Dentists usually recommend 2-3 checkups per year. Mechanics recommend an oil change roughly every 5,000 miles.

In every industry we have set times where we recommend checkups. Cyber security is no different.

In general, we recommend running a penetration test (also known as a pen test) at least once a year. But depending on the size of the attack surface, and various changes you make to your network, your tests might be more frequent. In some cases, you are forced to conduct regular pen tests just to comply with industry regulations.

At EliteSec, we’ve helped dozens of companies enhance their cyber security profile. But as you’ll soon find out, our clients have diverse motivations for pursuing pen tests. This article will help you find out what those are.

What is Pen Testing and How Does It Work?

A pen test is when a penetration tester, who acts as a type of white-hat hacker, attempts to break into your network with your permission.

So, why would you give the tester permission to do this?

Likely because they’re a certified professional that is accustomed to carrying out this sort of thing. Typically, pen testers follow a rigorous 5-step process to carry out penetration tests.

1. Reconnaissance: Before even beginning to think about a test, the pen tester hunts for information about your software, ie, the target system. First, they might try to gather publicly available info about your software, this is known as passive reconnaissance. However, they might interact directly with the software to delve deeper, which is known as active reconnaissance.
2. Vulnerability Scanning: Pen testers identify vulnerabilities using both manual and automated tools. You might have heard of vulnerability scanning software, this is the best time to use it. Basically, these tools will detect open ports and any other entry points where hackers can gain access.
3. Gain Unauthorized Access: Here comes the (not so) scary part. Armed with the information collected in the previous two phases, the pen tester sets out to breach your system’s defenses. To start, they will try static analysis to evaluate the source code of the app without actually running it. However, any pen tester worth their salt will also use dynamic analysis in which they run the code and monitor incoming and outgoing transactions. Here, various exploits become clear.
4. Holding Access: The tester will attempt to find as many avenues to breach the target system as possible. But part of the challenge after gaining access is to up the ante and grant themselves administrator privileges. This allows them to see just how far they can stretch your security protocols.
5. Analysis: With the penetration test wrapped up, the client should receive a report on the extent of the breach made. Alongside this, the tester should provide specific recommendations for how to eliminate vulnerabilities and improve your security infrastructure. Employee training is often involved in the aftermath.

7 Benefits to Regular Pen Testing

Hopefully you’re starting to see the value in pen tests. It’s quite important to ensure that you protect your tech infrastructure from malicious actors.

But pen tests are definitely not just a “once every few years” kind of thing. In fact, we believe they’re a “do as much as possible” thing, so long as time constraints and budgets permit it.

Quickly Discover New Vulnerabilities

Sometimes, your first penetration test can be an eye-opening experience. You’ll more than likely discover a bunch of vulnerabilities that you didn’t expect. It could even take you weeks just to work through addressing all the new problems that the penetration test found.

So, whenever you take your second test, you might feel a little disappointed seeing that there are fewer vulnerabilities to patch up. This might lead you to feel as though the pen test was a waste of time and money.

That’s far from the case. In fact, if you’re constantly improving your security posture, then seeing reduced cyber security risks is good news. It means that your pen tests and overall security strategy is working!

That said, new vulnerabilities are quite likely to arise

Secure Your Reputation

More than anything, data breaches tend to threaten your customers' data. So while a pen test is important for helping you protect your own assets, it’s also a favour that you owe to your clients. Without question.

While the adage “any publicity is good publicity” exists. It does not apply at all in the case of cyber security attacks. In many cases, affected customers will be hesitant to work with you in the future. If you want to quantify the harm a data breach does to your reputation, typically, a company’s stock price will fall 3-5% in the immediate aftermath.

The worst scenario is when people hear about your brand for the first time as they’re hearing about the breach. While a well-established company can usually shake it off, some newer companies never recover.

Therefore, the only way to be sure that you’re managing your reputation effectively is to consistently run penetration tests. Otherwise, you can’t be sure what perils are lurking around the corner.

Deep Preparation

Penetration tests are meant to simulate real-world attacks. As we outlined earlier, the pen tester does everything they can to make the attack realistic. That’s why they often talk with your IT employees or run code instead of taking a hands-off approach with automated tools.

This brings us to an important point, penetration tests are supposed to involve all relevant parties in your organization. And above all, these parties need to be educated on how to respond to threats. Reviewing your internal security protocols with your employees every month is a significant part of this. It will help keep everyone sharp.

Assess Your Security Posture

If you’re thinking about a penetration test, you’re probably already quite forward thinking when it comes to cybersecurity. However, even if you already have security controls in place, that doesn’t mean they’re anywhere close to perfect. In fact, you should see penetration testing as an opportunity to test the mettle of your security infrastructure and your employees in the event of an attack.

The thing about pen testing is that when done properly, the tester will assess risks from multiple angles.

Here are just a few of those angles:

• Network security
• Application security (web and mobile)
• Endpoints
• User behavior and awareness
• Data security
• Cloud
• Encryption

There are a lot more!

Manage Risk

Penetration tests will give you a lot of insight into where your security budget should be allocated. As such, this helps you a lot with managing risk as a whole. Just quantify the potential financial losses that you could incur during a cyber attack, and figure out how much you’re willing to spend on preventative measures. Keep in mind that SMBs spend an average of up to $650,000 on remedying damages from cyber attacks.

Comply With Regulatory Requirements

It’s a sad reality that some industries have more data to protect, and are therefore at a higher risk of a cyber attack. As a result, the government has teamed up with private industry to ensure that critical security standards are being met.

Take the medical industry for example, 93% of healthcare organizations say they’ve experienced at least 1 data breach in the 3 years prior. So if you’re working in the healthcare industry, you’ll likely need to follow HIPAA regulations.

Some other industries that have regulatory requirements include:

• PCI DSS: for eCommerce sites that store customer payment data.
• GDPR: Generally applicable to companies that process data from EU citizens
• SOX: for financial services and public companies
• FERPA: for educational institutions
• GLBA: for financial institutions
• COPPA: for online services dealing with children under 13

Stay on Top of Trending Threats

Cyber attackers never take a vacation. In fact, they’re always developing new tactics to find and exploit security vulnerabilities. The rise of AI in cybersecurity only makes these threats evolve more quickly.

Thankfully, pen testers are working hard to stay ahead of these attacks and develop new penetration testing methods. To give you an example, over three quarters of cybersecurity professionals agree that remote work poses a major threat to companies' security. In this case, a penetration tester would take stock of remote infrastructure like VPNs and ensure that they test those attack vectors during the pen test.

Best Practices for Cybersecurity Penetration Testing

Take All Attack Surfaces into Account

Your most sensitive data can be found in the most unexpected places. As we mentioned earlier, pen testers are likely to take your apps, network, cloud, and much more into account. Make sure that you’re using established cybersecurity software for each attack vector. Certain pen testing tools are more specialized than others.

Create a Clear Plan of Action

Your penetration tests should be designed in the context of your wider security strategy. So when you hire a penetration tester, you can sit down with them to discuss where you currently stand, and figure out what needs to be enriched. They’ll often have had experience working with organizations like yours and be able to give you specialized tips that you wouldn’t have otherwise thought of.

All that should come before you even run a pen test. But following the test, you’ll likely come away with new insights that you need to incorporate too. Most importantly, your pen tester will tell you which issues to prioritize handling first based on their overall risk.

Follow Up Regularly

Of what use is a plan of action if you don’t follow it correctly? Here are some tips to keep you on track:

• Create tasks and delegate responsibility: This is an important first step. You might already have an IT team, or maybe you’ll need to outsource. Either way, you need to consult with your pen tester that you have the right people to execute your cybersecurity plan.
• Set deadlines: Once again, in consultation with your testing partner and the rest of your team, figure out realistic deadlines for when each action item must be completed.
• Identify KPIs: Figure out which metrics are important to you and track them. An example would be vulnerability remediation time, which is the average amount of time it takes for your team to identify vulnerabilities and address them.
• Document everything: As you’re meeting your security goals, keep a log of which changes you made and who made them. Explain how you fixed certain vulnerabilities or errors, and make sure your explanations adhere to a standardized format to make it easy for your team members to interpret.

Conduct Regular Penetration Testing with EliteSec

Of course, we left the most important best practice for the end:

Work with an experienced penetration tester.

Most IT teams are already being worked to the bone, the last thing you want to put on their plate is penetration testing, a sophisticated security practice that takes years to master.

Working with EliteSec is incredibly simple. Just sit down with us for a free 30-minute consultation where we’ll assess your testing needs and whether we’re a fit. Having decades of experience in the cybersecurity field helping companies such as LogiSense and Magnet Forensics, you can rest assured your network is in the right hands.