Pentesting for vCISOs: What Works, What Doesn’t, and What Changed in 2025

If you’re an MSP offering vCISO services, you’re not just managing firewalls and EDRs anymore. You’re guiding clients through complex frameworks like SOC 2, PCI DSS, and HIPAA where penetration testing isn’t just a checkbox, it’s a trust signal. But as these frameworks get looser on guidance the line between a real pentest and a recycled Nessus scan keeps getting blurrier.

Your client’s CPA won’t know the difference. A 10-page report full of low-severity issues might look just fine to an auditor. But you’re the one accountable to the client when things go wrong.

It’s your name, your guidance, and your vendor which means it’s on you to deliver testing that actually protects your client’s systems and their customer data.

The problem? Many of these frameworks now leave key testing decisions up to interpretation. The AICPA (Who created SOC2), for example, has relaxed its guidance around penetration testing in SOC 2 audits and most if not nearly all CPAs aren’t cybersecurity experts. If your pentest report looks like a slightly polished Nessus scan, it may still pass. But that doesn’t mean your client is secure.

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1. Not All Pentesters Are Equal

There’s a massive boom right now in entry-level cybersecurity education. You’ve probably seen the wave of penetration testers with new degrees from WGU or getting certs from TCM, Hack The Box, INE, etc.

But here’s the truth:
A cert does not equal experience.
And a resume does not equal rigor or communication skills.

Your clients need more than someone who knows how to run Burp Suite. They need testers who understand business impact, chaining vulnerabilities, and real exploitation not just reporting a list of informational CVEs.

Even if you’re using a third-party vendor (which you should be... self-attested pentests is the CFO giving himself an audit), you still need to vet their team. Who’s actually doing the testing? What is their process? Is the report going to help your client reduce risk or just help someone pass an audit?

2. AI and Automated Pentests Have a Place... But Also a Ceiling

We’re fans of automation when it’s used responsibly. In fact, for some SMBs that simply can’t afford a full manual pentest, automated testing is better than nothing.

But if you’re running a Nessus scan and calling it a pentest? Or sadly in many cases like Horizon3, Vonahi, and others we have seen a nessus scan have more findings than the automated pentest.

If your “report” is just a list of low-severity findings with generic remediations?

If your output doesn’t go beyond CVSS scores and lacks real-world impact analysis?

Or doesn't show steps to remediation with screenshots.

Then let’s be real you’re not pentesting.

Bundling a few open-source tools into a shell script doesn’t make it proprietary. And it definitely doesn’t make it equivalnt to a manual pentest.

3. Reports That Help Auditors And Clients

A lot of pentest reports are written for other security pros. They’re full of acronyms, payload logs, and assumptions about the reader’s knowledge. But for your clients and their auditors; that kind of report can be confusing at best and useless at worst.

A good pentest report should do three things:

1. Give the auditor what they need to know in order to explain the results of the test to a non technical client ( Ex: You can be hacked because hackers can inject code through your sign up page see findnging x)
2. Give the client what they need to fix the issues (Remediation guidance)
3. Give you what you need to guide future improvements via a retest (Security posture description and check to see findings have been patched)

That means clear executive summaries. Severity ratings that reflect actual business risk. Ticket-ready remediation steps with context and reproducibility. Bonus points for reports that segment assets by environment, asset owner, or data classification.

Pentesting is one of the most valuable security services in your vCISO stack; if the report actually helps people make decisions.

4. Pricing Doesn’t Always Equal Quality

Some legacy firms are charging high five-figure retainers for pentests that are largely outsourced, mostly automated, and low on findings. The branding is polished. The sales pitch is tight. But the report is just the same as many other firms.

At MSP Pentesting, we’ve had clients come to us shocked by the difference in pricing and depth.
We use many of the same methodologies (OWASP Top 10 for example). We work with many of the same contractors.
The difference is:
We focus on real findings. We vet every report. We keep costs sane and execution sharp.

Final Pentest Findings

Compliance doesn’t always mean security. And security theater doesn’t keep your clients safe.

If you're offering vCISO services, you're not just a consultant. You're the line between checkbox compliance and real cyber protection.

So when it comes to pentesting, ask better questions.

Because at the end of the day, your clients don’t just want to pass an audit.

They want to sleep at night knowing they’re protected.

And that starts with a real pentest.

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