What is Penetration Testing? Ultimate Explainer

Cyber security isn’t something that should be based on one installation and the expectation of long-term success. It’s something that you have to push the limits of to discover the blind spots. In a world where cyber crimes are becoming increasingly common, it’s important to actively seek out vulnerabilities. Penetration testing is one of the best ways to discover your company’s weakest points. 

But what is penetration testing really? A “pen test” for sure is an authorised, simulated cyber attack on a company’s computer systems, covering everything from the networks and web applicatiosn to smart installations in the physical facility. It’s the best way to identify the company’s digital weaknesses, before any malicious hackers or opportunistic criminals can exploit them. 

What is a penetration test?

Information security penetration testing is a step beyond automated security scans. The pen test is enacted by a white hat hacker who actively tries to break into your systems, using the same exact tools and techniques that a criminal would use. 

The average penetration test follows a fairly standardised process: 

• Reconnaissance & scoping. Testers gather the intelligence on the target system, covering everything from domain names to employee infos, before setting the boundaries of the test.

• Scanning & probing. Then, the tester applies automated and manual tools to identify any network services, as well as open ports and potential security weakness. 

• Exploitation testing. Testers then attempt to exploit any vulnerabilities, such as misconfigured firewalls, as well as outdated software, weak passwords and SQL injection, to gain unauthorised access and extract dummy data. 
• Reporting & improvement. This final step involves creating a proper detailed report of what vulnerabilities were found, touching on how severe they are and how they were exploited. Then, the organisation can use this data to fix them. 

It doesn’t matter what sort of business you’re running or what sort of technology you have in your digital infrastructure, because the process is likely to be fairly similar on a macro level. It is worth noting that, while the process is going to be about the same, there are different forms of tests. 

Different forms of penetration testing

A penetration assessment will follow a general procedure, but there are a range of different actual tests that can take place. 

• Social engineering is the testing of the employees themselves, thorough using phishing emails, phone scams and tailgating. 
• Web & mobile application testing evaluates any custom software, APIs and web portals for coding flaws, such as the OWASP Top 10 vulnerabilities.
• Network testing assesses firewalls, routers, servers, switches and wireless networks for any easy entry points. 
• Physical security tests are digital methods designed to gain access to server rooms, offices or locks to evaluate physical security controls.

Levels of testing

It’s also worth understanding that there are different levels of penetration testing, designed to see how your systems respond to different standards of attacks. 

• Black box testing is approached with minimal insight, to see what an attacker might discover going in blind.
• Grey box testing includes some partial information, such as system architecture diagrams, to simulate the experience of an inside threat.  
• White box tests start from a place of complete access, such as source code and network maps, to simulate a thorough deep-dive internal audit. 

Going through a comprehensive, multi-layered approach to pen testing is essential if you want to properly understand where your vulnerabilities lie in the business. Make sure to hire a company with a strong history in the field of testing, check for compliance (ISO 27001, SOC 2 or UK Cyber Essentials Plus) and be totally honest about your existing security measures before the process starts. Clocking your vulnerabilities and seeing just how weak your company is is the perfect place to start rebuilding your security suite.