Best IT MSP · Buyer's Guide

Penetration Testing Services: Types, Process, and How to Choose

Penetration testing services hire ethical hackers to safely simulate real attacks on your systems and find vulnerabilities before criminals do. Tests come in several types (network, web app, wireless, social engineering, physical) and follow a structured process: reconnaissance, exploitation, and a findings report you act on. Many businesses need them for compliance and assurance.

Reviewed by the Best IT MSP research team · Updated 2026-06-18

What is penetration testing?

Penetration testing, or pen testing, is a security exercise where ethical hackers run planned, authorized attacks against your systems to find and safely exploit vulnerabilities, so you can fix them before a real attacker finds them. It is the difference between hoping your defenses work and proving whether they do.

The stakes make it worthwhile: the average data breach cost $4.88 million in 2024[1], and reported cybercrime losses topped $16 billion in a year[2]. Finding a weakness in a test is far cheaper than finding it in a breach. Penetration testing is a key part of cybersecurity services.

Best IT MSP does not perform penetration tests. We are an independent directory that vets and merit-ranks providers. This guide explains what to buy, then helps you shortlist verified firms.

The types of penetration tests

  • Network penetration testing. External (internet-facing) and internal tests of your network defenses.
  • Web application testing. Probes your apps for flaws like injection and broken access control.
  • Wireless testing. Checks Wi-Fi and wireless access for weaknesses.
  • Social engineering testing. Tests whether staff can be tricked via phishing or pretexting.
  • Physical security testing. Attempts physical access to facilities and devices.
  • Firewall and configuration testing. Validates that controls are set up correctly.

Tests are also classified by how much the tester knows up front: black-box (no information), white-box (full information), and gray-box (partial), which trade off realism against thoroughness.

How a penetration test works

  1. Scoping. Define what is tested, the rules of engagement, and the goals.
  2. Reconnaissance. Gather information about the target systems.
  3. Exploitation. Safely attempt to exploit vulnerabilities, using the same tools attackers use.
  4. Reporting. Document findings, rank them by risk, and recommend fixes.
  5. Remediation and retest. Fix the issues, then verify the fixes held.

Penetration testing vs vulnerability assessment

These are often confused. A vulnerability assessment scans broadly to list known weaknesses, automated, frequent, and wide. A penetration test goes deeper: a human expert actively exploits weaknesses to show real, demonstrated risk and how far an attacker could get. Many providers offer both together as VAPT (vulnerability assessment and penetration testing). Vulnerability scanning belongs in your ongoing program; pen testing is a periodic, point-in-time deep check.

Compliance and how often to test

Several frameworks require or expect penetration testing, including PCI DSS (card payments), and it supports SOC 2, HIPAA, and ISO 27001. As a rule, test at least annually and after any major change to your systems. The shortage of about 4.8 million cybersecurity professionals[3] is one reason most businesses buy testing as a service rather than building the capability in-house.

How to choose a penetration testing provider

  • Are their testers certified (for example OSCP, CREST), and will they say who tests?
  • Do they scope to your real risks and the compliance framework you need?
  • Do they deliver a clear, prioritized report with remediation guidance, not just a tool dump?
  • Do they offer a free retest after you fix the findings?
  • Can they show references and sample (redacted) reports?

Shortlist three, ask each the same questions, and compare. To start from a vetted, merit-ranked list, browse providers by city in the Best IT MSP directory.

Frequently asked questions

What is penetration testing?
Penetration testing is an authorized security exercise where ethical hackers simulate real attacks on your systems to find and safely exploit vulnerabilities. The goal is to discover weaknesses and prove real risk before a genuine attacker does, then fix them. It is also called pen testing or ethical hacking.
What are the types of penetration tests?
Common types include network (external and internal), web application, wireless, social engineering, and physical security testing, plus firewall and configuration checks. Tests are also categorized by tester knowledge: black-box (none), white-box (full), and gray-box (partial).
What is the difference between a penetration test and a vulnerability assessment?
A vulnerability assessment scans broadly to list known weaknesses, automated and frequent. A penetration test goes deeper, with a human expert actively exploiting weaknesses to demonstrate real risk and attack paths. Many providers combine both as VAPT. Use scanning continuously and pen testing periodically.
Is penetration testing required for compliance?
Yes, for some frameworks. PCI DSS requires penetration testing, and it supports SOC 2, HIPAA, and ISO 27001 programs. Even where not strictly mandated, regular testing is a recognized best practice and is often expected by customers, partners, and cyber insurers.
How often should we run a penetration test?
At least once a year, and after any significant change to your systems, applications, or network. High-risk or regulated environments may test more frequently. Pairing annual pen tests with continuous vulnerability scanning gives both point-in-time depth and ongoing coverage.
How much does a penetration test cost?
Cost depends on scope, the type of test, and the size and complexity of your environment, ranging from a few thousand dollars for a focused test to much more for a broad, multi-target engagement. A clear scoping conversation produces a fixed quote before any work begins.

Related insights

Vulnerability Assessment vs Penetration Testing

Sources

  1. IBM, Cost of a Data Breach Report 2024. https://www.ibm.com/reports/data-breach
  2. FBI Internet Crime Complaint Center (IC3), Annual Internet Crime Report. https://www.fbi.gov/news/press-releases/fbi-releases-annual-internet-crime-report
  3. ISC2, 2024 Cybersecurity Workforce Study. https://www.isc2.org/research

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