Blog Post November 29, 2022

Penetration Testing for Enterprises FAQ

Penetration Testing FAQ

By: Brittany Demendi, Corporate Communications Manager

How and when did penetration testing begin?

The concept of penetration testing, commonly known as ‘pentesting’ or ‘ethical hacking,’ first started around the 1960s, when cybersecurity experts informed the government that its computer communications lines were not as secure as they thought. To further investigate, the government brought in what they called “Tiger Teams,” named after special military teams, according to Infosec Institute, to hack their own network. Most government systems failed fast, however, they learned two things: first, that they could be accessed, and second, penetration testing was a valuable technique to identify any weak points in networks, systems, hardware, and software that needed to be further developed, thought out, and studied.

Is penetration testing considered a “luxury” tactic?

If penetration testing has been around since the 1960s, why is it a relatively new practice organizations implement into their security plan? It is estimated, by Infosec Institute, that $6.4 billion is spent on security checks and tools each year, with penetration tools not even skimming that surface. It is also considered to be only about a decade old, formally established in 2009. In addition, it mainly comes down to the lack of proper resources.

Penetration can be expensive trying to source in-house. Yes, there are penetration testers out there, but when our country is hitting an all-time high of open cybersecurity jobs, it can be tough to find the right experts to facilitate a penetration test properly, effectively, and consistently.

What is the difference between pentesting and scanning for vulnerabilities?

Vulnerability scanning, and penetration testing are sometimes mistaken as the same type of service. One of the main issues many organizations have is whether they will utilize or purchase one when they really need both to have the best proactive protection. A vulnerability scan is a high-level automated test that looks for vulnerabilities. It is a more passive approach to vulnerability management.

As it is possible to take vulnerability scanning to the next level with Continuous Vulnerability Management, it is still essential to add penetration testing in the mix because they work hand-in-hand. Continuous Vulnerability Management is continuous, while penetration testing is customized with various deployment options. Both programs play a critical role in building a healthy cybersecurity plan.

Do I need pentesting in my cybersecurity strategy?

Penetration testing allows organizations to evaluate the overall security posture of their IT infrastructure. An organization may have a robust security plan and strategy in place in one area but could be lacking in another. A successful cyberattack can be detrimental to most organizations, which means, no organization should wait for a real-world attack before utilizing its offense. Penetration testing exposes holes within every security layer, allowing cybersecurity experts to proactively act on shortcomings before they become a liability. Testing is focused on finding out how cybercriminals can get in.

This technique should not be a one-and-done type of effort. It is most efficient if it is a part of an ongoing vigilance. It is best to look for every possible open door into a network rather than finding one way in and calling it a day. Whenever there are security patch updates, which is a part of vulnerability scanning and patching as a service, or new applications used by employees, unknown risks open the door for cybercriminals. The most proactive way to slam those doors shut is to uncover any new security weaknesses by working on the offensive side of the game.

In addition to proactive cybersecurity protection, here are a few more reasons penetration testing is becoming a non-negotiable aspect of security plans:

  • Checking the box of compliance standards: penetration testing allows organizations to maintain industry standards and compliance regulations.
  • Improve security posture: penetration testing helps prioritize and address vulnerabilities with actionable results.
  • Hunting real-world vulnerabilities: weak endpoints are exposed in an organization’s computer system.

How do I perform a penetration test?

Penetration testing involves identifying an exploit, designing an attack, and performing a simulation of that attack to determine the best strategies to overcome a digital adversary. The nature of the exploit will often determine the resources that will be required to mitigate the risk. It combines manual and active attempts by pen testers to hack networks alongside automated tools that scan 24×7 for vulnerabilities.

Together, this is thought to offer a broader security review and has since evolved into cybersecurity services. This approach allows organizations of all sizes that may not be able to expand their IT team internally to a wide array of penetration tools and services like a Progressive Penetration Testing Program with experts to manage them.

In general though, penetration testing can be offered affordably, all while providing the utmost security protection. Specifically, Progressive Penetration Testing simulates different vantage points to see if any critical data can be accessed. In addition, documentation is provided and explained for each vulnerability, evidence, impact, recommendation, and observed instance.

Sometimes your IT teams are too close to the network to carry out effective tests, so turning to external cybersecurity experts to carry out a progressive penetration program can be the best way to monitor from different angles. Penetration tests transform into results with actionable insights for the stakeholder and decision-makers. There becomes more of an emphasis on the weak points exposed, better preparing a defense, and strengthening the offense.

For more information on progressive penetration programs, visit Or, if you are ready to get started with a demo or free trial, contact a cybersecurity expert today.