The Complete Skr1pt Kiddie Guide to Elite Hacker Games

The learning curve for information security (aka hacking) can be pretty steep. In addition to understanding tools, exploits, coding, and attack vectors, there's also absorbing the subversive thinking it takes to be a hacker. Nature vs. Nurture: Perhaps people are born with these traits, or perhaps they can be taught. I'd argue that if you're curious enough to try to learn, you've got the proper nature. Now it's time to nurture.

Example of old school hacking,
From the true-to-life 1983 documentary, Hackerman.

Back in the day, we had to learn these concepts by word of mouth, by finding a mentor or have hacker friends, or by brute-force figuring it all out our own damned selves. Moreover, computer equipment was expensive, so experimentation was prohibitive for most of us. To learn, we had to crack live systems which were someone else's property, which was both unethical and illegal.

Today, in this magical virtual world built by us old school hackers, we have the luxury not only of wikis, videos, training programs (some at actual colleges!), cheap hardware, and virtual machines to learn on, but we also have a fine collection of hacker games.

There are three categories of hacker games:

1. Technical games involve the practice of actual coding or cryptanalysis.
2. Hacker logic games which teach hacker thinking processes, but the interface and skill bears little resemblance to real-life hacking. 
3. Hacker-motif games full of green-on-black facades, but with little relation to real hacking.

This list includes games in the first two categories, that is, games of substance that teach something about real hacking.

Click to embiggen.
(Remember to say "Enhance!")

And a quick note about what I mean by "hacking". I define hacking as "any attempt to subvert the designed purpose for a technology, to use it in a way that was not originally intended." This stereotypically include infosec, that is, breaking and entering computers and networks (and defending against said breaking and entering), but it also includes all manner of opening things up, figuring out how they work, and changing them. If you've ever soldered tiny cargo bays to your quadcopter so you can glitterbomb tourists in downtown Seattle*, you're a hacker.

* No confirmed sightings have been reported, however, if someone were to happen to create such a thing, I am completely not responsible.

I've not played all of these, so my description and categorization of them might be off. A listing with a checkmark means I've played it for at least 5 hours.

And listing of the game does not mean I vouch for it.

One last point: If you want to get the full value from these games, don't resort to walkthroughs! Googling how to do something is useful, because you're learning a skill and applying it to a new problem. But looking up the answer in the back of the book teaches you nothing. If you're "stuck", you should spend at least a few days pondering it — then and only then should you go looking for a hint. And I said *hint*, not walkthrough. Looking up the answer should be a last resort.

Lower Tech, Hacking Themed Games:

Look like a hacker, without all the mess!
(Seriously, he's wearing a TIE?!)

Most of these require download and install, for various platforms, including Windows, Linux, Android, and iOS. Some are web-based.

• ✔ Digital: A Love Story —
  http://scoutshonour.com/digital/
  Story-based adventure game that simulates a 1988 computer environment. Solved through email and dialing into BBSes. Loved this game.
• ✔ Uplink —
  https://www.introversion.co.uk/uplink/
   Simulated hacking environment, which simplifies hacking tools but retains the logic. Awesome game.
• ✔ The Secret World —
  http://www.thesecretworld.com/
  An MMORPG that requires a hacker brain. Set in a dark version of the modern world of conspiracies, werewolves, and Lovecraftian bliss, it's a regular MMO in many ways: You have a character, get gear, and level up. But to get through the story, you have to solve actual puzzles, including cracking passwords on real (staged) websites. There's Morse Code in the early game that you have to transcribe in order to progress. (Which is harder than it seems if you don't know Morse Code.) As with Telehack, if you want to really learn the hacker mentality, you should solve all puzzles yourself (even if you're stumped) rather than fall back to the wikis and walkthroughs.
• ✔ Hacker Evolution —
  http://www.exosyphen.com/page_hackerevolutionuntold.html
  A story-based game which, like Digital: A Love Story, immerses you by placing you at a simulated computer console. The story unfolds as you receive emails and take on hacking tasks. Again, the tech is simplified, but you still have to explore and think like a hacker.