Penetration Testing for Healthcare: How to Get Started

BY Paul Kubler

Stolen medical data can fetch up to 50 times more value than financial data on the black market, making healthcare data a high-value target for cyber criminals ^[1]. Thanks to a rising tide of breaches, healthcare companies are facing extreme costs and strict compliance mandates like HIPAA. With the average data breach in healthcare costing over 10 million USD ^[2], penetration testing has become a critical defense measure for companies looking to avoid disruption and costly breaches.

If you’ve never conducted a penetration test, getting started may seem daunting. In this guide, we’ll walk you through the essentials, show you how to start a testing program, and cover why healthcare is vulnerable, what a test entails, and how to choose a partner to protect patient data and meet your security and compliance goals.

The Unique Security Challenges in Healthcare Environments

Healthcare IT environments face unique challenges that make cybersecurity especially complex. One primary challenge has to do with any legacy systems or outdated medical devices that can’t easily be upgraded or taken offline. For instance, hospitals and clinics often rely on equipment and software that are decades old. A recent study found 73% of healthcare providers still use medical devices running on legacy operating systems ^[3].

Third-Party and Vendor Risks

Another challenge revolves around the fact that modern healthcare is highly interconnected, with hospitals relying on third-party vendors for critical services like electronic health records, payment processing, imaging, and laboratory systems. This supply chain connectivity expands the attack surface. In fact, nearly 70% of healthcare records breached in 2023 were exposed through incidents at third-party partners or business associates ^[4].

Cloud Adoption and Telehealth Expansion

Healthcare has widely adopted cloud services and telemedicine, particularly after the COVID-19 outbreak. The increase in telehealth usage was over 3000% across 2020 while COVID -19 was in full swing and virtual care is still far more than prior to 2020. While cloud-based EHRs, patient portals and telemedicine applications improve access, they bring new security threats. Information stored within cloud applications may not be secure sufficient, improperly configured, or vulnerable without sufficient network security.

Balancing Security with Patient Care

Lastly, healthcare IT systems are life-critical, meaning they absolutely have to be up at all times to enable patient care. This makes hospitals an attractive target for ransomware and denial-of-service attacks. Healthcare providers are unable, unlike other industries, to bring down system after system with prolonged maintenance or security patches, nor are they capable of withstanding downtime. The attackers are aware of this squeeze, and given that over 57% of healthcare organizations have reported cyberattacks that impaired patient care, penetration testers are also aware of such high stakes and design engagements with caution so that no disruption occurs.

The Top Cybersecurity Threats in Healthcare Today

Healthcare faces many of the same cyber threats as other industries, but some attack types are especially prevalent and damaging in this sector. Below, we highlight a few of the main threats to the healthcare industry and how penetration testing can help address them.

Phishing

Phishing means that the attackers are sending spoof emails or messages pretending to be a credible source with the aim of tricking people into providing credentials or downloading malware. When it comes to healthcare, a common example of such phishing email could be one that is falsely claimed to have originated from the IT department, asking employees to reset their VPN password via a fake portal, and therefore stealing their login. Penetration testing may include simulated phishing among social engineering penetration tests.

Information Breaches

Data breaches and ePHI theft in healthcare typically refer to unauthorized access or theft of electronic protected health information (ePHI). This could be via hacking into databases, exfiltrating data through malware, or even insider wrongdoing. Penetration testers are trained to think like attackers and attempt to find the same cracks in your defenses. A pen test will probe your external network and web applications for common breach vectors and help close any gaps.

DDoS Attacks

Ransomware is a form of malware that encrypts files or systems and demands payment for the decryption key, while DDoS attacks overwhelm a system or website with traffic to knock it offline. For ransomware, pen testers often attempt the same techniques ransomware gangs use to see how far they can get and whether they can access critical systems. For DDoS, while a pen test doesn’t typically involve flooding your network, consultants can review your DDoS mitigation measures and even perform limited stress tests.

Obsolete technology

In addition to containing legacy programs and medical equipment, legacy systems also contain any other uses of software and operating systems that are still in operation based on compatibility requirements or money. These legacy systems are most often void of up-to-date security, meaning they have vulnerabilities that have long been resolved with newer technology. Penetration tests are capable of highlighting vulnerable areas by attempting to exploit commonly-known vulnerabilities of legacy programs, making practical recommendations designed to help eliminate risks while avoiding significant business disruption.

Vulnerabilities in Medical Applications and Devices

Healthcare penetration testing identifies potential critical vulnerabilities in custom applications, such as mobile health applications or telemedicine websites, before they are targeted by attackers. For instance, vulnerabilities in a patient portal may grant unauthorized access to protected health information (PHI). Penetration testing recreates real-world attacks, checking for vulnerabilities such as insecure APIs or broken authentication so that organizations discover and address risks, keeping patient data safe and secure.

Assets that Commonly Get Tested in Healthcare

When planning a healthcare penetration test, it’s important to define what will be in scope. Healthcare organizations have a broad range of IT assets, and a mature security program should eventually test all of them. However, there are a number of common focus areas, such as:

Internal and External Networks

In healthcare, network tests often reveal issues like open ports on outdated systems, weak Windows domain configurations, or flat networks with minimal segmentation. And since the hospital’s internal corporate network, clinical networks, and any outward-facing networks are the backbone connecting all devices and systems, a single misconfigured server or firewall rule can open the door to an institution-wide breach.

Common attacks like ransomware often start by exploiting a network-facing service, so regularly testing your network can catch those weak points before attackers do. Pen testers will typically perform external network testing, such as simulating an attacker probing your public-facing IPs for vulnerabilities, and internal network testing, simulating an insider or someone who breached the perimeter.

Web and Mobile Applications

Healthcare organizations have numerous applications, ranging from patient portals, scheduling, and telehealth video platforms, through mobile apps for tracking or messaging and so forth. Many of the applications touch sensitive patient data and are required to be available across the internet by patients and providers, which by itself raises risk.

Pen testing web and mobile apps can uncover vulnerabilities such as SQL injection, broken access controls, or inadequate encryption of data in transit. Testing apps ensures that this layer of your environment – the one directly used by patients and doctors – is secure against the most likely attacks.

Medical Devices and IoT

From MRI machines and infusion pumps to “smart” IV drips and patient wearables, the Internet of Medical Things (IoMT) is vast in a modern hospital. Pen testers can typically evaluate live medical devices in isolated instances, or verify new technology before it becomes widespread in the organisation.

This is important, since compromised medical devices can not only expose data but potentially threaten patient care. There have even been FDA alerts about device vulnerabilities. Regular penetration testing and risk assessment for IoMT helps identify those weaknesses so you can work with vendors to patch devices or put compensating controls in place

The Role of HIPAA Compliance in Healthcare

Compliance requirements loom large in healthcare security strategy. HIPAA is the main legislation in the U.S. on setting standards for protection of health care information. HIPAA’s Security Rule doesn’t specifically call for penetration tests or even vulnerability scans. But HIPAA does require covered entities to conduct periodic risk analysis and take appropriate action to reduce the identified risk. Penetration testing is widely regarded as an “addressable” measure under HIPAA; in other words, if it’s reasonable and appropriate for your organization, you should be doing it as part of meeting the requirement to “protect against reasonably anticipated threats” ^[5]. In fact, NIST (National Institute of Standards and Technology) offers guidance for HIPAA that specifically recommends penetration testing to validate the effectiveness of security controls. Pen tests provide real-world evidence that you’ve reviewed your security and remediated vulnerabilities, exactly what the auditor requires. It’s far better to find and remediate weakness via a controlled pen test than have it turned against you via breach, which comes with investigations and non-compliance fines, but that’s above and beyond the damage from the breach itself.

How Your Organization Can Engage in Penetration Testing

Ready to start penetration tests at your healthcare organization? By following the guide’s instructions, the tests will be effective, safe, and aligned with your goals.

Step 1 Identify Critical Assets and Risks

First, identify your most critical protection needs. In healthcare, this usually relates to systems that store or operate on ePHI (an electronic form of protected health information), life-critical medical devices, their core network infrastructure, and high-value web applications. Include participants from IT, security, compliance, and clinical divisions while creating an asset inventory.

Step 2: Define Goals and Scope of the Test

Next up, you should work on figuring out your requirements and overall goals. Are you trying to uncover as many vulnerabilities as possible across your entire network (broad assessment)? Or are you targeting a specific area, like a new patient mobile app or a recently deployed network segment (focused assessment)? A well-scoped test will concentrate on the highest-risk areas without accidentally disrupting sensitive operations.

Step 3: Choose the Right Penetration Testing Partner

Choose the right penetration testing partner if you don’t have qualified internal red teamers yourself. Remember that not all pen testing providers are equal, so look for one with healthcare experience, knowledge of compliance, and a methodology that fits your needs. Does your candidate have references in healthcare? What certifications do their testers hold? Will they provide a detailed report with remediation guidance?

Step 4: Plan the Engagement

When articulating plans and regulations, make certain that you coordinate with your chosen partner, setting up tests at such a time that disruption of operations is held to the minimum, with all legal and contract documents signed and finalized. Schedule with your IT personnel so that they don’t mistake the activities of the tester with an attack, nor make unintended changes within the test time span.

Step 5: Conduct the Test

Now you’re ready to let the pen testers do their real job, according to the plan that’s been agreed. While they test, they’ll generally employ some combination of automated scanners and manual methodologies aimed at discovering and taking advantage of vulnerabilities. They may, for instance, perform port scans and vulnerability scans of your network, attempt SQL injection, or probe default passwords of medical equipment.

Step 6: Review Findings and Remediate Vulnerabilities

Review findings and remediate vulnerabilities after testing, as the penetration testers will provide a detailed report of their findings that helps you determine the next steps. Also consider scheduling a debrief meeting with the testing team to walk through the report. This is your chance to ask questions and truly understand each finding, how difficult it was to exploit, what a real attacker could do with this, etc.

Step 7: Re-Test and Establish an Ongoing Testing Cycle

Once your review is complete, it is important to test some more and establish an ongoing testing cycle once your fixes are applied. Ideally, your penetration testing partner will include a follow-up test of the critical findings to confirm that vulnerabilities have been successfully remediated. For instance, if they found they could breach a web app via SQL injection, after you fix the code, they will try that attack again to ensure it’s truly resolved. Once everything is verified, you have a baseline of security.

Cybri: Your Partner for HIPAA and Healthcare Penetration Testing

As we discussed, healthcare penetration testing is rich in many aspects; security expertise, understanding of healthcare’s unique landscape, and a sensitive approach that considers patient safety and compliance. After looking at the challenges and steps above, you may be interested in finding a suitable partner. This is where Cybri comes in.

At Cybri, we have deep pen testing healthcare sector experience. Our approach checks all the boxes we’ve outlined in this guide, such as deep healthcare compliance expertise (e.g., HIPAA, HITRUST, and HITECH frameworks), highly qualified professionals, and a light-touch testing process.

Our US-based team ensures patient safety and uptime through a transparent, disruption-free process managed via our BlueBox PTaaS platform. And you receive comprehensive, actionable reports and remediation support tailored to your specific environment, from medical IoT to cloud apps, to not only pass audits but truly improve security.

Ready to fortify your healthcare cybersecurity? Get in touch with Cybri for a consultation. We can assess your needs and propose a penetration testing plan that fits your organization’s size, budget, and regulatory requirements. With Cybri’s support, you can confidently uncover hidden vulnerabilities before attackers do, strengthening your defenses and keeping your focus on delivering quality patient care.

Frequently Asked Questions

How often should healthcare orgs conduct penetration testing?

At a minimum, healthcare organizations should perform a full-scope penetration test once per year. Annual testing is recommended by industry best practices, and as of 2025, HHS is considering moving to yearly pen tests for HIPAA compliance ^[6]. Many organizations choose to test even more frequently or in a rolling fashion: for example, doing quarterly vulnerability scans plus targeted pen tests on different segments throughout the year.

What's the difference between a penetration test and a HIPAA security risk assessment?

A HIPAA Security Risk Assessment (SRA) is a broad evaluation required by HIPAA where an organization reviews all aspects of security risks to ePHI, including administrative, physical, and technical safeguards. It often involves checklists, policy reviews, and maybe high-level technical scanning. A penetration test, on the other hand, is a focused technical examination where testers actively try to exploit vulnerabilities in your systems.

Do pen tests disrupt patient care?

When done correctly, penetration tests should not disrupt patient care. Professional penetration testing firms take extensive precautions to avoid impacting production systems. Engagements are planned in coordination with your IT team, for example, scheduling testing during low-usage periods or maintenance windows. Critical life-safety systems can be excluded from direct testing or only tested with passive methods.

Are healthcare pen tests just about compliance?

When approached properly, penetration tests are about improving real security first and foremost, with compliance being a beneficial byproduct. It’s true that many healthcare organizations initially pursue pen testing to “check the box” for HIPAA, HITRUST, or a cybersecurity insurance requirement. But the true value comes in the security insights gained, as a penetration test will almost always uncover something that previously was unnoticed..

References

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