BTBreaktrailSecurity
Independent application security · Casper, Wyoming

Find the pathbefore an attacker does.

Breaking trail means going first through difficult terrain. We bring that mindset to applications, APIs, and AI systems—finding the routes attackers could take before they become incidents.

Map your exposure Explore services
BUSINESS RISKONLINE EXPOSURE → UNAUTHORIZED ACCESS → BUSINESS LOSS
  1. 01
    ONLINE ENTRY POINTWebsite or online accountWhere an attacker first gets in
  2. 02
    SECURITY GAPUnauthorized accessOne weakness opens the next door
  3. 03
    BUSINESS CONSEQUENCEData theft, fraud, or downtimeCustomers, operations, and revenue are affected
FIND THE GAPA small security weakness can become a costly business problem.BREAK THE PATH
01 THE TERRITORY

Security for the territory ahead.

You do not need to arrive with a map. Start with what you are building, changing, or worried about—we will define the right route through it together.

01

Application security assessments

A focused review of how your web application or API could be abused, with findings your team can actually act on.

  • Web applications
  • APIs
  • Source-assisted
02

Independent penetration testing

Hands-on testing that goes beyond a scanner to uncover real attack paths across your exposed systems and applications.

  • Black box
  • Authenticated
  • Evidence-led
03

Threat modeling

Find the dangerous assumptions early. We map what matters, how it could fail, and where security effort will have the most impact.

  • Architecture
  • Abuse cases
  • Prioritization
04

AI & agent security

Adversarial testing for systems that connect language models to data, tools, identities, and consequential business actions.

  • Agentic systems
  • Tool abuse
  • Data exposure
02 BUILT FOR THE NEXT MOVE

For teams moving into new territory.

LOCAL / WY

Casper & Wyoming businesses

A nearby, independent partner who can navigate risk without burying you in enterprise jargon.

BUILD / SHIP

Software & product teams

An offensive perspective before a launch, customer review, acquisition, or major architecture change.

NEW / GROUND

Teams adopting AI

Practical adversarial testing when models begin touching private data, tools, or business workflows.

03 THE ROUTE

Map. Test. Mark the way forward.

Breaking trail is deliberate work. We scope the terrain, investigate the paths that matter, and leave your team with a route it can follow.

  1. 01 / MAP

    Understand the terrain

    We define what changed, what matters most, and what a useful answer looks like before testing begins.

  2. 02 / BREAK TRAIL

    Go where scanners cannot

    We combine structured coverage with manual exploration to uncover exploitable conditions and connected attack paths.

  3. 03 / MARK

    Leave a clear route forward

    You receive evidence, prioritized findings, and a plain-language walkthrough—plus support for questions and retesting.

FIELD CREDENTIALS / OFFENSIVE SECURITYOSWE + OSWA

Advanced, hands-on certification in white-box web application testing—paired with real-world application security and threat-modeling experience.

04 ABOUT BREAKTRAIL

A clear route through complex security questions.

Breaking trail means going first through difficult terrain. Breaktrail Security brings that mindset to applications and connected systems—exploring how they can be misused and finding the paths others overlook.

Breaktrail is led by Jon Otano, an independent security practitioner in Casper, Wyoming. Jon works directly with every client across offensive testing, application security, threat modeling, and AI-connected software.

Currently mapping select projects

Let’s find the path before an attacker does.

Tell us what you are building, what changed, or what has you concerned. You do not need to know which kind of assessment to request.

Email hello@breaktrailsecurity.com