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From what i know and from what i already tryed, if i install VPN i saw i can connect to the internet with another ip and with another browser that VPN has, i am at work and i wanted to know if the ip connections from my pc can be tracked by the it man or by any other kind of software if i hide the connection with the vpn.. ? is it possible?

I always deteled my history and from what i understood from antoher person usually the browser saves caches and i enterd to documents and settings/(My account)/application data/macromedia/flash player and i deleted all in that folder since there it save all the connections, caches and all others...

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  • It's possible. While a VPN connection uses encryption to protect data in transit, network administrators might still be able to see that encrypted tunnel being established if they're monitoring your connection. It depends to a large extent on both the type of VPN used and the extent of monitoring. Nothing is completely secure. Dec 3, 2014 at 9:21
  • He is not "Heavly" tracking down all the connections, from what my collegue at work told me, he sometimes look at the connections, i don't know how and my collegue sayd that there it appears the ip of the one who connected, since all the 5 pc's from the offices are connected to one router, or something like that.. so he only occasionaly looks and if the boss is asking, he gives him the connections, any other helphful tips you got? anyways it would be better to use the vpn than the browser from my pc right? and btw i don't think he is able to do all that stuff, see the encrypted tunnel all that
    – Alex
    Dec 3, 2014 at 9:29
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    It would be even better not to waste company time doing stuff you shouldn't be doing. What you are trying to do is circumventing company policy and could get you fired.
    – R-D
    Dec 3, 2014 at 9:37
  • Yes i know... i work at an office where i have to make offerts of prices.. and sometimes i got dead times and usually spend time on Steam.. nothink more..
    – Alex
    Dec 3, 2014 at 9:44
  • It is a little more than trivial from a technical stand point to place a fake certificate in-between the VPN and your computer. By doing this your connection while still being encrypted but wouldn't be secure. Since IT has total control over your system configuration, and has the ability to install any certificate they want, they can do this without a much trouble.
    – Ramhound
    Dec 3, 2014 at 12:00

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Using a VPN connection can be tracked only if your connection to the VPN end server is not encrypted which is not usually the case, most VPNs use IPSec to encrypt your traffic, as you connect through a VPN, all of your requests pass to the VPN end server then the server redirects them to the real end point destination.

Now to answer your question, there are two scenarios:

  • if the connection is not encrypted then by monitoring your traffic and investigating I may be able to see the VPN headers inside and know where you are connecting to.
  • if your connection is encrypted then by monitoring your traffic and investigating I can know that you are connecting to a VPN server (whois lookup can do it), and will obviously assume that it's illegal and start a forensic investigation.

For the deleting history part, just use chrome incognito mode and don't worry about cached data, even opened documents (let's say a PDF) that will download a copy of it to temp directory in order to open it, it will be deleted right after you close your browser.

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  • How can i use the chrome incognito mode? so would you recommend me use vpn? as i sayd above, sometimes boss is asking the it man about the connections, he wants to see if anyone has connected anywhere else, and there are 5 pc's in the office togheter with my collegue that are connected to one router, is that possible to track down every pc from that room? i usually connect to steam to pass my time while i do work on offerts.. but my collegue sayd that sometimes the it man looks and the ip's are shown where you connected..
    – Alex
    Dec 3, 2014 at 9:33
  • 1- Open incognito mode by pressing ctrl+shift+N. 2- I don't recommend breaking office rules at all, I was explaining how VPN works in an easy way. 3- Even if your VPN provider is good enough and implemented encryption to the connection (you can check that from their website), you can still be identified by looking to IPs you are connecting to, if the IT guy is smart then he'll search the destination IP and know you are connecting to a VPN which is - from what you wrote - a violation of office rules.
    – Ash
    Dec 3, 2014 at 9:42
  • Thanks for explaining, last question, if i use the incognito mode, will the browser delete automatically the history? And i know, i am violating the office rules, but i am working as an offertant, if i wrote that correctly and while i make price offerts, i usually have dead times and would like to spend my time on Steam, nothink more..
    – Alex
    Dec 3, 2014 at 9:46
  • I am not in a position to judge so in the end no explanation is required, yes incognito mode makes it like you were never there.
    – Ash
    Dec 3, 2014 at 9:49

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