Cloud config, app logic, and human error: What penetration tests really catch & why it matters

From the outside, a penetration test might seem like a checkbox exercise: a routine security assessment, a report with technical findings, yet another compliance box ticked. But today’s threat landscape, and the approach to penetration testing and broader assurance services, is anything but routine. 

In fact, modern penetration testing has evolved far beyond perimeter scanning. With today’s complex cloud architectures, bespoke applications, and constant human oversight, effective penetration testing digs deeper. It uncovers business logic vulnerabilities, cloud misconfigurations, and chained exploits that automated scanners simply can’t detect. 

The demand is justified. IBM’s “Cost of a Data Breach” report uncovered that the average cost of a data breach in Australia is $3.92 million AUD. Some of the most frequent, and costly, data breach causes are the result of vulnerabilities that penetration testing is designed to uncover. Examples of pen test outcomes that reduce breach risk include hardening internal systems and processes to minimise malicious insiders, enhancing the resilience of third-party and supply chain integrations, and strengthening the security of user credentials. As such, proactive penetration testing has become a critical safeguard to identify vulnerabilities before attackers do. 

In this article, we explore what modern penetration tests are designed to catch, and why human expertise still matters. We also examine how Australian businesses can ensure they’re investing in testing that improves their security posture, not just their paperwork. 

Types of penetration testing

Penetration testing is no longer a one-size-fits-all approach. Depending on business needs, threat models, and environment complexity, there are several types of pen tests, including: 

•  External Network Penetration Testing: To find and assess your organisation’s internet facing systems from the point-of-view of an internet-based attacker with minimal starting information (aka a “black-box” test). 
•  Internal Network Penetration Testing: Finds vulnerabilities affecting devices on your organisation’s private corporate network that an attacker could exploit if they have breached the perimeter. Our approach goes beyond pure infrastructure testing, emphasising identity risks in your on-premises Active Directory.
• Web Application Penetration Testing: Focuses on flaws like SQL injection, XSS, authentication and authorisation weaknesses, and business logic issues.
• API Penetration Testing: Examines APIs for broken authentication, insecure endpoints, excessive data exposure, and logic flaws like broken object-level authorisation (BOLA).
• Mobile Application Penetration Testing: Identifies vulnerabilities in mobile apps such as insecure storage, improper session handling, weak encryption, and potential reverse engineering risks. 

Each approach uncovers different layers of risk. The most impactful engagements often combine several techniques to simulate real-world adversary behaviour.

Why a network perimeter scan isn’t enough

Traditional vulnerability scans were built to check firewalls, open ports, and known weaknesses in on-prem infrastructure. But today’s environments are cloud-native, API-driven, and highly dynamic. 

Industry experts report that many successful cloud breaches stem from misconfigurations or identity and access management (IAM) errors, not from perimeter attacks. Gartner reinforces this, projecting that through 2025, 99% of cloud security failures will be caused by customers failing to meet their shared responsibility obligations for cloud services. 

While perimeter scans are still relevant, they fail to account for: 

• Cloud-native risks, such as over-permissive IAM roles or exposed storage buckets.
   
• SaaS integrations, where lateral movement can occur across third-party platforms.
   
• Microservices, where internal APIs and service-to-service trust relationships can be exploited.

The reality is clear: organisations can no longer rely solely on network scans. Cloud penetration testing and application-layer insight are essential to finding the risks that, when overlooked, lead to breaches. 

Low quality threats vs real threats

There are certain “easy wins” that show up in almost every pen test report: SSL/TLS configurations, outdated JavaScript libraries, or missing HTTP headers. These aren’t irrelevant, but they’re also not what keeps CISOs up at night. 

Here’s how we break it down:

The Cloud Security Alliance’s 2024 State of Application Security report found that eight of the ten largest data breaches in 2023 were linked to application-layer vulnerabilities, not flaws in encryption or headers. Those breaches exposed nearly 1.7 billion records, illustrating just how costly misconfigurations and insecure logic can be. 

Real threats often hide in business logic, misconfigured permissions, and complex chains of minor weaknesses, the kinds of issues automated scanners rarely catch in full context. 

Vulnerabilities in business logic

Business logic flaws are the crown jewels of manual penetration testing. 

These are vulnerabilities that arise from your application’s functionality: the flows, rules, and decisions it makes when processing user input or managing transactions. 

Examples include: 

• Abusing a discount engine to get free or near-free products.
• Escalating privileges by modifying role parameters in a workflow.
• Skipping payment verification by manipulating API sequences.
• Draining funds by abusing refund or loyalty points logic.
   

These aren’t bugs you can find with a scanner. Instead, they require a deep understanding of the business context. It also takes the creativity, experience and cyber smarts to think like an attacker, and spot the unintended consequences of application logic. 

Chaining low-risk flaws into breach paths

Sometimes, the real risk isn’t in any single flaw, but in how they combine. 

Imagine this chain: 

1. Verbose error message exposes internal stack trace.
2. Misconfigured S3 bucket is publicly readable.
3. Hardcoded credential found in a backup file.
4. Credential reuse allows lateral movement into production environment.
    

Individually, none of these items might raise red flags. But together? They open the door to a full-scale compromise. 

Effective penetration testing models this attacker mindset, showing not just isolated findings, but how small cracks can be chained together to form a major business risk. 

Why human insights are still essential

As AI and automation take over more tasks, it’s fair to ask: do we still need human penetration testers?  

Here’s the truth: 

• AI can’t contextualise risk: It flags issues but doesn’t know your business priorities or the real-world impact of an exploit.
• Scanners over-report: False positives waste time. Human experts will triage penetration test results to ensure only relevant results are presented for action. unless triaged by a human.
• Attackers are creative: So, your testers need to be too.

Human experts provide: 

• A holistic, intuitive, and creative approach to problem-solving.
• Accuracy, being easily able to detect minor differences in text that change its meaning drastically, especially in a technical context.
• Independence and leadership, with the ability to offer important advice without being prompted.
• Context-aware testing that evolves with your systems .

Turning penetration testing insights into action

A good penetration test doesn’t just dump findings on your desk; instead, it helps you act.

Slipstream Cyber recommends:

• Risk-based prioritisation, with clearly communicated logic behind each risk assessment.
• Clear technical evidence supporting each finding included in the report.
• Remediation guidance that includes a best-practice fix, but also a secondary option when appropriate.
• Clear categorisation, separating valuable informational findings from directly exploitable vulnerabilities.

The goal is to spot vulnerabilities, but also to reduce your attack surface in measurable ways and to provide useful security advice.

Choosing a modern pen-test partner

When selecting a penetration testing provider, look for:

• Proven expertise in infrastructure and application testing.
• A human-led approach, rather than one that places specific tools above all else.
• Reports that include clear and detailed evidence, risk assessments, prioritisation, and remediation steps.
• Support for retesting and verification.
• Australian data sovereignty.

These are non-negotiables for organisations serious about security outcomes.

Insights and actions with Slipstream Cyber

Slipstream Cyber approaches penetration testing with one goal: make it useful, not just compliant. Our value comes from the diligence we apply to every report. We ensure each one is accurate, relevant, and clearly reasoned. That way, security teams, developers, executives, and boards all understand every risk, what matters, and why.

We go beyond automated tools, providing:

• Manual testing that uncovers business logic flaws, not just surface-level noise.
• Contextual insights tailored for technical and non-technical audiences.
• Chained exploit discovery with clear remediation guidance.
• Reports that drive action, not confusion or checkbox exercises.

With fully Australian-based operations and access to multi-disciplinary expertise, we help businesses make real security gains and understand the “why” behind every finding.

Essentially, Slipstream helps you move from reactive fixes to proactive risk reduction, with complete clarity at every step.

Want to see what a modern, premium, and comprehensive pen test can really uncover?

Explore our full range of penetration testing services or get in touch with Slipstream Cyber today.