Penetration testing that finds weaknesses before attackers do

Winmill pairs AI-driven testing with senior human testers to simulate real-world attacks across your systems, applications, and people, giving you clear visibility into your vulnerabilities, your true risk exposure, and the issues that need attention.

Continuous testing

Continuous, scalable security testing

Modern cyber threats evolve too quickly for annual or one-time penetration testing to be enough. The Penetration Testing Stream is Winmill’s continuous testing program, built for organizations that need ongoing visibility into their security posture rather than a point-in-time snapshot.

A subscription gives you recurring, targeted penetration testing aligned to your environment, technology stack, and risk profile. Our security engineers deliver prioritized findings, remediation guidance, and ongoing collaboration, so vulnerabilities are identified and addressed before attackers can exploit them.

Explore the Penetration Testing Stream

The Penetration Testing Stream is ideal for teams that want

  • Continuous coverage instead of yearly penetration testing.
  • Faster validation after code releases or infrastructure changes.
  • A predictable cost structure for recurring security testing.
  • A partnership with experienced penetration testers who learn your environment over time.
What you receive

A Winmill penetration test

The best way to know how intruders will attack your systems is to simulate a real-world attack under controlled conditions. You pinpoint actual vulnerabilities from the perspective of a motivated attacker, and most importantly, the test tells you how to fix the problems.

Our testing approach is based on industry standard methodologies such as PTES, NIST, OWASP WSTG, and OWASP IoTTG, along with our own proprietary checklists and exploits. We always include technical details with enough information to reproduce our findings, and every engagement comes with a complimentary readout call to review your assessment.

Every engagement includes

  • Executive summary report.
  • Full technical report.
  • Remediation action plan.
  • Retest to validate remediation.
AI-accelerated testing

Tested with AI, verified by humans

Modern attack surfaces are too large for manual testing alone. Winmill incorporates AI throughout the Penetration Testing Stream to expand the breadth and depth of every engagement, and every finding is validated by senior testers before it reaches your report.

Broader coverage

AI-assisted reconnaissance and scanning explore more of your attack surface, so endpoints, integrations, and edge cases that manual testing would miss still get examined.

Deeper testing

AI-generated attack variations probe authentication, business logic, and APIs with far more permutations than human hours alone could cover.

Verified by humans

Every AI-surfaced finding is manually validated and proven by our senior testers. Your report contains real, exploitable issues, not false-positive noise.

Key benefits

What penetration testing does for you

A complete view of vulnerabilities

You receive a prioritized list of issues, based on the exploitability and impact of each finding using an industry-standard ranking process.

Regulatory compliance

Detailed reports help you avoid fines for non-compliance and demonstrate due diligence to auditors by maintaining required security controls.

Avoiding the cost of system downtime

Our team provides specific guidance and recommendations to avoid financial pitfalls by identifying and addressing risks before attacks or security breaches occur.

Ensuring the stability of new assets

For organizations that rapidly develop and adopt new applications and infrastructure, regular testing gives stakeholders confidence that new assets and upgrades are not introducing new security flaws.

Team certifications
GPENGWAPTOSCPOSCEOSWPCEHCISACISSPCompTIA CASP+CompTIA Secure Infrastructure SpecialistMITRE ATT&CK Cyber Threat IntelligenceMITRE ATT&CK Purple Teaming Methodology
Why Winmill

Why enterprises choose Winmill as their testing partner

Extensive knowledge and experience

Our team has deep experience in penetration testing of external and internal networks, web applications, application infrastructure, and APIs, along with social engineering attacks such as physical security and phishing campaigns. We have tested for companies in healthcare, financial services, telecom, energy, and other industries.

High-quality reports

Penetration assessments are always peer-reviewed and edited by professional technical writers before delivery. In addition to comprehensive technical detail, we provide condensed information security summaries for executive and senior management.

Valuable, actionable insights

Our assessments provide actionable insight into discovered vulnerabilities, potential attack paths, the business impact of breaches, and remediation steps, so stakeholders can quickly digest what matters and act on it.

Certified, research-driven testers

To stay one step ahead of attackers, each of our team members devotes over 400 hours per year to research and the security community: publishing articles, participating in conferences, developing custom testing tools, and writing new exploit code.

Coverage

Five types of penetration tests

Web apps

Web applications are a common target for attackers exploiting flaws in authentication, session management, input validation, and access controls. Our testing simulates real-world attacks to uncover weaknesses before they can be abused, with detailed findings and prioritized remediation guidance tailored to your environment.

Mobile apps

Mobile apps introduce unique security challenges across both iOS and Android. We evaluate risks such as insecure data storage, improper permissions, weak encryption, and exposed APIs, assessing both the application and its interaction with backend services.

Connected products

A connected product is only as secure as its weakest layer. We examine device firmware, communication protocols, hardware interfaces, and cloud integrations together as one engagement, securing the whole ecosystem against both remote and physical threats.

Network & cloud infrastructure

Misconfigurations and overlooked vulnerabilities can leave the backbone of your operations exposed. Our testing simulates internal and external threats across firewalls, endpoints, identity and access management, and cloud services, so your infrastructure stays resilient, segmented, and aligned with best practices.

AI security

AI and machine learning models present new threat surfaces, from adversarial input manipulation to model theft and data poisoning. Our assessments identify and test for vulnerabilities in your AI pipelines, deployment environments, and data workflows.

Our work

Penetration testing success stories

Labor Union

Labor union secures member portal with Winmill’s Penetration Testing Stream

Critical vulnerabilities eliminated ahead of the member portal expansion, with immediate clarity into security posture.

Read the story
Professional Sports

Penetration testing for a national sports league

Manual testing on the league release cadence caught high-risk issues that automated scanners had missed.

Read the story
Technology Services

Winmill assists hybrid cloud management developer with cybersecurity services

DAST scanning and a structured remediation workflow built into every release of the platform.

Read the story
Winmill delivered comprehensive, high-quality penetration tests that exceeded our expectations. Their expertise and guidance made a measurable impact on our security.
Winmill Client
Common questions

Frequently asked questions

What does a Winmill penetration test include?

Every engagement includes an executive summary report, a full technical report, a remediation action plan, and a retest to validate remediation. We include technical details with enough information to reproduce our findings, and every engagement comes with a complimentary readout call.

What systems can Winmill test?

We test web applications, mobile apps, IoT devices, network and cloud infrastructure, and AI systems. Our team is also experienced in social engineering attacks such as physical security testing and phishing campaigns.

What is the Penetration Testing Stream?

The Penetration Testing Stream is Winmill’s continuous testing program. A subscription gives you recurring, targeted penetration testing aligned to your environment, technology stack, and risk profile, instead of a point-in-time snapshot once a year.

What certifications does the Winmill team hold?

Our team members have earned industry certifications including GPEN, GWAPT, OSCP, OSCE, CEH, PMP, CISA, and CISSP. Each team member devotes over 400 hours per year to security research and community contributions.

How does Winmill use AI in penetration testing?

We use AI throughout our testing to expand coverage and depth. AI-assisted reconnaissance explores more of the attack surface, and AI-generated attack variations probe deeper than manual testing alone. Every finding is then validated by our senior testers before it reaches your report. We also test AI systems themselves, from adversarial inputs to data poisoning.

Interested in starting a project with our pen testing experts?

Tell us what you’re working on and we’ll connect you with the right team.