Software Secured Company Logo.
Services
Services
WEB, API & MOBILE SECURITY

Manual reviews expose logic flaws, chained exploits, and hidden vulnerabilities

Web Application Pentesting
Mobile Application Pentesting
Secure Code Review
Infrastructure & Cloud Security

Uncovers insecure networks, lateral movement, and segmentation gaps

External Network Pentesting
Internal Network Pentesting
Secure Cloud Review
AI, IoT & HARDWARE SECURITY

Specialized testing validates AI, IoT, and hardware security posture

AI Pentesting
IoT Pentesting
Hardware Pentesting
ADVANCED ADVERSARY SIMULATIONS

We simulate attackers, exposing systemic risks executives must address

Red Teaming
Social Engineering
Threat Modelling
PENETRATION TESTING AS A SERVICE

PTaaS provides continuous manual pentests, aligned with release cycles

Penetration Testing as a Service
OWASP TOP 10 TRAINING

Practical security training strengthens teams, shifting security left effectively

Secure Code Training

Ethical Hacking

Services Overview

Black arrow icon

Enterprise Deal Support

Services Overview

Black arrow icon
Ready to get started?
Identify real vulnerabilities confidently with zero-false-positive penetration testing
Learn More
Industries
Industries
INDUSTRIES
Data and AI

AI pentesting uncovers adversarial threats, ensuring compliance and investor trust

Healthcare

Penetration testing protects PHI, strengthens compliance, and prevents healthcare breaches

Finance

Manual pentests expose FinTech risks, securing APIs, cloud, and compliance

Security

Penetration testing validates SecurTech resilience, compliance, and customer trust

SaaS

Pentesting secures SaaS platforms, proving compliance and accelerating enterprise sales

CASE STUDY

“As custodians of digital assets, you should actually custodize assets, not outsource. Software Secured helped us prove that our custody technology truly delivers on that promise for our clients in both the cryptocurrency and traditional finance”

Nicolas Stalder,
CEO & Co-Founder, Cordial Systems
Black arrow icon
Ready to get started?
Our comprehensive penetration testing and actionable reports have 0 false positives so you can identify
Learn More
Compliance
Compliance
COMPLIANCE
SOC 2 Penetration Testing

Pentesting validates SOC 2 controls, proving real security to auditors and customers

HIPAA Penetration Testing

Manual pentesting proves HIPAA controls protect PHI beyond documentation

ISO 27001 Penetration Testing

Pentests uncover risks audits miss, securing certification and enterprise trust

PCI DSS Penetration Testing

Pentesting validates PCI DSS controls, protecting sensitive cardholder data

GDPR Penetration Testing

GDPR-focused pentests reduce breach risk, regulatory fines, and reputational loss

CASE STUDY

“Software Secured’s comprehensive approach to penetration testing and mobile expertise led to finding more vulnerabilities than our previous vendors.”

Kevin Scully,
VP of Engineering, CompanyCam
Black arrow icon
Ready to get started?
Our comprehensive penetration testing and actionable reports have 0 false positives so you can identify
Learn More
PricingPortal
Resources
Resources
resources
Blogs
Case Studies
Events & Webinars
Partners
Customer Testimonials
News & Press
Guides and checklists
About Us
cybersecurity and secure authentication methods.
Black arrow icon
API & Web Application Security Testing

Attack Chains: The Hidden Weakness in Modern API & Web Application Security

Alexis Savard
November 21, 2025
Ready to get started?
Our comprehensive penetration testing and actionable reports have 0 false positives so you can identify
Learn More
Login
Book a Consultation
Deal Blocked?
Guides and checklists
/
Technical Fact Sheets

AI Penetration Testing Fact Sheet

This technical fact sheet explains how penetration testing approaches AI-integrated applications, including LLM APIs, Retrieval-Augmented Generation (RAG) systems, Model Context Protocol (MCP) servers, AI agents, and AI-generated code.

Download document

Key Takeaways

  • Understand the five major AI attack surfaces tested during an AI pentest.
  • Learn how security researchers evaluate LLM APIs, RAG pipelines, MCP servers, AI agents, and AI-generated code.
  • See real examples of vulnerabilities discovered in AI-integrated applications.
  • Understand how prompt injection, cross-tenant access, privilege escalation, and tool abuse occur.
  • Learn why securing the application around the model is often more important than testing the model itself.
  • Understand the differences between traditional application pentesting and AI-specific security testing.
  • Identify where AI features create new opportunities for unauthorized access, data exposure, and unintended actions.
  • Learn what enterprise buyers and security teams expect from AI security testing.
  • Penetration Testing for AI-Integrated Applications – Software Secured
    Software Secured · Technical Fact Sheet

    Penetration Testing for
    AI-Integrated Applications

    Who this is forEngineering leads, CTOs, and security teams shipping products that use LLMs, RAG pipelines, AI agents, or MCP-connected tooling.
    01LLM API Integrations
    Testing Approach
    We treat the LLM as an untrusted component in the application stack, not as a black box. Testing focuses on how user input reaches the model, how model output is handled downstream, and whether the boundary between the application and the LLM provider is properly enforced. We probe prompt construction logic, test system prompt confidentiality, and evaluate whether the application trusts model output in ways it shouldn't.
    Sample Vulnerabilities
    System prompt extraction via indirect prompt injection in user-supplied content
    Model response passed to a downstream function (e.g., code executor, SQL builder) without sanitization
    API key exposure through verbose error handling when provider calls fail
    Unbounded token consumption leading to denial-of-service via inflated inference costs
    Sensitive data (PII, internal instructions) reflected back in model completions due to poor context management
    02Retrieval-Augmented Generation (RAG)
    Testing Approach
    RAG systems introduce two attack surfaces that LLM-only integrations don't have: the document ingestion pipeline and the vector retrieval layer. We test both. On ingestion, we evaluate whether malicious content embedded in source documents can influence model behavior at query time. On retrieval, we test whether users can manipulate queries to surface documents they shouldn't have access to, and whether the retrieval results respect tenant or role boundaries. We also evaluate how the application handles conflicting or adversarially crafted retrieved chunks.
    Sample Vulnerabilities
    Prompt injection embedded in ingested documents (PDFs, emails, knowledge base articles) that hijacks model behavior when retrieved
    Cross-tenant document retrieval: user in Tenant A retrieves chunks belonging to Tenant B through crafted semantic queries
    Retrieval manipulation that forces the model to ignore its knowledge base and respond from injected context
    Metadata leakage: document filenames, author fields, or internal IDs exposed in cited sources
    No re-ranking or relevance threshold, allowing low-quality injected content to dominate retrieved context
    03Model Context Protocol (MCP)
    Testing Approach
    MCP dramatically expands what an AI system can do - and therefore what it can be made to do. We test MCP servers as network-exposed services with their own attack surface, evaluate tool definitions for overly permissive capability declarations, and assess whether the host application enforces meaningful human-in-the-loop controls before executing sensitive tools. We also test for prompt injection paths that could cause an LLM client to invoke MCP tools without user intent.
    Sample Vulnerabilities
    MCP server exposes tools (file write, shell exec, API calls) without enforcing caller authentication
    Tool descriptions crafted or manipulated to mislead the LLM into invoking higher-privilege operations
    Prompt injection in external content (emails, documents) causes the LLM to silently invoke destructive MCP tools
    Tool results returned to the LLM contain adversarial instructions that redirect subsequent tool use
    No rate limiting or scope restriction on MCP tool execution, enabling automated abuse at scale
    04AI Agents
    Testing Approach
    Agents operate with greater autonomy, longer task horizons, and more real-world side effects than single-turn LLM calls. Testing focuses on whether agents can be diverted from their intended task, whether they enforce scope boundaries across multi-step workflows, and whether their actions are reversible when something goes wrong. We simulate adversarial inputs at each step in multi-agent pipelines and evaluate whether orchestrator-to-subagent trust is properly scoped.
    Sample Vulnerabilities
    Task hijacking via adversarial content in the environment (a webpage, file, or API response the agent reads mid-task)
    Privilege escalation: subagent granted broader permissions than the initiating user holds
    Persistent memory poisoning - injecting false context into agent memory that influences future sessions
    Unbounded action loops triggered by malformed tool results, consuming credentials or budget without user awareness
    Orchestrator blindly trusts subagent output, allowing a compromised subagent to direct orchestrator behavior
    05AI-Assisted Developer Tooling & Platform-Generated Code
    Testing Approach
    AI-generated code introduces risk at the point of deployment, not at the point of generation. We review codebases and infrastructure where AI tooling (Copilot, Claude Code, Cursor, platform scaffolding) has contributed material functionality, focusing on the vulnerability patterns that appear most frequently in LLM-authored code. We also test platforms that generate executable output - workflow builders, low-code tools, AI-authored scripts - treating generated artifacts as first-class attack surface.
    Sample Vulnerabilities
    Generated authentication code that omits token expiry, scope validation, or revocation logic
    AI-scaffolded API endpoints with missing authorization checks (the model implements the happy path, not the security path)
    Over-permissioned IAM roles and cloud policies produced by AI infrastructure tooling
    Generated SQL or shell commands built from user input without parameterization
    Platform-generated code deployed without review, containing hardcoded credentials or insecure default configurations
    XSS and unsafe HTML rendering from AI-generated UI components that embed dynamic content without sanitization
    About Software Secured
    Software Secured is a premium manual penetration testing firm serving Series A/B SaaS companies. Every finding we deliver is confirmed exploitable. Zero false positives. Reports accepted by SOC 2 auditors and enterprise security teams.
    Get in touch
    softwaresecured.comsales@softwaresecured.com

    Ready to Test Your AI Application?

    Book a free consultation to find the right pentesting strategy for your AI-enabled product.

    Book a Consultation →

    Ready to get in touch? Get started by booking a consultation now.

    Book Consultation

    Get security insights straight to your inbox

    Continue your reading with these value-packed posts

    Security standards and compliance concept illustration
    Black arrow icon
    Penetration Test Reports & ROI

    Internal vs External Penetration Testing: What's the Difference?

    Kaycie Waldman
    Kaycie Waldman
     min read
    May 10, 2026
    Cybersecurity incident response lessons by Software Secured
    Black arrow icon
    API & Web Application Security Testing

    The Good, The Bad and the Ugly? Lessons from Incident Responses

    Omkar Hiremath
    Omkar Hiremath
    9 min read
    October 31, 2022
    4 Ways to Meet Your Deadlines
    Black arrow icon
    Vulnerability Management & Scoring

    Mastering SLAs: 4 Ways to Meet Your Deadlines

    Shimon Brathwaite
    Shimon Brathwaite
    7 min read
    July 13, 2023

    Helping companies identify, understand, and solve their security gaps so their teams can sleep better at night

    Book a Consultation
    Centralize pentest progress in one place
    Canadian based, trusted globally
    Actionable remediation support, not just findings
    Clutch logo
    Web, API, Mobile Security
    Web App PentestingMobile App PentestingSecure Code Review
    Infrastructure & Cloud Security
    External Network PentestingInternal Network PentestingSecure Cloud Review
    AI, IoT & Hardware Security
    AI PentestingIoT PentestingHardware Pentesting
    More
    PricingPortalPartnersContact UsAbout UsOur TeamCareers
    More Services
    Pentesting as a ServiceSecure Code Training
    Industries
    Data and AIFinanceHealthcareSecuritySaaS
    Compliance
    GDPR PentestingHIPAA PentestingISO 27001 PentestingPCI DSS PentestingSOC 2 Pentesting
    Resources
    BlogsCase StudiesEvents & WebinarsCustomer TestimonialsNews & PressWhitepapers
    More
    PricingPortalPartnersContact UsAbout UsOur TeamCareers
    Resources
    BlogsCase StudiesEvents & WebinarsCustomer TestimonialsNews & PressWhitepapers
    Security & CompliancePrivacy PolicyTerms & Conditions
    2026 ©SoftwareSecured