Observe Correlate Explain Submit

APJ SE Offsite - Capture the Flag

Observe. Prove.

A hands-on investigation workshop for APJ SE Offsite. Work through incident-style challenges, use Datadog evidence to explain what happened, and submit the exact answers in CTFd.

How to Play

  1. 1

    Confirm your workshop context

    Use the Datadog organization, team, and environment specified by the facilitators for this workshop.

  2. 2

    Open a challenge

    Start from Challenges. Each prompt describes a customer symptom, operational question, or investigation target.

  3. 3

    Investigate in Datadog

    Use the products and pivots implied by the prompt, such as APM, Logs, RUM, DBM, LLM Observability, Feature Flags, or Security views.

  4. 4

    Use pawfolio when it helps

    The app is available as the investigation target, but most answers should be supported by Datadog telemetry rather than by guessing from the UI.

  5. 5

    Submit the exact answer

    Submit the exact value requested by the prompt, such as a service name, attribute, status code, variant, or Datadog value.

Rules of Engagement

  • Use only the Datadog access, CTFd team, and workshop environment assigned to your team.
  • Do not brute-force answers, tokens, or application endpoints.
  • Do not change shared Datadog configuration, feature flags, Synthetics tests, dashboards, monitors, or CTFd settings unless a facilitator asks you to.
  • Do not delete data, reset shared resources, or disrupt another team's investigation.
  • Discuss investigation techniques freely, but keep final answers private while the game is active.

Solving Approach

  • Treat the CTFd prompt as the source of truth for scope, answer format, and rounding rules.
  • Keep your Datadog time window, service filter, environment, and team context aligned with the prompt.
  • Use pivots such as trace IDs, session IDs, user identifiers, status codes, routes, feature flag keys, and error messages.
  • When two signals disagree, prefer the source that directly observes the value being asked for.