Penetration Testing: Why Your Internet-Facing Systems Need a Real-World Security Test

Most businesses have firewalls, antivirus and email filtering in place. Many also believe that because they’re using reputable platforms like Microsoft SharePoint or other cloud services, their data is inherently secure.

Unfortunately, that’s not how attackers think.

If your systems are accessible from the internet, whether that’s a website, remote access portal, cloud application, VPN, or document platform, they are being scanned constantly. Not once a month. Not once a day. Constantly.

That’s where penetration testing becomes essential.

What Is Penetration Testing?

Penetration testing (or “pen testing”) is a controlled, authorised simulation of a cyberattack against your systems.

Instead of guessing where your weaknesses are, ethical security professionals actively try to:

• Break into your internet-facing systems
• Exploit vulnerabilities
• Access sensitive data
• Escalate privileges
• Move between systems

The goal isn’t to cause damage, it’s to uncover real-world risk before a threat actor does.

Think of it as hiring a professional burglar to test your locks before an actual criminal shows up.

Why Internet-Facing Systems Are High Risk

Any system exposed to the internet dramatically increases your attack surface. This includes:

• Company websites
• Client portals
• Remote Desktop or VPN gateways
• Cloud services
• Email platforms
• Document collaboration tools like Microsoft SharePoint

Attackers don’t need to know who you are. Automated bots continuously scan IP ranges looking for:

• Unpatched vulnerabilities
• Weak passwords
• Misconfigured services
• Open ports
• Outdated plugins or software

If they find an opening, exploitation can happen within hours.

“But We’re in the Cloud, Isn’t That Secure?”

Cloud platforms like Microsoft 365 are highly secure at the infrastructure level. However, security is a shared responsibility.

Microsoft secures the platform.
You are responsible for:

• User permissions
• Data access controls
• Conditional access policies
• Multi-factor authentication
• External sharing settings
• Integration with third-party apps

We regularly see:

• SharePoint sites publicly accessible
• Over-permissioned document libraries
• Guest access left enabled
• Legacy authentication still active
• Users without MFA

A penetration test identifies these configuration weaknesses before they become a breach.

What About SharePoint and Data Exposure?

Platforms like Microsoft SharePoint often contain:

• Financial records
• Contracts
• HR documentation
• Intellectual property
• Client data

If misconfigured, data can be:

• Indexed by search engines
• Accessed by unauthorised external users
• Exposed via compromised credentials
• Retrieved through token abuse or API misuse

A pen test doesn’t just check if someone can log in, it evaluates whether your data can be discovered, accessed, or extracted through real attack techniques.

Compliance, Insurance & Due Diligence

More cyber insurance providers now require:

• Regular vulnerability assessments
• Penetration testing reports
• Evidence of remediation

Similarly, many industry frameworks and compliance standards expect proactive testing of internet-facing infrastructure.

Pen testing demonstrates:

• Due diligence
• Risk awareness
• Active governance
• Board-level accountability

It moves security from “we think we’re secure” to “we’ve tested and validated our exposure.”

The Cost of Not Testing

A single exposed web application or misconfigured cloud environment can lead to:

• Ransomware
• Business email compromise
• Data theft
• Regulatory penalties
• Reputational damage
• Loss of client trust

The average breach is rarely caused by “sophisticated nation-state actors.” It’s usually:

• An unpatched vulnerability
• A forgotten test server
• A publicly exposed SharePoint site
• Weak authentication controls

All preventable. If identified early.

How Often Should You Pen Test?

Best practice for internet-facing systems is:

• Annually at minimum
• After major infrastructure changes
• After cloud migrations
• After deploying new public applications
• Following significant security incidents

For organisations handling sensitive data, twice-yearly testing is becoming common.

Final Thoughts

Cybersecurity is not just about tools, it’s about validation.

You wouldn’t deploy a new building without checking its structural integrity. Internet-facing systems deserve the same scrutiny.

Penetration testing provides clarity:

• Where are we exposed?
• How could we be breached?
• What is the real business impact?
• What must we fix first?

If your website, remote access, or cloud data platforms are accessible from the internet, penetration testing isn’t optional, it’s responsible governance.

If you’d like to understand your current exposure or schedule an external penetration test of your internet-facing systems, our team can help you assess risk and prioritise remediation before an attacker does.