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Many social networking and popular websites are blocked where I live. There are certain workarounds to access these services however, including VPN services provided by certain local providers with servers abroad located in several countries. However, these workarounds are getting increasingly unreliable so one has to switch between various applications such as Open VPN, OpenConnect, Cisco AnyConnect, etc. though they only seem to work for a certain period. I recently faced an IE notice when opening YouTube through one of these VPN services saying the connection is insecure, as shown in the following screen shot:
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Can the government track and intercept my online activity even when using VPN?

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    Anything you do at home with the Internet goes over a connection to your Internet provider. What if your surveilance agency taps on that connection? I suppose the only viable solution is to employ an IP-address that is not of your own and has no relation to you at all. – Mok-Kong Shen Nov 21 '15 at 10:39
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    The warning you are seeing is nothing to do with accessing the site through a VPN. IE is warning you the protocol used by the site is old and has known weaknesses that can be exploited. Have you considered using Tor and Onion? – Max Vernon Nov 21 '15 at 15:03
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    That's the entire gist of the problem. You can have secure, and cheap, but not fast, fast and secure, but not cheap, or fast and cheap, but not secure. How much do you trust the owner of the other side of your vpn connection? Can you be sure they are not offering the VPN as a honey pot? – Max Vernon Nov 21 '15 at 15:12
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    If you give me several billion dollars, I'll personally put a satellite into orbit for you that runs a connection only you have access to. I'll also give you 100% admin access to the box along with the source code for all parts. That is fast and secure, but not very cheap. – Max Vernon Nov 21 '15 at 15:17
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    @JasonStack: As I argued, using Tor etc. doesn't eliminate the risk I indicated earlier. – Mok-Kong Shen Nov 21 '15 at 17:55
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I also reside at a location, where the government blocks a number of websites related to security, and although the majority of their effort is around blocking pornographic content, I am sometimes bothered by the categorization of the content filter, or their choice of blocked sites. But it's not the blocking that bothers most, it's the fact that their Internet use is generally monitored and recorded in this country.

If your question is "can governments decrypt my VPN traffic", the answer is "depends". There is a concentrated effort by the Five Eyes intelligence agencies, and the effort (and partially its results) has been brought to us thanks to Ed Snowden (check out the Turmoil/APEX projects high-level info here (Der Spiegel magazine dumps), mainly focused on IPSEC). OpenVPN's TLS use also depends heavily on the implementation at hand, although 2048-bit RSA still is considered "out of reach" for the big guys.

Having said that, the other things that a government can do:

  1. The government agency that monitors Internet communications knows you are using a VPN. They may interpret this as "this person has something to hide". So you've probably ticked the first box in the "surveillance target" selection scheme.

  2. Using various techniques and patterns they would be able to ascertain and identify you from other VPN users across a variety of locations - a coffee shop, a friend's house, etc.

  3. Using these patterns they will try and track your non-VPN activity to build a profile and to start using other methods to monitor your posts, etc.

  4. They may try to run VPN disruptive techniques to bump you off the VPN, so your browser and/or other programs leak unencrypted packets in the immediate aftermath of the VPN going down. That will give them an idea what are you up to, e.g. hosts you're sending packets to, or even limited content.

  5. There have been attacks on VPN traffic that may help them discover certain patterns (e.g. when do you come back home from work).

In general many commercial VPN providers do not provide you with measures that will ensure maximum protection - they're not going to give you the strongest encryption, because that's more overhead for their servers. Also, because of their commercial activities, they do attract a lot of undesired attention.

My general recommendation is to run your own server - rent a cloud server for something like $19 a month within a country that generally won't be as keen on eavesdropping on your funny cat pics surfing habits over social media. In addition to that, run a legitimate mail server on it, and a WordPress site, and if anyone asks - you're just securing your connectivity to your mail/business server. You'll be using the VPN for legitimate business reason. Not that it will be a deterrent, but may win you the benefit of the doubt.

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The short answer is YES the Government can see your VPN traffic. Simply put the method used to encrypt the traffic is uses a key exchange based on a cipher. Most VPN use des/3des and various others which are licensed by the product owner who hands over the keys to a Government.If said government makes a request for the cipher keys they will be given but generally they don't need that either. They have devices and software that decrypt the keys. The only true way to evade surveillance is to use an encryption that is truly personal to you that is not publicly available.

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    "Most VPN use des/3des" - citation needed. "The only true way to evade surveillance is to use an encryption that is truly personal to you that is not publicly available." - this is the worst idea becaue you cannot possibly create a strong encryption. The true way to evade surveillance is to use a strong and tested algorithm. – schroeder Mar 29 at 10:12
  • How about vpn providers that connect you to the Tor network? – codezombie Mar 29 at 12:03
  • Can you explain this comment "various others which are licensed by the product owner who hands over the keys to a Government." a bit better? It looks like you're saying that the people who designed DES/3DES (and other algorithms) "give keys" to governments, but that isn't possible. – Xander Mar 29 at 12:41

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