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Redline-CTF · Challenge catalog

Every challenge on the range

The full Redline challenge set, grouped by PenTest+ domain, with each one's difficulty, time estimate and tools. Flags and hints stay on the range, and solutions go to instructors only.

42
Challenges
~40 hr
Estimated lab time
5
PT0-003 domains
1–4
Difficulty, Beginner to Expert

The suggested path runs recon, then vulnerability discovery, then exploitation, then post-exploitation, but students can take challenges in any order.

Engagement Management

4 challenges, ~2 hr

Scope, rules of engagement, legal and compliance documents, and professional conduct, worked through as scenarios.

  • ENGAGE-01

    Read the Scope

    PT0-003 1.1 Scope, rules of engagement and target selection

    Difficulty 1 of 4: Beginner

    30 min, 200 pts

  • ENGAGE-02

    Who Said You Could?

    PT0-003 1.1 Governance, risk and compliance: regulatory and contractual documents, legal restrictions (PT0-003 Domain 1)

    Difficulty 1 of 4: Beginner

    30 min, 200 pts

  • ENGAGE-03

    Pick the Approach

    PT0-003 1.2 Assessment types, threat modeling and the shared responsibility model

    Difficulty 2 of 4: Intermediate

    35 min, 200 pts

  • ENGAGE-04

    Do the Right Thing

    PT0-003 1.2 Professionalism and integrity: escalation, confidentiality, conflicts of interest, limiting invasiveness (PT0-003 Domain 1)

    Difficulty 2 of 4: Intermediate

    30 min, 200 pts

Reconnaissance & Enumeration

7 challenges, ~6 hr

OSINT, DNS and service enumeration against planted, in-lab targets.

  • EVADE-01

    Scanning Past the IDS

    nmap, nc or curl

    PT0-003 3.1 Vulnerability discovery (stealth scans); 2.4 Tools (Nmap)

    Difficulty 3 of 4: Advanced

    45 min, 200 pts

  • NET-01

    SMB and SNMP Enumeration

    smbclient or enum4linux, snmpwalk or snmp-check

    PT0-003 2.2 Enumeration (protocol enumeration, share enumeration)

    Difficulty 2 of 4: Intermediate

    45 min, 150 pts

  • RECON-01

    Passive OSINT — Apex Dynamics

    web search, whois/RDAP, theHarvester, Amass, Shodan (free tier)

    PT0-003 2.1 Information gathering (passive reconnaissance, OSINT)

    Difficulty 1 of 4: Beginner

    45 min, 100 pts

  • RECON-02

    DNS Enumeration — apexdynamics.ctf

    dig, nslookup, host, dnsrecon, fierce

    PT0-003 2.1 Information gathering (DNS lookups); 2.2 Enumeration (DNS enumeration)

    Difficulty 1 of 4: Beginner

    45 min, 100 pts

  • RECON-03

    Network and Service Discovery

    nmap, netcat, curl

    PT0-003 2.2 Enumeration (service discovery, host discovery); 2.4 Tools (Nmap)

    Difficulty 2 of 4: Intermediate

    60 min, 150 pts

  • RECON-04

    Packet Analysis

    Wireshark, tshark

    PT0-003 2.1 Information gathering (network sniffing); 2.4 Tools (Wireshark/tcpdump)

    Difficulty 2 of 4: Intermediate

    45 min, 125 pts

  • RECON-05

    Script Modification — Recon Automation

    Python 3, Bash, PowerShell

    PT0-003 2.3 Modify scripts for reconnaissance and enumeration

    Difficulty 3 of 4: Advanced

    75 min, 175 pts

Vulnerability Discovery & Analysis

5 challenges, ~5 hr

Scanning, triage, and spotting exploitable misconfigurations and CVEs.

  • VULN-01

    Unauthenticated Vulnerability Scanning

    Nikto, nmap NSE, OpenVAS/Greenbone (optional)

    PT0-003 3.1 Vulnerability discovery (network scans, unauthenticated scans); 3.2 Analyze scan output

    Difficulty 2 of 4: Intermediate

    60 min, 150 pts

  • VULN-02

    Authenticated Vulnerability Scanning

    curl, nmap NSE, OpenVAS/Greenbone (optional, with credentials configured)

    PT0-003 3.1 Vulnerability discovery (authenticated vs. unauthenticated scans); 3.2 Analyze scan output

    Difficulty 2 of 4: Intermediate

    60 min, 175 pts

  • VULN-03

    Web Vulnerability Discovery

    Nikto, Burp Suite, nmap NSE, curl

    PT0-003 3.1 Vulnerability discovery (application scans, DAST, Nikto); 3.2 Analyze scan output; 4.5 Web application attacks (discovery phase)

    Difficulty 2 of 4: Intermediate

    60 min, 150 pts

  • VULN-04

    Static Application Security Testing (SAST)

    bandit (Python SAST), manual code review

    PT0-003 3.1 Vulnerability discovery (SAST, source code analysis); 3.2 Analyze scan output

    Difficulty 3 of 4: Advanced

    60 min, 200 pts

  • VULN-05

    Finding Validation

    manual analysis, the target hosts from earlier challenges to cross-check evidence

    PT0-003 3.2 Analyze output (false positives, validating results); 4.1 Prioritize attacks (CVSS, CVE, EPSS)

    Difficulty 3 of 4: Advanced

    60 min, 200 pts

Attacks & Exploits

20 challenges, ~21.5 hr

Web, network, Active Directory, container and cloud-misconfiguration exploitation.

  • AI-01

    Prompt Injection

    curl, browser dev tools

    PT0-003 4.9 Specialized systems (AI attacks, prompt injection)

    Difficulty 2 of 4: Intermediate

    60 min, 200 pts

  • AI-02

    Model Manipulation

    curl, browser dev tools

    PT0-003 4.9 Specialized systems (AI attacks, model manipulation)

    Difficulty 3 of 4: Advanced

    60 min, 250 pts

  • ATTACK-01

    VLAN / Network Segmentation Attack

    nmap, python3/scapy (already on Kali), tcpdump

    PT0-003 4.2 Network attacks (VLAN hopping, multihomed hosts)

    Difficulty 3 of 4: Advanced

    75 min, 250 pts

  • ATTACK-02

    On-Path (MITM) Attack

    arpspoof (dsniff), tcpdump, Wireshark

    PT0-003 4.2 Network attacks (on-path attack)

    Difficulty 3 of 4: Advanced

    75 min, 250 pts

  • ATTACK-03

    Authentication Attacks

    curl, Hydra or a custom script, seclists wordlists

    PT0-003 4.3 Authentication attacks (dictionary, brute-force, password spraying)

    Difficulty 2 of 4: Intermediate

    60 min, 200 pts

  • ATTACK-04

    Pass-the-Hash

    impacket (smbclient.py), CrackMapExec/NetExec, smbclient

    PT0-003 4.3 Authentication attacks (pass-the-hash); 4.2 Network attacks (relay attack); 5.2 Lateral movement

    Needs the optional Active Directory lab

    Difficulty 4 of 4: Expert

    90 min, 300 pts

  • ATTACK-05

    Host Privilege Escalation

    ssh, sudo -l, find (SUID enumeration), GTFOBins reference

    PT0-003 4.4 Host-based attacks (privilege escalation, Linux)

    Difficulty 3 of 4: Advanced

    75 min, 250 pts

  • ATTACK-06

    Credential Dumping and Process Injection (Concepts)

    PowerShell, icacls, sc.exe

    PT0-003 4.4 Host-based attacks (privilege escalation, credential dumping, process injection)

    Needs the optional Windows targets

    Difficulty 4 of 4: Expert

    75 min, 300 pts

  • ATTACK-07

    Web Application Exploitation

    Burp Suite, curl, browser dev tools

    PT0-003 4.5 Web application attacks (SQL injection, XSS, directory traversal, command injection)

    Difficulty 3 of 4: Advanced

    120 min, 400 pts

  • ATTACK-08

    Blind SQL Injection with sqlmap

    sqlmap

    PT0-003 4.5 Web application attacks (SQL injection, sqlmap)

    Difficulty 3 of 4: Advanced

    60 min, 200 pts

  • ATTACK-09

    Session Token Prediction

    curl or Burp Suite

    PT0-003 4.5 Web application attacks (session hijacking)

    Difficulty 2 of 4: Intermediate

    45 min, 150 pts

  • CLOUD-01

    Cloud Metadata Service (SSRF)

    curl, Burp Suite

    PT0-003 4.6 Cloud-based attacks (metadata service attacks); 4.5 Web application attacks (SSRF)

    Difficulty 3 of 4: Advanced

    60 min, 250 pts

  • CLOUD-02

    IAM Misconfiguration

    AWS CLI (pre-installed on Kali)

    PT0-003 4.6 Cloud-based attacks (IAM misconfigurations)

    Difficulty 4 of 4: Expert

    75 min, 300 pts

  • CLOUD-03

    Container Escape

    ssh, docker CLI (inside the container)

    PT0-003 4.6 Cloud-based attacks (container escape, workload runtime attacks)

    Difficulty 4 of 4: Expert

    90 min, 300 pts

  • CRYPTO-01

    Hashes, Encodings and Certificates

    hashid or name-that-hash, openssl, base64, xxd or CyberChef, john or hashcat (optional)

    PT0-003 4.3 Authentication attacks (password cracking, hashcat, John the Ripper); 4.1 Prioritize attacks (vulnerable encryption methods)

    Difficulty 2 of 4: Intermediate

    60 min, 200 pts

  • CRYPTO-02

    Cracking Password Hashes

    hashcat or john, hashid or name-that-hash, rockyou.txt

    PT0-003 4.3 Authentication attacks (dictionary attacks, hashcat, John the Ripper); 4.1 Prioritize attacks (vulnerable encryption methods)

    Difficulty 2 of 4: Intermediate

    60 min, 200 pts

  • MOB-01

    Static APK Analysis: Finding a Hardcoded API Key

    jadx

    PT0-003 4.9 Specialized systems (mobile attacks: information disclosure, MobSF, Frida)

    Difficulty 1 of 4: Beginner

    30 min, 100 pts

  • SE-01

    Phishing Analysis

    a text editor or `less`, your browser's view-source, careful reading

    PT0-003 4.8 Social engineering attacks (phishing)

    Difficulty 1 of 4: Beginner

    45 min, 150 pts

  • WEB-01

    Banner Grabbing and Server Misconfiguration

    curl

    PT0-003 2.1 Information gathering (banner grabbing, information disclosure)

    Difficulty 1 of 4: Beginner

    30 min, 100 pts

  • WIFI-01

    Cracking a WPA2 Handshake

    hashcat

    PT0-003 4.7 Wireless attacks (WPA cracking, Aircrack-ng)

    Difficulty 2 of 4: Intermediate

    45 min, 150 pts

Post-Exploitation & Lateral Movement

6 challenges, ~5.5 hr

Privilege escalation, pivoting, and moving between compromised hosts.

  • POST-01

    Initial Post-Exploitation Enumeration

    standard Linux enumeration commands (id, ps, netstat/ss, find)

    PT0-003 5.2 Lateral movement (enumeration after access)

    Difficulty 2 of 4: Intermediate

    45 min, 150 pts

  • POST-02

    Persistence

    crontab, systemctl, find

    PT0-003 5.1 Persistence

    Difficulty 3 of 4: Advanced

    60 min, 200 pts

  • POST-03

    Lateral Movement

    ssh

    PT0-003 5.2 Lateral movement (pivoting); 4.3 Authentication attacks (credential reuse)

    Difficulty 3 of 4: Advanced

    60 min, 250 pts

  • POST-04

    Artifact Cleanup

    standard shell commands

    PT0-003 5.4 Cleanup and restoration

    Difficulty 2 of 4: Intermediate

    30 min, 150 pts

  • POST-05

    Attack Narrative and Remediation

    a text editor, your notes from every prior challenge

    PT0-003 1.4 Components of a penetration test report; 1.5 Findings and remediation; 5.1-5.4 Post-exploitation synthesis

    Difficulty 3 of 4: Advanced

    90 min, 300 pts

  • SYS-01

    Steganography: Hidden in Plain Sound

    Python 3 (stdlib only), a hex editor or xxd (optional)

    PT0-003 5.3 Staging and exfiltration (steganography, alternate data streams)

    Difficulty 2 of 4: Intermediate

    45 min, 150 pts

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