Pentesting: What It Is, How It Works & Ways to Do It (Right)

Cyber attacks happen every 39 seconds. Sure, most business leaders know they need protection, but too many still operate in reaction mode: wait for a breach, then scramble to fix it. That approach is becoming downright dangerous as attackers get more sophisticated.

That’s where penetration testing (pentesting, for short) can help. Think of it as hiring professional hackers to break into your systems before the malicious ones do. Unlike basic security scans that just check boxes, pentesting actively tries to exploit your weaknesses.

A vulnerability scan might tell you that your door is unlocked. A pentest shows you exactly how an intruder could walk in, what they could steal, and how much damage they could do while inside.

Below, we’ll walk you through everything you need to know about pentesting: what it is, why your business needs it, and how to implement it (properly). Whether you’re a CISO looking to strengthen your security program or a business owner trying to protect what you’ve built, you’ll find the actionable insights you need to stay ahead of threats.

What Is Pentesting?

Penetration testing is essentially a controlled cyberattack on your own systems. It’s like hiring professional thieves to break into your building, but instead of stealing, they document every vulnerability they find.

Pentesting is the practice of actively attempting to exploit vulnerabilities in your digital environment. These tests are conducted by security professionals (often called ethical hackers) who use the same tools, techniques, and mindset as malicious hackers—but with your explicit permission and for your benefit.

A proper penetration test mimics real-world attack scenarios but in a controlled, documented way that helps you understand exactly where your vulnerabilities lie. It also shows (most importantly) how to fix them before actual attackers can exploit them:

• Pentesting is legal and authorized: The key difference between a penetration tester and a criminal hacker is permission. Pentesters operate with detailed contracts, scopes of work, and authorization documents.
• Pentesting is controlled: Good pentesters work carefully to avoid disrupting your business operations while still thoroughly testing your systems.
• Pentesting is documented: Unlike actual attackers who try to cover their tracks, pentesters document everything they do and provide detailed reports on their findings.

Why Pentesting Matters for Your Business

When Colonial Pipeline was hit with ransomware in 2021, they didn’t just lose data. They shut down operations, paid a $5 million ransom, and watched fuel prices spike across the eastern US.

This is why pentesting matters. It finds the holes in your defenses before attackers do.

When your systems get breached, the costs pile up quickly:

• Average downtime after a ransomware attack: 24 days
• Average data breach recovery costs for small businesses: $120,000 to $1.24 million
• Business relationships damaged or lost: incalculable
• Reputation damage: often permanent

Too many businesses discover their vulnerabilities only after they’ve been exploited. By then, it’s too late. Plus, if you handle sensitive data, you likely face regulatory requirements:

• HIPAA requires regular security evaluations for healthcare organizations
• PCI DSS mandates annual penetration testing for payment processors
• GDPR and CCPA impose massive fines for data breaches
• Industry-specific frameworks like NIST 800-53 and ISO 27001 all call for regular penetration testing

Non-compliance penalties are steep, often reaching millions of dollars. Ultimately, the bigger risk is thinking you’re compliant when you’re not—a false sense of security that pentesting eliminates. Fixing vulnerabilities found through controlled testing costs a tiny fraction compared to when cybercriminals find them first.

This doesn’t even account for the business continuity costs, legal expenses, and reputation damage that come with actual breaches.

How Does Penetration Testing Work?

Penetration testing is more than just random hacking. It’s a methodical process with clear phases. Professional pentesters follow structured approaches that balance thoroughness with safety:

1. Planning and Preparation: Every good pentest starts with documentation. This includes written authorization, defined scope of systems to test, testing timeframes, emergency contacts, and rules of engagement. Skipping this phase turns a legitimate test into an unauthorized attack.
2. Reconnaissance: Before attempting any exploits, pentesters collect information about your organization, including public data, network details, and technology stack information. This mimics how real attackers operate (they rarely attack blindly).
3. Vulnerability Scanning: Next comes the systematic search for weaknesses through port scanning, application scanning, configuration reviews, and authentication testing. This phase combines automated tools with human expertise.
4. Active Exploitation: This is where pentesting differs from basic security scanning—pentesters actually try to exploit the vulnerabilities they’ve found by gaining unauthorized access, escalating privileges, and moving through your systems. Each successful exploitation is carefully documented.
5. Post-Exploitation Assessment: Once inside your systems, pentesters evaluate what’s actually at risk by determining what sensitive data could be accessed, how far an attacker could move within your network, and what business impacts a breach would cause.
6. Reporting and Remediation: The pentest culminates in a detailed report with an executive summary, technical findings with severity ratings, proof-of-concept details, and step-by-step remediation instructions. Good pentesters also provide a debrief session to explain findings.

Methodologies vary between providers, but this phased approach guarantees thorough coverage of your systems while maintaining the control and documentation that separates professional pentesting from malicious attacks.

6 Types of Penetration Tests

Think of these as different angles of attack. Each one reveals unique vulnerabilities that others might miss. Let’s take a look at the main types of pentests and when you should consider using each one.

1. Network Penetration Testing: Focuses on identifying vulnerabilities in network infrastructure, including firewalls, routers, and servers.
2. Web Application Testing: Targets vulnerabilities in websites and web applications, looking for issues like injection flaws and broken authentication.
3. Mobile Application Testing: Evaluates security of iOS, Android, and other mobile apps, including how they store data and communicate.
4. Social Engineering: Tests human vulnerabilities through techniques like phishing, pretexting, and physical access attempts.
5. Cloud Penetration Testing: Examines vulnerabilities in cloud-based infrastructure, applications, and storage.
6. Physical Penetration Testing: Attempts to gain unauthorized physical access to facilities, equipment, and sensitive areas.

1. Network Penetration Testing

Network pentesting focuses on your core infrastructure. Testers examine your firewall configurations, network devices, servers, and workstations. They’re looking for misconfigurations, weak passwords, unpatched systems, and improper network segmentation. This type of testing is important for businesses with complex networks or those that maintain on-premises infrastructure.

2. Web Application Testing

Your websites and web applications are often your most exposed assets. Web app pentesting identifies vulnerabilities like SQL injection, cross-site scripting, broken authentication, and insecure APIs. These tests can be conducted on production sites (carefully) or staging environments. 

A thorough web application pentest examines the entire application ecosystem, including the database, authentication systems, and integrations with other services. We’ve seen cases where a single vulnerability in a web form led to complete compromise of customer databases.

3. Mobile Application Testing

Mobile app pentesting examines how your applications store sensitive data, communicate with back-end systems, and implement authentication. Testers look for issues like insecure data storage, weak encryption, excessive permissions, and vulnerable communications. 

A mobile app test often includes both the app itself and its interaction with cloud services. The most common finding: apps storing authentication tokens and passwords in plaintext (essentially leaving the keys to the kingdom unprotected).

4. Social Engineering Testing

Sometimes the biggest vulnerability isn’t in your technology: it’s in your people. Social engineering tests check human susceptibility to manipulation through phishing campaigns, phone calls (vishing), and even physical impersonation. These tests help identify training gaps and process weaknesses.

5. Cloud Penetration Testing

Cloud pentesting examines your AWS, Azure, Google Cloud, or other cloud environments for misconfigurations, weak access controls, and insecure storage settings. This testing requires cloud-specific expertise since the attack vectors differ from traditional infrastructure. 

Cloud tests often find excessive permissions, unpatched instances, and publicly exposed storage, and these issues can lead to massive data breaches.

6. Physical Penetration Testing

Digital security means nothing if an attacker can simply walk into your building. Physical pentesting attempts to gain unauthorized access to your facilities, server rooms, workstations, and physical documents. Testers might use social engineering, lock bypassing, or other techniques to test your physical security controls. These tests often find surprising vulnerabilities—from tailgating opportunities to unsecured server rooms.

Red Team vs. Blue Team: What’s the Difference?

Red Team and Blue Team exercises are different approaches to testing your security.

The Red Team acts as your adversaries. They take an offensive approach, attempting to breach your systems by any means necessary within the defined scope. Their goal isn’t to find every vulnerability but to demonstrate how real attackers might compromise your most critical assets. Red Teams typically operate with minimal knowledge sharing, sometimes even working without the IT team’s awareness (though always with executive approval).

The Blue Team is your defensive unit. They’re responsible for detecting and responding to the Red Team’s activities. They’re evaluated by how quickly they can identify, contain, and remediate intrusions. For many organizations, the Blue Team is simply your existing security operations staff, put to the test during exercises.

Some organizations also implement Purple Team exercises—this is where Red and Blue teams collaborate openly, sharing techniques and findings in real-time to improve overall security posture.

Use AirAudit™ to Get Your Pentesting Right

Pentesting is too important to leave to chance. The difference between effective testing and a checkbox exercise can mean the difference between security and a business-ending breach.

Fortunately, you don’t have to go it alone.

AirAudit™ brings enterprise-grade penetration testing to organizations of all sizes. Our approach combines methodical testing procedures with real-world attack expertise gained from thousands of hours on the front lines of incident response.

Unlike generic security vendors, our penetration testers have direct experience remediating actual breaches. This gives them unique insight into how attackers think, what they target, and how they move once inside your systems. We’ve seen firsthand what happens when vulnerabilities go undetected, and we’re committed to finding them before attackers do.

Our testing goes beyond technical findings to deliver actionable intelligence about your security posture. Each AirAudit™ assessment includes:

• Clear, jargon-free executive reporting
• Detailed technical findings with proof-of-concept documentation
• Prioritized remediation recommendations
• Post-assessment consultation to answer questions
• Verification testing after remediation

Don’t wait for attackers to test your defenses. Take control of your security posture with a professional penetration test from Airiam. Contact us today to schedule your AirAudit™ assessment.