deadwood-sec 0.5.2

A self-hosted web-security range, leveled tutorial-to-impossible — the practice town for wraith and hickok.

deadwood

A self-hosted web-security range that doubles as a tutorial — graded levels from the first trivial injection to the deliberately near-impossible. It's the practice town for the dead man's hand: scout each room with wraith, take it with hickok, capture the flag, then read the vulnerable source and the fix.

Dependency-free (stdlib + SQLite). Runs on 127.0.0.1 only.

⚠️ deadwood is intentionally vulnerable, by design. It refuses to bind anything but loopback unless you force it. Never expose it to a network, a VM bridge, or the internet. Attack only this app, on your own machine.

• Install
• Run it
• Take your first flag
• How a level works
• The levels
• Pairing with wraith & hickok
• Tests

Install

pipx install deadwood-sec      # gives you the `deadwood` command

Or from a clone: pip install -e . — or run it with no install: PYTHONPATH=src python3 -m deadwood.

Run it

deadwood serve                 # http://127.0.0.1:8666  (the town map)
deadwood levels                # list the rooms and your progress
deadwood learn first-blood     # a level's briefing: objective, hints, source, the fix
deadwood flag first-blood 'DEADWOOD{...}'   # submit a captured flag

Open the map in a browser, pick a room, and point your tools at the app URL it gives you (e.g. http://127.0.0.1:8666/l/first-blood/app?id=1).

Take your first flag

Room 1 is a staff directory that drops your id straight into the SQL. The query returns three columns, so a UNION SELECT of three values reads any table you like — here, the hidden secrets:

$ deadwood serve &
$ curl 'http://127.0.0.1:8666/l/first-blood/app?id=0 UNION SELECT 1,label,value FROM secrets'
...
DEADWOOD{first_blood_825bb8670d30d32c}

$ deadwood flag first-blood 'DEADWOOD{first_blood_825bb8670d30d32c}'
  ✓ First Blood — taken. that's the hand.

That's the whole loop: find the flaw, read the flag, submit it. Flags are unique to your install, so the one above won't match yours — capture your own. Stuck? deadwood learn first-blood walks you in, one hint at a time.

How a level works

Every room is the same shape, easy to the hard:

• a realistic app (the fictional Deadwood Telegraph & Trust Co. — employees, customers, accounts, telegrams) with one real flaw;
• a flag to capture (DEADWOOD{...}, unique to your install);
• progressive hints — reveal them one at a time, only if you want them;
• the vulnerable source and how to fix it, once you ask (spoilers).

Play blind for the CTF, or lean on the hints and learn for the tutorial. Your captures are tracked locally.

The levels

Fifteen rooms, Tutorial → Endgame. Each maps to a technique you can practise by hand or drive with hickok/wraith:

#	Room	Tier	Vector
1	First Blood	Tutorial	SQL injection — UNION (in-band)
2	Whispers	Easy	SQL injection — boolean-blind
3	The Ledger	Easy	SQL injection — error-based (extractvalue, 32-char windows)
4	The Strongbox	Medium	SQL injection — UNION (double-quote context)
5	The Telegraph	Medium	SQL injection — time-based blind
6	The Bouncer	Medium	SQL injection — authentication bypass
7	Back Door	Medium	OS command injection → shell
8	The Watchman	Hard	SQL injection — time-based (parenthesised func('…') context)
9	Sleight of Hand	Hard	UNION behind a quote/catalog filter
10	The Gauntlet	Hard	UNION behind a keyword WAF (case/comment evasion)
11	The Cipher	Hard	Server-side template injection → RCE
12	The Annex	Brutal	SQL injection — cross-database (ATTACH)
13	Dead Man's Hand	Brutal	Blind injection behind a WAF denylist
14	The Vault	Impossible	Second-order (stored) SQL injection
15	The Whole Hand	Endgame	Full chain — recon → SQLi → session pivot → BAC → the vault

The world behind the rooms is deliberately the edge-case data a real dump hits, not a toy table: NULL cells that drop rows from a naive dump, a group_concat capped at 1024 bytes like MySQL, values longer than 32 chars, unicode, and a second ATTACHed database. That's where a tool's real bugs show up.

Pairing with wraith & hickok

deadwood is the range the tools grew up on. Scout the whole town, then take it:

deadwood serve &                                                  # the town
wraith 127.0.0.1:8666 --sessions examples/deadwood_sessions.json  # recon the whole surface
hickok sql -u 'http://127.0.0.1:8666/l/first-blood/app?id=1' -p id --dump secrets

The Whole Hand (room 15) is the live company app, end to end: recon it with wraith — it lights the IDOR, the broken access control, the XSS, the open redirect, the reflective CORS, the missing headers and the injectable directory — then dump the sessions table with hickok, ride a live admin token to the vault. SQLi → a real credential → broken access control → the house's deepest secret. A genuine discovery, on the one target that's yours.

When a tool can't take a room, that's a bug to fix in the tool; when a room is too easy, that's a room to harden. They sharpen each other.

Tests

pip install -e ".[dev]" && pytest

The suite checks the engine (flags, registry, per-level isolation, the seeded world) and that each level's flaw behaves as taught. See CONTRIBUTING.md to add a room and SECURITY.md for the responsible-use policy.

License

MIT.

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Deadwood, 1876 — where the dead man's hand was dealt.