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SOLVED Help setting up a proxy in a VM

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Mar 18, 2015
Hi folks,
I am looking for some help in setting up a proxy in a VM, as the title says. THe hardware is listed in my sig (Nas/Etc). I am using virtualbox in a Ubuntu Host and the VM guest is Ubuntu server. The big reason for using the vm in this fashion is just to keep things clean and neat for the Host OS. I just dont want to run into complications with conflicts or anything and I am also hoping to add a layer of security.

As of now I have the VM up and running, I have the firewalls on both machines set to speak allow contact back and forth for http/https etc, and I have also allowed the port the proxy is said to work on. I suppose I should mention the proxy is dual function. I am hoping to improve network communication with its caching abilities as well as filter/log web content. <-- is the end result. Right now I cant get anything to work even at default.

Troubleshooting that I have done:
Checked configs in the proxy (ie, what port it is set to run on, that the network interface is set to my network and that access is allowed) and that the service is started after changes
Checked browser configs (ie set the browser to use the proxy from the appropriate IP)
made sure to allow communication between the VM and the Host through every means that I can think of (ufw, iptables and changing the network adapters for the VM...currently bridged or NAT because I am testing both to see what works best)

Edit: AND THE SOLUTION WAS......*drumroll please* .........

The machine I use currently has a USB3/ethernet adapter because of a different problem I had with the OS/on board network. I added another USB3/ethernet adapter and configured the VM to use that connection :) Working like a charm now.

And it only took a day and a half of opening and closing ports and testing different configs. Networking is AEWSOME! :D
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