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Imagesqlnerd wrote in Imageitsecurity

Sidestepping Websense

EDIT:
I've done a few things since I originally posted this.
1. I installed SecureIM on a colocated server and changed my AIM proxy to the internal IP and port
2. I used my own certificate server to create a PFX file and now all my AIM is encrypted
3. I installed Privoxy as suggested by an LJer and edited firefox and IE to use it
4. I setup a Google VPN connection and that's my new gateway. I checked and all my stuff is going through there now.

I'd say I probably only needed to do #2 and #4. The VPN isnt allowing Yahoo (competition?) though so I'm using VPN for AIM and SecureIM for Yahoo.

Original post
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I'm in the IT department so I don't need to do this..but its a challenge for me.

Webense can track crap hardcore. From AIM to Web traffic. I want to install an AIM proxy on port.. 81 that perhaps looks like web traffic isnterad of AIM. I'd also like to install a proxy server (windows/linux doesnt matter) that would trick websense into not sniffing out port 80 hits.

Any suggestions? i'm not a security nerd so if my concepts are way silly, please forgive.

thanks