Penetration Testing
What Is Penetration Testing?
Penetration testing, or pen testing, is an attempt to evaluate the security of an IT infrastructure by safely trying to exploit vulnerabilities. These vulnerabilities may exist in operating systems, services and application flaws, improper configurations or risky end-user behavior. Such assessments are also useful in validating the efficacy of defensive mechanisms, as well as end-user adherence to security policies.
It might be helpful to think of penetration testing as hiring someone to attempt to break into your house to see how difficult it might be for them. Penetration testers, also known as ethical hackers, evaluate the security of IT infrastructures using a controlled environment to safely attack, identify, and exploit vulnerabilities. Instead of checking the windows and doors, they test servers, networks, web applications, mobile devices, and other potential entry points to find weaknesses.
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Why Is Pen Testing Important?
Cyberattacks continue to increase in volume and sophistication, and the amount of research and experience required to get ahead of these attacks is expanding the gap between the time of attack and the time of discovery. That's why traditional defensive cybersecurity isn't enough on its own. Pen testing is a type of offensive cybersecurity that equips organizations to see their systems from a ***'s perspective and close gaps in security before they're discovered by bad actors. Here are six further reasons pen testing is important:
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Identify and Prioritize Security Risks
Pen testing evaluates an organization’s ability to protect its networks, applications, endpoints and users from external or internal attempts to circumvent its security controls and gain unauthorized or privileged access to protected assets.
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Intelligently Manage Vulnerabilities
Pen tests provide detailed information on actual, exploitable security threats. By performing a penetration test, you can proactively identify which vulnerabilities are most critical, which are less significant, and which are false positives. This allows your organization to more intelligently prioritize remediation, apply needed security patches, and allocate security resources more effectively to ensure that they are available when and where they are needed most.
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Leverage a Proactive Security Approach
These days, there's no one solution to prevent a breach. Organizations must now have a portfolio of defensive security mechanisms and tools, including cryptography, antivirus, SIEM solutions, and IAM programs, to name a few. However, even with these vital security tools, it's difficult to find and eliminate every vulnerability in an IT environment. Pen testing takes a proactive approach, uncovering weaknesses so that organizations know what remediation is needed, and if additional layers should be implemented.
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Verify Existing Security Programs Are Working and Discover Your Security Strengths
Without the proper visibility into your environment as a whole, changing your security posture may result in you eliminating something that was not actually problematic. Pen tests don't only tell you what isn't working. They also serve as quality assurance checks, so you'll also find out what policies are most effective, and what tools are providing the highest ROI. With these insights an organization can also intelligently allocate security resources, ensuring that they are available when and where they are needed most.
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Increase Confidence in Your Security Strategy
How can you be confident in your security posture if you do not effectively test it? By regularly putting your security infrastructure and your security team through their paces, you won't have to wonder hypothetically what an attack will look like and how you'll respond. You'll have safely experienced one, and will know how to prepare to ensure your organization is never caught off guard.
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Meet Regulatory Requirements
Penetration testing helps organizations address the general auditing and compliance aspects of regulations and industry best practices. By exploiting an organization’s infrastructure, pen testing can demonstrate exactly how an attacker could gain access to sensitive data. As attack strategies grow and evolve, periodic mandated testing makes certain that organizations can stay one step ahead by uncovering and fixing security weaknesses before they can be exploited. Additionally, for auditors, these tests can also verify that other mandated security measures are in place or working properly. The detailed reports that pen tests generate can help organizations illustrate ongoing due diligence to maintaining required security controls.
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- Assess the Effectiveness of Your Security Controls with Penetration Testing
- How Manture is Your Vulnerability Management Program?
Transform Your Cybersecurity Approach
Get the latest insights from the 2024 Penetration Testing Report! With 72% of respondents indicating that penetration testing has successfully prevented breaches, its value is undeniable.
How Does Pen Testing Work?
Penetration testing is typically performed using manual or automated technologies to systematically compromise servers, endpoints, web applications, wireless networks, network devices, mobile devices and other potential points of exposure. Once vulnerabilities have been successfully exploited on a particular system, testers may attempt to use the compromised system to launch subsequent exploits at other internal resources, specifically by trying to incrementally achieve higher levels of security clearance and deeper access to electronic assets and information via privilege escalation.
One way to think of pen testing is to imagine using a found set of keys to attempt to enter an office building containing sensetive information. A pen tester will not only see if that building can be entered with the keys, but will also find out how many other internal office doors can be opened within that building to access even more privileged data.
Information about any security vulnerabilities successfully exploited through penetration testing is typically aggregated and presented to IT and network system managers to help those professionals make strategic conclusions and prioritize related remediation efforts. The fundamental purpose of penetration testing is to measure the feasibility of systems or end-user compromise and evaluate any related consequences these incidents may have on the involved resources or operations.
Through penetration testing, you can proactively identify the most exploitable security weaknesses before someone else does. However, there’s a lot more to it than the actual act of infiltration. Pen testing is a thorough, well thought out project that consists of several phases:
- Planning & Preparation - Figure out goals and scope accordingly.
- Discovery - Perform different types of reconnaissance on their target.
- Penetration & Exploitation - Test security weaknesses, gain access, and elevate privileges.
- Analysis & Reporting - Report what is putting an organization most at risk.
- Clean Up & Remediation - Leave no trace of testing activities and fix discovered weaknesses.
- Retesting - Ensure fixes were implemented and discover new weaknesses.
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Want to learn more about pen testing?
Check out our pen testing toolkit which is designed to guide you through all the steps of managing an effective penetration testing program.
How Often Should You Pen Test?
Penetration testing should be performed at least annually, but a quarterly frequency is even better. A pen-tester will reveal how newly discovered threats or emerging vulnerabilities may potentially be exploited by attackers. In addition to regularly scheduled assessments required by regulatory mandates, pen tests should also be run whenever:
Network infrastructure or applications are added
Security patches are applied
Upgrades to infrastructure or applications are done
End user policies are modified
New office locations are established
What Is Red Teaming?
The number of attacks are increasing and the amount of research and experience that’s required to get ahead of these attacks is expanding the gap between time of attack and time of discovery. That’s where teaming comes in. Teaming exercises simulate real-life attack scenarios — with one team attacking, and another defending.
Red Teams
A red team is on the offensive side. A red team is formed with the intention of identifying and assessing vulnerabilities, testing assumptions, viewing alternate options for attack, and revealing the limitations and security risks for that organization.
Blue Teams
The blue team is tasked with defending the organization. Blue teams are in charge of building up an organization’s protective measures, and taking action when needed.
Purple Teams
Recently, the concept of a purple team has become more popular in teaming exercises. This is the mindset of seeing and treating red and blue teams as symbiotic. It’s not red teams vs. blue teams, but rather one large team focusing on the one overarching goal: improving security. The key to becoming a purple team comes down to communication between individuals and their teams.
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What Are Pen Testing Tools?
Attackers use tools in order to make their breach attempts more successful. The same is true for pen testers. Penetration testing software is intended for human augmentation, not replacement — they allow pen testers to focus on thinking outside the box by taking over tasks that take time, but not brain power. When it comes to pen testing, it’s never a choice between penetration testing tools vs. penetration testers. Instead, it’s a choice of what penetration tools will help a penetration tester most.
Penetration testing is typically completed using a portfolio of tools that provide a variety of functionalities. Some are open source, while others are commercial. Some of these tools are the same as those used by threat actors, allowing for the exact replication of an attack. Others highlight the needs of an ethical ***, allowing for a stronger emphasis on features that prioritize the end goal of validating security weaknesses without affecting production environments, and prioritizing remediation.
Security teams are also turning to penetration testing tools to advance their in-house programs through strategic automation. Automation can elevate the skills of inexperienced testers with wizards that safely guide them through critical standard tests; experienced testers can maximize their time by automating the routines.
So what should you look for when it comes to an automated pen testing solution? Penetration testing tools should be simple, efficient, reliable, and centralized. Key types of penetration testing tools include (but are not limited to):
- Adversary simulation tools: These tools emulate real attackers embedded within systems to mimic post-exploit behavior to identify security weaknesses.
- Certified exploit tools: Tools that leverage expert-validated certified exploits save time using libraries of common vulnerabilities and exposures (CVEs).
- SQL injection testing tools: SQL injection tools disrupt application database queries with SQL statements that can provide access to sensitive information.
- Brute-force testing tools: Brute-force tools use bots to test enormous quantities of letter and number combinations to *** passwords and encryption keys.
- Credential capturing tools: Tools like keyloggers installed via malware or *** schemes with *** login pages can steal privileged credentials.
Keep reading:
- The Human Element of Pen Testing and the Role Tools Can Play
- How Commercial Pen Testing Tools Can Make Your In-House Testing Program More Effective and Efficient
- Three Things You Need in a Penetration Testing Tool
How to Choose Between a Penetration Testing Tool or Service
Pen testing software and services are one of the top ways to evaluate an organization’s ability to secure networks, applications, endpoints, and users from exploitation of security weaknesses. However, depending on your circumstances, you may have to choose between software and services. Other times, you’ll need both. So how do you determine which approach you need?
First, you’ll need to evaluate your company’s size and structure. If you have on-staff security analysts, perhaps automated tools are the best option. External pen testing services can give an outside perspective of your cybersecurity needs. The combination of both is the best way to ensure some of the strongest coverage.
The guide When to Use Penetration Testing Software, Services, or Both gives detailed advice to help determine what level of pen testing your company needs, by examining pen testing scope, organization size and structure, tools and resources available, analyst skills and experience, and implementation timeline.
How Are Exploits Used in Pen Testing?
A common tactic of attackers trying to breach an environment is to use an exploit against a known vulnerability in an application or device present in a targeted infrastructure. Exploiting a vulnerability can provide an attacker with privileges or capabilities they would not normally be granted. In order to provide insight into what threat actors might be able to do, pen testers also use exploits.
Usually, attackers have to write exploits as they find vulnerabilities. Others are readily available on the internet, usually posted anonymously by other attackers. Some common types of exploits are operating system exploits, social engineering, and web application exploits.
On the ethical hacking side, exploit development can be an advanced penetration testing skill that takes time to master. Additionally, when on a job, pen testers often don’t have the resources to create a new exploit. Many resort to searching for and using pre-written exploits they find online—oftentimes the same ones attackers use.
Because exploit writing takes time and expertise, both attackers and pen testers alike are always looking for exploits or exploit libraries that can save them the effort. Access to enterprise exploit libraries are often a benefit that comes with owning an enterprise pen testing tool.
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Think Like a Cyberattacker
Cybersecurity isn’t just about building walls; it’s about understanding how to outsmart the attackers. Our comprehensive guide, Decoding the Attacker Mindset: Pen Testing Revelations, dives into 5 real-world scenarios that reveal the strategies hackers use to breach defenses.