Exercise: Dark Web Chat

This post is not a HOWTO. Frankly it’s not even really a challenge — though you’re more than welcome to try! It’s more of a reflection and a question. I’ll explain that later.

First, though, let’s throw the gauntlet for this post:

If you’re anywhere near technically competent, you should be able to create a nearly anonymous, nearly untraceable, fully encrypted, leave-no-trace chat service for a handful of users.

It’s no joke. I’m not kidding. In MindOfJoe’s Digital Dojo ranking, I’d put the task around Brown Belt. It would serve as a good capstone demonstration, building on a lot of knowledge and techniques someone of your experience already has, but adds some next-level complexity. If I toss you a laptop, maybe a thumb drive, and the wifi password, you should be able to get it done and demonstrate that it works.

If you start getting a little too close to the edge of the mats, expect to get whacked by a jo staff. You’re not going to just have everybody login to some third-party service and rely on their EULAs, Privacy Policies, Good Will, and Website Promises, to keep your communications safe. This is not a “Pay Someone Else” exercise in project management. This is the “Get it done! Right now! What are you looking at?!? Clock’s ticking!”-type test environment — about as close to “Real World” conditions as possible.

Go ahead, give it a go! Build it. Test it. Tell me when you’re ready. If you succeed, your service just might be able to federate with mine so we don’t even have to have accounts on each other’s boxes.


Well, a couple of answers come to mind:

  • If in today’s world you can’t even imagine a scenario where something like this is necessary, you’re out of touch. Where would we even start?
  • If it doesn’t strike you as an interesting exercise and get your creative juices flowing, you’re just not inspired. No harm, no foul — you’ve just walked through the wrong dojo door.
  • If it’s interesting and you can see how it could be important, but maybe it’s a bit outside your reach? Well, that’s okay. Are you inspired enough to rough out a solution? Maybe complete some pieces, know what to research, and know when to ask for help? Maybe we can work with that…
  • You already have something like this running, just in case? Now we’re talking!

So there are no “right” answers, right? These are more like gates — a bit of a self-check on where you fit in. If you’re interested in building a cohort of communications guerillas or networking ninjas who can operate independently to solve complex solutions in constrained environments, or if you’re interested in ensuring that people and communities can always communicate freely and securely — even in hostile environments, even without commercial infrastructure — then maybe these are the types of questions you’d ask to find the types of people who can get it done. Maybe.

How many of these folks do you think we’d need — per capita, per square mile, per community, your choice — to ensure we could always have connections?

Solutions? Different Puzzles?

It’s not my intention to post a solution, only to state I spent some time putting one together today. Why? I think it’s important to know how to do it, and better yet to have the capability on the shelf — just in case. “No really — why?” Uhh… Well, that’s just what I do. And frankly I’m interested in finding some other people who are just wired this way too! For those people, I’m curious: What are your ideas for “capstone exercises” like this? Those “You should be able to ___” challenges that have practical use, demonstrate breadth & depth of skill and experience?

Feel free to comment — or maybe we’ll chat 😉

By Joe

Puzzle Wrestler & Mountain Herder. Math & Computer Nerd since the 80s. Longtime linux (current debian, ubuntu, raspian, centos, gentoo), currently fighting feebsd. Over-complicates networks for fun, occasionally secures them for profit. Develops own tools & services (cli, web services, and lately some android). Degrees in Math, Belts in Aikido. Zen, Motorcycle, Ham Radio, Homebrew (Ale, not Radio), Coffee & Tea, some Mandolin & Fiddle, MDA Advocacy (son with Duchenne), …

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