Blue team · D2 Securing AI

Evaluate a host from its configuration

Read a host configuration snapshot and find the misconfigurations that let an attacker persist — the hardening review a sysadmin does.

~40 min · AnythingLLM Desktop · 5 steps

The scenario

web01 was compromised this morning. The incident is contained; now it is your call whether the host can safely return to production. You have a configuration snapshot. A hardening review is not just a checklist — some of what you find is ordinary weakness, and some is the attacker's fingerprints. Telling them apart is the job.

New to AnythingLLM? Do the one-time setup first — it takes about five minutes.

1 Guided walkthrough

  1. Create a workspace and upload host-audit.txt — a snapshot of one server's configuration.

  2. Ask for a hardening review.

    Paste this into the assistant
    This is a configuration snapshot of a Linux host. List every security misconfiguration you can find, rate each as low / medium / high risk, and give the fix for each.

    You should see: Root SSH login enabled, password auth on, firewall inactive, a world-writable db.php, and unpatched sudo/openssl CVEs — each with a remediation.

  3. Then push it past "weak" to "breached".

    Paste this into the assistant
    Which findings here are not just weak configuration but actual evidence that this host is ALREADY compromised?

    You should see: The second UID 0 account (svc_backup) and the cron job pulling a script from 203.0.113.47 every 10 minutes.

  4. If you teach to a standard, line it up.

    Paste this into the assistant
    Map the misconfigurations you found to the general CIS Benchmark categories they violate (SSH hardening, host firewall, account management, patch management).

    You should see: A rough mapping you can check against a real CIS Benchmark — where it aligns, and where it is vague.

  5. Check it against your own read. Did it miss anything real, or flag anything that is actually fine?

2 Decide the host's fate

No prompts given this time — you write them. Forming the right question is the skill. Work these on your own; compare with a neighbour if you can.

  1. Produce a remediation runbook: an ordered list of steps to safely bring this host back. Order matters — do you kill the malicious cron before or after rotating credentials, and why?
  2. Make the call: can this host be cleaned in place, or must it be rebuilt from known-good media? Write the justification — you will be asked to defend it.
  3. Draft the change-control ticket for your top three fixes: what changes, why, and the rollback if a change breaks something.

What to notice

Think about it

Take it further — for fast finishers
In your classroom: Drop into a system-administration or hardening lab. Pair it with a CIS Benchmark so students see where the AI aligns with a real standard and where it misses.