HackTheBox for Beginners: Getting Started Guide
What Is HackTheBox?
Section titled “What Is HackTheBox?”HackTheBox (HTB) is an online cybersecurity training platform with vulnerable virtual machines that teach penetration testing skills. Unlike guided platforms, HTB drops you into a realistic environment and expects you to figure things out — mimicking what professional pentesters do daily.
The platform offers two modes. HackTheBox Labs present vulnerable machines (“boxes”) to enumerate, exploit, and escalate privileges on. HTB Academy provides structured modules with hands-on exercises, covering basic Linux enumeration through advanced Active Directory attacks.
HTB maintains active machines (rotated weekly, no walkthroughs) and retired machines (VIP-only, with writeups). Active machines force independent methodology; retired machines let you learn from official solutions.
Legal notice: All HTB machines are legally authorised practice environments. Never use techniques learned here against systems you do not own or lack explicit written permission to test. Unauthorised access is a criminal offence under the Computer Fraud and Abuse Act (US), Computer Misuse Act (UK), Criminal Code Act 1995 (AU), and equivalent laws worldwide.
How Does HackTheBox Compare to TryHackMe?
Section titled “How Does HackTheBox Compare to TryHackMe?”Both platforms are excellent but serve different stages of your learning journey.
HackTheBox vs TryHackMe — Last verified: March 2026
- Difficulty — Medium to Hard — less hand-holding
- Format — Machines + challenges + Academy
- Best For — Building real pentest skills
- Free Tier — 2 active machines, Starting Point
- Community — Competitive, ranking system
- Career Value — Respected by hiring managers
- Difficulty — Easy to Medium — guided rooms
- Format — Step-by-step rooms + learning paths
- Best For — Complete beginners learning fundamentals
- Free Tier — Many free rooms available
- Community — Supportive, learning-focused
- Career Value — Good for showing initiative
Recommended path: Complete TryHackMe’s Pre-Security and Complete Beginner paths first. When you can finish TryHackMe medium-difficulty rooms without hints, you are ready for HTB.
How Do You Get Started with HackTheBox?
Section titled “How Do You Get Started with HackTheBox?”Create your account at hackthebox.com. The free tier includes Starting Point machines and two active machines. Choose a professional username — your HTB profile is public.
Connect via VPN. Unlike TryHackMe’s browser-based AttackBox, HTB requires a VPN connection:
# Connect to the HackTheBox VPNsudo openvpn --config ~/Downloads/lab_username.ovpn
# Verify connection — look for a 10.10.x.x addressip addr show tun0Alternative: Pwnbox. HTB offers a browser-based Parrot OS instance, though using your own Kali Linux builds stronger skills.
Start with Starting Point — HTB’s guided introductory machines covering VPN setup, Nmap scanning, service enumeration, and flag submission. Complete these before attempting regular active machines.
What Does Your First Machine Look Like?
Section titled “What Does Your First Machine Look Like?”Every HTB machine follows a consistent methodology:
Your First HackTheBox Machine
Step-by-step approach for beginners
The most common beginner mistake is rushing to exploit before enumerating thoroughly. A thorough scan reveals the attack path; a rushed scan leaves you guessing.
What Is the Difference Between Free and VIP?
Section titled “What Is the Difference Between Free and VIP?”| Feature | Free | VIP ($14/month) | VIP+ ($18/month) |
|---|---|---|---|
| Active machines | 2 at a time | All active machines | All active machines |
| Retired machines | None | Full library + writeups | Full library + writeups |
| Starting Point | Full access | Full access | Full access |
| Pwnbox | Limited hours | Extended hours | Extended hours |
| Servers | Shared | Shared | Dedicated |
Start free. Upgrade to VIP when you exhaust Starting Point and want retired machines with writeups — the best learning resource on the platform. Student discounts available.
Pricing verified March 2026. Check hackthebox.com for current information.
What Does HTB Academy Offer?
Section titled “What Does HTB Academy Offer?”HTB Academy provides structured modules with reading material, hands-on exercises, and completion certificates. Tiers include Free (introductory modules), Student (discounted intermediate access), and VIP (full access including Active Directory and exploit development).
Topics include Linux/Windows fundamentals, network scanning, web attacks (SQLi, XSS, SSRF), privilege escalation, AD exploitation, and incident handling. Certificates map to PenTest+, eJPT, and OSCP objectives.
Which Machines Should Beginners Start With?
Section titled “Which Machines Should Beginners Start With?”| Machine | Difficulty | What You Learn |
|---|---|---|
| Meow | Very Easy | Basic connectivity, Telnet enumeration |
| Fawn | Very Easy | FTP enumeration and anonymous login |
| Dancing | Very Easy | SMB enumeration and share access |
| Redeemer | Very Easy | Redis enumeration and database interaction |
| Explosion | Very Easy | RDP and credential-based access |
| Preignition | Very Easy | Web directory enumeration, default credentials |
After Starting Point, move to Easy-rated active machines. Focus on Linux machines first — they reinforce foundational command-line skills. When you upgrade to VIP, retired Easy machines with writeups become your best learning tool.
What Skills Will You Build?
Section titled “What Skills Will You Build?”- Enumeration and reconnaissance — port scanning, service detection, information gathering
- Exploitation techniques — leveraging CVEs, misconfigurations, weak credentials
- Privilege escalation — Linux (SUID, cron, kernel exploits) and Windows (tokens, service misconfigs)
- Web application testing — SQL injection, XSS, SSRF, authentication bypass
- Active Directory attacks (advanced) — Kerberoasting, pass-the-hash, BloodHound
These skills align with CompTIA PenTest+ (PT0-002) and OSCP certification objectives.
What Are the Best Tips for Success?
Section titled “What Are the Best Tips for Success?”Take detailed notes for every machine. Record commands, output, and decisions in a consistent format. These notes become portfolio evidence and interview preparation.
Struggle before looking at hints. Spend at least 30 minutes trying different approaches before checking forums. The struggle is where real learning happens.
Use HTB forums for nudges, not solutions. Hints point you in the right direction without spoiling the machine.
Build a repeatable methodology. Connectivity, port scan, enumeration, research, exploitation, escalation, documentation. Refine with every machine.
Track progress on your profile. Your HTB rank and completed machines are shareable proof of practical skills.
What Should You Do After Getting Started?
Section titled “What Should You Do After Getting Started?”- SOC analyst roles: Combine HTB with TryHackMe defensive rooms
- Penetration testing: Progress through Easy and Medium machines, then attempt HTB Pro Labs
- General readiness: Build a home lab alongside HTB for unrestricted practice
Individual results vary. HackTheBox is one part of a broader strategy including certifications, portfolios, and networking.
HTB machines teach you a ton, but without a plan it is easy to jump between random boxes. This tracker helps you align your lab practice with the skills your certifications actually test.
Career Roadmap & Study TrackerAvailable Now
Step-by-step roadmap with study tracker worksheets and certification decision framework.
Frequently Asked Questions
Is HackTheBox good for complete beginners?
Starting Point machines are beginner-friendly with guided instructions. However, regular HTB machines assume foundational Linux and networking knowledge. If you are a complete beginner, start with TryHackMe first and move to HackTheBox when you can complete medium-difficulty rooms without hints.
Is HackTheBox free?
HackTheBox has a free tier with Starting Point machines and 2 active machines. VIP costs approximately $14 USD per month and unlocks all active machines, retired machines with writeups, and extended Pwnbox hours. Student discounts are available.
Do I need Kali Linux for HackTheBox?
You need a machine with penetration testing tools. Kali Linux or Parrot OS are the most common choices. HTB also offers Pwnbox (browser-based), but connecting from your own VM builds more practical skills.
How long does it take to complete a HackTheBox machine?
Starting Point machines take 15-45 minutes. Easy active machines take 2-6 hours for beginners. Medium machines can take 4-12 hours. Speed improves as you develop a repeatable methodology.
What is the difference between HackTheBox and TryHackMe?
TryHackMe provides guided rooms for beginners. HackTheBox offers challenge-based machines with minimal guidance for intermediate users. Most career changers benefit from using both -- TryHackMe first, then HackTheBox.
Can I put HackTheBox on my resume?
Yes. Include your HTB profile link and mention your rank, machines completed, and any Pro Labs finished. Hiring managers for security roles recognise HackTheBox as strong evidence of practical skill.
What is HTB Academy?
HTB Academy offers structured modules with reading material and hands-on exercises, covering topics from Linux fundamentals to Active Directory attacks. Modules award completion certificates that map to PenTest+, eJPT, and OSCP objectives.
Should I pay for HackTheBox VIP?
Start free. Upgrade to VIP when you exhaust Starting Point and want retired machines with official writeups. At $14 per month, VIP is worthwhile if you practice at least 5 hours per week.
More resources
Official HackTheBox platform — create your free account and start with Starting Point machines.
HTB AcademyStructured learning modules covering penetration testing fundamentals through advanced techniques.
HTB DiscordCommunity Discord server for hints, study groups, and connecting with other learners.