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When I'm on a public network that I don't trust, I use a combination of ConnectBot and ProxyDroid (with "Global Proxy" enabled) to tunnel my phone's traffic through a trusted server that I control. However, I have to set that all up manually, and I'm sure plenty of other data leaks out around that tunnel (at the very least, apps will check in between the time I connect to a network and the time I set up the tunnel). Also, the process is involved enough that I usually only go through it when I'm on a public network and I get SSL errors from the browser telling me google.com is using a certificate signed by GoDaddy.

I'd like to set something up that smooths the process out a bit, such that a tunnel is automatically established whenever I connect to a network, all traffic is routed through it, and apps aren't able to connect to the Internet unless the tunnel is open (very important). Obviously, it should verify the authenticity of the server before connecting (though I haven't seen a VPN that doesn't). I'd like something that uses SSH since that's the simplest to set up, but anything will do. What sorts of solutions like this are out there? My server runs Ubuntu 12.04, and I can install extra software on it if needed.

Again, the most important part here is that no app can access the network unless it's going through the tunnel, and if the tunnel hasn't been established yet, no traffic escapes. Obviously, the one exception would need to be whatever app is actually making the initial connection to establish the tunnel.

I'm currently using a rooted HTC Incredible running CyanogenMod 7. I'm in the market for a new phone though, so if anyone knows of any solutions that require something newer than Android 2.3, those would be welcome as well.

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Maybe shadowsocks? There are different os client/servers, even for routers. http://www.shadowsocks.org/

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Proxies by design aren't meant to be set system-wide. Apps are supposed to make proxied connections if they want to. And mostly apps fall back to no-proxy mode if for some reason proxy server isn't accessible. Also there are other limitations. http proxies can't handle UDP traffic and SOCKS proxies can't handle ICMP echo (which ping uses). A VPN network, however operates at lower level and forwards all traffic to remote end. For details see Why proxy set on Android does not work when used as hotspot?

it should verify the authenticity of the server before connecting (though I haven't seen a VPN that doesn't)

Mostly http proxies support basic authentication, and obviously SSH and VPNs do.

I'd like something that uses SSH since that's the simplest to set up

You can create a SOCKS5 tunnel using SSH dynamic port forwarding, it can forward UDP traffic too. But you need to use third party apps, Android doesn't support SOCKS proxies. For details see: How to set up a socks5 with Android cli?

I'd like to set something up that smooths the process out a bit, such that a tunnel is automatically established whenever I connect to a network, all traffic is routed through it, and apps aren't able to connect to the Internet unless the tunnel is open (very important).

Android by-default doesn't offer such functionality but you can use automation apps in combination with VPN based apps to hopefully achieve the desired result.

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