Think of your business like a bank. You have valuable assets such as data, systems, customer relationships, brand reputation and more – with strong defences at the front door. But how can you be sure those defences will hold?
Just as a bank regularly runs security checks on its vaults, cameras and alarm systems, penetration testing (or “pen testing”) is your digital security check, probing systems from the outside in to find out exactly where an attacker could potentially slip through.
Unlike standard cyber security assessments that provide a snapshot of your security posture, pen tests go a step further. They simulate real-world attacks to actively exploit weaknesses and assess how far a threat could reach if your defences were breached. This hands-on approach can help to uncover vulnerabilities you may not even know exist, so you can fix them before they’re exploited.
Let’s explore the key benefits of penetration testing, the different types of tests, how the process works and what to consider when choosing the right provider, so you can make informed, proactive decisions about your organisation’s security.
The Importance and Benefits of Penetration Testing
Penetration testing is both a technical exercise and strategic investment in your organisation’s resilience. By simulating real-world attacks, your business can gain critical insights that guide smarter security decisions and protect your bottom line.
Consider key benefits, such as:
- Supporting regulatory compliance – aligning with industry standards and regulations by demonstrating proactive security measures.
- Managing risk – by identifying and prioritising vulnerabilities before they can be exploited.
- Preventing breaches – mitigating potential threats by uncovering hidden gaps in your defences.
- Protecting trust and reputation – demonstrating to clients, partners and other key stakeholders that your business takes cyber security seriously, reinforcing confidence in your brand.
An Overview of the Penetration Testing Process
A structured, step-by-step approach by a cyber security expert can deliver thorough coverage and clear outcomes. Here’s what typical penetration testing involves.
1. Scoping & Reconnaissance
Your Inspired IT cyber security expert will collaborate with you to define objectives, identify target systems and establish rules of engagement, then gather information about networks, applications and users to map potential entry points.
2. Exploitation
Next, your penetration tester will actively deploy tools and techniques to breach identified weaknesses (just as a real attacker would) to demonstrate the impact of vulnerabilities.
3. Post‑Exploitation
Your specialist will explore how far a potential intruder could progress, elevate privileges or access sensitive data once inside your environment.
4. Reporting & Remediation
They will then compile a clear, actionable report detailing each finding, its risk rating and step‑by‑step recommendations so you can prioritise and implement fixes.
5. Retesting
Your tester may rerun targeted tests against previously exploited areas to confirm remediations are effective and your defences are more solid.
Common Types of Penetration Testing
To address different risk profiles, let’s explore a few different types of penetration testing in cyber security, based on information available and attack vectors.
1. Information Availability
The amount of information shared with a tester before an engagement can influence its outcomes. The style of test is typically described as white box, black box or grey box penetration testing.
Open‑Box (White‑Box)
In open-box testing, your tester receives some security information ahead of time, such as network diagrams and configuration files.
Closed-Box (Black-Box)
In closed box testing, your tester will start without prior knowledge – just as an external attacker might. This method can evaluate how well your perimeter defences can withstand an unknown adversary.
Covert (Grey‑Box)
In grey box penetration testing, testers only receive partial insight (for example, user credentials or network maps). This balances depth and realism, focusing on high‑risk areas without full disclosure.
2. Attack Vector
To understand how real attackers might breach your defences, tests also focus on key attack vectors – different pathways and methods that may be used to gain unauthorised access to systems, networks and applications. Some examples of different attack vectors include the following.
External Network Penetration Testing
These tests target your internet‑facing infrastructure (e.g. firewalls, VPN gateways, mail servers and public web portals) to reveal how an outside attacker might gain entry.
Internal Network Penetration Testing
These tests simulate an insider threat or compromised device to uncover paths for privilege escalation, lateral movement and access to sensitive information.
Web Application Penetration Testing
These tests review your customer‑facing and internal apps to identify and exploit vulnerabilities relating to authorisation, security configuration and data protection mechanisms.
Mobile & APIs Penetration Testing
These tests simulate hacking attempts against mobile applications (such as iOS/Android) to identify and exploit vulnerabilities in the way it interacts and transfers data with backend systems – such as insecure data storage, flawed authentication flows and excessive permissions.
Wireless Penetration Testing
These tests examine your Wi‑Fi networks, access points and connected IoT devices to identify weak encryption, misconfigured access points and weak security protocols.
Physical Security Penetration Testing
A tester may target physical security controls to gain unauthorised access to restricted areas or server rooms, for example, through door locks or badge systems.
Social Engineering Penetration Testing
These types of tests may target employees to gain unauthorised access to protected systems, such as through:
- phishing – sending fraudulent email links or other messages to induce employees to reveal personal or business information.
- tailgating – attempting to follow employees into secure areas.
- pretexting – impersonating an employee and attempt to persuade employees to divulge confidential information.
- baiting – leaving USBs infected with malware inside and outside buildings for employees to find and insert into a computer.
This exercise can expose gaps in human awareness and response protocols.
By selecting the right mix of tests, you can determine your greatest risk areas, as well as remediation pathways to strengthen your business’s overall security posture.
Penetration Testing vs. Vulnerability Assessment
If you’re familiarising yourself with penetration testing, you may also come across the concept of vulnerability assessments. Before choosing the right security exercise, it can help to understand how penetration testing and vulnerability assessments differ, and how they can complement each other.
| Type | Penetration Testing | Vulnerability Assessment |
|---|---|---|
| Objective | Exploit weaknesses to demonstrate real-world impact. | Identify and catalogue known vulnerabilities. |
| Approach | Hands-on, simulated attack by skilled testers. | Automated scans and manual verification of known issues. |
| Scope | Focused on critical systems or high-value targets. | Broad coverage of network devices, applications and configurations. |
| Depth | In-depth exploitation, lateral movement and privilege escalation | Surface-level checks for missing patches, misconfigurations |
| Outcome | Detailed vulnerability report and results, with risk context and remediation recommendations. | Comprehensive list of vulnerabilities with severity ratings |
Together, these assessments can create a powerful “one‑two punch”.
- Vulnerability assessments map out your “attack surface” by pinpointing potential weak spots at scale.
- Penetration tests can then take a closer look at these critical areas, showing exactly how a potential attacker might exploit them and how to prioritise fixes.
By combining both, you can build a proactive, layered defence that’s wide‑ranging and informed.
Frequency and Timing of Penetration Testing
Determining the right cadence for penetration tests can help you stay ahead of evolving threats and meet regulatory obligations. As a rule of thumb, it’s good practice to conduct testing as follows:
- annual testing – at least one full test per year to maintain baseline security
- after significant changes – re‑test following major system upgrades, new technology roll‑outs or infrastructure migrations
- quarterly – for high‑risk environments (such as organisations utilising public‑facing portals or critical applications), or as required by industry standards
- in line with regulatory requirements – such as organisations in industries driven by frameworks that mandate specific testing frequencies.
Consider using this checklist to tailor your schedule:
- Have you deployed new hardware or software?
- Have you experienced a security incident in the last 12 months?
- Does your industry standard or client contracts specify testing intervals?
- Are you planning significant architectural or network changes?
Answering “yes” to any of these questions may mean it’s time to schedule your next pen test.
Selecting the Right Penetration Testing Provider
Choosing the right partner is critical to successful penetration testing. Look for firms with recognised credentials, proven methodologies and a track record in your industry. Be wary of providers who offer “one‑size‑fits‑all” services or lack transparency.
Provider Qualifications & Considerations
Look for providers with:
- CREST, OSCP or CISSP certifications
- documented methodology (e.g., OWASP, PTES)
- case studies or references in your sector (e.g., mining, construction, professional services)
- clear scope definition and rules of engagement
- detailed reporting format with risk ratings and remediation guidance.
Red Flags to Avoid
There are a few indicators to watch out for that may indicate a questionable penetration test provider, including:
- vague proposals or no formal engagement contract
- overly cheap, bundled “scan + pen test” packages
- lack of post‑test support or retesting options
- unsubstantiated claims/no evidence of ethical hacking best practices.
Use this checklist to vet prospective providers and ensure you get thorough, reliable testing professionals.
Learn how Inspired IT’s ethical, transparent certified cyber security experts can tailor a penetration test to your organisation’s unique needs. Find out more on our Penetration Testing Service page.
Common Myths and Misconceptions
Don’t let common misunderstandings leave your organisation’s vulnerabilities exposed. Let’s clear up a few myths about penetration testing.
Myth: “Only large organisations need pen tests.”
Businesses of all sizes hold valuable data. Even small breaches can have devastating impacts.
Myth: “Compliance means we’re secure.”
Meeting standards is a baseline. Real security comes from actively finding and fixing gaps.
Myth: “One‑time tests are enough.”
Threats evolve constantly. Regular testing can help you keep pace and uncover new vulnerabilities.
Myth: “Pen tests uncover every flaw.”
While penetration testing can be invaluable at identifying and addressing gaps, no test is exhaustive. Combining assessments and ongoing monitoring can provide your organisation with better coverage.
Myth: “Penetration testing is too disruptive.”
Skilled providers can minimise business impact by planning around your operations and windows of downtime.
Real-World Examples of Penetration Testing Impact
Curious how pen tests can deliver tangible results? Let’s explore a few example success stories.
A Financial Services Firm Thwarts Ransomware
A mid‑sized accounting practice invited a cyber security specialist to conduct a pen test after hearing of a local ransomware surge. Testers uncovered an exposed remote desktop port, then implemented a critical patch and MFA (multi-factor authentication) controls – blocking a real‑world attack that arrived days later.
Mining Operation Secures its Network
A regional mining company faced growing concerns over its operational technology. Through tailored network and wireless testing, their tester identified a backdoor into its network, sealed the vulnerability and delivered staff training – preventing potentially costly downtime and safety risks.
NFP Protects Donor Data
A local not‑for‑profit providing community support engaged a security expert to review their web application. The tester discovered a vulnerability that could expose donor and client information. They helped them patch the gap and strengthen access controls – keeping donor and community members’ personal data safe, and preserving their trust and reputation.
Hopefully, these examples demonstrate how proactive testing can transform hidden risks into actionable security improvements.
Steps to Get Started with Penetration Testing
With a clearer understanding of how penetration testing works and why it matters, perhaps you’re ready to take the next step. Follow these simple steps to get started.
1. Define Your Scope
Identify the systems, applications and networks you want tested – for example your corporate network, customer portal or other critical technology environments.
2. Gather Key Stakeholders
Bring together key departments, such as IT, security, legal and operations to agree on objectives, timelines and any compliance requirements.
3. Select a Trusted Provider
Vet partners for relevant experience, certifications and a clear methodology (such as Inspired IT).
4. Plan & Prepare
Draw on your trusted provider’s expertise to confirm the scope. Schedule tests around business windows, share necessary credentials and finalise rules of engagement.
5. Execute & Review
Your tester will work with you to provide results, interpret findings, prioritise remediations and implement improvements.
Final Thoughts
Penetration testing is one of the most effective ways to stay ahead of evolving cyber threats. It gives you a clear view of where your defences stand, before malicious actors can find the cracks.
By combining technical rigour with real-world insight, penetration testing can help you make smarter security decisions, protect your most valuable assets and build long-term resilience. For organisations looking to navigate compliance, safeguard client data or simply strengthen your digital foundation, it’s a proactive step that pays off.
Ready to secure your organisation? Inspired IT is here to help you turn insight into action. Find out more about customised penetration testing and get in touch with our cyber security experts to strengthen your organisation’s digital defences.
