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Certified Canadian testers combine automation with hands on validation to secure your chatbots, copilots, and AI agents.

AI Penetration Testing & Security Assessment Services in Canada

Your AI systems make decisions, touch customer data, and call internal tools, a new and often untested way in. PlutoSec delivers AI penetration testing that pairs AI pen testing agents with certified testers, so every finding is proven before it reaches your report.

  • Certified AI Penetration Testers

    OSCP, OSWE and GPEN certified engineers lead every LLM, agent and AI application assessment.

  • AI Speed, Human Judgment

    AI agents widen coverage while our testers prove and rate every finding.

  • Developer Ready Reporting

    Every finding follows the OWASP LLM Top 10 and comes with clear steps for your developers.

  • Confidential & Secure

    Prompts, code and findings stay under strict NDA on Canadian hosted systems.

About AI Penetration Testing

AI Penetration Testing Built Around Real Attacks

AI penetration testing is a hands on assessment of the models, prompts, data sources, and connected tools behind your AI features. It asks a simple question: what happens when someone tries to trick, overload, or quietly pull data out of your chatbot, copilot, or agent? Standard web testing rarely answers that, because AI systems can respond differently every time.

Pen testing AI tools and autonomous agents are quick at mapping targets and firing thousands of payloads, yet they can't judge business impact. A support bot that reveals another customer's order, or an agent that deletes records after a cleverly worded request, needs a human who understands your workflow. We use AI for speed and certified engineers for judgment, then map results to PIPEDA, Quebec's Law 25, and OSFI expectations.

Full AI Attack Surface Coverage

Human Validated Findings

OWASP LLM Top 10 Alignment

Canadian Compliance Mapping

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Ready to Strengthen Your Cybersecurity?

Protect your business with expert led security assessments, penetration testing, and managed security services. Talk to our specialists today.

Book a Free Consultation

Our AI Testing Methodology

  1. 1.

    Scoping and Planning

    We list your models, agents, and data sources, then set rules of engagement.

  2. 2.

    AI Attack Surface Mapping

    We trace every prompt, API, and connected tool an attacker could reach.

  3. 3.

    Adversarial Testing

    Agents fire prompt attacks at volume while our testers craft the ones tools miss.

  4. 4.

    Proof and Validation

    A certified tester reproduces every finding, so false positives never reach your report.

  5. 5.

    Risk Analysis and Retest

    We rank issues by business impact, map them to your frameworks, then retest fixes.

Why Choose PlutoSec?

A Safer Way to Adopt AI

Teams are shipping chatbots, copilots, and agents faster than they can secure them. PlutoSec, based in Etobicoke, Ontario, helps organizations across Canada secure AI powered products and adopt AI pen testing with certified engineers, clear reporting, and no sensitive data sent to outside AI platforms.

AI Security Specialists

Our engineers understand classic exploitation and how language models fail when someone pushes them.

Humans Behind the AI

Agents widen coverage, but a certified tester proves every finding before it reaches you.

Canadian Compliance Focus

Reports reference PIPEDA, Quebec's Law 25, OSFI B 13, and ITSG 33 wherever they apply to you.

Senior Led Delivery

One senior engineer owns your project from first call to final retest, with no junior handoffs.

What We Cover

LLM and Chatbot Testing

We test chatbots and internal copilots for prompt injection, jailbreaks, and system prompt leakage.

AI Agent and Tool Testing

We check whether agents can be talked into unauthorized actions or risky tool calls.

RAG and Data Pipeline Testing

We probe retrieval layers for data leakage, poisoned documents, and weak access control.

Model and API Abuse Testing

We test model endpoints for extraction attempts, weak rate limits, and exposed keys.

AI Assisted Penetration Testing

We use AI agents on your apps and networks, then confirm every result by hand.

Pre Release and Vendor AI Testing

We test new copilots and vendor AI plugins before launch, so fixes arrive before customers do.

How We Test AI Systems

  • Prompt Injection and Jailbreak Testing
  • Sensitive Data Leakage Testing
  • Agent Permission and Tool Abuse Testing
  • RAG and Vector Store Access Review
  • Model Extraction and Training Data Review
  • AI Pentesting Agent Recon with Manual Validation
  • Validated AI Risk Findings
  • Proof of Concept Evidence
  • Prioritized Remediation Plan
  • Free Retest Included

Tools We Use for AI Testing

  • Garak
  • PyRIT
  • Promptfoo
  • Agentic Security
  • Adversarial Robustness Toolbox
  • Burp Suite Professional
  • Postman
  • Custom Python Scripts

Get Started

Ready to Strengthen Your Cybersecurity?

Protect your business with expert led security assessments, penetration testing, and managed security services. Talk to our specialists today.

Book a Free Consultation

Why AI Penetration Testing Matters

Stop Data Leaks

Find the prompts and retrieval paths that could expose customer records, source code, or internal files.

Keep Agents in Check

Confirm that agents cannot be talked into actions or permissions they should never have.

Protect Your Reputation

Catch manipulated or harmful outputs before a public chatbot becomes a screenshot on social media.

Show Due Diligence

Give auditors, insurers, and regulators documented proof that qualified people tested your AI.

CLIENT VOICES

What our clients say

5.0 / 5based on 20 verified reviews
GoodFirms

Their team conducted a thorough security assessment and penetration testing of our website, keeping us informed throughout the process. What really stood out was how they presented technical findings in straightforward language rather than jargon — our entire team could understand the vulnerabilities and risks without needing to decode complex terminology. The final report included practical remediation recommendations we could actually implement.

Rachel CohenOwner, StantVerified
GoodFirms

Their team used a hands-on approach to identify vulnerabilities and security weaknesses that automated scans had missed, risks that could have exposed sensitive user information. Each finding was clearly explained, prioritized by severity, and paired with practical remediation recommendations. They remained available to answer questions and guide us through remediation.

Adam KowalskiOwner, Viva-menteVerified
GoodFirms

Their team took the time to understand our sustainability platform, performed a thorough security assessment, and kept us informed throughout the engagement. The final report clearly prioritized each finding and included practical remediation steps that our technical team was able to implement without confusion, significantly improving our platform's security posture.

Luca MorettiIT Security Manager, GEA.viteVerified
GoodFirms

Their team conducted a thorough penetration test and security assessment, identified vulnerabilities across our infrastructure, and provided clear, actionable steps to address them. Communication was professional and responsive throughout, and the final report was detailed yet easy to understand without unnecessary technical jargon. We especially appreciated their hands-on approach and meticulous attention to detail.

Maya EllingtonIT Manager, Pescara Blu B&BVerified
GoodFirms

Their team strengthened our cloud infrastructure, improved our access controls, and addressed security risks while providing ongoing monitoring. Communication was consistently clear, their support was responsive whenever we needed it, and their recommendations were practical and straightforward to implement.

Julian MercerIT and Cybersecurity Director, NovellowinesVerified
GoodFirms

Their team uncovered vulnerabilities in our web application that we would have missed and explained each one clearly with practical remediation steps. They stayed responsive throughout the engagement and made the entire process straightforward.

Wyatt CallahanCEOVerified
GoodFirms

Their team continuously monitored our hospitality operations for vulnerabilities and threats, flagging potential issues early with clear recommendations before problems escalated. They were responsive and knowledgeable, making security guidance practical and actionable for our specific needs. They've become a trusted partner we rely on.

Riley EastwoodIT Manager, CrodadalagoVerified
GoodFirms

Their team conducted a thorough penetration test and vulnerability assessment of our web environment, uncovering vulnerabilities we'd missed entirely. They communicated findings clearly, provided practical remediation guidance we could actually implement, and remained professional and responsive throughout the engagement.

Ava WhitmoreDirector of IT Operations, IlpassaggioVerified
GoodFirms

Working with PlutoSec was smooth and professional from start to finish. Their team manually tested our WordPress website, clearly explained each vulnerability they found, and gave us actionable steps to fix them, which made remediation straightforward instead of overwhelming. They were responsive to our questions and guided us through the process.

Sara MahmoudCTO, Andrea BaccoliniVerified
GoodFirms

Their team took time to understand our website, conducted a thorough security assessment and penetration test, then clearly explained each vulnerability they found. They provided practical remediation guidance we could actually implement to address the findings and strengthen our defenses. Communication was responsive throughout, and we felt confident in their technical knowledge and approach.

Aisha RahmanIT Security Manager, IlmiobeautyVerified
GoodFirms

Their team conducted a detailed penetration test and vulnerability assessment, identifying security weaknesses and clearly explaining the business risks behind each finding. What impressed us most was their hands-on approach — they manually validated vulnerabilities rather than relying solely on automated scanning. Beyond the initial assessment, their managed security services helped us maintain stronger ongoing security.

Zoya KhanCTO, FProgettiVerified
GoodFirms

Their manual penetration testing caught vulnerabilities that automated scanners had missed, and their final report was detailed with practical remediation recommendations we could actually implement. The team demonstrated strong technical expertise and remained responsive throughout the project, answering our questions during remediation and completing everything on schedule.

Adam Al-MasriIT Manager, FoggiaitVerified
GoodFirms

PlutoSec provided proactive managed security, vulnerability management, and ongoing monitoring that meaningfully strengthened our security posture. The team was responsive and professional, addressing concerns quickly and giving us confidence that our systems and business data are properly protected.

AnonymousVerified clientVerified
GoodFirms

Their team helped us improve IT security, system reliability, and day-to-day support, while always being responsive when we needed assistance. We especially appreciated their practical approach, clear communication, and cybersecurity knowledge.

AnonymousVerified clientVerified
GoodFirms

Their cybersecurity team took time to understand our environment and performed a detailed penetration test, going beyond automated tools to manually validate findings and explain the potential business impact clearly. The final report was well-structured with practical remediation recommendations our team could easily follow.

AnonymousVerified clientVerified

Insights & Research

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Frequently asked questions

Answers to the questions we hear most. Still unsure how it applies to your environment? Our engineers are happy to talk it through.

What is AI penetration testing?
It covers two things, and we do both. We test the AI systems you run for prompt injection, data leakage, and abuse. We also use AI to speed up wider testing, with a certified tester checking every result.
Can an AI pentester replace a human penetration tester?
Not today. An AI pentester is great at repetitive work like reconnaissance and payload volume, but it struggles with business logic. That's why certified testers prove each issue and judge what it means for your business.
What are the best AI tools for penetration testing in 2026?
It depends on the target. Autonomous agents suit continuous web and API coverage, while red teaming tools like Garak and PyRIT suit LLM applications. The best AI for penetration testing is whichever mix fits your environment, verified by hand.
What does an AI pentesting agent actually do?
It plans and runs test steps on its own, like mapping endpoints, trying payloads, and chaining weaknesses. We keep each agent inside a locked scope with rate limits, and a tester confirms every result.
How does AI penetration testing help with Canadian compliance?
Our reports support PIPEDA safeguard duties, Quebec's Law 25 rules on automated decisions, and OSFI guidance like B-13 and E-23. They also supply evidence for SOC 2, ISO 27001, and ISO 42001 audits.
How long does AI penetration testing take?
Most engagements run one to three weeks, depending on how many models, agents, and integrations are in scope. We test in staging where possible so live customers never notice.

Get Started

Ready to See What Your Current Security Is Missing?

Book a short consultation with PlutoSec and get a practical view of where your current security model may be exposed.

Book Your Free Security Consultation