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Request: The question must assumed to be hypothetical and answers be limited to technical only. (no ethics and other things)

I am in an organization (school) that has very strict network policies. We can access internet only through a squid proxy. Stackoverflow is banned and I want to access it somehow.

Now I own a machine in some cloud connected directly to internet backbone. I have root access to this machine. Needless to say it's outside my organization's network. This machine is accessible through HTTP from my organization network.

Now tell me is there anything that I can install on the cloud machine so that I can surf whatever I want from organization's network?

I think this reduces to asking : Basically the way we have SSH tunneling is HTTP tunneling possible ?

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Do you know for a fact that the proxy server is in fact Squid? The nature of the proxy server changes the approach.

School law can get quite complicated (and IANAL), but the bottom line is that the school district is responsible for making a best effort to appropriately filter content (which is the reverse of standard college policy). That means that the school needs some way of constantly updating which sites are accessible (unless of course they just throw their hands up and institute a very strict whitelist policy, which they might have done if they are just using Squid). In many organizations, a dedicated proxy device is used that subscribes to a service which constantly updates web site categorization. These services have gotten very good over the years at detecting and preventing the standard sorts of ways around your institutional proxy (such as setting your own proxy server up outside the network and using that to view Stack Overflow, which is essentially Bruno's answer).

It is possible to use VNC over an HTTP proxy, which might accomplish what you want (remote into your outside machine and then run a web browser inside it). I have also seen some people have success with SSH tunneling through HTTP proxies (Craig notes that it shouldn't work, and maybe it doesn't with Squid, but I have seen it done with other proxy devices although I've never tried it myself). Again, unless they really are using a fairly static Squid configuration, don't be surprised if the admins catch on fairly quickly as to what you are up to.

Since I am, in fact, employed to prevent precisely the kind of thing you are describing, I should note that violating your institution's Acceptable Use Policy will get you into a lot of hot water. Yes, you said to ignore the ethics but this post is appearing under my name and will be eminently Googleable. :)

That said, even when I was a student and not an employee, I found that some problems are best solved organizationally. There is a procedure somewhere for unblocking websites, and there are people authorized to submit to that procedure (i.e. teachers, professors, etc.). If you can make the case to them that some sites should be unblocked, then they can make the case to the IT Department. Provided that no one has previously offended the BOFH, you should be able to get access to the site. After all, it is quite well known and dedicated to intelligently solving technical issues rather than trading ways of attacking your network.

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+1 For paying attention to the Acceptable Use Policy. That was excluded from the initial question, but it can matter indeed (it may also depend whether the site is blocked by default or by an actual policy). Discussing it with those who make the policy is a better approach indeed. – Bruno Sep 15 '10 at 17:42

Do you need a website on that server? If not, why not run sshd on port 80 and then use an SSH tunnel? If that's not possible, this may be of interest but I've not tried it.

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That won't work. Squid is an HTTP proxy it should only allow the HTTP protocol through. – Craig Sep 14 '10 at 19:54
Fair point, sorry for the misleading answer! – James L Sep 14 '10 at 20:16
Also I need a website to work there. – Eastern Monk Sep 15 '10 at 17:31

If your box is running something like Apache Httpd, you could probably configure a path on your box to relay the requests to the server of your choice using mod_proxy and its reverse proxy functions.

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This sounds most appropriate. – Eastern Monk Sep 15 '10 at 17:30
This may help too: – Bruno Sep 15 '10 at 17:35

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