I’ve recently been running a 5e-based game with my usual role-playing nerd circle on Sunday nights. The game is called The Spy Game. It started off as a Kickstarter campaign and doubled it’s original funding goal (well done!) It’s been fairly successful, but I’m not here to talk about that. This post is about how I’ve incorporated Capture the Flag elements to our role playing.

Yes, I’m a grown man who plays D&D-style games. We play D20 games, which are role-playing games that use dice to determine the outcomes of certain actions. They have become increasingly popularized in the media, with Stranger Things being a large contributor. I did not grow up playing D&D, but started playing when my poker group decided to mix it up. Yes that is true.

What is The Spy Game?

The Spy Game is a role-playing game that is built around telling stories set in a today-like world with… spies. That means your players pick what type of spy they want to play, and make up back stories, choose classes (Infiltrator, Assassin, Medic, etc.) Then the Game Master (me) makes up scenarios and missions for them to go on. The players decide what they want to do (e.g. attack a security guard) and they roll a die to see how devastating their attack on the poor guard was. And while this is a gross over-simplification, it’s good enough for our purposes.

Quickly, What is Capture the Flag?

Capture the flag (commonly CFP), is a style of network and systems security penetration-testing simulation for fun. The idea is that a security expert creates a small, simulated computer system that players try to break into, or crack a code to find a “flag”. The flag is the indicator of the player’s success. For example, you might be given a website that has some sort of password protection that is beatable with certain techniques. Once you bypass the security, you discovery a flag. These are often written as {Flag-name} or something similar to allow the players to know they have been successful. You can read all about them on Wikipedia, or play there with Hacker101 or even Google.

Combining CTFs and Role Playing

My roleplaying group is fairly nerdy (does that go without saying?) So I wanted to make the game a little technical and different from our usual swords and sorcery chaos romps. I thought it would be interesting for those in the group who are less technically minded to learn a little about actual hacking, rather than the “roll the dice to try and hack the system” that is built into the game. The more experienced computer-people in the group could screen share as they worked, and the team could work out the problems together. Everyone wins!

It has worked out really, really well. Everyone has enjoyed these CTFs, including me. I’ve only written a few so far, but they include:

  • Breaking a password to get into a security camera interface
  • Finding the GPS coordinates of an arms deal that is going down, hidden in a base-64 string
  • Decoding a message between two terrorists, hidden in an image
  • Cracking a cipher (spoilers) to get the code words for the security team on duty needed for a break-in!

You can find them the few I’ve written so far here on Github.

These ideas were heavily influenced by the excellent CTF run by the one and only Connor Tumbleson, at Sourcetoad.

Writing CTFs with ChatGPT

I would highly recommend adding a real world CTF to your next role playing adventure. But who has the time? Enter AI with ChatGPT. One of the scary things about ChatGPT is that it writes decent code, but it is only as good as the prompts you give it, and it is NOT secure. So basically anything you tell the bot to write for you has an exploit big enough to drive a bus through. This should be scary to anyone using it for production work, but it is amazing for CTFs.

I’ve also used ChatGPT to write quick and dirty interfaces (like the security camera on-off switch). Is it pretty? No! Would I use anything like that for a client or anywhere near a production environment? Hell no! But it’s MORE that good enough for a fun evening with friends, gathered around a Zoom table, working out how to hack into a secret vault.

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I help companies turn their technical ideas into reality.

CEO @Sourcetoad and @OnDeck

Founder of Thankscrate and Data and Sons

Author of Herding Cats and Coders

Fan of squash, whiskey, aggressive inline, and temperamental British sports cars.

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Is Anyone Working on Agentic Authentication?

Everyone is building AI-powered tools, even people who shouldn’t be. Agents seem to be the next obvious (and big?) step. But these little bots need a secure way to act on behalf of users without causing chaos.

Richard Dulude at Underscore VC wrote about the lack of identity standards for AI agents in this LinkedIn article. I don’t know Richard or Underscore VC (sorry). But, he’s right, traditional authentication assumes either a human or a machine with static credentials, and that doesn’t work for AI agents that need to make decisions and take actions. Companies want accountability (and probably liability), and users need control of what their potentially psychedelic robot is doing on their behalf. This balance doesn’t exist yet.

This is probably for another blog post, but right now, everyone, including the bots, are using human interfaces as a stopgap. OpenAI’s Operator is a great example, agents pretending to be humans to interact with systems that weren’t built for them. That’s fine for now, but eventually, the human interfaces will be an afterthought. Like how “mobile-first” design took over, we’ll be doing “agent-first” design with human-accessible backups. Having a dedicated standard for agentic authentication might be a good first step in that machine-to-machine way of thinking and designing systems.

Agentic Proxy Credentials (APC): A Solution (A Term I Totally Made Up)

I made this up. It’s probably a bad term, but naming things is fun. This doesn’t exist… if you are a large battery and power supply company, don’t sue me. I’m spitballing here.

One possible fix is the “sucked out of my thumb” Agentic Proxy Credentials (APC). This would let users grant their AI agents secure, limited permissions to interact with systems while making sure the right level of oversight are in place. There are things that I wanted to do this very week, but I don’t trust my bots with my actual usernames and passwords:

Stop me talking to Airline Idiot Bots

Talking to airline chatbots is painful. Right now, they can only regurgitate FAQ answers. With an APC, my AI assistant could log into my airline account, check flights based on my loyalty status, and rebook me without you having to touch anything. This would make AI actually useful instead of just a slightly smarter help page.

Paying for small things without having to deal with entering my ACH data AGAIN

I don’t want to give an AI full access to my bank account. But I wouldn’t mind letting it handle small transactions in a controlled way. With APCs, I could grant my assistant time-limited access to approve payments or move money within strict limits. The AI does the work, I stay in control, and my bank account doesn’t mysteriously empty overnight… unless I’m Ambien shopping again.

AI Dungeon Master’s Assistant

D&D is great, but session prep is a time sink. I want an AI that logs into my D&D Beyond account, manages stat blocks, generates lore-friendly content, and even takes session notes. The AI handles the boring admin work, and you get to focus on making your players cry (or cheer, if you’re nice). Yes, serious stuff here.

How It Could Work

There are a few ways to make this happen, I think. I’m no longer allowed to do actual engineering at my own companies I founded, so this blog is my outlet. Everyone needs a hobby.

Is Someone Already Building This?

Honestly, I wouldn’t be surprised if Okta, OAuth, or OpenAI are already working on this and I’m just ranting for no reason. But if they aren’t, they should be. The pieces are all there, someone just has to put them together.

I need this, but I can’t find it. If anyone is working on it, let me know. I’m too busy trying to solve employee gifting at scale at Thankscrate, implementing AI into every existing business at Sourcetoad, and making sure passengers can watch TV and book dinner reservations in the middle of nowhere at OnDeck.