Home› Services› Penetration Testing
Service
AI-Enhanced

Penetration
Testing &
AI Red-Teaming

Find your vulnerabilities before adversaries do. Citadel Africa's penetration testing combines certified offensive security expertise with AI-assisted attack simulation — including adversarial testing of your AI systems, LLMs, and ML pipelines.

Request a Pentest Our Methodology ↓
100% Findings Validated
0 False Positive Tolerance
CEH Certified Testers
Live Simulation
citadel-recon v2.4 — target: [CLIENT ENVIRONMENT]
$ ./citadel-scan --target scope.conf --mode full
# Initialising AI-assisted reconnaissance...
[*] Enumerating external attack surface
[+] Open ports discovered: 22, 80, 443, 8080
[+] Web application fingerprinted: Apache 2.4.51
[!] CVE-2021-41773 — Path traversal (HIGH)
[!] Exposed .env file — credentials at risk
[*] Scanning LLM API endpoint...
[!] Prompt injection vector identified
[!] System prompt leakage — CRITICAL
[✓] Report generating: 14 findings (2 CRIT, 5 HIGH)
$
What It Is

Offensive Security Testing That Mirrors Real Attacks

Penetration testing is controlled, authorised hacking — carried out by Citadel Africa's certified analysts to identify and exploit vulnerabilities in your environment before real attackers do. We don't just scan for known issues. We think and act like the adversaries targeting your sector.

Every engagement is scoped to your environment, risk profile, and objectives. We deliver clear, prioritised findings with actionable remediation guidance — not a raw list of CVEs your team can't action.

In the age of AI, traditional penetration testing is no longer enough. Our engagements now include adversarial testing of AI systems, LLM implementations, and ML models — covering the attack surfaces most firms have never assessed.

Network & Infrastructure
Internal and external network testing — firewalls, servers, cloud infrastructure, VPNs, and Active Directory environments.
Web & Mobile Applications
OWASP Top 10 and beyond — authentication, session management, injection flaws, API security, and business logic vulnerabilities.
AI / LLM Adversarial Testing
Prompt injection, jailbreaking, system prompt extraction, model inversion, and data poisoning attacks on your AI implementations.
Social Engineering
Phishing simulations, pretexting, and human-layer testing — because your people are the most targeted attack vector.
AI-Enhanced Capability
We Test What Other Firms Ignore
Prompt Injection Testing

We attempt to hijack your LLM's instructions through malicious inputs — testing whether attackers can override system prompts, extract sensitive training data, or make your AI act against its design.

Model Jailbreaking

We test whether your AI guardrails hold under adversarial pressure — using known and novel jailbreak techniques to evaluate if your model can be manipulated into unsafe or policy-violating outputs.

System Prompt Extraction

Many organisations embed confidential business logic in LLM system prompts. We test whether an attacker can extract this information — exposing proprietary instructions, internal data, or security controls.

API & Integration Testing

AI-powered applications connect to external services, databases, and APIs. We test every integration point for authentication weaknesses, data leakage, and privilege escalation vectors.

ML Model Inversion

We test whether attackers can reconstruct training data or extract sensitive information from your ML models through carefully crafted queries — a growing risk for finance, healthcare, and HR applications.

MITRE ATLAS Aligned

Our AI red-teaming methodology is aligned to the MITRE ATLAS framework — the industry standard for adversarial ML threat intelligence — ensuring complete, structured coverage of your AI attack surface.

How We Work

Our Penetration Testing Methodology

A structured, intelligence-led approach aligned to PTES, OWASP, and MITRE ATT&CK — every step documented, every finding validated.

Step 01
Scoping & Rules of Engagement

We define target systems, test boundaries, timelines, and emergency contacts. You sign off on scope before a single packet is sent.

Planning
Step 02
Reconnaissance & OSINT

AI-assisted intelligence gathering on your digital footprint — subdomains, exposed credentials, technology stack, employee data, and threat actor interest.

AI-Assisted
Step 03
Vulnerability Discovery

Automated scanning combined with manual analysis to identify vulnerabilities, misconfigurations, and logic flaws that automated tools alone will miss.

Technical
Step 04
Exploitation & Post-Exploitation

We safely exploit confirmed vulnerabilities to demonstrate real-world impact — privilege escalation, lateral movement, and data access — stopping only where scoped.

Offensive
Step 05
Report & Debrief

A detailed report with CVSS scores, risk ratings, evidence, and actionable remediation steps. Followed by a live debrief with your security team.

Reporting
What You Get

Deliverables

Executive Summary Report
A non-technical overview of findings, risk posture, and strategic recommendations — written for board and leadership audiences.
Technical Findings Report
Full technical detail on every finding — CVSS score, evidence, proof-of-concept, affected systems, and step-by-step remediation guidance for your engineering team.
Risk-Ranked Vulnerability Register
A prioritised list of all findings, rated Critical / High / Medium / Low — so your team knows exactly what to fix first.
Live Debrief Session
A walkthrough of findings with your technical team — we explain attack chains, answer questions, and help you build a remediation plan.
Retest & Letter of Attestation
After remediation, we verify fixes are effective and issue a letter of attestation — accepted for compliance, audits, and board reporting.
Sample Report Summary
Penetration Test — External Network Assessment
Critical
2
High
5
Medium
8
Low
12
Scope External Network + Web App
Duration 5 Days
Methodology PTES + OWASP
AI Testing Included
Retest Included (30 days)
Why Citadel Africa

What Sets Our Pen Testing Apart

01
Zero False Positives Policy

Every finding in our reports is manually validated. We never deliver scanner output dressed up as a pentest. If we report it, we've confirmed it exploitable.

02
AI Attack Surface Coverage

We are one of the only firms in East Africa offering adversarial AI testing. If you've deployed LLMs, AI agents, or ML models — we test them with the same rigour as your network.

03
Kenya-Context Intelligence

Our reconnaissance uses threat intelligence specific to the Kenyan and East African threat landscape — meaning we test for the attack techniques actually used against your sector, not generic global patterns.

Get Started

Ready to Find Your Vulnerabilities First?

Request a scoping call today. We'll assess your environment and recommend the right penetration testing engagement for your risk profile and budget.

Request a Pentest View All Services
Active breach? Call our emergency line immediately: +254 797 907 510 — 24/7