Penetration testing (or pentesting) is a critical part of maintaining and fortifying your IP, network, and physical security. It involves giving professional pen testers permission to hack, test, and identify potential vulnerabilities in existing and new systems, networks, and apps, to secure against unauthorized access by malicious actors. This article looks at penetration testing, its benefits, and how to get started.

What is Penetration Testing?

IT penetration testing (or pen testing) refers to the process of methodically hacking into your system and network to identify and expose as many vulnerabilities as you possibly can, from multiple vantage points. Ethical hackers and security researchers perform these tests with the full knowledge and authorization of the client.

Penetration testers use internal and external attacks on your servers, intranets, web applications, wireless networks, mobile devices, network devices, and other available entry points (on-site or remote). After hacking your assets, pen testers generate reports on their findings and, in some cases, offer remediation advice.

Penetration testing has been around since the ‘90s but has definitely changed over the years. The practical value of attack simulation hasn’t gone away, but deficiencies in the way these programs are deployed have caused many security leaders to view penetration tests as a ‘necessary evil’.

You should perform a penetration test if you:

  • Discover or suspect new IT security threats
  • Create or update a new company intranet or software
  • Relocate your office and network or move to a fully remote work environment 
  • Set up a new internal data storage site, or relocate
  • Were recently attacked through ransomware or adware
  • Set up a new end-user policy or program

Protecting the organization and its assets isn’t the only reason to invest in penetration testing. With penetration testing, you can protect customer data, reduce cyber risk, satisfy stakeholder requirements, and preserve the organization’s image and reputation. 

It’s important to note that compliance is no longer the top reason for penetration testing. According to a recent study of cybersecurity engineers, managers, and CISOs, only 16% of organizations test purely for compliance purposes, while 61% of respondents cited best practice as a reason for testing. 


Types of Penetration Testing

A range of penetration testing types are available to uncover vulnerabilities across key areas of your IT infrastructure. Below are some types of pen tests you could perform:

  • Web app test to find any potential security holes in your software and applications
  • Network test to expose the vulnerabilities within your host network and all network devices
  • A wireless security test to help you identify insecure holes and hotspots in your Wi-Fi network and ensure you not vulnerable to attacks like business email compromise
  • Social engineering test to identify if your employees follow the training and procedures you have in place to protect against phishing or other similar cyber threats
  • Infrastructure test to check for vulnerabilities
  • IoT pen tests to protect user data globally.
  • PCI pen test to assess the technical and operational components of your system to ensure cardholder and payment data security systems meet the set PCI compliance standards

Ways to Perform Pen Tests

The following are four ways of performing a pen test:

  • Internal testing: Simulates the damage that employees could wreak on your systems
  • External testing: Simulates outside attacks on your visible DNS, web servers, email servers, and firewalls
  • Blind testing: Simulates how attackers would go about gathering company information and attacking it. Your penetration testers have no information about your company when they attempt to attack it
  • Double-blind testing: Simulates a real attack by giving no information to the pen tester and no notice to almost everyone on your organization of the test

When your pen tester gives you an overall measure of your risk assessment, you can start understanding and appreciating your organization’s overall readiness to identify, prevent, mitigate, and respond to cyber threats.

Your pen testing strategy should help you answer these questions:

  • How well prepared are you against potential attacks?
  • Have you identified all your potential vulnerabilities?
  • Can you recover from an attack?

These questions are excellent high-level discussion points to have with your senior management team.


Penetration Testing: The 5 Biggest Benefits

1.  Analysis of IT  Infrastructure

A pen test allows an in-depth analysis of your IT infrastructure and your ability to defend your applications, systems, networks, endpoints, and users from external and internal attempts to cause disruption and data losses or gain unauthorized access to protected assets.

Below are some advantages of using pen tests to analyze your security infrastructure:

  • Reveals system vulnerabilities: Pen tests show weaknesses in your target environments. After the test, you will receive a report detailing the problematic access points and vulnerabilities in your system and networks. It also includes suggestions for software and hardware improvements to upgrade your security.
  • Reveals Hackers’ methods: A primary goal of pen testers is to simulate real attacks on your system using black hat methods. After identifying vulnerabilities, they exploit them as black hat hackers to help you identify parts of your systems and network that need improvement.
  • Tests your response to real cyber threats: If you know your system’s vulnerabilities, you can prepare tactics and tools to prevent and mitigate attacks.
  • Reveals your current IT spending problems: It shows which areas to allocate your IT budget and where you lose money. Discovering your system’s weaknesses shows your overall security posture and how to amplify, modify, and optimize it.

2.  Protection from Financial Damage

A single breach of your company’s security system can lead to millions of dollars in damages. Security faults and associated disruptions in the performance of your network, applications, and services can cause debilitating financial harm to your organization. It could hurt your reputation and customer loyalty, generate negative press, and incur unanticipated penalties and fines.

Frequent penetration testing helps avoid these expenses by preventing and mitigating IT infrastructure invasions. It is far better for your organization to proactively maintain its security, irrespective of the high cost than to face extreme losses to its brand equity and financial stability.

Therefore, you should carry out a pen test whenever you change your network infrastructure and have highly qualified experts do it. Penetration testers will scrutinize your internet-connected systems for weaknesses and potential information vulnerabilities that hackers could use to compromise your data and network’s confidentiality, integrity, and availability.

3.  Protects Clientele and Partnerships

A security breach can significantly affect your organization, clients, partners, and other third parties. However, if you schedule penetration tests regularly and take the necessary actions and prevention steps needed to ensure data and system security, you build trust and confidence.

4.  Protects Company Image and Reputation

You build an excellent company reputation and public reputation after years of consistency, hard work, and a lot of investment. However, all your hard work can change overnight due to a single security breach. Irrespective of the breach’s cost and whether you resolve it quickly, it can significantly hurt your reputation, trust, and confidence.

These destructive consequences could take years to repair and cost you a lot of business. Hence, scheduling regular penetration tests and taking the right mitigation steps to avert security breaches can prevent such outcomes. Remember that there are many malicious actors and hackers always on the prowl of vulnerable company IT environments, looking to gain access by any means necessary.

5.  Compliance with Regulation and Security Certification

IT departments address the overall compliance and auditing facets of procedures such as PCI DSS, HIPAA, GLBA, SARBANES – OXLEY, and report penetration testing necessities recognized in the PCI DSS or NIST/FISMA commands. The complete records of your pen tests can help you evade substantial penalties for non-compliance. It also allows you to illustrate ongoing due diligence by maintaining the required security controls.

PCI DSS addresses pen testing to relevant systems, and qualified penetration testers perform it. The ISO27001 standards have a compliance section that requires system owners and managers to perform regular penetration tests and security reviews – at least every six months. They also need competent pen testers with the right tools to conduct these tests.

How to Get Started with Penetration Testing Services

Performing a thorough IT penetration test is a complex process that entails:

  • Gathering information about your organization and its systems
  • Scanning your systems, network, and website for vulnerabilities
  • Exploiting the vulnerabilities to gain access to your network and system
  • Pivoting from the malicious actor vantage point to seek new weaknesses to exploit
  • Generating detailed data reports of your simulated breaches
  • Translating your data into action steps for increased security

The entire process requires a team of skilled IT professionals with years of experience in Windows and Linux environments, networking, scripting and coding skills, application development and assessment, and database management. They also need skills and expertise in hacking and pen test methodologies.

Furthermore, pen-testing helps your organization align with set industry security standards. Whether you need to meet PCI DSS, HIPAA, FISMA, GDPR, FFEIC, GLBA, or any other compliance and regulation needs, a pen test can help you identify the gaps preventing you from reaching compliance certification. It will offer you specific deliverables that you can improve, and you need the technical know-how to map them to particular industry security standards. Alternatively, you can hire a security consultant for help.


Unfortunately, not all penetration tests are equal. These tests’ results vary depending on several factors, including your testers’ skill, the test’s length, system changes during the test, as well as active and inactive web applications and firewalls during the test.

Hence, when you hire a company offering penetration tests and vulnerability disclosure and scanners, ensure that their pen testers are seasoned experts who perform multiple tests periodically to identify all the vulnerabilities in your system.

Before beginning with penetration testing, you need to determine which method of penetration testing is right for your organization. The four primary methods are traditional penetration testing, crowdsourced security penetration testing, internal testing, and a mixed testing approach. Each method has its pros and cons depending on your goals, resources, timeline, and budget.


Hire the Right Penetration Testing Professional

Certified penetration testers range from thorough, razor-sharp, and helpful to oversold, irresponsible, and negligent. Below are some critical things to know when looking for the right professionals:

  • The pen testers should have strong communication skills. They should easily switch from in-depth and technical discussions to a high-level overview of concepts depending on their audience. They should also present reports in clear language.
  • Beware of “secret sauce” consultants who cannot repeat findings or give clear reports on how to recreate issues they identified. The pen testers should be technically well-versed in enterprise development framework, multi-platform system administration, networking protocol, MiTM, password storage (NTLM, LM, and shadow), ARP spoofing, scripting (Ruby, Perl, and Python), database systems, and essential security toolsets.
  • Get involved with the IT security community and have active participants in hacker conferences, open-source software (OSS) security tools development projects, local information security chapters, and other InfoSec communities to gain better insight.
  • Hire reputable pen testers who are thorough and methodical. They should also be passionate about hacking and willing to go off-script to cover all the bases.

Alternatively, instead of taking on the challenges of pen testing, you could hire a trusted IT security company with an experienced team of experts in all things IT. By leveraging the power of crowdsourced penetration testing, you’ll find benefits such as rapid setup and time to value, realtime results, SDLC integration, and the option to ‘pay for results’ instead of time. 

A recent survey found that crowdsourced penetration tests identify on average 7X more high-priority vulnerabilities than traditional penetration tests. If you want your penetration tests done ASAP and receive a detailed report of your systems’ health, Bugcrowd can help. We are a top-tier crowdsourcing security company offering the complete security coverage you need.

Get started with Bugcrowd today, or get a copy of the “2020 Ultimate Guide to Penetration Testing.”