AI & LLM Penetration Testing
Typical delivery
5–7 business days
Why this matters
Attackers craft inputs that override your system prompt, extract confidential instructions, or force your model to act outside its guardrails. Traditional security tools are blind to this entire attack class.
Vynox runs 40+ prompt injection and jailbreak techniques per engagement, covering the full OWASP LLM Top 10, and delivers two reports: a technical report for engineers and an executive summary for leadership.
“We extracted your full system prompt in under 10 queries.”
How Vynox tests
- Direct prompt injection to override system instructions
- Indirect injection via documents and tool outputs
- Role-play and persona exploits
- Token manipulation and boundary attacks
- Multi-turn attack chains — 40+ techniques total
What's at stake if this goes untested
System prompt leakage
Competitors recover your IP and model instructions.
Guardrail bypass
Brand damage via harmful or off-policy outputs.
Data disclosure
Sensitive data surfaced to unauthorized users.
Compliance event
Regulatory penalties if PII is exposed.
Frequently asked questions
What is LLM penetration testing?
LLM penetration testing is the manual, adversarial probing of a large language model application for vulnerabilities such as prompt injection, jailbreaks, system prompt leakage, and guardrail bypass. Unlike automated scanners, it uses human-crafted attack chains that map to the OWASP LLM Top 10.
How is this different from a normal application pentest?
A traditional pentest targets code-level flaws like injection and broken auth. LLM penetration testing targets the model's behaviour — how natural-language inputs can override instructions, extract data, or bypass safety controls. Both are needed for an AI product; they cover different attack surfaces.
What do I receive at the end of an LLM pentest?
You receive two reports: a technical report with every finding, reproduction steps, and OWASP LLM Top 10 mapping for engineers, and an executive summary for leadership. Each finding includes severity and developer-ready remediation guidance.
Your AI Ships Fast. Attackers Move Faster.
Book a 30-minute call. We'll map your AI attack surface, scope the right engagement, and give you a clear picture of what an attacker would find — before they do.