LLM Penetration Testing
Manually test your chatbot with 40+ prompt injection and jailbreak techniques to identify system-prompt leakage, guardrail bypasses, sensitive-data disclosure, and other OWASP LLM Top 10 risks.
Protect your AI chatbot before attackers turn prompts, documents, or connected tools into pathways for data exposure. Vynox Security performs manual, adversarial testing of LLM-powered chatbots to uncover prompt injection, jailbreak, system-prompt leakage, guardrail bypasses, and unsafe tool actions. Receive clear evidence, prioritized findings, and developer-ready remediation guidance so your team can ship with greater confidence.
Targeted adversarial assessments for chatbot models, retrieval layers, connected tools, and proprietary AI assets.
Manually test your chatbot with 40+ prompt injection and jailbreak techniques to identify system-prompt leakage, guardrail bypasses, sensitive-data disclosure, and other OWASP LLM Top 10 risks.
Assess whether direct, indirect, encoded, role-play, token-manipulation, and multi-turn attacks can override chatbot instructions or cause unsafe responses and unintended behavior.
Test the full retrieval path for restricted-document exposure, cross-tenant retrieval, access-control bypasses, vector database poisoning, and embedding-inversion risks in chatbot knowledge bases.
Evaluate chatbots that invoke tools or agents for tool-call injection, task hijacking, privilege escalation, unsafe API actions, and data exfiltration through legitimate channels.
Simulate determined adversaries pursuing realistic objectives across chatbot inputs, models, tools, and pipelines through structured threat modeling and multi-step exploit chains.
Measure whether targeted queries can reveal proprietary training data, fine-tuning signatures, model behavior, or intellectual property that competitors or attackers could exploit.
AI chatbots introduce attack paths that conventional application testing often overlooks. Vynox Security probes your live application as an adversary would, testing how prompts, retrieved content, integrations, and user interactions can be manipulated. Each engagement covers the relevant OWASP LLM Top 10 risks and delivers reproducible evidence, CVSS-scored findings, and stack-specific fixes. Choose Rapid Secure for fast assurance or Deep Secure for broader adversarial coverage.
See why security-conscious teams rely on Vynox for responsive, actionable AI security assessments.
AI-native testing that turns complex chatbot risks into practical next steps.
Purpose-built testing addresses LLM, RAG, and agent vulnerabilities traditional pentests commonly miss.
More than 40 prompt injection and jailbreak techniques test real-world chatbot resilience.
Reproduction steps, evidence, CVSS scores, and stack-specific guidance accelerate remediation for engineering teams.
PTaaS aligns testing with model updates and sprints, with same-day staging retests after fixes.
AI security specialists focused on clear, effective engagements.
Discovery Call Lead / Founder or Senior Team Member
Karan Singh is a founding team member and senior security professional at Vynox Security, where he leads discovery calls and security assessment scoping for prospective clients. As the primary booking contact for new engagements, Karan plays a pivotal role in helping organizations understand their AI and infrastructure security needs before any testing begins. With deep expertise in AI-native security testing — including LLM penetration testing, RAG pipeline security, and autonomous agent assessments — he ensures every engagement is precisely scoped to deliver maximum value. Karan is committed to making the onboarding process clear and efficient, setting the foundation for thorough, developer-ready security assessments that help clients ship AI products with confidence.
Point of Contact / Security Engagement Lead
Shubham serves as a Security Engagement Lead and primary point of contact for client engagements at Vynox Security. Known for his prompt responsiveness and seamless coordination, Shubham ensures that every security testing engagement runs smoothly from kickoff through final delivery. He acts as the bridge between Vynox's technical security team and client stakeholders, keeping communication clear, timelines on track, and deliverables aligned with each organization's specific compliance and remediation goals. Clients consistently praise Shubham for making the entire security testing process efficient and stress-free. His dedication to collaborative, responsive client engagement reflects Vynox's core commitment to being a trusted security partner for AI-powered businesses and security-conscious development teams.
AI chatbot testing combines manual adversarial prompting with application-level security validation. Testers attempt direct and indirect prompt injection, jailbreaks, system-prompt extraction, sensitive-data disclosure, guardrail bypasses, and multi-turn attack chains. They also evaluate retrieval sources, authentication, authorization, connected APIs, and tool calls. Vynox maps applicable findings to the OWASP LLM Top 10 and provides reproducible evidence and remediation guidance.
Talk with a specialist about your chatbot’s testing scope and risks.
4.6/5 from 10 verified reviews
Mapped testing across AI security risks
SOC 2 and ISO 27001 mapping
Book a 30-minute discovery call to review your AI attack surface, prioritize testing needs, and receive clear scope, timeline, and pricing guidance.
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