Windward Labs

Security Research & Tooling Lab

Stay upwind of your adversaries.

Windward Labs is a security research and tooling lab. We build the tools, automation, and processes the modern researcher and penetration tester needs, and we prove them on real engagements across web, API, cloud, and internal networks. We build for the AI-native era and release our work as it matures.

We are open about how we work. When a test needs a tool that doesn’t exist, we write it, then publish it and the method behind it so the rest of the field can use it too.

Research & Open Source

We build the tooling our own testing needs, then we open it up.

We believe radical transparency about how we work, our process and our methods, is the best way to advance security assessment and give defenders what they need to stay ahead of the adversary. A lot of firms treat tooling as a cost of running the assessment. For us it is the main line of work, and we publish the parts of it useful beyond a single client.

01

Tooling & automation

Off-the-shelf scanners only get you so far. We write offensive tooling and automation for each engagement, then generalize the parts that hold up into tools we reuse on the next one.

02

Built for the AI-native era

We use AI in the work itself: assisted recon and triage, LLM analysis across large result sets, and the experience to test AI systems and agent pipelines, which are now part of the attack surface.

03

Open source

We publish the tooling and the methods behind it. We are hardening both across our first engagements, working toward a public toolkit and methodology any researcher or pentester can pick up and use.

04

Repeatable method

We write down how we work: documented methodology, repeatable workflows, and automation your team can run after we leave.

The toolkit is still in progress, built and refined through our first engagements. If you want early access, or to collaborate as it ships, get in touch.

Engagements

Where the research gets proven

These engagements are where the tooling actually gets used. We scope each one around what you need rather than a template, senior people do the work, and you see the methods we use, not only the findings.

Offensive Security Testing

Penetration testing across web, API, cloud, and internal networks. We research each target and build tooling specific to it, the same work that feeds our open-source toolkit, so testing goes deeper and faster than a scanner can.

  • Web application penetration testing
  • API penetration testing
  • Cloud security assessments (AWS, GCP, Azure)
  • Internal network penetration testing

Application Security

Security designed into how your engineers ship, from first design through deploy, so problems are fixed at the source instead of patched later.

  • Application security assessments
  • Secure design & threat modeling
  • Source-assisted code review
  • Developer-facing remediation guidance

Advisory & Resilience

Senior security guidance on architecture and readiness, plus retained advisory when you want a standing team to call.

  • Security architecture reviews
  • Tabletop exercises & incident readiness
  • Fractional / retained security advisory
  • Threat-model & roadmap review

How we work

Built to be the team you wish you had in-house

Most assessments optimize for page count over real risk. We stay small, senior, and tools-first, and what we learn on one engagement gets built into the next. The work has to earn your trust, and so do the people doing it.

01

Builders who operate

The person who scopes your engagement is the one doing the work and writing the tooling behind it. Senior operators who build their own tools rather than only running other people's scanners.

02

Research-driven, AI-native

We research each target and build custom tooling and automation during the engagement, increasingly with AI in the loop. That goes deeper and faster than a checklist, and what we learn carries into the next engagement.

03

What we learn, we open up

We are open about our process and our methods, not only our findings. We generalize and release the strongest tooling from our engagements, so you start from everything we have already built.

04

More than a report

You get a clear list of risks, a specific fix for each one, and tooling you can keep using. We measure success by whether you are harder to attack after we leave.

Why “Windward”

To be to windward is to hold the advantage. You are upwind, in control, free to pick your next move.

That is where security teams should sit relative to their attackers, and it is rarer than it should be. We started Windward Labs as a research and tooling lab because we were tired of assessments that optimized for deliverable size over the tools and decisions a team could actually keep. We also believe the field only moves forward when methods are shared, so we work in the open by default.

We are a small, senior team that builds. We do our own research, write the tooling and automation our tests need, and increasingly build for the AI-native era, then release the strongest of it. We would rather have a few long-term clients and a solid public toolkit than many one-off engagements. We judge the work by one thing: whether you are harder to compromise after we leave than before.

Senior-led
Builders, every engagement
Tooling-first
Research into reusable tools
AI-native
Built for the new surface
Open source
In the works, by intent

Get in touch

Let’s talk about your threat model

Tell us what you’re protecting and where you’re worried. We’ll reply within one business day with scoping questions and next steps.

Helpful to include if you can:

  • Systems or assets in scope
  • Timeline and any compliance drivers
  • Whether this is a one-time or ongoing need

Prefer email? hello@windwardlabs.io

Reporting a vulnerability in our systems? security@windwardlabs.io

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