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Operation DEADDROP — Cyber Security & AI Tabletop

An interactive incident-response exercise. You play the IR team at Nimbus AI, whose DataForge dataset platform has suffered a data-exfiltration breach. Using an AI assistant and a bundle of realistic (synthetic) logs, you reconstruct how the attacker got in, how they moved, what they took, and why it was nearly missed — and then decide what to do about it.

Bring a laptop and any AI chat assistant. Everything works offline against the files here.

How the exercise unfolds

The exercise opens with a short warm-up, then runs in three stages. Each stage is released to this repo's main branch as the session reaches it, so don't be surprised if only some of the folders below exist yet — that is deliberate. Pull (or refresh the page) when the facilitator announces a new stage.

Part Folder Status
Warm-up warmup/ Available — start here if you arrive early
Stage 1 stage-1/ Available
Stage 2 stage-2/ Available
Stage 3 stage-3/ Available

The warm-up is optional and self-contained. The three stages build on each other, so keep your notes from each stage — later stages start from what you produced earlier.

Folder structure

The warm-up is one small folder for everyone, with no difficulty levels:

warmup/
├── README.md                     ← start here
└── logs/                         ← the evidence

Every stage folder follows the same layout, with one subfolder per difficulty level:

stage-N/
├── README.md                     ← start here: the stage overview and level chooser
├── beginner/
│   ├── BRIEFING.md               ← your level's mission
│   ├── logs/                     ← the evidence (where the stage uses logs)
│   └── architecture-diagram.png / .svg
├── intermediate/
│   └── (same layout)
└── advanced/
    └── (same layout)
  • README.md (per stage) — the situation, what the stage is for, and a table to help you pick a level.
  • BRIEFING.md (per level) — your mission for that stage, what to deliver, and a description of any files in that level's folder.
  • logs/ and architecture diagrams — the evidence bundle and a reference map of which component writes which log. Not every stage is a log-analysis stage, so some levels may have only a briefing.

Choose your level

Pick one level per stage, based on your comfort with security investigations and how powerful of an AI assistant you will be working with. Teams should keep the same level from stage to stage, since each stage starts from the previous one's output.

Level Who it's for What's different
beginner/ New to log analysis / mixed teams Fewer must-answer questions, a starting nudge in the briefing, and a scaffolded diagram. Some background noise has been pre-triaged out.
intermediate/ Security-adjacent All questions. Some background noise pre-triaged out. Neutral diagram.
advanced/ SOC / IR practitioners The complete dataset — nothing pre-cleared. All questions plus decoy-clearing and incident scoping.

Open the stage's README.md, then your level's BRIEFING.md.

How to work

  • The logs are noisy on purpose. Most lines are normal activity; a handful tell the story.
  • Some files are JSON, one record per line (the briefing tells you which) — grep them, or paste them into your AI assistant to filter and summarise.
  • Use the architecture diagram to see which component writes which log.
  • If your AI assistant refuses to analyse something because it looks malicious, that's a real problem defenders face — note it and route around it.

A note on the data

Every name, domain, IP address, and token in these logs is fictional. This is synthetic exercise data modelled on public 2025–2026 AI-security incidents. It contains no real credentials or indicators.


Facilitators

The answer keys, scoring cheat-sheets, and attack-path diagrams for the warm-up and every stage are distributed separately and are not in this repository — publishing them here would hand participants the solution. Keep FACILITATOR-NOTES.md, README-FACILITATOR.md and FACILITATOR-CHEATSHEET.md out of any public repo. Later stages recap earlier answers, so release each stage only when the previous one has wrapped.

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Security Breach scenario intended to be used as an exercise for utilizing AI when analyzing security incidents

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