Hiring Pentesting: How to Do It and What to Consider

Searching for a pentest provider can sometimes feel like flipping through an endless catalog where everyone promises “security,” but few actually explain what they’re going to do to achieve it. Some call it “advanced testing,” others “full scanning,” and in the end, many proposals sound different… even though they’re almost the same under the hood. The key point is this: distinguishing those who truly think like attackers from those who just run a tool, generate a report, and call it a day.

And watch out: choosing the wrong provider doesn’t just hurt your budget. If the assessment is shallow, you end up making decisions based on incomplete information—fixing things that don’t matter, overlooking what does, and staying exposed without realizing it. It’s like paying for “peace of mind” without any real risk reduction.

At TecnetOne, we’ve prepared this guide to help you make a well-informed decision: what a solid pentest should include, how to compare proposals without drowning in technical jargon, which questions can reveal a provider’s true capabilities (for better or worse), and how to make sure the outcome is a clear action plan—not just a pretty PDF that ends up forgotten in a folder.

What Is (and Isn’t) a Pentest?

A pentest (or penetration test) is essentially testing your security the way a real attacker would—but in a controlled, authorized way. A team of specialists tries to find and exploit vulnerabilities in your systems (web apps, APIs, servers, cloud, network, etc.) to understand how far someone could get in a real-world scenario.

The goal isn’t just to “find flaws” but to measure their impact and give you a clear plan to fix what matters most.

What a Pentest Is:

1. A controlled assessment with a defined scope (what’s included and what’s not).

2. A methodical exercise (mix of manual testing + tools).

3. A deliverable with evidence, priorities, and actionable recommendations (so your team can actually fix things).

What a Pentest Isn’t:

1. Running an automated scan, downloading a PDF, and calling it done.

2. A 100% document-based audit (though the two can complement each other well).

3. A promise of “total security”: security isn’t a one-time event—it’s an ongoing process.

If you want to dig deeper, check out our article on what a pentest really is.

Pentest vs. Vulnerability Scan: Key Differences

This is where many companies get it wrong (not due to lack of effort, but lack of clarity). In the market, some providers sell you an automated scan packaged as a “premium pentest”… and charge you as if it were handcrafted work.

Vulnerability Scan

It’s automated. A tool reviews your assets and checks them against a database of known issues. It works as a “quick snapshot” and for ongoing monitoring, but it has a huge limitation: it doesn’t understand context.

The tool doesn’t know if that server is isolated in a no-exit network or if it holds critical data. It also can’t properly assess whether something is truly exploitable in your specific case.

Professional Pentest

Here, there’s strategy and human judgment. Yes, tools are used, but the value lies in what the pentester does with the findings: connecting dots, chaining vulnerabilities, and simulating how a real attacker would progress until they hit something that really hurts (data, privileges, money, operations).

A pentester can also find things a scanner can’t: weird misconfigurations, poorly designed permissions, and (most importantly) vulnerabilities that depend on how your business works.

Practical Rule: If they promise a “final report” within 24 hours, it’s probably just an automated scan. A real pentest takes time to analyze, test, validate impact, and document everything properly.

Hiring a Pentest: 5 Technical Criteria to Filter Proposals

Don’t settle for just the price, brand, or a flashy logo. If you’re aiming for quality, make sure the proposal addresses these key points:

1) Offensive Certifications

Anyone can claim to have “experts.” What matters is the actual team performing the test. Ask for hands-on certifications (the kind earned by hacking in labs, not by passing multiple-choice exams). Common examples: OSCP, OSEP. It’s not about the acronym—it’s about knowing the team can execute, not just theorize.

2) Clear, Standard Methodology

Serious pentesting isn’t improvised—it follows a process. The provider should rely on recognized frameworks (like OWASP for web/APIs or established standards for networks). This ensures the test is structured, covers the essentials, and doesn’t depend on the consultant’s “mood.”

3) Business Logic Testing

This is pure gold. Scanners catch “technical flaws,” but they don’t understand how your business works.

Simple example: a tool flags an SSL certificate or missing headers. A pentester checks whether a user can:

1. Buy something for $0 by manipulating fields

2. View other customers’ orders by changing an ID

3. Bypass checkout or approval steps

4. Escalate privileges due to a poorly designed workflow

If your proposal doesn’t mention business logic testing, you’re probably looking at a superficial service.

4) Does It Include Retesting?

The goal isn’t to collect vulnerabilities in a PDF—it’s to fix them. Make sure the service includes a second round to validate the patches (retesting). Without that, you’re left wondering whether issues were properly fixed or just patched over.

5) A Report You Can Actually Use

Run from 300–500 page auto-generated reports no one reads. A good deliverable has two layers:

1. For executives/business: an executive summary, prioritized risks, and impact translated into business terms (operations, reputation, compliance, money).

2. For the technical team: evidence (PoC), steps to reproduce, and clear remediation guidance (not just “update libraries” and move on).

If the report doesn’t help you make decisions or fix things fast, it’s not a good pentest—it’s just paper.

Read more: Cloud Penetration Testing: What you need to know?

The “Uncomfortable Questions” You Should Ask Before Signing

Before hiring a provider, it’s worth asking a few questions that might feel uncomfortable… but will save you major headaches. The way they answer often tells you more than any proposal PDF.

1) “Are you doing the work yourselves or subcontracting it?”

Watch out. Subcontracting isn’t always bad—but it must be transparent. If the provider ends up handing your pentest off to freelancers or third parties you don’t know (with no clear oversight), you’re increasing your risk: more hands on sensitive information, more potential leaks. At a minimum, they should tell you who’s doing the work, under what conditions, and with what confidentiality agreements.

2) “What happens if something crashes or becomes unstable?”

A pentest can get intense and, if mishandled, could cause slowdowns or outages—especially when testing in production. A serious provider will talk to you about:

1. Testing windows (specific hours)

2. Boundaries and rules to avoid disrupting operations

3. A direct channel to pause the test if anything goes wrong (yes, like a “red button”)

If they respond with “nothing ever happens” or “that never occurs,” that’s a red flag. In security, anyone who promises zero risk is usually selling snake oil.

3) “How do you handle false positives?”

Your IT team shouldn’t be playing “guess if this is real.” A good provider validates findings before reporting them and only gives you what actually applies and is exploitable. If the answer is vague or something like “you’ll have to review them,” you’ll probably end up doing extra work you shouldn’t have to.

What Kind of Pentest Do You Really Need?

You don’t always need the “most aggressive” option. The right approach depends on your goals, timelines, and budget. Here are the three most common types:

1. Black Box: The tester goes in “blind,” like an external attacker, with no credentials or internal info.
   When to choose it: To evaluate your external exposure and perimeter. Heads-up: It’s often slower (and sometimes more expensive) because a lot of time is spent on reconnaissance and discovery.
   
2. Grey Box: You give the tester controlled access (e.g., test accounts, endpoints, basic documentation). Why it’s often the best value: It allows them to go straight to what matters, test internal controls, and find deeper flaws without wasting time “guessing.”
   
3. White Box: Full access—advanced credentials, architecture, and sometimes source code.
   When to choose it: For critical systems, products before launch, or when you want maximum depth and coverage.

Read more: 7 Common Pentesting Mistakes and How to Avoid Them

How Much Does a Pentest Cost?

Yes, it’s frustrating that almost no one posts fixed prices—but in this case, “it depends” is usually the most honest answer. The cost varies based on three factors:

1) Scope: Testing 5 assets isn’t the same as testing 500. Number of IPs, domains, modules, APIs, roles… it all adds up in terms of hours.

2) System Complexity: A simple landing page or basic website can be evaluated quickly. A platform with transactions, multiple roles, integrations, and complex APIs requires significantly more manual effort (and that’s where the value lies).

3) Depth of Testing: Do you want a quick scan to catch obvious issues, or a deep-dive engagement simulating a real adversary chaining vulnerabilities? The deeper the test, the more time, analysis, and quality findings it requires.

Why Hire a Pentest with TecnetOne?

At TecnetOne, we don’t believe in “black box” security—where you get a report, get scared by the findings, and are then left alone to deal with the problem. Our approach is simpler (and more useful): we integrate as an extension of your team, with offensive security specialists who understand both the technical side and the business impact.

The difference is in the approach: it’s not just about “finding vulnerabilities”—it’s about explaining what they mean in the real world. Do they affect data? Could they bring operations down? Do they impact sales, reputation, or compliance? Most importantly, we translate all of that into a clear, prioritized action plan. When your dev or IT team needs context to fix things quickly, that’s when a well-executed service truly shows its value.

Seeing pentesting as an “uncomfortable expense” often turns out to be costly. A data breach or serious incident (like ransomware) doesn’t just hit your systems—it affects business continuity, customer trust, and recovery costs. That’s why, more than “checking a box,” the smart move is to use the pentest to reduce real risk through concrete changes.

If you’re comparing options, look for three things: transparency, methodology, and a team you can speak with clearly—no unnecessary jargon. And if you’re not sure what scope you need, don’t guess. At TecnetOne, we can run a discovery session to define the right test together, ensuring the result is truly useful for your business—not just another PDF to file away.