Guardrails are only as strong as the attacks they've survived. We systematically evaluate your model's safety controls and content filters against current and novel bypass techniques, for Cyprus businesses launching public-facing AI.
We map exactly where your guardrails hold and where they fail, giving you reproducible cases to harden against and a clear view of residual risk.
What we test
- Guardrail & content-filter bypass
- Policy evasion techniques
- Harmful-output elicitation
- Refusal-boundary mapping
- Encoding, role-play & multi-turn attacks
- System-prompt & safety-layer probing
Common vulnerabilities we uncover
- Content-filter and guardrail bypass
- Policy and safety-instruction evasion
- Multi-turn and role-play jailbreaks
- Encoding and obfuscation-based bypass
- Harmful or restricted output elicitation
- System-prompt and safety-layer disclosure
How we run your LLM Jailbreak & Guardrail Testing
- Kick-off & scoping. A short call to agree goals, in-scope assets and rules of engagement, so your llm jailbreak & guardrail testing is safe, authorised and aimed at your real business risk.
- Mapping & discovery. Before touching anything we map the full attack surface in scope, so nothing exploitable slips through.
- Hands-on testing. Cyprus-based specialists exploit and chain weaknesses manually — the flaws scanners walk straight past — to show genuine impact.
- Reporting. Each issue is verified, CVSS-rated and documented with a step-by-step reproduction and a practical fix your team can apply.
- Free retest. Once you have remediated, we re-test at no extra cost to confirm the attack path is truly closed.
What you receive
- Guardrail coverage assessment
- Reproducible bypass cases
- Hardening & policy recommendations
- Residual-risk summary
Your deliverables
When your llm jailbreak & guardrail testing wraps up, you receive a clear, audit-ready report plus a walkthrough call with your team. Inside you will find:
- A concise executive summary that management and the board can act on
- Every technical finding with a reproducible, copy-paste proof of concept
- CVSS v3.1 ratings and plain-language business impact for each issue
- Practical, prioritised remediation your developers can implement straight away
- A free retest and updated finding status once fixes are in place
- A signed attestation letter for clients, auditors, GDPR, NIS2 and ISO 27001
Standards & frameworks
OWASP LLM Top 10
MITRE ATLAS
NIST AI RMF
EU AI Act readiness
What you gain
By the end of your llm jailbreak & guardrail testing, you will know exactly which weaknesses a real attacker could exploit, what it would cost your business, and the precise order in which to fix them — backed by evidence, not a scanner’s guesswork. Cyprus firms use our findings to close critical gaps, satisfy client and regulator security questionnaires, and demonstrate due diligence for GDPR and NIS2. With a free retest included, you also get documented proof the issues are resolved.
Working with us
Every llm jailbreak & guardrail testing begins with a short, no-obligation scoping call to understand your goals, environment and constraints, followed by a fixed-price proposal. Most work is delivered remotely, and because we are based in Cyprus we work in your timezone with on-site visits across Limassol, Nicosia and island-wide where it helps. We keep you updated throughout and flag any critical finding immediately rather than waiting for the report. Everything is covered by a signed NDA and safe, non-disruptive testing that protects your production systems. You receive your report, a walkthrough and a complimentary retest once fixes land. Engagements are typically booked one to three weeks ahead, and urgent testing can often be arranged — just email hi@cypruspentest.com.
Why Cyprus businesses choose CyprusPentest
Your llm jailbreak & guardrail testing is run by senior offensive-security specialists who test the way genuine attackers do — manually, creatively and focused on proving real impact. What sets us apart:
- Based in Cyprus — local, in your timezone, with on-site coverage across Limassol and Nicosia.
- Manual, exploit-led testing that chains vulnerabilities the way an attacker would, well beyond automated scanners.
- Reproducible proof for every finding, with copy-paste steps your team can independently verify.
- Compliance-ready reporting that supports GDPR, NIS2, ISO 27001 and CySEC expectations.
- A free retest so you have documented evidence your fixes actually hold.
- Fixed-price and responsive, with a named point of contact from scoping through to retest.
Explore related services
LLM Jailbreak & Guardrail Testing pairs well with our other Cyprus penetration testing services for fuller coverage. You may also want:
- Prompt Injection Testing — Prompt injection testing in Cyprus. Direct and indirect injection testing across every untrusted input for Cyprus…
- AI Agent Penetration Testing — AI agent penetration testing in Cyprus. Tool-abuse, goal-hijack and sandbox-escape testing for Cyprus companies deploying autonomous…
- AI Supply Chain Security Audit — AI supply chain security audit in Cyprus. Model provenance, plugin and dataset-integrity review for Cyprus AI…
Frequently asked questions
Do you test vendor or custom guardrails?
Both — vendor guardrails, custom classifiers and your system-prompt defences together.
Why does this matter for my brand?
Bypassed guardrails can produce harmful output attributed to you, creating reputational and legal exposure.
Do you deliver reusable tests?
Yes, each bypass is documented for your safety-regression suite.