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If, theoretically, one was using a network that force-disconnects your device from itself if you are detected using a proxy (such as a network configured with Cisco Umbrella or similar), but a proxy is necessary to avoid censorship of content or to maintain privacy, which kinds of proxies are the most resistant to detection?

So far I know about OpenVPN and third party proxies such as Ultrasurf and Opera VPN, but those are relatively trivial to detect and block.

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    Just to clarify it, proxies and VPNs are NOT the same thing. The terms cannot be used interchangably. You can read about the differences on google.com/amp/s/www.howtogeek.com/247190/… – Jesse P. Aug 10 '18 at 3:33
  • @JesseP. Thanks, sorry for the inconsistency. It doesn't really matter to me which one I am using as long as it effectively cloaks my network traffic. – laptou Aug 10 '18 at 13:50
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If all you're looking for is a proxy, I'd recommend Tor.

If you're looking for a VPN, I personally use and recommend PureVPN. NordVPN is also one of the top VPNs available.

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    Tor usage is easily detectable by the network operator because all Tor nodes have their IPs published. You should use a private bridge (torproject.org/docs/bridges.html.en) in order to hide the fact that you're using Tor. – Macil Aug 10 '18 at 4:06
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    @Macil Above and beyond that, the Tor protocol has a very obvious footprint and is detectable even when used inside of a VPN. Consistent packets of 512 bytes of data should jump right out to most packet scanners. – Adonalsium Aug 10 '18 at 12:32
  • @Adonalsium I believe Tor bridges have obfuscation features that take timing into account too to make them less detectable than Tor over a VPN. – Macil Aug 10 '18 at 17:03
  • @Macil Ah, I wasn't aware of that. Good to know. – Adonalsium Aug 10 '18 at 17:14
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If you want to hide on the internet I would suggest a combination of different software. First of all you shouldn't use Windows anymore and switch to Tails.

If you are just looking for a good VPN, I would suggest one which proves that it doesn't log your traffic. Not even timestamps. You can find a good list here. Take care that you can pay with XMR, BTC or cash to hide your payment. I personally prefer mullvard because you don´t even need an account. But it´s your choice and you can take whatever you want. Just look if they are storing logs of you.

If you have your VPN, try TOR. It's easy to use and kind of safe (not for sure but better if you use your normal internet browser).

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