How Often Should You Pentest Your Company?

by | Jul 7, 2023 | Penetration Testing

Why your business needs a pentest?

The big question is, how often should you pentest your company? Penetration testing has become an increasingly standard practice, with businesses and organizations using either pen testing services or in-house security teams to uncover weaknesses and assess their security posture.

Companies choose pentesting services to maintain their proactive approach to safeguarding their IT infrastructure and demonstrate compliance with regulations and industry standards. While most cybersecurity professionals conduct a pen test once or twice a year, there is a growing need to consider more frequent testing. It’s crucial to explore why organizations should conduct penetration testing more frequently and how to strike a balance between testing frequency and practicality.

Conducting penetration testing is essential for several reasons:

  1. Identify vulnerabilities: Penetration testing helps to identify vulnerabilities in systems and applications that attackers could exploit. Organizations can take steps to address these weaknesses and reduce the risk of a successful attack by identifying them.
  2. Test security defenses: Penetration testing allows organizations to test their security defenses against simulated attacks, providing a realistic view of their security measures’ effectiveness and identifying areas needing improvement.
  3. Comply with regulations: Many industries and regulations require regular penetration testing to ensure compliance. Penetration testing can help organizations meet regulatory requirements and avoid potential fines or penalties.
  4. Protect sensitive data: Organizations that handle sensitive data, such as financial data, healthcare records, or personally identifiable information (PII), are at a high risk of cyber-attacks. Penetration testing can help identify vulnerabilities in systems that hold sensitive data and ensure they are adequately protected.
  5. Improve incident response: Conducting regular penetration testing can help organizations prepare for a potential cyber-attack and improve their incident response capabilities. Organizations can develop and refine their incident response plans by identifying weaknesses in their systems and applications, reducing the impact of a successful attack.
  6. Identifying weaknesses in hardware infrastructures, software applications, and human errors to develop successful controls.
  7. Exposing security bugs in existing software, such as patches and updates, can bring along new vulnerabilities and eliminate bugs by installing patches and regular updates.
  8. Ensuring implemented controls are effective and functioning correctly.
  9. Discovering “backdoors” and misconfigurations that can create vulnerabilities for cybercriminals to exploit.

When do you need a penetration test

According to our research, most organizations (44%) run a penetration test once or twice a year, and about 15% never had an actual penetration test. But is annual testing enough? Let’s talk about why businesses should conduct penetration testing more frequently and how to find the right balance.

So how often should you run a pentest: daily, weekly, monthly, quarterly, or yearly?

Performing penetration tests daily is not practical and realistic due to the considerable strain on an organization’s resources, including time, budget, and talent. Although let’s be honest here: who does that? However, certain aspects and types of penetration testing can be automated, and of course, a human element is still crucial in the process. Vulnerability scans executed frequently by in-house specialists can effectively find basic vulnerabilities and misconfigurations, but vulnerability scans cannot understand logic. Therefore, a vulnerability scanner cannot find any vulnerability that requires a multi-step process to exploit the vulnerability or contains logic flaws. For example, permissions set on shares that are too open and allow anyone in the organization access when only specific groups or users should access these shares will not be found by a vulnerability scan.

Keep in mind that it is also recommended that every so often, vulnerability scans will be performed by third-party penetration testers. So, what’s the difference between a Penetration test and a vulnerability scan?

Vulnerability Scanning vs Manual Penetration Testing

  1. Process: Vulnerability scanning is automated, while manual penetration testing involves a skilled professional manually testing an organization’s systems and applications.
  2. Level of Analysis: Vulnerability scanning is limited to known vulnerabilities and configuration issues, while manual penetration testing involves identifying new or unknown vulnerabilities that automated tools may miss.
  3. Insights: Vulnerability scanning provides basic insights into an organization’s security posture. In contrast, manual penetration testing provides a more comprehensive analysis and simulates real-world attacks, providing valuable insights into an organization’s overall security defenses.

It’s common for vulnerability scans to be confused with penetration tests, but they are different security practices that serve different purposes. Vulnerability scans aim to identify and report known vulnerabilities present in an IT environment. If running an authenticated vulnerability scan, the scanner will look at the Windows registry and view which patches were installed and which are missing. The vulnerability scanner will not try to exploit the vulnerability, move laterally across the network, or obtain additional password hashes or cleartext passwords for further exploitation.

Effective vulnerability management solutions involve an ongoing process that regularly detects, assesses, reports, and prioritizes network systems and software vulnerabilities, presenting the information in a clear and easy-to-understand format. This allows organizations to protect their critical assets efficiently and effectively.

Seek a Qualified Penetration Testing Company

Penetration testing is typically performed manually by qualified penetration testers (usually a third-party company) with a deep understanding of cybersecurity. They possess specialized skills and certifications, such as the OSCP, OSCE, OSWP, and GIAC certifications. Pen testers use various tools and techniques to simulate real-world attacks on an organization’s systems and identify vulnerabilities that automated tools may not detect.

Working with a penetration testing company like Artifice Security can provide additional benefits, such as access to a team of experts with diverse backgrounds and experience and the latest tools and technologies. The testing process typically involves examining multiple issue types, including network, mobile, and system vulnerabilities, application flaws, and social engineering attacks like phishing.

Ensure Companies Perform Manual Penetration Testing

A manual approach to pentesting is much more precise than just a vulnerability scan. It involves simulating real-world attacks to assess the security posture of an organization’s systems and networks. Unlike vulnerability scans, which only identify potential risks, penetration testing can validate whether those risks are actual threats and provide specific guidance on how to remediate those threats.

Manual penetration testing can help organizations identify vulnerabilities that may not be visible through vulnerability scanning, such as those hidden or buried deep within an organization’s infrastructure. Additionally, penetration testing can provide insights into the impact and likelihood of exploitation of identified vulnerabilities, which can help organizations prioritize their remediation efforts.

After the testing, the pen tester provides a detailed report with findings and prescriptive suggestions for remediation. Specialists at Artifice Security may also perform a root cause analysis to identify the underlying factors contributing to the vulnerabilities and make strategic and tactical recommendations to address them.

While vulnerability scanning can be useful for identifying potential risks, it should not be relied upon as the sole method for assessing an organization’s security posture. Regular penetration testing can help organizations better understand their risk profile and ensure that they have adequate controls in place to prevent attacks.

It is a common misconception that penetration testing must always be comprehensive, testing the whole IT environment from top to bottom. While it is important to conduct complete testing of the entire IT environment, it may only be necessary to do so quarterly or twice a year, especially for larger organizations with complex infrastructures. Pen testing can be done at any scale. Organizations and businesses can take a risk-based approach to determine which systems or applications are most critical or high-risk and prioritize testing in those areas.  For example, you can have external and internal penetration tests, or just social engineering pen tests, or test certain IPs. This can help to ensure that limited resources are used effectively and efficiently to address the most pressing security concerns.

Does the Size of your Company Matter When Deciding How Often You Should Pentest Your Company?

Does the Size of your Company Matter When Deciding How Often You Should Pentest Your Company

How Often Should You Pentest Small Businesses?

In case you are wondering if the small size of your organization or business could be more attractive to cyber-criminals. Well, the truth is that the size of an organization is no longer a factor that plays a role in how attractive your company is to hackers.  In fact, the consequences of a cyber-attack can be particularly devastating for small businesses. According to reports, 60% of small companies that have been hacked close within six months. This is a significant concern as small businesses are the backbone of many economies worldwide, and their success is critical to overall economic growth. According to CNBC, 43% of attacks are targeted at small businesses, but only 14 percent of small businesses are conducting regular pentests.

  • Cybercriminals often perceive small businesses as easier targets because they may have fewer resources and less sophisticated security defenses in place. This can make them more susceptible to attacks, as cybercriminals see them as low-hanging fruit.
    • For example, small businesses can have a custom application not on a proven framework. Therefore, it is easier for a malicious actor to gain access to the critical data.
  • Additionally, small businesses often hold valuable data, such as customer information or financial data, making them attractive targets for cybercriminals looking to steal sensitive information. This data can be used for various malicious purposes, including identity theft, financial fraud, and extortion.
  • Many small businesses and organizations, due to their size, do not have sufficient policies and procedures in place. For example:
    • Change management approval for changes in a system.
    • No policies or security checks for hardening systems before deployment.
    • No regular patch management policy.
    • No dedicated security team that continuously checks for vulnerabilities in the company.

Because of all these factors, small businesses should really have more pentests than larger organizations. However, with a limited cybersecurity budget that does not allow for expensive penetration testing, what is the solution?

Below are some options for small organizations needing penetration testing and security consulting:

  • Conduct a limited scope penetration test once a year for critical infrastructure.
  • Hire system and network administrators who know security and can configure systems with security in mind.
  • Perform internal penetration testing and vulnerability scanning in-house.
  • Train employees on creating secure password phrases, using multi-factor authentication, and ensuring you have policies in place to update your systems and employee systems regularly.
  • Ensure you are using security tools to their fullest instead of buying separate security tools to perform one function. Deploy free security solutions from trusted vendors (e.g., Microsoft LAPS).

More than half of all cyberattacks are committed against small-to-midsized businesses (SMBs), and 60 percent of them go out of business within six months of falling victim to a data breach or hack.

US National Cyber Security Alliance

A Better Business Bureau survey found that for small businesses — which make up more than 97 percent of total businesses in North America — the primary challenges for more than 55 percent of them in order to develop a cybersecurity plan are a lack of resources or knowledge.

Better Business Bureau survey

How Often Should You Pentest Medium and Large Organizations?

According to projections, the global economy is expected to suffer a loss of $10.5 trillion by 2025 due to cybercrime, which indicates a year-on-year increase of 15%. With this alarming growth rate, businesses are at higher risk than ever, and even large organizations with robust cybersecurity measures are susceptible to cyber attacks.

In fact, as of today (March 2023), multiple Fortune 500 and other large companies confirmed that they experienced cyber attacks and data breaches.

  • Chick-fil-A: March 2023
  • Activision: February 2023
  • Google Fi: February 2023
  • T-Mobile: January 2023
  • Norton Life Lock: January 2023

… and the list goes on.

Why Are Medium and Large Organizations Becoming More Prone to Hacks?

Why Are Medium and Large Organizations Becoming More Prone to Hacks
Industrial worker in protective uniform operating forklift in big warehouse distribution center.

  • Increasing Attack Surface

Large organizations have many employees, devices, and physical locations that need to be secured. Their extensive network and cloud environments also provide numerous access points for cybercriminals to exploit. The shift towards remote and hybrid work models, accelerated by the pandemic, has further expanded the attack surface. With employees working from home, organizations must now secure devices outside their corporate network, making tasks like software updates and patch deployment more challenging.

For medium and large organizations, all it takes is one vulnerable system to compromise the entire company.

  • Alert Fatigue

Medium and large businesses may have an in-house security operations center, but finding qualified security experts to run it can take time and effort. Analysts are often tasked with monitoring and tuning multiple cybersecurity tools generating thousands of daily alerts. This can lead to cybersecurity alert fatigue, where analysts become overwhelmed by the sheer number of alerts, making it difficult to distinguish the important from the unimportant. When a security team is impacted by alert fatigue, over a quarter of alerts may be ignored every week, leaving the organization vulnerable.

Having the latest defensive security tool is not enough. Each organization has to fine-tune their systems to detect malicious traffic properly. A penetration test performed regularly helps organizations fine-tune their incident detection systems and response capabilities by testing controls and training security analysts on how an attack looks versus false positives.

  • Potential Profit or Scope of Damage

Medium and large organizations have larger budgets and high-profile operations, making them attractive targets for cybercriminals, ransomware gangs, and nation-state actors. These experienced cybercriminals execute sophisticated attacks that are well-researched and carefully planned. Breaches can lead to massive fallout for large organizations, including significant financial losses and reputational damage.

  • Extensive Vendor Partnerships

Large organizations often work with a vast network of vendors and third-party partners to scale their operations rapidly. However, these relationships also increase the organization’s exposure to risk, as there is no guarantee that their partners can adequately protect their data. A breach in a third-party partner’s system can unlock access to the large organization’s network, compromising its security.

For example, in 2013, the company, Target, was compromised by a third-party HVAC vendor where the vendor was compromised through a phishing attack. The attackers then used these stolen credentials to access Target’s corporate network, ultimately installing malware on POS devices.

High-Risk Organizations

How Often to Pentest: High Risk Organizations

In 2020, the world witnessed unprecedented cyberattacks, which set new records. As the COVID-19 pandemic triggered a massive surge in Internet usage, cybercriminals targeted industries that depend on online services and data storage. As a result, cybercrime has risen by 300% since the pandemic’s start, as reported by the U.S. FBI. And this number didn’t go down; it is still rising.

Some industries are more vulnerable than others due to the nature of their business.

  • Banking/Credit/Financial
  • Education
  • Energy/Utilities
  • Healthcare/Medical
  • Government/Military

How Often Should You Pentest the Financial Industry?

The financial industry has always been a top target for cyberattacks due to the high value of the data stored by these institutions. Cybercriminals target banks, investment firms, and other financial services companies to steal money, personal information, and other sensitive data.

According to a report by Accenture, financial services experience the highest number of cyberattacks compared to any other industry, with a total cost of $18.3 million per company per year. In 2020, there was a 118% increase in cyberattacks on financial institutions compared to the previous year.

These attacks can come in various forms, including malware, phishing, and ransomware. The impact of a successful cyberattack on a financial institution can be catastrophic, leading to financial losses, reputational damage, and loss of customer trust.

That is why it is crucial for businesses in the financial sector to perform a thorough penetration test regularly. At Artifice Security, we regularly see our first-time clients who have already had a few penetration tests done by other companies with critical and high-rated vulnerabilities existing or unresolved issues that were not fixed after previous pentests.

We recommend that these organizations perform quarterly or semi-annual pentests at a minimum for the financial industry. This is not only required many times by compliance but helps the organization stay safe and current from trending vulnerabilities. At a minimum, any organization that changes its network or systems should perform a penetration test to find its vulnerabilities.

How Often Should You Pentest the Education Sector?

The education sector has become an increasingly attractive target for cybercriminals in recent years. Educational institutions, from K-12 schools to universities, often have large databases of personal and financial information, making them an appealing target.

In 2020, the K–12 had a record-breaking number of incidents, with 408 reported across 377 school districts in 40 states. In 2021, there were a total of 1,043 schools between all the impacted districts. In 2022, that number nearly doubled to 1,981. These attacks can disrupt classes, damage school systems, and compromise sensitive information.

Additionally, the sudden shift to remote learning during the COVID-19 pandemic has created new vulnerabilities for educational institutions. The need for virtual classrooms and online learning platforms has increased the amount of data transmitted and stored online, making them more susceptible to cyberattacks.

Why are higher education institutions getting hit by cyber attacks?

Higher education institutions are a goldmine for PII (Personal identification numbers: social security number (SSN), passport number, driver’s license number, taxpayer identification number, patient identification number, financial account number, or credit card number. Personal address information: street address or email address. Personal telephone numbers). They have large student populations with fresh credit histories, plus alumni and employee data.

As many of these educational systems don’t emphasize security with continuous investments in cybersecurity and professional training, they are seeing severe consequences of being a new favorite target for hackers.

At a minimum, higher education organizations should perform a penetration test annually. A penetration test should be conducted afterward if the organization is expanding or changing its systems or networks.

After a large increase in schools getting hit by ransomware attacks, Artifice Security is seeing an increase in higher education organizations requesting penetration tests, with many admitting that their test is the first of its kind.

How Often Should You Pentest Energy and Utility Companies?

Energy and utility companies have been increasingly targeted by ransomware attacks, as demonstrated by the May 2021 Colonial Pipeline outage. This incident caused gas shortages across the East Coast when hackers were able to take down the largest fuel pipeline in the United States.

Although the Colonial Pipeline attack is one of the most significant ransomware attacks of 2021, it is just one example. Recent cyber securities reports across the industry suggest that this industry will remain a prime target for cybercriminals due to its crucial role in national and economic security. According to the research, most (71%) utility organizations are confident they will avoid a security breach in the upcoming year. However, the data also reveals that 87% of utility companies have suffered at least one security breach within the last three years.

Based on all of the Red Team assessments and penetration testing performed by Artifice Security, it was found that all energy and utility companies could be breached when physical social engineering was involved. Once breached, our consultants could gain access to the network and ultimately have full control of the systems for that organization.

Having organizations provide consistent training and security assessments are vital to preventing attacks.

How Often Should You Pentest the Healthcare Sector?

Healthcare sector continues to be at risk of cybersecurity attacks. Over 90% of healthcare organizations have reported security breaches within the last three years, including denial-of-service attacks, malicious code, and ransomware incidents. Nearly 300 Hospitals Impacted by Ransomware in 2022.

The COVID-19 pandemic exacerbated the problem in 2020, with cyberattacks on healthcare organizations more than doubling compared to the previous year. Approximately one-third of those attacks involved ransomware (malicious software) that blocks access to data or systems until a ransom is paid. Ransomware attacks are particularly alarming in the healthcare industry because they can impede critical processes and jeopardize patient safety.

Does HIPPA require pentesting?

Technically, the Health Insurance Portability and Accountability Act of 1996 (HIPAA) does not specifically require penetration testing. It is important to note some crucial details here. Although vulnerability scans or penetration testing are not explicitly mentioned in the HIPAA regulations, various industry experts and standards organizations (such as NIST) suggest that conducting penetration testing, wherever possible, is an effective approach to fulfilling several HIPAA requirements. The HIPAA Security Rule specifies several goals, all of which are supported by frequent security testing, such as vulnerability scanning and penetration testing.

  • HIPAA requires periodic technical and non-technical evaluations (internal and external penetration tests)
  • NIST recommends external/internal penetration testing to meet technical evaluation requirements
  • Penetration testing helps evaluate security measures related to access control
  • Security testing supports HIPAA objectives of confidentiality, integrity, availability of e-PHI
  • Security testing helps identify and protect against threats and impermissible uses/disclosures of e-PHI

Healthcare organizations are generally difficult, as many organizations, such as hospitals, have an average of ~100 vendors that work within the hospital. For example, Hill-Rom might be the hospital bed manufacturer, which has network connections within the hospital and data transmitting out to a wireless router, which might be controlled by another vendor, who then ultimately moves metadata back to Hill-Rom.

As you can see, healthcare organizations’ networks and systems are difficult to track and can be overwhelming for the organization with the vendors in them.

To determine how often a penetration test should be done is determined by the scope of the assessment, what type of pentest is needed, previous pentests performed, current policies and procedures in place, and how often the organization is changing its network or systems. On average, we find that a semi-annual or annual pentest is sufficient for healthcare organizations to find and remediate vulnerabilities.

How Often Should You Pentest the Government Sector?

The government sector also faces significant cybersecurity threats due to the highly sensitive and confidential information they handle. Hackers target government networks and systems to steal data, leaving individuals and state and local governments vulnerable to attacks.

The cost of these attacks is substantial. In 2020 alone, 79 ransomware attacks were launched against US government organizations, resulting in $18.8 billion in recovery costs and downtime. Despite this, only 38% of state and local employees have received training on ransomware prevention.

Therefore, all organizations, regardless of size, should take cybersecurity seriously and conduct regular penetration testing to identify vulnerabilities and mitigate the risk of cyber-attacks. Working with qualified professionals who can help identify and address potential security threats is important in protecting your organization’s assets, reputation, and customers.

When is the best time to perform a pentest?

The best time to perform a penetration test, or pentest, depends on various factors, including the organization’s specific needs and circumstances. Here are some general guidelines to consider:

  1. Before deploying a new system or application: Penetration testing can identify vulnerabilities and weaknesses in a new system or application before it goes live, allowing for any necessary remediation to be carried out before an attack occurs.
  2. After significant changes to the system: Any changes or updates made to the system can introduce new vulnerabilities. A pentest after such changes can ensure that no new vulnerabilities have been introduced and that the existing vulnerabilities have been adequately addressed.
  3. Regularly scheduled intervals: A periodic penetration test (e.g., quarterly, semi-annually, or annually) can help ensure the organization’s security posture remains effective and up-to-date. It can also help to identify new or evolving threats.
  4. In response to a specific threat or incident: If there has been a security incident or the organization has received intelligence about a specific threat, a pentest can help identify any vulnerabilities the threat could exploit.

Ultimately, the timing of a pentest will depend on the specific needs and circumstances of the organization, and it is recommended to consult with a qualified security professional to determine the best approach.

How Often to Perform a Pen Test

The frequency of performing a penetration test, depends on various factors, including the organization’s industry, the regulatory environment, the size and complexity of the infrastructure, and the threat landscape. Here are some general guidelines to consider:

  1. Compliance requirements: Many regulatory frameworks and compliance standards require regular pentesting. For example, the Payment Card Industry Data Security Standard (PCI DSS) mandates that organizations that handle payment card data perform pentesting assessments at least annually.
  2. Industry best practices: Some industries have established best practices that recommend regular pentesting. For example, the National Institute of Standards and Technology (NIST) recommends that organizations perform pen testing periodically or after significant system changes.
  3. Risk assessment: Organizations should perform a risk assessment to identify the assets that need to be protected and the potential threats they face. Based on the risk assessment results, they can determine the appropriate frequency of pen testing.
  4. Business changes: Significant changes to the business, such as mergers and acquisitions or the adoption of new technologies, may require additional pentesting to ensure that the security posture remains effective.

In general, organizations should perform penetration testing regularly, at least annually, or more frequently if required by regulatory requirements or risk assessment. However, it’s important to note that pentesting is just one part of a comprehensive security program. It should be supplemented with other security measures, such as vulnerability scanning, security awareness training, and incident response planning. Artifice Security recommends that pen testing be done at least annually and preferred semi-annually based on how often major vulnerabilities are related. Quarterly penetration tests are recommended for organizations with a larger attack surface or regularly change their network or applications.

Need a consultation for penetration testing services? Book a call with Artifice Security today!

Artifice Security is an expert cybersecurity services provider that specializes in penetration testing. Consider the following reasons for companies to hire Artifice Security for pen testing services:

  1. Expertise and Experience: Artifice Security’s penetration test team comprises highly skilled and experienced professionals with a deep understanding of the latest threats and attack techniques. They have worked with numerous clients in diverse industries, giving them a broad perspective on security challenges and solutions.
  2. Comprehensive Testing: Artifice Security’s pen testing methodology is extensive and covers all aspects of a company’s security posture. They use a combination of automated and manual testing techniques to identify vulnerabilities and assess the overall effectiveness of the security controls in place.
  3. Customized Approach: Artifice Security takes a personalized approach to pen testing, adapting the test’s scope and depth to meet each client’s specific needs. They collaborate closely with the client to comprehend their objectives and goals before developing a testing plan to meet them.
  4. Actionable Results: Artifice Security delivers detailed and actionable reports that clearly identify vulnerabilities and provide recommendations for remediation. The reports are designed to be easily understood by both technical and non-technical stakeholders, providing clear guidance on improving the organization’s security posture.
  5. Compliance: Artifice Security’s pen testing services are designed to meet the requirements of various compliance regulations, such as PCI DSS, HIPAA, and GDPR. By engaging Artifice Security to conduct a pen test, companies can ensure they meet the necessary compliance requirements and avoid potential fines and legal issues.

Artifice Security is a reliable and trustworthy partner for companies that take the protection of their assets and data from cyber threats seriously. Our expertise, comprehensive testing approach, customized methodology, actionable results, and experience make Artifice Security an excellent option for any company looking to enhance its security posture.

Have more questions about choosing the best penetration testing company? Visit our Ultimate Guide to Penetration Testing page

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