Organizations that handle sensitive data should be diligent in their security efforts, including regular penetration testing. Even minor data breaches can cause significant damage to an organization’s reputation and bottom line.

There are two main reasons why regular penetration testing is necessary for secure web application development.

  • safety: Web applications are constantly evolving and new vulnerabilities are discovered all the time. Penetration testing helps identify vulnerabilities that can be exploited by hackers so you can fix them before they do harm.
  • compliance: Depending on your industry and the type of data you work with, you may need to comply with specific security standards (PCI DSS, NIST, HIPAA, etc.). Regular penetration testing helps ensure that your web application meets these standards and avoids penalties for non-compliance.

How often should I pen test?

Many organizations, large and small, Have an annual penetration testing cycleBut what is the best frequency for penetration testing? Is once a year enough or should it be done more often?

The answer depends on several factors, including the type of development cycle, the importance of your web application, and your industry.

More frequent penetration testing may be required if:

Have an agile or continuous release cycle

Agile development cycles are characterized by short release cycles and rapid iteration. This makes it harder to track changes made to the codebase and increases the chances of introducing security vulnerabilities.

If you only test once a year, it’s likely that vulnerabilities will go undetected for a long time. This can expose your organization to attack.

To mitigate this risk, the penetration testing cycle should be aligned with the organization’s development cycle. For static web applications, testing every 4-6 months is sufficient. However, frequently updated web applications may need to be tested more frequently, such as monthly or weekly.

Web applications are business critical

Systems that are critical to an organization’s operations require special attention when it comes to security. This is because a compromise of these systems can have a catastrophic impact on your business. potential loss.

For example, let’s say your organization’s e-commerce site is down for an hour due to a DDoS attack. Not only do you lose potential sales, but you also have to deal with the cost of attacks and negative publicity.

To avoid this scenario, it’s important to ensure that your web application is always available and secure.

Non-critical web applications typically need only be tested once a year, while business-critical web applications should be tested more frequently to ensure there is no risk of major outages or data loss .

Web applications are for customers

If all your web applications are internal, you may be able to reduce the frequency of penetration testing. However, if your web application is open to the public, you should pay particular attention to your security efforts.

Web applications that are accessible to external traffic are more likely targets for attackers. This is due to the growing pool of attack vectors and the potential entry points that attackers can exploit.

Also, customer-facing web applications tend to have more users. This means security vulnerabilities are exploited more quickly. For example, a cross-site scripting (XSS) vulnerability in an external web application with millions of users can be exploited within hours of being discovered.

To protect against these threats, it’s important to penetrate customer-facing web applications more often than internal ones. Depending on the size and complexity of your application, monthly or weekly pen tests may be required.

you are in a high risk industry

Certain industries are more likely to be targeted by hackers due to data confidentiality. For example, healthcare organizations are often targeted because they hold protected health information (PHI).

If your organization is in a high-risk industry, you should consider conducting penetration tests more frequently to ensure your systems are secure and compliant with regulations. This helps protect your data and reduces the chance of costly security incidents.

No internal security operations or pen test team

This may sound counterintuitive, but if you don’t have an in-house security team, you may need to conduct penetration tests more frequently.

Organizations without a dedicated security staff are more likely to be vulnerable to attack.

If you don’t have an in-house security team, you’ll need to rely on external pen testers to assess your organization’s security posture.

Depending on the size and complexity of your organization, pen testing may need to be done monthly or weekly.

You are focused on mergers and acquisitions

There is often a lot of confusion and confusion during mergers and acquisitions. This can make it difficult to keep track of all the systems and data that need to be secured. As a result, it is important to conduct penetration tests more frequently during these times to ensure all systems are secure.

M&A also means adding new web applications to an organization’s infrastructure. These new applications may contain unknown security vulnerabilities that could put your entire organization at risk.

In 2016, Marriott acquired Starwood, unaware that hackers had exploited a flaw in Starwood’s reservation system two years earlier. Over 500 million customer records compromised.This put Marriott in hot water UK Watchdog ICO andresulting in a fine of £18.4m in the UK. According to Bloomberg, more problems lie ahead as hotel giants could “face up to $1 billion in regulatory fines and legal costs.”

To protect against these threats, it is important to conduct penetration tests before and after acquisition. This allows you to identify potential security issues and fix them before the migration is complete.

The Importance of Continuous Penetration Testing

Regular penetration testing is important, but not enough in today’s world. Continuous penetration testing becomes more important as companies increase their reliance on his web applications.

There are two main types of penetration testing: time-boxed and continuous.

Traditional penetration testing occurs on a set schedule, such as once a year. In today’s world where companies are relying more and more on his web applications, this kind of penetration testing is no longer enough.

Continuous Penetration Testing is the process of continuously scanning a system for vulnerabilities. This allows you to identify and fix vulnerabilities before they can be exploited by attackers.Continuous penetration testing helps find and fix security issues as they happen Instead of waiting for regular evaluations.

Continuous penetration testing is especially important for organizations with agile development cycles. Because new code is deployed frequently, the potential for introducing security vulnerabilities increases.

Penetration testing as a service model is where continuous penetration testing stands out. Outpost24’s PTaaS (Penetration-Testing-as-a-Service) platform Enterprises can easily conduct continuous penetration testing. The Outpost24 platform keeps up with your organization’s latest security threats and vulnerabilities, so you can be confident that your web applications are secure.

  • Manual and automatic pen tests: Outpost24’s PTaaS platform combines manual and automated penetration testing to give you the best of both worlds. This means you can find and fix vulnerabilities faster while still enjoying the benefits of expert analysis.
  • We offer comprehensive coverage: Outpost24’s platform covers all OWASP Top 10 Vulnerabilities and more. This means you can be confident that your web applications are safe against the latest threats.
  • cost effective: At Outpost24, you only pay for the services you need. This makes continuous penetration testing more affordable, even for small businesses.


Regular penetration testing is essential for secure web application development. Depending on your organization’s size, industry, and development cycle, you may need to modify your penetration testing schedule.

An annual penetration testing cycle is sufficient for some organizations, but not most. For business-critical, customer-facing, or high-traffic web applications, continuous penetration testing should be considered.

Outpost24’s PTaaS Platform Conduct ongoing pentesting in an easy and cost-effective manner. Contact us today to learn more about our platform and how we can protect your web applications.

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