Cyber threats directed against the healthcare sector are at unprecedented levels. In fact, healthcare data breaches reached an all time high with 168 million patient records compromised in 2023 [1]. This illustrates that cybersecurity in healthcare is not merely an issue of data protection, but one of continuity of care and patient safety.
Hospital breaches can literally endanger lives, and the average cost of a breach in healthcare is nearly $10 million, which is the highest of any industry [2]. Because of that, healthcare organizations need more than basic IT security – they need specific penetration testing to find risks before attackers find them.
This buyer’s guide will discuss why healthcare requires a distinct approach to penetration testing, profile the best organizations in this space, and lay out what to consider when selecting a partner.
Why Healthcare Requires Specialized Penetration Testing
Due to the sensitive personal information that hospitals and clinics handle on a daily basis, a set of unique security challenges in healthcare IT environments dictate the need for a special form of penetration testing. Furthermore, many healthcare staff report that they are still using older technology. In fact, about 73% of healthcare organizations report that they rely on legacy systems [3], since they cannot possibly introduce any change into critical devices or software that would potentially disrupt care.
These two factors combined create a set of serious vulnerabilities, only made worse due to the nature of those systems, as they may not be easily patched or taken down without disrupting the services they provide [4]. A penetration tester with experience in the healthcare space realizes these limitations and understands how to work around them, assessing for vulnerabilities without the risk of unintended downtime.
The compliance and regulatory factors contribute to the need for specialization as well. Healthcare organizations must comply with laws such as HIPAA, HITECH, and often HITRUST frameworks. A generalist security assessment may overlook compliance gaps, while specialized healthcare pentesters know these regulations and will ensure tests adhere to requirements and help keep conduct compliant.
Going even further, there is another set of distinct threats currently on the rise in the healthcare industry; ransomware gangs that specifically target hospitals and clinics, since the attackers know that their victims cannot tolerate extended outages. The American Hospital Association called 2023 the “worst year ever” for healthcare cyberattacks, with 2024’s breaches even more “profound” in scale [3]. Seeing as this trend is not likely to step anytime soon, it is extremely important to consider the security of all networks and systems in the healthcare industry.
Penetration testers with the knowledge and experience dealing with the particular demands and requirements of medical workflows and devices, third-party EHR systems, and patient-safety considerations are often the best option, as they bring a unique set of skills to the table that generic pentesting firms simply are not capable of matching.
Therefore, choosing a specialized provider that employs a set of technical experts in legacy systems as well as modern EHR platforms, while also being aware of the operational realities of clinical care is a solid strategy that typically provides the best results overall, ultimately building a more resilient defense against the numerous threats that currently plague the industry.
Best Penetration Testing Companies for Healthcare (Vendor List)
1. Cybri
Best for: Healthcare organizations seeking a highly collaborative and transparent penetration testing partner with deep, certified expertise in healthcare compliance and security.
Cybri distinguishes itself as a premier penetration testing firm through its unwavering commitment to the healthcare sector. The company’s industry expertise is proven by its testers’ specialized knowledge in probing EHR systems, medical devices, and cloud-based healthcare applications with precision that avoids operational disruption. Their compliance alignment is exceptional, offering tailored assessments specifically designed for the HIPAA security rule and HITRUST CSF, ensuring that testing protocols directly map to regulatory requirements.
Cybri’s service offerings are enhanced by a highly collaborative model; clients engage directly with their 100% US-based Red Team through the proprietary BlueBox PTaaS platform. This tool provides real-time visibility into Cybri’s testing process, embodying transparency and enabling client IT teams to engage actively. A key strength is their client support & remediation, which includes clear, actionable guidance and complimentary retests to validate that vulnerabilities are resolved effectively.
Finally, Cybri brings detailed reporting to executives without losing track of risk and remediation for the technical teams and executives. The combination of a deep focus on healthcare, certified depth of expertise, and partnership-driven approach positions Cybri as a leading option for providers who prioritize security as a strategic necessity.
2. Drummond Group
Drummond Group provides healthcare penetration testing services that involve manual exploitation and real-world attack emulation beyond the vulnerability assessments. The purpose of the approach is to understand the likelihood of compromise and reporting with actionable items to remediate the issues, to improve the organization’s cybersecurity posture and reduce the risk of a data breach.
Drummond Group’s Comprehensive Healthcare Risk Assessment (CHRA) can support a variety of regulations. But while their CHRA is valuable for demonstrating compliance, organizations primarily seeking a nimble, adversarial perspective might find the process better suited for audit preparation than for pure, unvarnished security testing.
They offer cloud penetration testing, social engineering, security awareness training, application testing, and IoMT / medical device testing. Drummond emphasizes trust, quality, and integrity, with experts who understand how to create solutions to fit each healthcare environment. They can thus be suited for large health systems that require rigorous, audit-ready compliance reporting. However, their comprehensive, framework-heavy approach might be more process than smaller organizations and startups with a straightforward tech stack actually needs.
3. Depth Security
Depth Security offers penetration testing services to provide realistic attacks to identify and exploit vulnerabilities in healthcare networks and applications. Their established methodology, developed through numerous assessments, delivers detailed exploitation paths and concrete proof of concepts. While thorough, this comprehensive approach can sometimes uncover a volume of technical detail that may exceed the immediate needs of organizations seeking a more high-level, strategic overview of their risk posture.
Their services consist of network and application penetration testing, adversary emulation, and customized assessments in healthcare environments. Depth Security’s evidence-based, deep-dive methodology can be great for finding obscure vulnerabilities, but their intense, king-of-the-hill style of testing might be more aggressive than what is required for a routine compliance check.
4. Red Sentry
Red Sentry does healthcare penetration testing, simulating attacker methodologies to discover risks in healthcare systems like EHRs, medical devices, patient portals, and vendor integrations. By combining automated scans with man attacks, Red Sentry evaluates for technical vulnerabilities, business logic vulnerabilities, and social engineering weaknesses. Red Sentry also provides documentation to support compliance efforts and suggests steps to address security risks.
Their team is familiar with the challenges of clinical workflows, medical device security, and regulatory requirements. Red Sentry offers penetration testing services across various areas, including infrastructure, Internet of Things (IoT), and compliance-related assessments. Red Sentry can generate detailed reporting in days instead of weeks, but while Red Sentry’s promise of rapid, detailed reporting is attractive for fast-paced environments, organizations seeking a more methodical and thorough testing pace might find their accelerated timeline less conducive to learning.
5. Software Secured
Best for: Healthcare SaaS companies and technology vendors requiring manual penetration testing with robust remediation support and compliance mapping.
Software Secured provides manual penetration testing for healthcare applications handling sensitive PHI. Their methodology maps vulnerabilities to frameworks such as OWASP Top 10, SANS Top 25, and NIST to facilitate HIPAA compliance. They provide detailed reports that include remediation suggestions, stating that they do not provide false positives. For vulnerability triage and tracking, the company provides continuous support via Slack for teams willing to engage in vulnerability management in a dynamic and asynchronous manner.
In terms of service, Software Secured conducts testing for network, web application, mobile and APIs, as standalone engagements or as Penetration Testing as a Service (PTaaS). Software Secured has a reputation for finding high risks (approximately 20% of findings were rated as high severity) and showing transparent pricing. However, their approach to engagement in supporting developers, provided via slack, may not be ideal for more traditional healthcare providers that might prefer formal communications or more standardized project management approaches.
Key Evaluation Criteria: How to Choose the Right Partner
| Criteria | What It Means | Why It Matters for Healthcare |
| Industry Expertise | A provider with proven experience working with healthcare systems like EHRs and medical devices. | They understand critical workflows and are less likely to disrupt patient safety or 24/7 uptime during testing. |
| Compliance Alignment | The firm is knowledgeable about regulations (HIPAA, HITRUST) and incorporates compliance checks into the test. | The pentest must not only find technical holes but also support mandatory regulatory risk assessments. |
| Service Offerings | The vendor can test all layers of your environment, from networks and cloud to medical IoT and social engineering. | Healthcare IT ecosystems are broad; multifaceted testing ensures no critical area is overlooked. |
| Reporting Quality | Clear, actionable reports that rank findings by risk and include detailed remediation instructions are provided. | Good reporting links vulnerabilities to compliance requirements and offers a roadmap for enhancing security. |
| Certifications & Credentials | Both the business and its testers possess the necessary qualifications, such as CISSP, OSCP, and HITRUST Assessor. | Certifications serve as a reminder that the supplier upholds strict standards and stays current with security best practices. |
| Client Support & Remediation | Retesting, remediation assistance, and debriefs are part of the post-test support provided by the vendor. | Having a partner to help plan fixes is essential for implementing significant security improvements with frequently overworked IT staff. |
Final Thoughts & Next Steps
Selecting a pen testing partner is a very important step for any healthcare organization. The costs are high: patient data, trust, and safety can be at risk. As we’ve described, the very best providers mix technical capability with domain knowledge specific to the healthcare space. Providers not only bring strong hacking skills, they also bring an understanding of the clinical workflows, the nuances of medical devices, and the compliance requirements. By selecting a true specialist in this space, healthcare organizations can identify where vulnerabilities exist, before it is discovered by an attacker, and the organization can continue to provide care to patients.
As a next step, healthcare security leaders should evaluate what testing they currently need and contact one of the approaches outlined in this guide. Talk to them about your environment and challenges; good partners will want to adapt their approach to your reality. For example, Cybri provides free consultations to scope healthcare penetration testing engagements and describes how their BlueBox platform keeps clients engaged during testing.
In the end, your aim should be to establish a permanent relationship with a security firm that will protect your organization from the next attack year after year. Cyber threats are constantly changing, so your company shouldn’t waste any more time. You can guarantee better protection for your patients and their data in the future by enhancing your security today with specialized penetration testing.
Frequently Asked Questions
References
- HIPAA Journal. (July 2025). Healthcare Data Breach Statistics
- HIPAA Journal. (July 2024). Average Cost of a Data Breach Rises to $4.88M; Falls to $9.77M in Healthcare
- Paubox. (June 2025). Modernization of healthcare legacy systems
- S2S Communications. (July 2025). Why Healthcare Needs Specialized Penetration Testing to Protect Patient Data
- Network Assured. (August 2024). How Much Does Red Team Penetration Testing Cost Today?
- Gartner. (2023). How frequently do you perform penetration testing of your web applications?
- Outpost24. (Aug 2025). Does HIPAA require penetration testing?
