Why would a company pay for a pen test?

Penetration testing, also known as pen testing or ethical hacking, is the practice of testing a computer system, network or web application to find security vulnerabilities that an attacker could exploit. Rather than waiting for an actual attack, organizations proactively hire security professionals to attempt to breach their systems and identify weaknesses before malicious hackers can find and take advantage of them.

Pen testing provides many important benefits and there are several key reasons why companies choose to invest in it:

Identify security gaps before criminals can exploit them

The primary goal of pen testing is to discover vulnerabilities in networks, applications, and systems before they can be leveraged for malicious purposes like data theft or service disruption. Skilled security testers use the same tools and techniques as real attackers, providing valuable insight into where the weak points are within an organization’s IT infrastructure. Performing pen tests on a regular basis allows companies to find and remediate security holes before cybercriminals become aware of them. This proactive approach significantly reduces the risk of a damaging breach.

Fulfill compliance requirements

Many government regulations and industry standards include mandatory pen testing requirements. For example, the Payment Card Industry Data Security Standard (PCI DSS) requires companies that process credit card payments to conduct annual pen tests on their networks and applications. Health care organizations regulated under HIPAA must also implement a schedule of regular pen tests. Adhering to compliance requirements ensures that companies avoid fines and other penalties.

Gain assurance for insurance policies

Cyber insurance providers commonly require pen testing results in order to qualify organizations for coverage. By providing validation of a strong security posture, pen testing can lower insurance premiums or allow companies to get approved for more comprehensive policies. Maintaining up-to-date records of pen test findings also helps demonstrate due diligence in the event of a claim.

Validate existing security controls

No prevention and detection controls are 100% effective, so pen testing evaluates real-world effectiveness and identifies potential gaps. For example, a web application firewall may appear to block SQL injection attacks based on scans, but hands-on pen testing may reveal ways for attackers to bypass the WAF protection. Pen testing validates that security tools and configurations are working as intended.

Prepare for real-world attacks

The findings from pen tests allow security teams to improve incident response plans by revealing exactly where their systems are vulnerable. Understanding how pen testers are able to infiltrate assets provides blueprints for the types of real-world attacks that could happen. Teams can shore up defenses and be better prepared to respond quickly to similar attack scenarios. Practicing detection and containment strategies during pen tests also sharpens skills.

Meet due diligence requirements

Publicly traded companies often need to demonstrate due diligence to shareholders around cybersecurity practices. Performing comprehensive pen testing shows that management is taking proactive steps to identify and mitigate risks. Having detailed reports with remediation plans indicates responsible stewardship over information assets and helps avoid potential shareholder lawsuits in the aftermath of a breach.

Obtain an objective assessment

While many organizations conduct internal vulnerability assessments and audits, pen testing brings an objective, real-world hacker’s perspective. Experienced pen testers think like criminals to identify hidden flaws and attack vectors that may be unknown to internal IT and security teams. External experts provide an unbiased evaluation of the organization’s security posture.

Types of Penetration Testing

There are several different types and scopes of pen testing that companies may choose from depending on their needs and budget.

External Network Testing

This involves remotely testing externally visible systems like firewalls, web servers, VPNs, DNS servers and more to find vulnerabilities that could allow malicious actors to gain unauthorized access. Testers act as external threat actors to identify ways to breach the network perimeter.

Internal Network Testing

Once testers gain access inside the network perimeter, they pivot to find vulnerabilities deeper within the organizational environment. Tactics focus on lateral movement throughout the network to determine what data and systems can be accessed from compromised machines.

Web Application Testing

Websites and web apps are probed for weaknesses like SQL injection, cross-site scripting (XSS), broken authentication issues and other OWASP top vulnerabilities. Tests verify that input validation, encryption and access controls are implemented properly.

Mobile Application Testing

This evaluates security posture of mobile apps across iOS and Android platforms. Assessing the network communications and data storage protections used by mobile apps is important for organizations with BYOD policies.

Wireless Testing

The discovery, exploitation and protection of Wi-Fi networks and other wireless systems like Bluetooth and NFC is tested. Attackers frequently target weakly secured wireless connections as an initial entry point into a company.

Physical Testing

Attempts are made to physically access facilities, hardware and data to identify vulnerabilities in physical security controls around locks, surveillance systems, alarms and more. Social engineering techniques may also be employed.

Client-side Testing

Examines weaknesses in client-side systems like workstations and laptops. Testing phishing susceptibility, USB drive infection risks and local privilege escalation flaws helps strengthen end user defenses.

Pen Testing Process and Methodologies

Skilled pen testers adhere to structured industry frameworks to carefully plan, scope and conduct their assessments. Some common pen testing methodologies include:

Open Source Security Testing Methodology Manual (OSSTMM)

A peer-reviewed methodology focused on operational security metrics and quantitative test results. Tests are conducted across five channels: human, physical, wireless, telecommunications and data networks.

NIST Special Publication 800-115

Outlines technical processes for preparing, conducting and analyzing the results of controlled pen tests against IT systems. Maintained by the U.S. National Institute of Standards and Technology (NIST).

Penetration Testing Execution Standard (PTES)

Details seven main phases of pen tests including pre-engagement, planning, reconnaissance, vulnerability analysis, exploitation, post-exploitation and reporting. Sponsored by the non-profit Institute for Security and Open Methodologies (ISECOM).

Open Web Application Security Project (OWASP)

Provides a framework for testing web apps and APIs. Breaks down assessment using the STRIDE model covering spoofing, tampering, repudiation, information disclosure, denial of service and elevation of privilege.

A typical pen testing engagement consists of the following general steps:

Planning

Requirements are established by determining scope, objectives, timeline and rules of engagement. Critical aspects include setting boundaries, defining successful breach conditions, and getting written permission to conduct tests.

Reconnaissance

Gathering background information on the target organization through public research and open source intelligence (OSINT) tools. Identifying technical systems, infrastructure and potential vulnerabilities.

Scanning

Using vulnerability scanners and other tools to map out networks, discover likely issues and detect entry points for gaining initial access. This passive scanning minimizes the risk of disruption.

Exploitation

Attempting to exploit known vulnerabilities to achieve penetration using techniques simulating real-world attacks. May include phishing, password cracking, denial of service and more. Typically performed in multiple phases of escalating intrusiveness.

Analysis

Assessing findings, validating vulnerabilities, determining exploitability and ranking risks based on severity and threat levels. Compiling results into a prioritized remediation report.

Reporting

Documenting all vulnerabilities found, how they were discovered/exploited, screenshots demonstrating access, sensitive data accessed and other relevant details. The deliverable includes an executive summary, technical details and a remediation roadmap.

Remediation

The client IT and security teams implement fixes and improvements based on the recommendations contained within the pen test report. Pen testing providers can also offer advice on effective remediation options.

Key Benefits of Pen Testing

Beyond fulfilling compliance requirements and validating security controls, pen testing delivers many advantages that directly reduce business risks and costs for organizations:

Cost savings

Pen testing is far less expensive than the financial damages and recovery costs following an actual breach. The Ponemon Institute pegs the average cost of a corporate data breach at around $4 million. Proactively finding and patching vulnerabilities can save organizations orders of magnitude more than the price of pen testing.

Improved risk awareness

Management, IT pros and end users often become more cognizant of security risks after seeing the results of a well-executed pen test. Real-world exploits events drive changes in mindset, priorities and behaviors.

Better resource allocation

Armed with objective pen test assessments, security leaders can more effectively prioritize projects and direct budgets into areas that will have the most impact in improving their organization’s security posture.

Enhanced incident response

Understanding how pen testers are able to infiltrate the environment makes security teams better prepared to detect and react to similar types of attacks. Practicing response workflows strengthens capabilities.

Competitive advantage

Robust security is increasingly used as a competitive differentiator. Organizations that proactively pen test convey trustworthiness to customers and business partners compared to those that don’t test or have experienced breaches.

Informed metrics

Pen testing provides concrete metrics like the time taken to breach systems, percentage of resources compromised, days to remediate findings and more. Quantifiable KPIs enable smarter security investments.

When Should Companies Consider Pen Testing?

While organizations can choose to pen test on an ad-hoc basis, it is most effective to conduct assessments on a periodic schedule as part of an overall vulnerability management program. Some common situations when organizations should perform pen testing include:

Annually

Performing network and application pen testing at least once a year provides ongoing validation of security posture and protections. Tests should cover critical systems, new environments and major upgrades.

After significant changes

Mergers, acquisitions, expansions, migrations and other IT transformations call for new pen tests to ensure controls remain strong amidst change. Specialized assessments may be required for new segments of the business or infrastructure.

To meet compliance mandates

Satisfying PCI DSS, HIPAA, SOX, GLBA and other regulatory compliance requirements necessitates regularly scheduled security testing and audits. Pen tests provide evidence of due diligence.

Following security incidents

Successful malware infections, data breaches and other security incidents should trigger additional pen testing to check for wider compromises or vulnerabilities that enabled exploitation. Tests validate remediation efforts.

To qualify for cyber insurance

Insurers nearly always require current pen test results to obtain cyber risk policies, particularly for higher coverage amounts. Ongoing testing also keeps premiums in check.

After infrastructure changes

Major IT projects like migrations to new networks or cloud environments warrant new rounds of pen testing to ensure controls work as expected. Stress testing for performance and scale is also useful.

Before public events

For companies making announcements at trade shows, conferences or other events that could make them a target, preemptive pen testing helps avoid being compromised at moments of elevated publicity and scrutiny.

Choosing a Pen Testing Provider

While some organizations conduct internal pen tests using their own IT security staff, most opt to hire an experienced third-party firm for assessments to take advantage of deep expertise and avoid conflicts of interest. The following criteria can help vet potential pen testing service providers:

Experience

Look for companies with a long track record of performing rigorous manual pen tests across diverse industries. Check references to confirm capabilities. Established firms with CREST, GIAC, OSCP and other certified testers demonstrate expertise.

Methodology

Providers should adhere to recognized industry standards like PTES or NIST. Request an overview of their pen testing methodology, processes and deliverables. A detailed project plan demonstrates systematic testing.

Reporting

The pen test report is one of the most critical deliverables. Evaluate sample reports to confirm they provide adequate technical evidence and risk ratings for all findings. Executive summaries should clearly translate risks for business leaders.

Remediation guidance

The best pen testing firms go beyond just reporting vulnerabilities by partnering with clients on fixes through actionable remediation advice. They may also offer post-assessment retesting to validate implementations.

Communications

Ensure the provider emphasizes maintaining ongoing contact during the full engagement lifecycle. Ask about communications policies and real-time reporting capabilities to keep stakeholders informed.

Staffing

Examine consultant backgrounds to verify advanced technical certifications related to networks, systems, applications and mobile devices. Also look for non-technical social engineering expertise.

Ethical conduct

Legitimate pen testing companies operate transparently under strict rules of behavior for minimizing business disruption. Confirmthey carry adequate liability insurance covering errors and omissions.

Pricing

Compare fee structures across providers keeping in mind that lowest cost options may carry more risk of incomplete testing. Optimal value involves methodical assessments balanced against budget realities.

Maximizing the Value of Pen Testing

To get the most value out of pen testing investments, organizations should:

Scoping

Carefully plan engagement scoping, objectives and success criteria aligned to key business risks. Continually evaluate which systems and resources to prioritize for testing within time and budget constraints.

Threat modeling

Work with the pen tester to incorporate current threat intelligence and high-risk scenarios into tests based on potential attackers and their capabilities, motives and resources. Customized threat modeling makes tests more meaningful.

Purple teaming

Bring together pen testers and IT/security staff to collaborate on tests in real time, share information and weigh defensive strategies. This “purple teaming” improves skills and detections on both sides.

QA testing

Conduct tests on release candidates of patches, upgrades and new code prior to deployment to confirm they do not introduce unexpected vulnerabilities compared to current production versions.

Integrated testing

Coordinate dynamic pen testing with other assessment types like static analysis, fuzzing, malware simulation and red team exercises for comprehensive results. Integrated testing provides multiple perspectives.

Ongoing remediation

Treat the remediation phase as an ongoing process versus a one-time event. Continue strengthening defenses over time based on learnings rather than just checking the box on immediate fixes.

Conclusion

Regular penetration testing provides Tangible risk reduction for any organization by identifying security gaps before attackers can exploit them. Beyond meeting compliance mandates, pen testing reduces costs, informs metrics, improves readiness and conveys trustworthiness. Companies should incorporate periodic assessments as part of an overall vulnerability management program and cyber resilience strategy. Partnering with an experienced pen testing provider yields optimal results based on proven methodologies and expert skills simulating real-world attacks. By continually investing in pen testing, companies can identify and remediate vulnerabilities before they turn into expensive breaches.