Everything You Need to Know About Penetration Testing

For organizations working to protect themselves from cybersecurity threats, looking at their IT environment through the eyes of a hacker can be the best way to spot unknown vulnerabilities. 

In what was already a tough year, 2020 saw cybercriminals wreaking havoc on some of the largest organizations in the world — organizations that you might think would be impenetrable. Microsoft suffered a breach of 250 million customer service and support records, LabCorp reported that 7.7 million patient records were stolen, and dozens of critical servers at the United Nations were successfully hacked.

Given this hostile digital landscape, private businesses and public organizations alike should be considering how they can take a more proactive approach to their own cybersecurity. While this likely includes shoring up IT defenses, investing in the right equipment and software, and ensuring assets have been appropriately patched, decision-makers can go one step further. To understand how prepared they are for an attack and a subsequent breach, teams should quite literally put themselves in their hacker’s shoes. 

This is where penetration testing comes in. Also known as pen testing, penetration testing calls for cybersecurity professionals to probe and attack IT assets as if they were cybercriminals, in an attempt to see how an organization would fare against an actual attack. Much like a fire drill in a school or office building, this strategy can simulate a real event and help organizations understand their disaster preparedness. But for penetration testing to produce helpful and actionable insights, it must be conducted properly. 

Why You Should Consider Penetration Testing

Penetration testing calls for IT professionals to look at an organization through the eyes of a cybercriminal. From network infrastructure and applications to individual devices and more, a pen test will consider how a wide range of attack vectors may grant bad actors access to a network. However, penetration testing doesn’t just stop at the level of probing — cybersecurity experts carrying out a pen test will really attempt to breach the network and see how IT defenses hold up against a sustained attack. 

By doing so, organizational teams can gain a more practical understanding of the health of their cybersecurity defenses. For example, recent updates might create vulnerabilities that IT experts wouldn’t know about on their own, or minor software bugs might go undetected in the larger hustle of organizational cybersecurity concerns. Undergoing penetration testing helps ensure that the right people are aware of every possible line of attack a bad actor might take.

To carry out a pen test, teams have a number of options at their disposal that can be used to understand defenses from multiple points of view. These include:

• • External testing will focus on assets that are the most visible online, such as the organization’s website, consumer-facing applications, and the DNS.
  • Internal testing simulates how assets behind the organization’s firewall will fare, such as when dealing with a rogue employee or a bad actor that acquired employee credentials through a phishing attack. 

• • Blind testing involves only providing the testers with the name of the target organization, allowing them to better simulate what a real assault might look like.

• • Double-blind testing involves an attack which cybersecurity personnel haven’t been warned about ahead of time, which also helps more accurately depict a real attack. 

• • Targeted testing calls for the tester and cybersecurity teams to work together in order to provide total transparency into what an attack looks like from both sides.

The Steps of Successful Penetration Testing

While investing in penetration testing is becoming increasingly important, it is an extensive and often complicated process that shouldn’t be undertaken without skilled support. To carry out a successful pen test, teams must first plan their overall goals for the assessment and specify what kind of information they want to gather. Next, testers will begin probing the specified targets to understand how they might respond during an attack — this process will help them carry out as effective an attack as possible to help gain valuable insights. 

Once this information is ready, testers will launch their attack and attempt to gain as much access as they possibly can. Depending on the kind of pen testing they’ve been tasked with carrying out, they will exploit any vulnerabilities to see what kind of damage real attackers might be capable of causing. Finally, after this process is complete, the tester and organizational parties will analyze the results of the attack, discuss vulnerabilities that were discovered and what damages might have occurred outside of a simulation, and plan how best to patch up those attack vectors. 

This type of information can benefit all types of organizations — from smaller teams looking to get the most out of their IT spend, to larger organizations that have a sprawling digital purview. In fact, the Pentagon recently hosted “Hack the Pentagon,” inviting hackers to test its networks, and discovered more than 100 previously unknown vulnerabilities as a result. 

Penetration Testing with a Trusted Cybersecurity Provider

If your organization is interested in testing its defenses, it’s important for you to work with a trusted cybersecurity consultant with prior pen test experience. By doing so, your team can be sure that you’ll gain the greatest possible insights from a professionally simulated attack — while enjoying the peace of mind that trained experts won’t do any actual damage in the process. 

By partnering with Turn-key Technologies, Inc. (TTI), organizations can gain clear visibility into just how effective their cybersecurity posture really is and enact recommendations from industry experts. Whether you’re just looking for a cybersecurity partner for pen-testing, or you’re in need of managed IT services with around-the-clock support, TTI has the track record and team to help.