10 Signs Your Organization Needs a Penetration Test Immediately
July 31, 2025
Over 2,200 cyberattacks hit businesses every day. Most exploiting known but unpatched vulnerabilities. These blind spots are why the average cost of a breach has climbed to $4.88 million, impacting not just finances but trust, compliance, and operations. One of the biggest signs you need a penetration test is the presence of undetected vulnerabilities lurking in your systems, despite existing security controls. Pen testing helps uncover these hidden risks before attackers do..
How do you know it is time for a pen test? Waiting for a breach is not an option. If you are unsure whether it is time to test your defenses, here are ten clear signs your organization cannot afford to ignore.
What Is a Penetration Test (and What It Isn’t)?
Many people confuse simple vulnerability scanning with penetration testing, but these are two very different processes.
A penetration test, or pen test, is a simulated cyberattack conducted by ethical hackers to uncover security vulnerabilities in your systems, networks, or applications just like a real attacker would. Unlike automated scans, pen testing mimics real-world tactics, exploiting weaknesses to assess how far an attacker could go and what damage they could cause.
| Penetration Test IS | Penetration Test ISN’T |
|---|---|
| A simulated real-world cyberattack | A basic vulnerability scan |
| Performed by skilled ethical hackers | Fully automated or tool-only |
| Focused on exploitation and impact | Focused only on detection |
| Context-aware and tailored to your environment | Generic or one-size-fits-all |
| Helps prioritize high-risk vulnerabilities | Generates long lists without context |
| Conducted at scheduled intervals (or after major changes) | A continuous or real-time monitoring tool |
| A valuable layer in your broader security strategy | A substitute for patching, monitoring, or other defenses |
| Often required for compliance and third-party assurance | A complete compliance solution on its own |
10 Definitive Signs You Need a Penetration Test
If any of the following scenarios apply to your organization, it is time to schedule a penetration test.
1. You have Never Had a Pen Test Before
If you have never tested your defenses through simulated attacks, you are essentially operating blind. Without knowing your weak points, you cannot fix them.
2. You have Recently Launched a New Application or Feature
Every new application or significant update introduces potential risks. Before going live with a new web or mobile app, a penetration test acts as a real-world security baseline assessment. This step helps catch vulnerabilities missed during development and ensures sensitive data is not exposed from day one.
3. You have Made Significant Network Infrastructure Changes
Among the top signs you need a penetration test is when infrastructure changes, like cloud migrations, introduce new attack surfaces your team has not yet fully assessed.
4. You Need to Meet Compliance Requirements
Several compliance frameworks mandate or endorse pen testing to ensure robust security practices.
- PCI DSS (Requirement 11.4 & 11.4.2): Requires organizations that handle cardholder data to perform external and internal penetration testing at least annually and after any significant changes to the environment.
- HIPAA (45 CFR §164.308(a)(1)(ii)(A) & (B)): While not explicitly requiring penetration testing, the Security Rule mandates regular risk analysis and risk management. Penetration testing is a widely accepted method to identify vulnerabilities during these assessments.
- CJIS Security Policy (Section 5.10.1.3): Requires agencies that access criminal justice information to perform periodic security testing, including vulnerability and penetration testing, to ensure systems are secure against evolving threats.
Penetration testing provides tangible evidence to auditors that your organization is actively identifying and mitigating vulnerabilities, a core expectation of most modern compliance standards.
5. You have Recently Experienced a Security Incident
If your organization experiences a breach, a follow-up pen test is vital to identify and fix remaining vulnerabilities. This test helps determine how attackers gained access and whether similar vulnerabilities remain. It validates that security holes have been patched and ensures your remediation efforts are effective, reducing the risk of repeat incidents.
6. Security Regulations in Your Industry Have Been Updated
When major security regulations change, such as the transition to PCI DSS 4.0 or new state privacy laws, your controls may need to be re-evaluated. A penetration test helps you understand the impact of new rules and identify any new security gaps that must be closed to remain compliant.
7. You Are Undergoing a Merger or Acquisition
Mergers and acquisitions introduce significant security risks. Integrating another company’s technology stack means inheriting their networks, applications, and potentially their vulnerabilities. A comprehensive penetration test of newly acquired assets is a critical due diligence step to understand and mitigate inherited risks.
8. You Need to Validate Your Security Investments
Organizations invest heavily in security tools and personnel, but are these investments effective? Penetration testing simulates real-world attack vectors to test whether your defenses such as firewalls, can detect and stop determined attackers. The results help you optimize security spending and focus on what truly matters.
9. You are Relying Solely on Automated Scans
Automated tools are great for surface-level checks, but they often miss business logic vulnerabilities, chained exploits, or real-world attack scenarios. A manual pen test fills that gap.
10. It Has Been Over a Year Since Your Last Test
The threat landscape evolves rapidly. New vulnerabilities are discovered daily, and attackers constantly refine their methods. Best practices from frameworks like NIST recommend conducting a penetration test at least annually. For high-risk applications or those handling sensitive data, more frequent testing is advised. Regular testing ensures your security posture remains current and effective.
How to Prepare for a Successful Penetration Test
To maximize the value of your penetration test, follow these steps:
- Define the Scope: Clearly outline which applications, networks, or IP ranges are in-scope and which are off-limits.
- Choose the Right Partner: Select a reputable firm with certified penetration testers and experience in your industry.
- Communicate with Your Team: Inform key stakeholders, including IT and incident response teams, about the planned test (unless conducting a blind test).
- Establish Rules of Engagement: Define the testing window, communication protocols, and procedures for handling critical vulnerabilities.
For a step-by-step guide, check out the detailed blog on how to conduct penetration testing to ensure nothing is overlooked during your prep.
Do not Wait: The Consequences of Skipping a Pen Test
Delaying a penetration test leaves your organization exposed to unknown vulnerabilities. The risks include data breaches, financial loss, reputational damage, and regulatory fines. Proactive cybersecurity testing is a cornerstone of modern risk management. If you recognize even a few of these signs you need a penetration test; you can shift from a reactive to a proactive security posture, protecting your business, customers, and reputation.
Ready to assess your risk? Get a Personalized Pen Test Scope & Quote. Or, see our automated website and API vulnerability scanner in action with a 14-day free trial.
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