resources at your workplace, without having to force all of your regular internet browsing traffic to run through the workplace WAN connection twice.

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