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I have some old black-box applications which emit HTTP requests, that now I need to transfer via a secure HTTPS connection to the destination server and get back its result and deliver to the emitting application with a minimal effort and system (re)configuration.

I have a moderate understanding of networking and security, but so far I had no luck in trying solutions with Squid and Mitmproxy, because there's no simple and straight-forward configuration for doing such a simple (from my point of view) task, and everything seems too complex since those tools are for more general tasks as far as I understand. After some more googling now there's Tinyproxy which seems to be able to do the same thing, but I'm not sure about the terminology and capabilities of proxies like SSL-bumping for example (http://www.squid-cache.org/Doc/config/ssl_bump/).

Could anybody shed some light please, or to provide a link to a minimalist tutorial, or ideally a ready-made solution with configuration files to reproduce what I want? Maybe it's impossible without coding a low-level networking application? I appreciate a professional opinion, not just a wild-ass guess. Thanks!

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    Are the requests always aimed at some specific servers? If so, this sounds more like a task either for Stunnel or standard Apache/Nginx reverse proxy. – user1686 Apr 26 at 20:51
  • No, the requests are intended for different destinations, and even may change some day. – Hack06 Apr 27 at 18:05
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So after a week of reading the Squid docs and trying out lot of things, I managed to accomplish the task with iptables redirection to Squid, using its SSL-Bumping feature and a URL-rewriting script. I'm not eager to post all the parts of the configuration files and commands used, but this answer post is just for reference in case someone is looking for the answer to my initial question of being it possible or not and which tools to use. Just take your time to read over the docs and understand completely what you're doing.

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