Advanced Penetration Testing for AI Systems

Vynox Security delivers expert-led advanced penetration testing for the AI systems and infrastructure your business depends on. We manually test LLM applications, RAG pipelines, agents, APIs, cloud environments, and more to uncover exploitable weaknesses automated scanners miss. Get clear evidence, practical reproduction steps, and developer-ready remediation guidance that helps your team ship securely and meet customer or compliance expectations.

Security expert testing an AI application

Our Advanced Penetration Testing Services

Focused, manual security assessments for AI applications, models, agents, data pipelines, and complex attack scenarios.

AI & LLM Testing

Manual adversarial testing for LLM applications using 40+ prompt injection and jailbreak techniques, full OWASP LLM Top 10 coverage, and developer-ready remediation guidance.

RAG Pipeline Testing

End-to-end testing of retrieval paths to identify document leakage, cross-tenant retrieval, access-control bypasses, vector database poisoning, and embedding inversion risks.

AI Agent Testing

Security testing for autonomous agents with tool access, including tool-call injection, goal hijacking, agent chaining, privilege escalation, and data exfiltration scenarios.

Prompt Injection Testing

A focused assessment of whether attackers can override system instructions, bypass guardrails, extract prompts, disclose sensitive data, or trigger unintended actions.

Model Extraction Testing

Measures whether targeted queries can recover proprietary training data, fine-tuning signatures, model behavior, or intellectual property from deployed models.

AI Red Teaming

Scenario-driven adversarial simulations that chain weaknesses across models, agents, and pipelines to demonstrate realistic business impact and strengthen defenses.

AI-Native Assurance

Security Testing Built for AI Risk

Advanced Penetration Testing from Vynox Security goes beyond automated scans and conventional application checks. Our specialists manually validate real attack paths across LLMs, RAG pipelines, autonomous agents, APIs, cloud services, and mobile or web products. Each engagement delivers technical evidence, CVSS-scored findings, reproduction steps, and stack-specific fixes. Choose Rapid Secure for fast compliance-ready assurance or Deep Secure for comprehensive adversarial coverage.

AI security testing review in progress
Trusted Security Partner

Client Success Stories

See how security-conscious teams use Vynox to test, remediate, and ship AI products with greater confidence.

"Shubham and the rest of the Vynox team were responsive and easy to work with throughout the engagement. The retest turnaround was impressively fast — fixes were verified the same day our engineer pushed them to staging."

Cody I.

"Communication during the engagement was outstanding — always clear, concise, and consistent. The shared documentation provided us with real-time updates on findings as they emerged, which proved to be extremely valuable."

Verified User in IT and Services

"I find Vynox Security very professional and appreciate their great availability throughout the engagement. Their POC, Shubham, was very prompt in responding and always ready to help, making coordination very smooth and efficient."

Arpit A.

"Shubham and the rest of the Vynox team were responsive and easy to work with throughout the engagement. The retest turnaround was impressively fast — fixes were verified the same day our engineer pushed them to staging."

Cody I.

"Communication during the engagement was outstanding — always clear, concise, and consistent. The shared documentation provided us with real-time updates on findings as they emerged, which proved to be extremely valuable."

Verified User in IT and Services

"I find Vynox Security very professional and appreciate their great availability throughout the engagement. Their POC, Shubham, was very prompt in responding and always ready to help, making coordination very smooth and efficient."

Arpit A.

"Shubham and the rest of the Vynox team were responsive and easy to work with throughout the engagement. The retest turnaround was impressively fast — fixes were verified the same day our engineer pushed them to staging."

Cody I.

"Communication during the engagement was outstanding — always clear, concise, and consistent. The shared documentation provided us with real-time updates on findings as they emerged, which proved to be extremely valuable."

Verified User in IT and Services

"I find Vynox Security very professional and appreciate their great availability throughout the engagement. Their POC, Shubham, was very prompt in responding and always ready to help, making coordination very smooth and efficient."

Arpit A.
The Vynox Difference

Why Choose Vynox Security?

Specialized testing that turns complex security risks into clear next steps.

AI-Native Expertise

Purpose-built methods assess LLMs, RAG systems, and agents beyond traditional penetration-testing coverage.

Actionable Findings

Developer-ready remediation includes reproduction steps, evidence screenshots, CVSS scores, and stack-specific guidance.

Compliance Evidence

Findings map directly to SOC 2 and ISO 27001 control evidence requirements.

Continuous Validation

PTaaS aligns testing with sprints, with same-day retests after fixes reach staging.

Meet the Vynox Team

Responsive security specialists focused on clear, practical AI assurance.

Portrait of Karan Singh, Discovery Call Lead and Founder at Vynox Security

Karan Singh

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.

Portrait of Shubham, Security Engagement Lead at Vynox Security

Shubham

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.

Frequently Asked Questions

What is advanced penetration testing?

Advanced penetration testing is an expert-led security assessment that simulates realistic attacker behavior rather than relying solely on automated vulnerability scans. Vynox Security manually investigates exploit chains, authentication and authorization weaknesses, business-logic flaws, cloud misconfigurations, and AI-specific risks. The final report documents validated findings with severity, evidence, reproduction steps, and practical remediation guidance for engineering and leadership teams.

How is AI penetration testing different from a traditional pentest?

What systems can Vynox Security test?

How long does an advanced penetration test take?

Will I receive remediation guidance with the report?

Can penetration testing support SOC 2 or ISO 27001 readiness?

What is PTaaS, and when should we use it?

Can you test production AI systems safely?

Still Have Security Questions?

Speak with our team to scope the right assessment.

Trusted Assurance

Awards and Recognition

G2 rating recognition

G2 Rating

4.6/5 from 10 verified reviews

OWASP LLM coverage badge

OWASP LLM Coverage

AI testing mapped to OWASP guidance

Compliance-ready reporting badge

Compliance-Ready Reporting

Evidence mapped for audit requirements

Ready to Test Your AI Attack Surface?

Book a free 30-minute discovery call to review your stack, discuss risk priorities, and receive clear guidance on scope, timing, and engagement options.

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