You’ve watched the conference talks, followed the security researchers on Twitter, maybe even completed a few TryHackMe rooms. The idea of getting paid to legally break into systems sounds like the dream job. And the salaries—$126,000 average, with senior pentesters clearing $150K+—make it even more appealing.

Here’s what most “how to become a pentester” guides won’t tell you: the path isn’t linear, the entry barriers are real, and the job itself looks nothing like the CTF challenges that got you interested in the first place.

This guide breaks down the actual journey from where you are now to landing that first pentesting role—including the uncomfortable truths about what it takes, who actually gets hired, and whether this career path makes sense for you.

What Penetration Testers Actually Do

Before diving into the “how,” let’s clarify the “what.” Pentesting has been romanticized by media and conference culture to the point where many aspiring pentesters have no idea what the day-to-day actually involves.

The Reality of the Job

A penetration tester’s job is to find security vulnerabilities before malicious attackers do. You’re essentially playing the role of a criminal—but legally, with written permission, and with the goal of helping organizations improve their defenses.

According to CBT Nuggets’ breakdown of pentester responsibilities, typical tasks include:

  • Scoping engagements: Understanding what you can and can’t test, negotiating boundaries with clients
  • Reconnaissance: Gathering intelligence about target systems before attacking them
  • Vulnerability assessment: Running scans, analyzing results, separating real risks from false positives
  • Exploitation: Actually breaking in—the part everyone fantasizes about
  • Report writing: Documenting findings in a way that non-technical executives can understand and act on
  • Client communication: Presenting results, defending findings, answering questions

Here’s the part nobody mentions: report writing and client communication often consume more time than actual hacking. One pentester described the hardest part of the job as “translating technical speak to easily actionable and understandable business language.”

If you hate writing and dread explaining technical concepts to people who don’t understand technology, this career might frustrate you more than you expect.

Pentesting vs. Red Teaming vs. Ethical Hacking

These terms get thrown around interchangeably, but they’re not the same thing:

RoleFocusScopeDetection
Penetration TesterFind vulnerabilities in specific systemsDefined targets (web app, network, etc.)Not a concern—client knows you’re testing
Red Team OperatorTest overall security postureBroader—may include social engineering, physical accessAvoid detection at all costs
Ethical HackerGeneral security assessment and improvementVaries widelyDepends on engagement

According to Synack’s comparison, penetration testing focuses on identifying as many vulnerabilities as possible within a defined scope, while red teaming simulates realistic attacks to test an organization’s detection and response capabilities.

Most entry-level security roles are pentesting, not red teaming. Red team positions typically require years of pentesting experience first.

The Skills You Actually Need

Forget the certification shopping lists for a moment. Here’s what you need to actually do this job.

Technical Foundation (Non-Negotiable)

Networking fundamentals: You can’t attack what you don’t understand. TCP/IP, DNS, HTTP/HTTPS, common ports and protocols—this isn’t optional. If you can’t explain what happens when you type a URL into a browser, you’re not ready.

Our subnetting tutorial and Wireshark guide cover networking fundamentals that every pentester needs.

Operating systems: Deep knowledge of both Windows and Linux. Not “I can use the command line” level—more like “I understand how Windows authentication works, where credentials are stored, what services run by default, and how to manipulate them.”

For Linux skills, Shell Samurai offers interactive command-line training that builds the muscle memory pentesters need. Our Linux basics guide and bash scripting tutorial are also essential reading.

Scripting and programming: Python and Bash at minimum. PowerShell if you’re doing Windows testing. You don’t need to be a developer, but you need to read code, modify exploits, and automate repetitive tasks.

Check out our PowerShell for beginners guide if you’re coming from a Windows background.

Web application security: Most pentesting engagements involve web apps. Understanding the OWASP Top 10, how injection attacks work, authentication bypass techniques, and common misconfigurations is essential.

Tools of the Trade

You’ll need hands-on experience with:

The PortSwigger Web Security Academy offers free, hands-on training that’s considered one of the best resources for learning web app pentesting.

Soft Skills (Yes, Really)

Technical skills get you in the door. Soft skills determine whether you succeed.

Communication: You’re selling security improvements to people who don’t want to spend money on things that aren’t broken yet. You need to explain risks in business terms, prioritize findings by actual impact, and write reports that executives will read and act on.

Our soft skills for developers guide covers communication strategies that apply directly to security roles.

Problem-solving under pressure: Engagements have deadlines. You won’t always find the vulnerability on the first try. Can you stay methodical when you’re stuck?

Continuous learning: Attack techniques evolve constantly. If you’re not spending personal time keeping up with new research, you’ll fall behind quickly.

Phase 1: Building Your Foundation (Months 1-6)

If you’re starting from zero, here’s where to begin.

If You Have No IT Background

Don’t jump straight into pentesting training. You need fundamentals first.

Option A: CompTIA pathway Start with CompTIA A+ for IT fundamentals, then Network+ for networking, then Security+ for security basics. This takes 6-12 months but gives you a solid foundation.

Option B: Faster route Get the Google IT Support Professional Certificate (3-6 months), then jump to Security+. This works if you’re disciplined and can fill gaps through self-study.

Either way, you need hands-on practice. Set up a home lab with virtual machines. Break things. Fix them. Break them differently.

If You Already Work in IT

You’re ahead of most aspiring pentesters. Your next step depends on your current role:

From help desk/support: Focus on networking and Linux skills. Get Security+ if you don’t have it. Start doing HackTheBox or TryHackMe in your spare time. Target a junior security analyst or SOC analyst role as your stepping stone—it’s easier to move from SOC to pentesting than from help desk directly.

Our IT support to cybersecurity guide covers this transition in detail.

From sysadmin/network admin: You have a huge advantage. You already understand how systems work, which makes learning how to break them much easier. Go straight to pentesting practice and certifications like PenTest+ or eJPT.

From development: Your coding skills are valuable, but you need to flip your mindset from “how do I build this securely?” to “how would I break this?” Focus on web app security—your development background makes PortSwigger’s Web Security Academy an ideal starting point.

Essential Practice Platforms

You can’t learn pentesting from books alone. These platforms let you practice legally:

PlatformCostBest For
TryHackMeFree/Premium ($14/month)Complete beginners, guided learning
HackTheBoxFree/VIP ($14/month)Intermediate learners, realistic machines
PortSwigger AcademyFreeWeb application security
VulnHubFreeDownloadable vulnerable VMs
PicoCTFFreeCTF-style challenges
OverTheWireFreeLinux and command-line skills

Shell Samurai complements these platforms with structured Linux and terminal training—skills you’ll use constantly as a pentester.

Phase 2: Getting Certified (Months 6-18)

Certifications matter in pentesting. Not because they prove you can hack, but because they get your resume past HR filters and signal to hiring managers that you’ve invested in the field.

The Certification Path That Actually Works

Start here: CompTIA Security+ Security+ isn’t a pentesting cert, but it’s often required for security roles and proves you understand defensive security concepts. Many government and contractor jobs mandate it. Get it out of the way early.

Prove you can pentest: eJPT The eLearnSecurity Junior Penetration Tester (eJPT) certification is 100% hands-on. You’re given a virtual network and 48 hours to find and document vulnerabilities. It’s affordable (~$200-300) and respected as proof that you have practical skills.

According to INE’s pentester roadmap, the eJPT is one of the best entry points because it tests real-world ability rather than memorization.

Level up: CompTIA PenTest+ PenTest+ validates vulnerability assessment and pentesting skills. It’s more theory-heavy than eJPT but widely recognized and often listed in job requirements.

The industry gold standard: OSCP The Offensive Security Certified Professional (OSCP) is the certification that separates serious pentesters from everyone else. It’s a 24-hour hands-on exam where you attack a network of machines and write a professional report.

OSCP is brutal. Most people fail the first time. But it’s also the most respected pentesting certification in the industry. When hiring managers see OSCP on a resume, they know the candidate can actually do the job.

Expect to spend 3-6 months preparing for OSCP, even with prior experience. The training alone (PEN-200) costs around $1,600.

Certifications to Skip (For Now)

CEH (Certified Ethical Hacker): Despite the name, it’s mostly theoretical and less respected than OSCP or even PenTest+. One security professional noted that “the OSCP is far more respected and sought after than the Certified Ethical Hacker (CEH) certification.”

CISSP: This is a management-level certification, not a technical pentesting cert. Useful later in your career, but premature for entry-level pentesters.

The Certification Timeline

CertificationTime to PrepareCostWhen to Get It
Security+1-2 months~$400Months 3-6
eJPT1-3 months~$250Months 6-9
PenTest+2-3 months~$400Months 9-12
OSCP3-6 months~$1,600Months 12-18

Phase 3: Getting Your First Job (Months 12-24)

Here’s where theory meets reality. The pentesting job market is competitive, and most “entry-level” roles aren’t actually entry-level.

The Entry-Level Paradox

According to Research.com’s pentester career analysis, entry-level penetration testing roles typically require 1-4 years of experience in IT functions like system, security, or network administration.

Nearly 10% of pentesters identify as entry-level, which means junior positions exist—but they’re rare and highly competitive.

Realistic Job Targets

Instead of applying exclusively to “Penetration Tester” roles, consider these stepping stones:

Junior Pentester / Associate Pentester: The actual entry point, but rare. When these roles open, they get hundreds of applications.

Security Analyst / SOC Analyst: Defensive roles that give you visibility into security operations. You’ll see attacks from the defender’s perspective, which makes you a better attacker later. These roles are more plentiful and have lower barriers to entry.

Check our cybersecurity career path guide for more on SOC analyst roles.

Vulnerability Analyst: Focus on finding and documenting vulnerabilities without full exploitation. Good stepping stone to pentesting.

Security Consultant: Some consulting firms hire junior consultants and train them in pentesting as part of broader security assessments.

Building a Portfolio That Gets Interviews

Your resume says you know pentesting. Your portfolio proves it.

Write-ups: Document your solutions to HackTheBox and TryHackMe machines. Show your methodology, not just “I got root.” Explain how you enumerated the target, what you tried, what failed, and why your successful approach worked.

GitHub presence: Scripts you’ve written, tools you’ve modified, custom automation. Nothing proves coding ability like code.

Blog posts: Technical deep-dives on vulnerabilities, tool reviews, CTF write-ups. This demonstrates communication skills and passion for the field.

Bug bounties: Finding real vulnerabilities in production systems through platforms like HackerOne or Bugcrowd is the ultimate proof of skill. Even a few valid findings show you can find real bugs in real systems.

Our homelab on resume guide covers how to present technical projects to employers.

Interview Preparation

Technical interviews for pentesting roles often include:

Live challenges: You might be given access to a vulnerable system and asked to find and exploit vulnerabilities in real-time. They’re watching your methodology, not just your results.

Scenario questions: “How would you approach testing a web application?” “Walk me through your enumeration process.” “Describe a time you got stuck during an engagement and how you solved it.”

Tool knowledge: Expect questions about specific tools, commands, and techniques. “What’s the difference between a TCP connect scan and a SYN scan?” “How does Metasploit’s payload selection work?”

Our technical interview preparation guide covers strategies that apply to security interviews.

Salary Expectations: The Real Numbers

Let’s talk money. Pentesting pays well, but the numbers vary more than most guides admit.

2026 Salary Data

According to multiple sources, here’s what pentesters actually earn:

Experience LevelSalary RangeMedian
Entry-level (0-2 years)$66,000 - $90,500~$78,000
Junior (1-3 years)$85,000 - $100,500~$92,000
Mid-level (4-6 years)$100,000 - $130,000~$114,000
Senior (7+ years)$130,000 - $180,000+~$150,000

Glassdoor reports an average total compensation of $153,759, including base salary and bonuses. ZipRecruiter’s data shows an average of $126,245.

The discrepancy comes from sample differences—senior roles at large enterprises skew Glassdoor’s numbers higher.

What Affects Your Salary

Location: Pentesters in San Francisco, New York, and Washington D.C. earn 20-40% more than national averages. Remote work has narrowed this gap, but it persists.

Industry: Finance, healthcare, and government contractors typically pay more than general consulting firms.

Certifications: OSCP holders command higher salaries. According to salary surveys, certifications can increase earning potential by 10-15%.

Specialization: Red team operators, cloud security specialists, and those with specific expertise (mobile app testing, IoT security) often earn premiums.

For context, compare these numbers to our cybersecurity analyst salary guide and cybersecurity salary overview.

Is Pentesting Right for You?

Before investing 1-2 years into this career path, honestly assess whether it matches your personality and goals.

You’ll Probably Love Pentesting If…

  • You genuinely enjoy puzzles and problem-solving under constraints
  • Breaking things feels more satisfying than building them
  • You’re comfortable with ambiguity and incomplete information
  • Writing and communication don’t feel like chores
  • You can handle working alone for extended periods
  • Continuous learning excites rather than exhausts you

Consider Other Security Roles If…

  • You prefer defensive work (detecting attacks, incident response)
  • You want more predictable work hours (pentesting deadlines can mean crunch time)
  • You’re more interested in policy and governance than hands-on technical work
  • You hate report writing and client communication
  • You want to specialize deeply in one technology rather than being a generalist

Blue team roles (SOC analyst, incident responder, security engineer) often have lower barriers to entry and can be just as rewarding. Our cybersecurity career transition guide covers alternative paths into security.

What’s Changing in 2026

Pentesting is changing. Here’s what’s different now:

AI Integration

According to Penligent’s 2026 AI pentesting guide, the industry has shifted from “automation” (doing the same thing faster) to “autonomy” (AI reasoning and acting independently).

This doesn’t mean AI is replacing pentesters. It means the tools are evolving. Pentesters who understand how to use AI-assisted tools effectively will have an advantage over those who don’t.

Cloud and Container Focus

Traditional network pentesting is declining. Most new applications live in AWS, Azure, or GCP. Container security (Docker, Kubernetes) has become a major specialization area.

Our cloud computing career path guide covers the cloud fundamentals that modern pentesters need.

Remote Work Permanence

CyCognito’s red teaming analysis notes that remote work has expanded pentesting job opportunities. You can now work for companies anywhere in the country, though some engagements still require on-site presence.

The Honest Bottom Line

Becoming a penetration tester takes 1-2 years of dedicated effort, significant financial investment in certifications, and genuine passion for security. The job market is competitive, entry-level roles are scarce, and you’ll likely need a stepping-stone security position before landing a pure pentesting role.

But for the right person, it’s worth it. Pentesters do intellectually challenging work, earn strong salaries, and play a genuine role in making systems more secure. The field is growing at 33% through 2033—much faster than most occupations.

If you read this guide and thought “that sounds hard but I still want it,” you’re probably the right kind of person for this career.

Start building your foundation today. The pentester you want to be in two years depends on the work you put in now.

FAQ

Can I become a penetration tester without a degree?

Yes. According to multiple industry surveys, only 28% of tech job postings require a degree, and pentesting is one of the fields where demonstrated skills matter most. Certifications like OSCP and a strong portfolio of write-ups can substitute for formal education. However, some government and contractor roles still require degrees for compliance reasons.

How long does it take to become a pentester from scratch?

Expect 18-24 months of serious effort if you’re starting with no IT background. This includes 6-12 months building fundamentals, 6-12 months on certifications and hands-on practice, plus job search time. Career changers from IT backgrounds can potentially move faster—12-18 months is realistic.

Is the OSCP certification necessary for entry-level pentesting jobs?

Not strictly necessary, but highly valuable. OSCP separates you from hundreds of other applicants and signals to employers that you have proven, hands-on skills. For competitive roles, it’s often the difference between getting an interview and getting ignored. Entry-level alternatives like eJPT or PenTest+ can get you started, but OSCP remains the industry gold standard.

What’s the difference between pentesting and bug bounty hunting?

Penetration testing is contracted work—companies hire you (or your firm) to test specific systems within a defined scope and timeline. Bug bounty hunting is freelance vulnerability research where you find bugs in organizations that have public bounty programs. Bug bounties offer flexibility but inconsistent income; pentesting provides stable employment but less autonomy.

Can I do pentesting remotely?

Yes, many pentesting roles are remote-friendly. According to FlexJobs research, computer and IT leads all industries in remote work adoption. Some engagements require on-site presence (especially those involving physical security testing or air-gapped networks), but pure network and web application testing can typically be done remotely.