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Before I begin, I'd like to state I am going to try and be as thorough as possible. Both so everyone offering help can know the full situation, and to ensure that I get accurate information.

Ok; I recently transferred to a new college, in a new city, and a new state. The method for accessing the internet is different from my prior University, and - although I'm confident in my current methods - I'd like to know for sure that my activities are as hidden as possible. Why? Because, although I live in the dorms, my dorm internet connection isn't currently working and they said it could be a month (!) until they get it fixed. So, the only internet I can get is through connecting to the Library's hotspot, where the rules are more strict and all that.

The set-up: I've my own laptop, but to access Wi-Fi one must log on with an assigned username & password. I've downloaded the TOR browser, set it up and it works fine (I get a different IP address and all that); but, will this be sufficient to keep my browsing private from the System Administrator? What if I opt to browse outside of encrypted mode?

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As long as you are using Tor, your system administrator won't be able to see what you are doing or what sites you are visiting. It does not matter if you are visiting encrypted sites or using plain HTTP.
However, you should keep in mind that Tor exit node owners will be able to see your traffic to unencrypted sites, even if they cannot tell who you are. There is an article on this topic on Wired.

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