How Often Should Your Company Conduct a Penetration Test? A Three-Part Practical Guide for CIOs

How Often Should Your Company Conduct a Penetration Test? 

CIOs often ask me how often they should do cybersecurity testing or penetration tests, but there isn’t a simple answer. “How often should our company conduct a penetration test?”

For most companies, testing at least once a year is a good starting point. However, annual testing should not be seen as the final goal.

A penetration test helps show how secure your company is at a given point in time. But after the test, new apps, cloud moves, acquisitions, infrastructure updates, identity changes, or new third-party tools can introduce new risks. NIST also says that how often you test should depend on your risk, and you may need to test more often as your systems and threats change.

For CIOs, the better question is often:

“What events should trigger a penetration test, and how should we prioritize testing across our environment?”

The answer depends on your company’s risk, technology environment, regulatory requirements, and rate of change.

This three-part blog post will help you decide when annual penetration testing is enough, when you should test more often, and how to create a testing schedule that fits your budget.

What Is a Penetration Test?

A penetration test is a security assessment in which skilled testers try to find and exploit weaknesses in your systems, apps, networks, cloud environments, and other technology.

The goal isn’t just to make a list of weaknesses.

A vulnerability scan might tell you that a weakness exists. A penetration test goes further by asking:

Can an attacker actually exploit it?

• What could they access?
• Could they move deeper into the environment?
• Could multiple weaknesses be combined into a more serious attack path?

This difference is important for IT directors and business leaders.

A report containing 50 vulnerabilities may sound alarming, but not every vulnerability represents the same level of business risk. Some, like a self-signed SSL cert, may be difficult to exploit or have limited impact. Others may provide an attacker with a path to sensitive information, administrative access, business-critical systems, or customer data.

Penetration testing helps you understand what those findings really mean for your business.

Tanner Security would test your systems the way an attacker would. This helps you see how weaknesses could be used against you, what you should fix first, and how to mitigate the problem in your IT environment.

How Often Should a Company Conduct a Penetration Test?

For most companies, doing a penetration test once a year is a good minimum standard and usually meets compliance standards.

However, you should also plan extra tests after big changes to your technology setup.

We normally recommend annual testing and additional assessments following major infrastructure changes, cloud migrations, acquisitions, major deployments, or security incidents. We also recommend conducting ongoing vulnerability assessments in addition to these tests.

Here’s a practical way to approach this:

Annual Testing: The Baseline

A full penetration test every 12 months lets your company verify that your key security controls are working as intended.

Annual testing helps you identify new weaknesses or security gaps, confirm that past fixes worked, and show customers, auditors, insurers, and leaders that you’re staying secure.

If your environment doesn’t change much, annual penetration testing may be enough to keep you confident in your security.

However, most companies today deal with frequent changes.

Why an Annual Calendar Alone Is Not Enough

Imagine your company conducts a penetration test in January.

The test goes well. Major vulnerabilities are identified and addressed.

In March, you migrate a critical application to AWS.

In May, you acquire another company.

In July, you deploy a new customer portal.

In September, you integrate a new third-party SaaS platform with access to sensitive data.

If you wait until next January to test again, important changes could go untested for months.

That’s why CIOs keep asking me how often they should perform tests: they should combine regularly scheduled tests with extra tests after major changes.

Your yearly test acts as a regular security check.

Major changes should prompt extra testing if the risk is high enough.

For companies subject to PCI DSS, this concept is more than a best practice. PCI guidance requires penetration testing at least annually and after significant infrastructure or application changes, with internal and external testing requirements defined for applicable environments.

How Penetration Testing Frequency Should Work

The best testing schedule depends on a few key factors.

1. How Quickly Your Technology Environment Changes

A company with a stable network will need a different testing schedule than one that launches new apps every month.

If your company often adopts new technology, you should consider testing more often or focusing on specific areas.

This may include businesses that regularly:

• Release custom developed web application features
• Deploy custom software
• Make significant changes to AWS or Azure
• Integrate new APIs
• Acquire other companies
• Add remote access systems
• Change identity and authentication platforms
• Introduce AI applications or third-party AI tools

You don’t need to run a full penetration test every time you make a small change.

Instead, match the scope of your test to the level of risk.

A major update to a customer-facing application may justify targeted web application penetration testing. A new cloud deployment may warrant an AWS penetration test or a cloud penetration test. A major network change may justify testing external and internal attack exposure.

The main goal is to test what has changed and see how those changes might affect your security.

2. The Value of Your Systems and Data

Not all systems need to be tested as often as others.

A public marketing website that does not process sensitive information generally poses a different level of risk than an application that contains financial information, healthcare data, government contract data, manufacturing designs, intellectual property, or customer records.

IT directors or CIOs should focus their testing on what matters most to the business.

If a system were compromised, ask:

“Could the company continue operating?”

“Could customer or employee data be exposed?”

“Could an attacker gain access to other critical systems?”

“Would the incident trigger legal or regulatory obligations?”

“Could the company lose an important customer or contract?”

The bigger the possible impact, the more often you should test.

3. Compliance and Customer Requirements

Compliance rules can significantly affect how often you need penetration testing.

PCI DSS, for example, requires applicable penetration testing at least every 12 months and after significant infrastructure or application changes.

Other frameworks may let you set your own schedule based on your risk, rather than applying a single rule to everyone.

This is where companies often make a mistake.

They ask:

“What is the minimum frequency required?”

A better question is:

“What frequency gives us reasonable assurance based on our actual risk?”

Compliance should establish a floor, not necessarily a ceiling.

If your company has important systems that change often, testing just once a year to meet the minimum requirement is not enough.

4. Your Company’s Threat Profile

Some companies are more attractive targets than others.

Healthcare companies hold large amounts of sensitive patient information. Financial services firms may be targeted for fraud and financial gain. Manufacturers may face ransomware and intellectual property theft. Defense contractors may be targeted by sophisticated threat actors seeking sensitive information.

Being a small business doesn’t always mean you have low risk.

Attackers often target smaller companies because they believe security resources and monitoring capabilities may be more limited.

How often you test should depend on who might target your company and what they could get if they succeed.

Penetration Testing Frequency Related Services

• External Network Penetration Testing: Evaluate your company’s internet-facing systems from the perspective of an external attacker. Testing may include public infrastructure, VPNs, remote access systems, cloud services, and other externally accessible assets. Tanner Security recommends annual testing and additional testing after significant changes.
• Internal Network Penetration Testing: Determine what an attacker could accomplish after gaining an initial foothold inside your network.
• Web Application Penetration Testing: Evaluate business-critical web applications for vulnerabilities involving authentication, authorization, session management, input validation, APIs, and business logic.
• Custom Application Penetration Testing: Assess proprietary applications with complex workflows, integrations, user roles, and functionality that may require deeper manual testing.
• Cloud Penetration Testing: Test AWS, Azure, and other cloud environments for exploitable weaknesses and misconfigurations.
• Vulnerability Assessments: Identify known vulnerabilities more frequently and use the results to support ongoing remediation between penetration testing engagements.
• Cybersecurity Risk Assessments: Evaluate the broader cybersecurity program and identify which systems, threats, and weaknesses should receive the highest priority.

Penetration Testing Frequency FAQ’s

How often should a company conduct a penetration test?

For most companies, conducting a penetration test at least once a year is a good starting point. However, companies should consider additional testing after significant changes to their environment, such as cloud migration, major application deployment, acquisition, significant infrastructure change, or cybersecurity incident. The right penetration testing frequency should be based on your company’s risk, the sensitivity of your data, compliance requirements, and how quickly your technology environment changes.

Is annual penetration testing enough?

Annual penetration testing may be enough for a company with a relatively stable, lower-risk technology environment. However, many companies make significant changes throughout the year that can introduce new security risks. A practical approach is to conduct a comprehensive penetration test annually and perform targeted testing when major changes affect critical systems, applications, cloud infrastructure, or identity and access controls.

What changes should trigger another penetration test?

A company should consider additional penetration testing after a major cloud migration, deployment of a new customer-facing application, significant application update, acquisition, network redesign, major change to remote access or identity systems, or a cybersecurity incident. The key question is whether the change creates a new attack surface or could affect the security of business-critical systems.

Should we perform a penetration test after moving to AWS or another cloud provider?

A major cloud migration is a good time to consider penetration testing or a cloud security assessment. Moving systems to AWS, Azure, or another cloud platform changes how identities, permissions, networks, applications, and data are secured. A penetration test can help determine whether an attacker could exploit weaknesses introduced during the migration, while a configuration or cloud risk assessment can identify broader security and governance gaps.

How often should web applications be penetration tested?

Business-critical web applications should generally be tested at least annually and after significant changes. This may include major feature releases, new APIs, authentication changes, new user roles, significant third-party integrations, or changes to how the application handles sensitive information. Companies that release major changes frequently may benefit from more regular or targeted application security testing.

Can a vulnerability assessment replace a penetration test?

No. A vulnerability assessment and a penetration test serve different purposes. A vulnerability assessment identifies known weaknesses and is useful for ongoing security monitoring. A penetration test goes further by determining whether weaknesses can actually be exploited and what an attacker could potentially accomplish. Many companies benefit from conducting vulnerability assessments more frequently while using penetration testing to validate real-world risk.

How do we determine the right penetration testing schedule for our company?

The right schedule should be based on risk rather than simply selecting a date on the calendar. Start by identifying your most business-critical systems, the sensitivity of the information they contain, how often the environment changes, and any compliance or contractual requirements. An annual comprehensive penetration test combined with targeted testing after significant changes is often a practical approach. A cybersecurity risk assessment can also help determine which systems should receive the highest testing priority and where your security budget will have the greatest impact.