TL;DR - I get told that I am too wordy, so if you want the summary, here are some steps to setup a virtual testing environment to test payloads to see if they can handle HTTP(S) proxies and if so, can they authenticate properly through them as well. This post will cover the proxy setup without authentication since that is the easier part, and I will do a second post shortly to hack together the authentication portion of it. Skip down to the actual setup here if you wanted to skip the fluff. Introduction: There have been times in my red teaming and pentesting experience that I have run into networks where direct outbound traffic to the internet (or in some cases out of the subnet) is completely restricted. When I say direct, I mean that all DNS traffic first goes to an internal DNS server, all web traffic goes through an internal proxy, email to an internal SMTP/IMAP server, etc. From the client workstation to any internet IP address is dropped for TCP, UDP, and ICMP.