We sit down with penetration tester Uzayr to discuss ethical hacking, cybersecurity, penetration testing, OPSEC, and what it takes to work in the field.

Penetration testing is often misunderstood. From the outside, it can look like simply “hacking into systems,” but the reality is far more complex. It involves identifying weaknesses, understanding how they can be exploited, and ultimately helping organizations strengthen their defenses.

For this interview, DarkDotWeb spoke with Uzayr, a penetration tester who gave us an inside look at the field, the mindset behind penetration testing, the challenges involved, and what it is really like to work on the other side of the screen.

We discussed everything from finding vulnerabilities and ethical hacking to OPSEC, cybersecurity, and the skills needed to succeed in the industry.

Could you introduce yourself and explain how you first became interested in cybersecurity and penetration testing?

I’m Uzayr. I’ve been hacking for the better part of a decade. I got into this field, like any other – by being a curious and stupid kid hacking random things for the fun/power.

What does your role as a penetration tester involve on a typical engagement?

Testing every function of a system. For a market, which is the most common engagement I get, it involves testing anything from the ordering system, registration and withdrawals, all the way to all the
potential ways someone can exploit market functions for profit. It is common for extorters to abuse missing rate limiting, captchas or features even, to take you down with targeted DDOS attacks, or to
exploit messaging functions to promote other markets through them. I generally look at every way a system can be misused with malintent. That is the root idea, and what guides me during all the tests
I run on any engagement.

Many people hear the term “hacker” and immediately think of criminals. How would you explain the difference between an ethical hacker, a penetration tester, and a malicious actor?

There isn’t a difference, really. Every good guy started by doing stupid, silly bad things with no impact. But generally, it’s their intent. Ethical hackers do it to help the companies get fixed, and to
stay safe from hackers. You can also add penetration testers here, as they are a subcategory of ethical hackers. A malicious actor is generally classified as any hacker performing malicious actions for
profit, personal gain, etc. You can say I am a malicious actor, since I help secure the very same illegal systems that law enforcement attempts to take down. The actual landscape is much more complicated
than just black, gray and white.

What skills or knowledge areas do you think are most important for someone wanting to become a penetration tester?

Investigative mindset. It’s a must. The technical skills come from learning, exercising/practicing on various labs or real targets, and with experience. But the investigative mindset – why is this system
desgined this way, why does it work like this, what happens if I do this – is something that cannot be taught, only discovered. On a technical level, start with the solid basics. You can never become good
if you don’t know the core basics to a level that no one can beat you on.

How important is understanding the fundamentals (networking, operating systems, programming, etc.) compared to learning specific tools?

It’s the most important thing. Tools are useless otherwise. You can’t build a house even with all the tools and materials in the world, if you don’t understand the basic fundamentals of how a house needs
to be built.

There are many people who focus heavily on tools. In your experience, what separates someone who knows how to use tools from someone who truly understands security testing?

That’s what separates me from my competition, in the penetration testing field on the dark web. I understand your needs, goals and your operation. Not just give you a list of vulnerabilities with no
clear impact.

Can you explain the general phases of a penetration test from the initial assessment to the final report?

Reconnaissance & Planning gathers passive intelligence (domains, IPs, employees, tech stack) and clarifies scope and rules of engagement; Scanning & Enumeration uses active tools like Nmap to identify live hosts, open ports, and services; Vulnerability Assessment analyzes findings to spot weaknesses using automated tools and manual analysis; Exploitation attempts to actually break in and escalate privileges to prove real-world impact; Post-Exploitation & Lateral Movement explores network reach, data access, and persistence; and Reporting & Remediation documents findings with severity ratings, proof-of-concept evidence, and actionable remediation steps for client discussion.

What are some common misconceptions people have about penetration testing?

People often think pentesting is just unauthorized “hacking,” when it’s actually authorized and contractually scoped work. Others assume pentesters find all vulnerabilities—we provide a point-in-time snapshot, not a complete audit. A dangerous belief is that “passing a pentest means you’re secure,” when really it’s just one measure at one moment; threats evolve and configurations drift over time. Some organizations treat it as a one-time checkbox rather than an ongoing practice, and many overestimate what automated tools can do, not realizing manual testing and business logic analysis are essential to surface real issues.

When testing an organisation’s security, what are some of the areas you pay the most attention to?

I focus heavily on authentication and access control mechanisms, external-facing applications (VPNs, APIs, web portals), unpatched or outdated systems, cloud misconfigurations (open buckets, overly permissive IAM roles), and network segmentation weaknesses that enable lateral movement. Third-party integrations and supply chain touchpoints often reveal overlooked risks, and I always assess whether defenders can detect and respond to intrusions a system with no monitoring or alerting is particularly dangerous.

How important is social engineering and the human element when assessing an organisation’s security?

Social engineering is arguably the highest-impact vector because humans remain the weakest link, a well-crafted phishing email or pretexting call can bypass firewalls, multi-factor authentication, and sophisticated tooling. I always include phishing simulations and credential-harvesting tests because they often succeed where technical defenses fail, and they reveal gaps in user awareness, incident response procedures, and security culture that no firewall can fix.

What are some of the most common security weaknesses you continue to see organisations making today?

Weak or reused passwords, lack of multi-factor authentication, unpatched systems, overly permissive access controls (users with more privileges than their role requires), poor cloud configuration (exposed storage buckets, misconfigured security groups), lack of network segmentation, and outdated or ineffective security awareness training are the biggest repeat offenders. These aren’t new problems they’re fundamentals that organizations consistently fail to execute properly due to competing priorities and technical debt.

Are there any types of vulnerabilities that you feel are underestimated by companies?

Supply chain and third-party risk is vastly underestimated; companies often have weak visibility into what vendors can access and how well those vendors are securing data. API security is another blind spot. APIs are often treated as internal tools and lack the same scrutiny as user-facing applications, yet they’re frequent attack vectors. Credential stuffing and account enumeration attacks exploit publicly leaked credentials that companies don’t detect or respond to quickly enough. Physical security gaps and “security through obscurity” are also regularly overlooked until they’re exploited.

Why do you think organisations continue to struggle with basic security issues despite increased awareness?

It comes down to competing priorities and resource constraints, security competes with revenue-generating projects for budget and engineering time, and it’s hard to justify spending money on preventing an attack that hasn’t happened yet. Organizational silos create friction (developers don’t talk to security, ops doesn’t prioritize patching), alert fatigue causes defenders to ignore warnings, and technical debt accumulates faster than it’s paid down. Many organizations also lack sufficient skilled staff to manage security effectively, and cultural change takes time even with awareness training, people reuse passwords and fall for phishing emails.

In your opinion, is poor security usually caused by a lack of knowledge, lack of resources, or poor security culture?

It’s rarely just one factor usually a combination. Some organizations lack knowledge (they don’t know what to prioritize), many lack resources (understaffed, underfunded), but the biggest barrier is culture. You can hire experts and allocate budget, but if leadership doesn’t champion security, if developers see compliance as a box to check, if incident response is slow, or if security teams lack a seat at the table, then nothing sticks. I’d say culture is the multiplier good culture makes limited resources go further, while poor culture wastes abundant resources.

How has the cybersecurity field changed during your time working in it?

The threat landscape has moved from script kiddies and isolated attacks to sophisticated, nation-state-backed actors and well-organized ransomware gangs targeting critical infrastructure. Cloud adoption has shifted the attack surface from on-premise data centers to distributed, API-driven environments where visibility is harder. The speed of threats has accelerated zero-days are discovered and exploited faster than patches are deployed. Tooling has become more accessible and powerful (both offensively and defensively), and the human element (social engineering, phishing, insider threats) remains constant but has scaled with remote work and third-party ecosystems.

What emerging threats or trends do you think organisations should pay more attention to?

AI-powered attacks (deepfakes for social engineering, automated vulnerability discovery, malware generation) and attacks on AI models themselves (poisoning training data, extracting proprietary models) are accelerating and under-prepared-for. Supply chain attacks and software dependency vulnerabilities are becoming the norm rather than the exception. Ransomware-as-a-service is lowering the barrier to entry for attackers, and the shift to decentralized identity and blockchain-based systems introduces new attack vectors that most organizations don’t yet understand. Cloud-native security and Kubernetes misconfigurations are also massive blind spots.

How do you think artificial intelligence will impact cybersecurity, both from an offensive and defensive perspective?

Defensively, AI can automate threat detection, anomaly detection, and incident response at scale, reducing alert fatigue and speeding up incident response to minutes rather than hours. Offensively, AI enables attackers to generate convincing phishing content, automate vulnerability discovery, adapt malware in real-time, and orchestrate sophisticated multi-stage attacks with minimal human involvement. The gap between offensive and defensive AI capabilities is currently in the attacker’s favor because it’s easier to automate attacks than to defend against them. Defenders will eventually catch up, but we’re in a window of asymmetric advantage for attackers.

Do you think companies are currently prepared for the increasing number of cyber threats? Why or why not?

Most are not, the gap between threat velocity and organizational response capacity continues to widen. Many still operate with reactive, incident-response-focused security rather than proactive threat hunting and prevention. Smaller and mid-market companies are particularly under-resourced, and even large enterprises struggle with visibility into their full attack surface (cloud, third-parties, legacy systems). Detection and response capabilities vary wildly; some organizations can detect a breach in hours, others in months. Until security is genuinely prioritized at the board and CEO level not just compliance theater most organizations will remain reactive rather than prepared.

What advice would you give to someone who discovers a vulnerability in a system and wants to report it responsibly?

First, don’t exploit it further or disclose it publicly document exactly what you found and how to reproduce it, then identify the organization’s security contact (security.txt file, security@ email, bug bounty program, or general press/legal contact if nothing else exists). Report it with clear steps to reproduce and business impact, give them reasonable time to patch (typically 90 days is standard), and maintain confidentiality throughout. If they’re unresponsive after multiple attempts and 90 days have passed, coordinated disclosure through a researcher or media outlet is sometimes necessary, but that’s a last resort and should be done professionally, not vindictively.

Why is responsible disclosure important for improving overall security?

Responsible disclosure builds trust between security researchers and organizations, incentivizing companies to actually fix vulnerabilities rather than hide them or shoot the messenger. If researchers immediately go public or sell exploits to criminals, organizations lose motivation to engage constructively, and vulnerabilities stay unpatched longer and more victims get harmed. It also protects researchers from legal liability and creates a sustainable ecosystem where vulnerability reports lead to patches, which benefit everyone. Without responsible disclosure norms, we’d have a race to exploit rather than a race to fix.

Have you seen attitudes towards ethical hackers and security researchers improve over the years?

Absolutely. Ten or fifteen years ago, security researchers were often treated as threats or nuisances by organizations; legal teams would threaten lawsuits, and disclosure attempts went nowhere. Now, most large companies have bug bounty programs, coordinated disclosure policies, and security research is increasingly respected as a career path. However, attitudes still vary wildly some organizations are genuinely grateful for reports, while others remain defensive or dismissive, especially smaller companies that lack security maturity. The professionalization of the field has helped a lot, but there’s still room for improvement in how organizations treat researchers.

Cybersecurity is often discussed after something goes wrong. What can individuals and organisations do today to reduce their risk before they become a victim?

For organizations: enforce multi-factor authentication everywhere, maintain an up-to-date asset inventory and patch schedule, segment your network, conduct regular security training (especially phishing simulations), implement robust logging and monitoring, and run regular penetration tests and red-team exercises to find gaps before attackers do. For individuals: use a password manager with unique passwords per account, enable MFA everywhere possible, be skeptical of unsolicited requests (emails, calls, messages), keep your devices and software updated, and don’t reuse credentials across sites. At both levels, the fundamentals, strong authentication, patching, monitoring, and awareness prevent the vast majority of breaches; it’s not about fancy tools, it’s about executing the basics consistently.

What has been the most interesting or challenging type of security assessment you have worked on?

Cannot disclose. But it was a market. They were compromised from top to bottom, in 3 days, by me. They were active for years. Got arrested a year later. No surprise, haha. Should have hired me earlier.

Is there a particular security lesson from your career that has stayed with you?

Don’t be a martyr. There are a few stories I’ve told about my past, on Dread, that shaped the way I am today. Don’t die for a cause that won’t die for you. Keep your friends close and enemies closer. And never underestimate the lengths someone would go to – in order to destroy you.

What is something you wish more people understood about cybersecurity?

It’s always a human problem. At the very core of it, humans are the ones who designed everything. Every flaw in every system comes from a lack in someone’s logic.

What advice would you give to someone starting their journey into penetration testing?

The list is long, really. I believe this interview is a great starting point to read. I’d say you need to be a sponge. Read everything from everywhere, understand it. Every single detail will help you later no matter how random it seems.

Where do you think cybersecurity will be five years from now?

Heavily corporate-backed, filled with AI and less human than it is now. And it won’t be good.

What skills do you believe will become increasingly valuable for security professionals?

I’ve previously answered that logic and an investigative mindset is the differentiating factor. I stand by it.

Is there anything about penetration testing or cybersecurity that you feel is misunderstood and deserves more attention?

It’s not a premium, or an extra cost. It’s a must. Whether it is for your clients to know you’re safe, for your investors, your peace of mind, or for attackers to know someone tested you before, and their chances are low.

What was it like sharing your knowledge and perspectives with the DarkDotWeb community?

One word. Fun. A little tricky, had to bring my best English and use a little AI to be able to answer them in a way that makes sense. But fun.

Uzayr’s PGP key and verified details can be found here below.

Uzayr PGP Signed Contact Details

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Uzayr Official Contacts

Dread: /u/Uzayr Jabber: [email protected]

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Uzayr’s PGP Key

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Interview with Penetration Tester: Uzayr