Confidentiality and Privilege Leakage Testing for Legal AI

• Chief Information Security Officer (Law Firm)
• Head of Knowledge and Innovation
• General Counsel
• IT Director (Legal)

Firms and legal departments are connecting AI copilots to document management systems, matter workspaces and data rooms. The features that make them useful, retrieval across documents and memory of past work, can expose one client's information to another matter team, reveal privileged advice, or follow instructions a counterparty has planted inside a document.

We run a confidentiality-focused security assessment of your legal AI tool. With your team we map matters, permissions and data flows, then seed canary documents into restricted test matters. Testers act as users on other matters and as external clients, trying direct questions, multi-turn social engineering, system-prompt extraction and indirect prompt injection through uploaded contracts, emails and data room files. We check whether retrieval honours matter permissions, what prompts and outputs are stored and where, and whether agent tools such as email or document export can be misused. Findings come with evidence, severity, mapping to the OWASP Top 10 for LLM Applications and fixes, followed by a re-test.

• Ethical wall testing with canary documents in restricted test matters
• Indirect prompt injection through contracts, emails and data room files
• Client-chatbot tests for disclosure of other clients' information and internal guidance
• System-prompt and configuration extraction attempts
• Review of logging, telemetry and vendor retention of prompts and outputs
• Tool-use abuse tests for email, export and document-sharing actions

1. 01Map matters and data flowsWe document matter permissions, connected repositories, vendors, logs and the tools the AI can use.
2. 02Seed canariesUnique canary documents are placed in restricted test matters with your IT team's approval.
3. 03Run attacksTesters attempt cross-matter retrieval, injection through documents, prompt extraction and tool misuse.
4. 04Check leakage pathsLogs, telemetry and vendor settings are inspected for retained privileged or client content.
5. 05Confirm findingsEach suspected leak is reproduced and reviewed with your security lead.
6. 06Report and re-testYou receive evidence, severity and fixes, and we re-test after remediation.

1. Scoping
   • Matter and permission map
   • Data flow and vendor inventory
   • Rules of engagement
2. Test assets
   • Canary documents for restricted matters
   • Injection payload library for contracts and emails
   • Test user personas across matters
3. Execution
   • Automated prompt and retrieval test runner
   • Manual multi-turn testing
   • Tool-use abuse scenarios
4. Analysis
   • Canary detection in outputs and logs
   • Reproduction and severity rating
5. Reporting
   • Evidence pack with transcripts
   • Mapping to OWASP LLM Top 10 and NIST AI RMF
   • Re-test tracker

Your security lead and our tester confirm each finding together before it is reported, and your risk and IT leadership decide on remediation and go-live. No real client documents are used as test material.

• Legal AI copilot or chatbot under test
• Document management system such as iManage, NetDocuments or SharePoint
• Identity provider and matter permission system
• Logging and SIEM tools
• Issue tracker for remediation

• Only synthetic canary documents and test matters are used
• Testing follows written rules of engagement and agreed time windows
• Findings and evidence shared only with named contacts
• Any real client data seen during testing is reported and not retained
• Re-tests reuse the same scenarios so results are comparable

• Helps you evidence the confidentiality safeguards expected under Bar Council of India rules and the protection of privilege under Indian evidence law.
• Supports DPDP Act 2023 security safeguard obligations and, for EU data, GDPR security requirements.

• Legal

  Contract Clause Extraction and Risk Flags

  Extract key clauses, dates and obligations from executed and incoming contracts, compare them with your playbook and flag deviations, with every item linked to the clause it came from.

• Legal

  Due Diligence Data Room Review

  Index a virtual data room against your request list, extract issues from contracts, corporate records and licences, and draft report tables and query lists for lawyers to confirm.

• SaaS & AI Product Companies

  RAG Data-Leakage and Access-Control Testing

  Test whether your RAG pipeline leaks documents across users, roles or tenants through retrieval, caching, citations or logs, using seeded canary documents and role-based test personas.

• Legal

  Client Intake Voice Agent

  Answer inbound enquiries in Hindi and English, record facts and parties for a conflict check, spot urgent matters for an on-call advocate and book consultations, without giving legal advice.