Chatbot Security Assessment

Security assessment for chatbot and conversational AI systems

About This Service

Our Chatbot Security Assessment tests a conversational AI system the way its users — and its abusers — actually reach it: through the conversation. We test whether the chatbot can be talked out of its rules (prompt injection and jailbreak), whether it leaks data from its context or from another user's session, whether its safety guardrails can be bypassed, and whether the backend actions it can trigger are properly gated. The work follows the OWASP Top 10 for LLM Applications and the OWASP AI Testing Guide, and draws on MITRE ATLAS. Because Persian text can slip past a filter tuned for English without changing what the model understands, we test the language-specific evasions too. Every finding is proven, rated with CVSS alongside its real impact, and written up with a concrete fix.

What's Included

Prompt injection and jailbreak against the conversation guardrails

Language-specific evasion: character variants, zero-width characters, and mixed-script obfuscation in Persian

Sensitive data leakage from the system context, the knowledge base, or another user's session

Safety and brand-guardrail bypass: unsafe, off-policy, or reputationally damaging output

Session and state handling: history bleed, cross-session leakage, and identity confusion

Backend integration: actions the chatbot can trigger, and whether they are authorized and gated

Input validation and output handling where the reply reaches another system

Authentication and authorization of the user behind the conversation

Privacy and PII handling in prompts, logs, and transcripts

Unbounded consumption: cost and denial-of-service through the chat interface

How It Works

1
Chatbot Discovery
We map the chatbot: its purpose and rules, the system prompt and guardrails, the knowledge base it draws on, the backend actions it can take, and how a user is identified across a conversation. This sets the boundary of what it should and should not do.
2
Conversation & Injection Testing
We try to talk the chatbot out of its rules — directly, and through content it reads from its knowledge base — and we test the language-specific evasions that a filter tuned for one language misses. The question is whether the guardrails hold when the user and the instruction disagree.
3
Data, Session & Guardrail Testing
We test whether the chatbot leaks its system prompt, its knowledge base, or another user's data; whether history bleeds between sessions; and whether its safety and brand guardrails can be pushed into unsafe or off-policy output.
4
Backend & Action Security
Where the chatbot can take an action — look up an order, change a setting, open a ticket — we test whether that action checks who is asking and stays within their permissions, so the conversation cannot become a path into the backend.
5
Validation, Reporting & Re-testing
Every finding is proven with a reproducible conversation, rated with CVSS and the real impact, mapped to the OWASP Top 10 for LLM Applications, and written up with a concrete fix. After you remediate, we re-test to confirm the fixes hold.
Deliverables
  • Executive summary with a risk overview for decision-makers
  • Detailed technical report, each finding with a reproducible conversation
  • Prompt-injection, jailbreak, and language-specific evasion findings
  • Data-leakage and session-handling findings
  • Safety and brand-guardrail bypass findings
  • Backend action and authorization findings
  • Findings mapped to the OWASP Top 10 for LLM Applications, with CVSS and business impact
  • Prioritized remediation guidance and re-testing after remediation

Why HafezSecure

Conversational AI Expertise
Current understanding of how chatbots fail — prompt injection, jailbreak, guardrail bypass, and session leakage — and of how a conversation becomes an attack surface onto the systems behind it.
Persian-Aware Testing
A safety filter tuned for English can be slipped with Persian character variants, zero-width characters, and mixed script that leave the model's understanding intact. We test those evasions, which an English-only assessment does not.
Past the Chat, Into the Backend
We do not stop at making the chatbot say something wrong; we test whether the actions it can take are properly authorized, so a clever conversation cannot reach data or operations behind it.
Reproducible and Actionable
Every finding comes as a conversation you can replay, mapped to a recognized standard, with a concrete fix for the guardrails, the session handling, or the backend gate.

Frequently Asked Questions

What is a Chatbot Security Assessment?

It evaluates a conversational AI system for security weaknesses reached through the conversation — prompt injection and jailbreak, data leakage, guardrail bypass, session flaws, and the security of the backend actions it can trigger — following the OWASP Top 10 for LLM Applications and the OWASP AI Testing Guide, with each finding proven and rated.

What is the difference between prompt injection and jailbreak?

Jailbreak is getting the model to ignore its own safety rules — to say what it was told not to say. Prompt injection is getting it to follow an attacker's instruction over the application's, often through content it reads rather than a direct request. They overlap, and a chatbot assessment tests both.

Why does testing in Persian matter?

Many safety filters are tuned for English. Persian character variants (ی/ي, ک/ك), zero-width characters, mixed script, and Finglish can change what the filter sees without changing what the model understands, letting a payload through. An assessment that only tests English misses these, so we test the Persian-specific evasions directly.

Can a chatbot leak data it should not?

Yes — through its system prompt, its knowledge base, or the history of another user's session if state is not properly isolated. We test whether the chatbot can be led to reveal its instructions, retrieve documents the user has no right to, or carry information across sessions.

Do you test the systems the chatbot connects to?

We test the boundary: where the chatbot can trigger a backend action, we check that the action verifies who is asking and stays within their permissions. A full assessment of the backend systems themselves is a separate scope we can add, but the chatbot-to-backend gate is part of this service.

Is testing safe for a live customer-facing chatbot?

Conversational testing is largely safe, but tests that could trigger a real action or reach real customer data are agreed in advance and run carefully. We prefer a staging instance that mirrors production, and when we must test the live system we set limits and keep a contact on your side to pause at once.

How is the severity of findings decided?

Each finding gets a CVSS score for a common baseline, adjusted by the real impact — what it leaks or triggers, how easily, and whether it crosses a user boundary — and is mapped to the OWASP Top 10 for LLM Applications. A guardrail slip that only affects tone is not the same as one that reaches customer data.

How long does a chatbot security assessment take?

Duration depends on the chatbot's complexity — its knowledge base, its backend actions, and the languages it serves. A typical assessment runs about one to three weeks, and we give a firm estimate after scoping. Re-testing after you remediate is included.

Ready to Get Started?
Contact our team to discuss your security assessment needs