Getting Started

New to cybersecurity? This is your roadmap from zero to hacking your first machine. No gatekeeping, no prerequisites, no degree required.

Step 1: Learn Linux

Most penetration testing happens on Linux. You do not need to be a sysadmin, but you need to be comfortable.

Learn the file system structure (/etc, /var, /home, /tmp, /proc)
Understand permissions (chmod, chown, sudo, SUID/SGID)
Master basic commands (ls, cat, grep, find, ps, kill, netstat, ss)
Learn bash scripting (variables, loops, conditionals, functions)
Practice on a Kali Linux or Parrot OS VM

Resources: HTB Academy "Linux Fundamentals" modules (3 modules, free with VIP). Alternatively, OverTheWire Bandit (free wargame that teaches Linux through progressively harder levels).

Step 2: Learn Networking

You cannot hack what you do not understand. Networking is the foundation.

OSI model (7 layers) and TCP/IP model (4 layers)
Common protocols: HTTP/HTTPS, DNS, SSH, FTP, SMB, RDP, SMTP
IP addressing, subnets, NAT, routing basics
TCP vs UDP (handshake, state, reliability)
Ports and services - know the common ones by heart

Protocol	Port	Use
HTTP	80	Web traffic
HTTPS	443	Encrypted web traffic
SSH	22	Remote shell
FTP	21	File transfer
SMB	445	Windows file sharing
RDP	3389	Windows remote desktop
DNS	53	Name resolution
SMTP	25	Email sending
MySQL	3306	MySQL database
PostgreSQL	5432	PostgreSQL database
Redis	6379	In-memory cache
WinRM	5985/5986	Windows remote management

Resources: HTB Academy "Networking Fundamentals" module. Alternatively, Cisco Networking Academy free courses or Professor Messer Network+ videos on YouTube.

Step 3: Learn Windows

A lot of targets are Windows. You need to understand how Windows works from an attacker and defender perspective.

Active Directory basics (domains, forests, OUs, GPOs, trust relationships)
Windows authentication (NTLM, Kerberos, ticket-granting tickets)
Windows file system and permissions (ACLs, DACLs, SACLs)
PowerShell (commands, scripting, execution policies)
Windows Event Logs and Sysmon
Common Windows services (IIS, MSSQL, WinRM, SMB)

Resources: HTB Academy "Windows Fundamentals" modules (3 modules). Microsoft Learn documentation for Active Directory.

Step 4: Learn Web Basics

Web applications are a massive attack surface. Understand how they work before trying to break them.

HTTP protocol (request/response, methods, headers, status codes)
HTML, CSS, JavaScript basics - enough to read source code
Cookies, sessions, authentication tokens
Common web vulnerabilities (OWASP Top 10: SQL injection, XSS, SSRF, CSRF, IDOR, file upload, command injection)
APIs (REST, JSON, authentication)

Resources: PortSwigger Web Security Academy - free, comprehensive, created by the Burp Suite team. This is the gold standard for web security learning.

Step 5: Start Hacking

Now you are ready for actual machines. Start easy and work your way up.

Hack The Box Starting Point

HTB Starting Point is the on-ramp. It covers:

Tier 0 machines (free, very easy, guided walkthroughs)
Tier 1 machines (free, easy, less guidance)
Tier 2 machines (harder, requires more independent thinking)

Do all of Starting Point before jumping into regular machines. It teaches the methodology: scan, enumerate, find vulnerability, exploit, escalate privileges, get flags.

HTB Academy Paths

HTB Academy offers structured learning paths:

Junior Penetration Tester - Beginner offensive path
Cybersecurity Analyst - Beginner defensive path (leads to CJCA exam)
Bug Bounty Hunter - Web-focused offensive path
SOC Analyst - Blue team career path

Each path is a sequence of modules with interactive exercises. You earn cubes for completing modules, which unlock more advanced content.

After Starting Point

Once you finish Starting Point, try:

Easy machines on HTB (filter by "Easy" difficulty, Linux first)
HTB Academy modules in your chosen path
Challenges (start with "Easy" web or crypto challenges)

Step 6: Learn the Methodology

Every machine follows roughly the same process. Internalize it:

Recon - nmap full port scan, service version detection, default script scan
Enumerate - Deep-dive every open port. Check for default credentials, version-specific vulnerabilities, misconfigurations
Exploit - Use what you found to get a foothold (low-privilege access)
Enumerate again - Now you are on the machine. Check sudo permissions, SUID binaries, cron jobs, interesting files, network connections
Privilege escalation - Use what you found to get root or admin
Document - Take notes and screenshots as you go. This is critical for reports and for going back if you get stuck

Step 7: Build a Home Lab

Practice safely in your own environment.

Install Kali Linux or Parrot OS in a VM (VirtualBox or VMware, free)
Set up Vulnhub machines (free, downloadable vulnerable VMs)
Or use HTB machines (no local infrastructure needed)
Install a SIEM at home: Elastic Stack (free) on a Linux VM, forward Windows Event Logs to it
Run Atomic Red Team tests against a Windows VM and see if your SIEM catches them

How Long Does It Take?

Linux + networking + Windows basics: 1-3 months (evenings and weekends)
First easy HTB machine solved independently: 1-2 months after basics
Comfortable with easy/medium machines: 3-6 months of regular practice
Ready for CJCA exam: 6-12 months of consistent practice, completing the 20-module Academy path

Everyone learns at their own pace. The key is consistency - 1 hour every day beats 10 hours once a week.

Mindset

Enumeration is everything. The more you enumerate, the more attack surface you find. Rush this and you will miss the vulnerability.
Read the output. Do not just run commands. Understand what they tell you.
Take notes. You will forget what you tried on a machine last week. Write it down.
Learn from writeups. After you solve (or give up on) a machine, read other people's writeups. You will learn techniques you never would have thought of.
Do not cheat yourself. Looking up the answer before you try is not learning. Try for at least an hour before checking hints.