GAUNTLET — CTF Writeups

METHODOLOGY-FIRST · RECONNAISSANCE TO ROOT · ONGOING — UPDATED AS CHALLENGES ARE COMPLETED

// ● ACTIVE · rev 2026-06-10 — 7 methodology stubs · TryHackMe + HackTheBox · live / growing

// Methodology First — What This Repository Is — The deliverable here is method, not
flags
. Each entry documents how a target is approached — what was observed, what was
inferred, what was tried, what failed, and what worked — because the reasoning is the part
that transfers to a real engagement. The current seven entries are preparation stubs:
structured from publicly documented information about well-known retired rooms, they capture
the attack path and methodology without reproducing live flag values or claiming an original
solve. They are study scaffolds that become full writeups as each room is worked under
account. Failure paths are documented deliberately — understanding why a technique did not
apply matters as much as knowing when it does.


Platforms

TryHackMe — Structured learning paths and guided rooms. Used for building systematic
knowledge of specific techniques — privilege escalation, web exploitation, SMB, Active
Directory. Immediate feedback loop.

HackTheBox — Competitive CTF environment with harder, less guided machines. Closer to
realistic engagements — the attack surface is defined, but the path from recon to root is not
signposted. Builds independent methodology.


Writeup Index

Machine Platform Difficulty Status Attack path Tools
Blue THM Easy Stub EternalBlue (MS17-010) → SMBv1 → SYSTEM shell → Hashdump nmap, metasploit, hashdump
Kenobi THM Easy Stub SMB + NFS enumeration → ProFTPD path traversal → SUID privilege escalation nmap, enum4linux, smbclient, netcat
Steel Mountain THM Easy Stub HFS 2.3 RCE → CVE-2014-6287 → msfvenom shell → PowerUp unquoted service path PE nmap, metasploit, msfvenom, PowerUp.ps1
Alfred THM Easy Stub Jenkins default credentials → Groovy script console RCE → token impersonation nmap, jenkins, nishang, metasploit
Basic Pentesting THM Easy Stub SMB enumeration → Samba username disclosure → SSH brute-force → SUID + sudo PE nmap, enum4linux, hydra, linpeas
Lame HTB Easy Stub Samba 3.0.20 username-map command injection (CVE-2007-2447) → direct root; vsftpd banner ruled out as a rabbit hole nmap, enum4linux, smbclient, metasploit
Jerry HTB Easy Stub Tomcat Manager default credentials → malicious WAR deploy → JSP shell as NT AUTHORITY\SYSTEM nmap, whatweb, msfvenom, curl

// Active — More Writeups Loading — This index grows as challenges are completed. Seven
structured stubs are in place (five TryHackMe, two HackTheBox); pending additions include
TryHackMe rooms (RootMe, Ice, Lian Yu) and further HackTheBox machines (Legacy, Devel). Each
writeup follows the methodology template in README — from initial recon to root, with failure
paths documented alongside successes.


Coverage Radar — Honest Self-Assessment

Category Score (/5) What the seven stubs actually cover
NETWORK 4 SMB/NFS enumeration and exploitation across four machines (Blue, Kenobi, Basic Pentesting, Lame).
PRIVESC 3.5 SUID, sudo abuse, unquoted service paths, token impersonation.
WEB 3 Jenkins console RCE, HFS CVE-2014-6287, Tomcat WAR deploy.
CRYPTO 1 Hash dumping and cracking only (hashdump → john/hashcat).
FORENSICS 0.5 Evidence-logging discipline, no dedicated forensics challenges yet.
PWN 0.5 Tooling familiarity (gdb, ghidra); no completed binary-exploitation writeups yet.

Scores reflect the current stub set, not aspiration — the low axes are the practice roadmap,
and the chart gets redrawn as entries land.


Methodology Notes

Enumeration Order — Full-port SYN scan → service + version fingerprinting → OS detection →
per-service deep enumeration. Web gets Gobuster/ffuf + Nikto. SMB gets enum4linux. Never skip
UDP where a UDP service is suspected.

Privilege Escalation — LinPEAS first pass → review SUID/SGID, sudo -l, cron jobs, writable
paths, kernel version, service permissions. GTFOBins for SUID/sudo vectors. Always check
service account permissions and unquoted service paths (Windows).

Shell Stabilisation — Python pty spawn → export TERM=xterm → stty raw -echo. Tab completion
and job control restored. Prevents accidental ctrl-C kills in reverse shells.

Documentation Standard — All commands logged with rationale. Failed attempts documented
with the reason they failed. Evidence screenshots where appropriate. Tools listed with purpose,
not just name.


What CTF Practice Maps To

CTF categories are not abstract puzzles — each one rehearses a capability that a security role
uses in the field. This is how consistent practice translates into job-relevant skill.

CTF capability Real-world equivalent Role
Service enumeration & version triage External attack-surface assessment; vulnerability validation Pentester · SOC L2
Web exploitation (SQLi, LFI, SSTI) Application security testing; OWASP-aligned review AppSec · Pentester
Privilege escalation (SUID / sudo / cron / token) Post-compromise impact assessment; hardening review Pentester · Red Team
SMB / Active Directory enumeration Internal network assessment; lateral-movement analysis Red Team · IR
Reading exploit code & mapping CVEs Threat intelligence; exploit triage; patch prioritisation Threat Intel · SOC
Evidence logging & SHA-256 integrity Chain-of-custody discipline; defensible reporting DFIR · Consultant
Documenting failed paths Reproducible methodology; report writing Every security role

Tool Stack

Category Tools
Recon / enumeration nmap, gobuster, ffuf, whatweb, nikto, enum4linux, dig
Web exploitation Burp Suite, sqlmap, manual injection, curl
Credentials hashcat, john, hydra, credential wordlists (rockyou)
Privilege escalation linpeas, winpeas, pspy, GTFOBins, PowerUp.ps1
Post-exploitation Metasploit (where appropriate), manual shell stabilisation
Binary / reversing gdb, pwndbg, ghidra, objdump, strings

Repository

// GitHub — Full writeups, methodology notes, and templates:
github.com/rootdrifter/gauntlet — one repository
in the github.com/rootdrifter portfolio.