Cyber attacks conjure up notions of shady programmers tucked away in a dark room typing away at their keyboards, furiously trying to siphon money from your bank account.

The reality is far more mundane.

47% of attacks go unnoticed simply because malicious activities are indistinguishable from regular user activities in the eyes of administrators.

If you want to prepare for a cyber-attack, you need to make decisions based on contextual information about your business and industry. This article from EliteSec will help you identify the main signs that indicate you need a penetration test.

Do I Need a Penetration Test?

We are biased, after all, penetration testing is our thing. We’ve counted 6 cases where penetration testing can help you fortify your cybersecurity posture.

These are:

• Recent infrastructure changes
• Compliance requirements
• Client requirements
• Your last pen test is outdated
• There has been a hack in your industry recently
• Your digital infrastructure has recently expanded

We’ll break down each scenario and some of the important security requirements to consider in each case.

Recent Infrastructure Changes

This one is pretty simple, if you’ve changed your IT operations significantly, you’re going to need some time to adapt. So will your security posture.

Typically, you need to engage in pen testing after recent:

• Cloud migrations: You can make all sorts of mistakes here. A company moving from on-premises to the cloud could misconfigure its IAM policies. Even a single permission error could expose you to a massive security risk. And if you’re moving to a hybrid cloud-on-prem environment, the connection points are usually a weakness.
• Software deployments: A new CRM or ERP system means a new data goldmine for hackers. API integrations are especially vulnerable.
• System updates: Most companies don’t have stable patch management procedures to help them.

Compliance Requirements

It feels like every year, there’s a new slate of security regulations introduced. At the very least, they’re constantly being expanded.

Companies that work with customer information, typically in healthcare and finance, usually have the most stringent requirements. And these are completely non-negotiable, you won’t be able to continue operating without meeting them.

There are some important pitfalls to look out for though. Some regulations, like HIPAA, do not explicitly require a pen test, but running one is simply the easiest way to comply.

Another big one is the PCI-DSS if you store cardholder information. A lot of pen testers can get this one wrong. They don’t isolate the cardholder data environment properly. Usually, this is due to a misconfiguration of their firewall. An attacker could then access the cardholder data environment simply through a phishing attack on an employee’s email.

Client Requirements

Enterprise clients do their due diligence, and software companies that can’t provide recent pen test results will lose out on big contracts. You usually need proof of a test within the last 6 to 12 months. Pen tests might seem like a big cost upfront, but they’re just an investment that you require if you want to compete for large B2B clients.

A weak security posture will have downstream effects on the whole ecosystem. So you’ll find that companies you collaborate with will increasingly require them too. For instance, an insurance provider might require proof of a pen test when you’re applying for cyber insurance. Some SaaS providers will require proof of a pen test to access their API. Everyone is looking to protect themselves first and foremost.

Your Last Security Assessment Is Outdated

Only 32% of companies conduct a penetration test annually or biannually. So if you haven’t run a pen test in 12 months, you’re in the majority.

Keep in mind that not every single business needs a pen test. That mom-and-pop store down the street doesn’t. But if you have lots of digital infrastructure, then cyber attackers see you as a target.

On the other hand, new security breaches are being discovered every day. Hackers move fast; they’re always trying to discover new vulnerabilities and exploit them.

One must imagine that the main reason companies avoid penetration tests is that they’re too costly. However, the average cost of a data breach is over 4 million dollars as of 2023. And in general, 60% of SMEs will go out of business within 6 months of a data breach. So, while the cost of preparation is high, it’s better to pay a little early rather than pay a lot later.

Plus, regardless of whether a data breach happens or not, you could still pay more in insurance premiums if you don’t present evidence of a penetration test. The costs can come from all angles.

Recent Security Incidents In Your Industry

The thing about cyber hackers is that while they’re malicious, there is some laziness that is fundamental to their role. Otherwise, they might pursue legal means of earning money.

Once hackers can find an “earning model” that works for them. They usually continue to double down on it until it’s completely exhausted. That often means they’ll try the same exploit on the same type of company. So if one company in your industry gets attacked, it’s likely that more will follow.

Here’s what the attack patterns look like in each industry:

Healthcare

Usually, the primary attack vector here is patient data. That’s why there are so many regulations for it when it’s stored on-premises. Attackers usually use phishing attacks as healthcare companies have a lot of administrators, which means a higher surface of security vulnerabilities available to attackers.

Financial Services

Fintech firms are another obvious target for a cyber security breach. After all, they have so much payment data. The main vector that a hacker will exploit here is the transaction systems. As any penetration tester will tell you, API vulnerabilities are the main target here, which is why you need to fix security holes at this point.

Manufacturing

The average downtime cost for a plant is usually in the hundreds of thousands. Industrial control systems have some connection to the internet. This allows them to be vulnerable to remote access exploitation attacks. The issue here is not so much about sensitive data. Rather, they are attempting to sabotage your factories to gain an advantage over you. Or worse, they hold your factory hostage until you pay a ransom.

You Recently Expanded Your Digital Infrastructure

This is a little different from changing your digital infrastructure. Basically, companies are adding new tools to their tech stack all the time. And in a world where SaaS sprawl is creeping in from all angles, you need to be extremely cautious about what software you’re onboarding. Every new application increases your attack surface by about 20%. Each API endpoint is a new vector for data breaches.

Of course, anytime you onboard new enterprise software, you should check that it complies with GDPR or other relevant regulations in your industry.

Beyond that, you need to talk to penetration testers to see if there are potential risks to that particular software if you’re not sure. The main risk factors are in the API integration points, but also in the extra data flow complexity that each software adds. Even if your customer data isn’t exposed directly to their APIs, it wouldn’t take long to get there if it’s not isolated.

To protect yourself from these risks, we recommend taking inventory of all your digital assets at least twice a year. And of course, consult a penetration tester when you’re unsure.

Best Practices for Penetration Testing

Whether you want to hire penetration testers or you’ll conduct everything in-house, you should be prudent. Here are some best pen testing practices that we’ve accumulated after decades of experience:

Define The Scope

You should never test blindly. Not every single attack surface needs to be tested - there should be boundaries. Make sure that you document the extent of the attack surface as well as the exact times when the testing should be done. Part of the goal here is minimal interference with your regular operations.

Here is an overview of the surfaces you should test:

External Testing

• Network Infrastructure
• Web Applications
• Cloud Configurations
• Email Security

Internal Testing

• Network Segmentation
• Access Controls
• Password Policies
• Privilege Escalation

Specialized Testing

• Wireless Networks
• Social Engineering
• Mobile Applications
• IoT Devices

Test as frequently as possible

We’ve said it already and we’ll say it again. You need to test at least once a year, and every 6 months is ideal. Some industries require you to test every quarter if you want to comply with their regulations.

Create A Culture of Cybersecurity

Make your security infrastructure a priority. You should collaborate with your IT team and cybersecurity experts to create an incident response plan. Furthermore, we recommend that you invest in real-time monitoring solutions to help you stay alert to threats as they arise. Meet with your IT team monthly and conduct an overview of any suspicious activity and new threats that could arise.

Conduct Penetration Testing with EliteSec

Still not sure if you need a penetration test? We specialize in ethical hacking for companies who are just at the beginning of their cybersecurity journey. Sit down with us to have a candid conversation about your main vulnerabilities and the best course of action for your team.