Service Overview
The AI LLM Security Assessment is a technical security assessment that tests the resilience and operational integrity of a specific, deployed AI-powered chatbot or LLM implementation, from an attacker's perspective. Through hands-on penetration testing, this assessment identifies exploitable vulnerabilities in the language model's behavior, its integration architecture, supporting applications, and backend systems. The service combines automated discovery techniques with deep manual testing—mirroring Sophos' industry-aligned methodology for application testing, which draws from recognized standards such as OWASP and OSSTMM.
Ideal For:
- Organizations deploying AI Chatbot/LLMs in customer support, internal operations, or product interfaces
- Teams integrating LLMs with proprietary data through RAG or agent frameworks
- Enterprises expanding automation through AI-driven tools or decision assistants
Organizations implementing generative AI, LLM-based assistants, retrieval augmented generation (RAG) pipelines, or Chatbot/LLM-driven automation gain insights into potential risks, model manipulation vectors, data leakage pathways, and ecosystem-level security gaps.
Benefits of the AI Chatbot/LLM Security Assessment:
- Identify model-level risks such as prompt injection and jailbreak vulnerabilities
- Prevent data leakage through model behavior or integration misconfigurations
- Strengthen guardrails, policies, and content moderation pipelines
- Validate safe RAG and plugin/tool integration
- Protect customer trust and reduce AI-related business risk
Service Methodology
The assessment follows a structured, multi-phase methodology inspired by Sophos’ approach to web application testing, balancing automated scanning with targeted manual analysis to eliminate false positives and uncover deeper logic-level weaknesses.
Listed below are components of the test:
Scoping & Rules of Engagement
Sophos will schedule an initial meeting to establish rules of engagement, level of effort, scope, risk acceptance, reporting requirements, testing timelines, and schedules. Sophos pre-engagement planning ensures testing is aligned with business and technical constraints. Scoping includes:
- Defining approved Chatbot/LLM instances, integrations, and environments
- Understanding model type (LLM, fine-tuned model, RAG, hybrid)
- Mapping integration layers such as APIs, plugins/tools, and vector databases
- Establishing acceptable risk boundaries, rate limits, and testing windows
- Identifying sensitive workflows and business-critical functionality
This phase establishes the foundation for structured, safe testing of the customer’s environment.
Reconnaissance & Attack Surface Mapping
Automated tooling is used to quickly enumerate and baseline the Chatbot/LLM ecosystem.
Automated testing includes:
- Endpoint enumeration, interface crawling, and integration discovery
- Automated prompt fuzzing to detect injection weaknesses and known attack patterns
- Scanning for exposed backup files, debug resources, or configuration artifacts
- Identification of known vulnerabilities in Chatbot/LLM frameworks and hosting platforms
Automated findings are validated manually to reduce false positives and highlight meaningful patterns.
Manual Testing & Adversarial Behavior Analysis
This phase mirrors Sophos’ deep manual application testing focusing on business logic, access control, and chaining low-severity issues into impactful attack paths.
Supporting Standards and Frameworks
- OWASP GenAI Red Teaming Guide: Lifecycle-based blueprint for red teaming
- OWASP AI Testing Guide: Structured testing for AI systems
- MITRE ATLAS: Tactics and techniques for adversarial threats to AI
- OWASP LLM Security Verification Standard: Security controls for LLM-backed systems
Manual AI-focused testing includes:
Prompt Injection Attacks
- Direct and indirect prompt injection
- Hidden or embedded instruction manipulation
- Context override attacks and system prompt disclosure attempts
Data Leakage Testing
- Attempts to extract confidential or personally identifiable information (PII)
- Retrieval of sensitive internal documents and content from RAG systems
- Probing for training data memorization
Access Control & Permission Abuse
- Circumventing role-based restrictions through phrasing
- Inducing unauthorized plugin/tool actions
- Model-as-proxy API abuse
Business Logic Manipulation
- Triggering unintended actions or workflows
- Generating harmful or inaccurate recommendations
- Inducing unsafe commands or misaligned outputs
Hallucination & Safety Filter Evaluation
- Stress-testing model guardrails
- Validating content moderation and policy enforcement
- Evaluating model consistency under adversarial conditions
Ecosystem & Integration Testing
- Plugin/tool injection and privilege escalation
- Manipulation of vector database content in RAG pipelines
- Testing session management and context isolation
Cloud-Native AI Platform Security & Governance
Before assessing the models themselves, we evaluate the security "wrapper" and orchestration layer provided by the Cloud Service Provider (CSP). This phase ensures that the underlying infrastructure is resilient against misconfiguration and unauthorized access. Some example technology assessments are:
- Azure AI Foundry Assessment
- AWS Bedrock Security Review
The goal: uncover vulnerabilities that are only identifiable through human-led, logic-driven testing.
Vulnerability Chaining & Impact Analysis
Similar to Sophos’ emphasis on combining otherwise low-impact findings into significant exploits, this phase explores:
- Chaining prompt injection with tool execution
- Poisoning retrieval sources to influence model output
- Multi-step attacks that escalate access or cause operational harm
This provides a realistic view of the attacker’s potential reach.
Remediation Validation
Sophos will conduct one (1) remediation validation ("RV") for only the high- and critical-severity findings listed in the final report. After primary test completion, Customer has ninety (90) days in which to remediate issues, schedule the RV, and have Sophos perform the RV. Customer must submit the RV request through email to the Sophos point of contact for the assessment within thirty (30) days of delivery of the final report or the RV is forfeited.
Note: Sophos only conducts RVs remotely, regardless of whether the assessment was conducted on-site.
Outcome
Presentation of findings and deliverables compiled by Sophos will be provided to you in the form of a report. The report will include the following:
- Executive summary
- Methods, detailed findings, narratives, and recommendations if any
- Attachments as needed for relevant details and supporting data
Customer shall have one (1) week from delivery of the report to provide comments to be included in the final report. If there are no comments received from Customer before the expiration of the review period, the report will be deemed final.
Upon completion of the Services, the Customer-designated contact will receive a secure/encrypted email confirmation from Sophos. Unless otherwise notified in writing to the contrary by the Customer designated contact, within five (5) business days of such email confirmation, the Services and this SOW shall be deemed complete.
Scoping information
External testing will be limited to pre-defined target systems or network ranges. For the purposes of scoping, a target system refers to a live system exposing at least one port/service to the Internet.
While we do perform some OSINT to find undocumented assets associated with the customer, no live testing of those systems will be performed without written approval. Any modifications to scope will be discussed and documented with Customer before proceeding, and may incur additional fees through a Change Order.
External penetration testing typically relies on a blackbox methodology adhering to an artificially compressed timeline. Supplying additional information allows for efficient testing which can remain focused on impactful results. Providing a set of valid credentials for a specified test account allows Sophos to perform more accurate password spraying, and to configure tooling for the most efficient testing possible.
| Scope | Description |
|---|---|
| AI Chatbot/LLM Security Assessment | Single Chatbot/LLM Implementation - testing focused on Implementation & Access Controls |
| AI/LLM - Add on Objective | Add-on Objective example: - Assessing Agentic Workflows |
| Custom AI/LLM Security Assessment | Contact Sophos Red Team for scoping to understand the total number of Service Units required. |
Work is conducted during business hours of the Sophos consultant. After-hours feature is available for an additional cost.