Penetration Testing

Offensive Security Engagements

Every engagement is tailored to your environment, risk profile, and threat landscape, ensuring you only test what matters most.

Secured foundations. Hardened networks.

Infrastructure Security

Network penetration testing - identify internal & external weaknesses
Internal/External attack simulation – validate real‑world threat pathways

Protected platforms. Secure code.

Application Security

Web, mobile, and API testing – uncover vulnerabilities across your applications
WAF bypass testing – assess whether attackers can evade your defences

Resilient people. Informed defense.

Human-Layer Security

Social engineering – test human resilience against manipulation
Credential harvesting tests – identify gaps in identity security

Think like hackers. Defend like pros.

Adversarial Simulation

SOC testing – evaluate detection and response readiness
Red teaming – full‑spectrum adversary simulation & tests

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What Our Clients Say

"We engaged Cyber Caddy for both their Managed Security Operations and Cyber Consulting, and the comprehensive value has exceeded our expectations. I’d highly recommend working with the Cyber Caddy team to anyone looking for a dependable and well-rounded cybersecurity partner."
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Joe Oliver

IT Manager / PTG Group

"In the development industry, reputation and data integrity are everything. Before Cyber Caddy, our digital security was a blind spot. They didn’t just provide a service; they built a culture of resilience within our firm. Now, with their 24/7 proactive vigilance, I have total confidence our operations are protected, allowing us to focus entirely on our next phase of growth."

Tim Black

CEO / Black Developments

“Cyber Caddy played a critical role in elevating our cyber security posture. Through their Virtual CISO service, they implemented key policies, developed essential business documents, and aligned our practices with a recognised cyber security framework. Their structured approach gave us clarity, confidence, and a strong foundation for ongoing security.”

Ivor Ryan

CFO / Results Legal

"Having Cyber Caddy monitor our technology and oversee our IT provider gives me the extra peace of mind I was looking for. I highly recommend having Cyber Caddy as your dedicated cyber partner for your business."
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Mark Aldridge

Director / EmandEm Accountants

Frequently Asked Questions (FAQs)

What is penetration testing and why do we need it?

Penetration testing (pen testing) is a controlled, ethical attack on your systems or applications to identify exploitable weaknesses before real attackers do. It gives you evidence‑based visibility of risk and a prioritised fix list you can act on immediately.

How is a pen test different from a vulnerability scan?

A vulnerability scan is automated and broad; a pen test is manual, targeted, and exploit‑focused. Pen testers validate findings, chain weaknesses, and assess real‑world impact, not just list potential issues.

How do you determine the right scope for our pen test?

We start with a short consult: business objectives, threat profile, compliance needs, asset inventory, and testing constraints. Then we propose a scope that maximises risk coverage for your budget (e.g., high‑value apps, internet‑facing assets, identity attack paths).

What do we receive at the end of the engagement?

A clear, executive‑ready report including: findings with evidence, risk ratings, business impact, exploit paths, and prioritised remediation guidance. We also deliver a technical appendix and a walkthrough session with your team.

Can you test our cloud environments and APIs?

Absolutely. We test AWS/Azure/GCP configurations, IAM paths, storage exposures, and service endpoints, as well as REST/ GraphQL/ SOAP APIs for authz/ authn flaws, input validation, and business‑logic weaknesses.

Do you perform social engineering as part of pen testing?

On request and within strict approvals. We can simulate phishing, MFA‑fatigue attacks, and credential harvesting campaigns to measure human‑layer resilience and report practical improvements.

What standards or frameworks guide your methodology?

We align with widely recognised practices (e.g., OWASP for application testing, reputable penetration testing methodologies, and structured kill‑chain thinking for adversarial simulations). The goal is consistent, repeatable quality with real‑world relevance.

How often should we conduct a pen test?

Common cadence is annually for core systems and before/after major releases for critical applications. Additional testing is recommended after significant architecture changes or new internet‑facing deployments.