How to setup forward proxy on Windows server for outgoing HTTP and HTTPS requests?

Question

I have a windows server 2012 VPS running a web app behind Cloudflare. The app needs to initiate outbound connections based on user actions (eg upload image from URL). The problem is that this 'leaks' my server's IP address and increases risk of DDOS attacks.

So I would like to prevent my server's IP from being discovered by setting up a forward proxy. So far my research has shown that this is no simple task, and would involve setting up another VPS to act as a proxy.

Does this extra forward proxy VPS have to be running windows ? Are their any paid services that could act as a forward proxy for my server (like cloudflare's reverse proxy system)?

Also, it seems that the suggested IIS forward proxy plugin, Application Request Routing, does not work for HTTPS.

Is there a solution for both types of outgoing (HTTPS + HTTP) requests?

I'm really lost here, so any help or suggestions would be appreciated.

Answer 1

If all you're trying to do is make the connections appear to be coming from a different IP, there are online cloud services you can use for that, such as hidemyass.com

running your own proxy is also possible, and most http proxies will work for http and https (using tunneling / CONNECT). These are available for pretty much any platform. For linux, there's Squid and some others (Privoxy is another well-known). For Windows there are more that I know of, including squid, and our own product WinGate.

I would suggest looking into the hosted option though, as that will be simpler, and you won't need to be the one that deals with DDoS attacks on the proxy.

Disclaimer: I work for Qbik who are the authors of WinGate