Understanding Software Penetration Testing

Worldwide, businesses are facing increasingly sophisticated cybersecurity threats – and the costs and potential reputational damage associated with them are growing, too.

What’s more, hackers are frequently exploiting weaknesses in software and applications – such as malware vulnerabilities, poor password management, and authentication flaws.

Thankfully, software penetration testing can help firms to take stock of potential weaknesses in their applications and uncover new ways to strengthen themselves against hackers and bad actors. Let’s explore what software penetration testing involves, why it’s important, and how you can get started.

What is Penetration Testing?

Penetration testing is a controlled, simulated cyberattack ordered by business owners to analyze the cybersecurity of their systems and software. Testers use typical hacking techniques and tools to assess how robust their clients are against internal and external threats.

Software penetration testing, in particular, covers a series of checks and measures to spot vulnerabilities in application code and access controls that could lead to security breaches.

At the end of the process, testers produce detailed reports that break down what they did and the weaknesses they found, and suggest ways to remedy problems and strengthen security.

Penetration testing remains extremely popular with our clients, who use our services to spot hidden flaws to prevent loss of data and business.

In fact, it’s heavily relied upon by businesses worldwide as threats continue to evolve:

“Cybersecurity Ventures predicts the global penetration testing product and service market will exceed $5 billion annually by 2031. This is based on vetting and averaging market forecasts from numerous industry sources.”

Steve Morgan, Cybersecurity Ventures

Why is Penetration Testing Important?

Penetration testing helps business owners spot exploitable flaws before hackers can and also allows them to keep data protection in line with compliance standards. Testing helps to protect customer data, and therefore prevent loss of business and reputational damage.

Cybercrime is set to cost global businesses upwards of $15.6 trillion by the end of the decade, and the average cost of a data breach is currently around $4.88 million. That’s money companies can easily avoid losing through penetration testing at least twice a year.

Therefore, many businesses adopt penetration testing as a service – which means outsourcing security analysis to seasoned experts, rather than hiring in-house.

Types of Software Penetration Testing

Software penetration testing splits into different types, such as web application, cloud, and mobile application testing. Other types outside of software testing include network, wireless, and social engineering analysis, however, these may also involve testing software for vulnerabilities.

Let’s break down these key types.

Web application penetration testing

Web application penetration testing focuses on software that’s accessible via the internet. For example, these tests often assess whether or not web forms and login screens are easy to exploit.

Cloud penetration testing

Cloud penetration testing is an analysis that can cover several applications that connect and communicate together via the cloud. This process often involves analyzing third-party services and applications that could put client data at risk.

Mobile application penetration testing

Mobile application penetration testing is a type of software analysis that focuses on the robustness of software developed specifically for smartphones, tablets, and wearable tech.

Network penetration testing

Network penetration testing analyzes the security of servers, IoT (Internet of Things) devices, and overall network infrastructure against cyberattacks.

Wireless penetration testing

Wireless penetration testing is similar to network testing – however, it predominantly focuses on wireless devices and whether or not attackers can easily exploit Wi-Fi connectivity.

Social engineering penetration testing

Social engineering penetration testing analyzes the knowledge and behavior of a client’s team – and whether or not they are likely to fall for confidence tricks, phishing scams, and other techniques.

In some cases, clients may arrange for a blend of several of the above testing types. For example, a business might arrange for a full mobile application penetration test, but also require social engineering checks to ensure their employees are trained and up to date on cybersecurity best practices.

We always remind our clients that there’s often no right or wrong answer when it comes to choosing a penetration testing type – which is why we focus on building custom plans and packages depending on what they need.

Key Penetration Testing Methods

Penetration testing splits into three key methods – black box, white box, and gray box. Black box penetration testing is “blind,” meaning testers have no prior knowledge of the software or network they’re breaking into, and white box testing is the opposite – they have complete knowledge of access points, security concerns, and connected systems.

Gray box penetration testing, meanwhile, is a blend of black and white. With this testing method, experts have some information on client software and systems, but not the complete picture.

Many businesses prefer black box testing out of the three because it closely resembles real-world attacks. However, white box penetration testing covers a broader scope, therefore considering all potential vulnerabilities.

Step-by-Step Software Penetration Testing Process

There’s no single process for software penetration testing, however, tests typically start with pre-engagement and reconnaissance, followed by vulnerability assessments, exploitation and controlled hacking, reporting, and remediation.

Here’s how each of these steps break down.

1. Pre-analysis and reconnaissance

We start each software penetration test with a close analysis of what our clients need, the software they’d like us to analyze, and what they expect from the process. It’s here where testers outline the scope, timescales, objectives, and tools to be used.

Once the client and testers agree on the process to be followed, the latter go ahead and start gathering information on the software and systems that fall in scope.

2. Vulnerability scanning and assessment

Testers run vulnerability scans and dive deep into software code and system architecture to find potential weaknesses they can exploit at the next step of the process.

3. Exploitation and controlled hacking

This stage forms the attack itself, where testers use tools to exploit the weaknesses found in the previous step. During this step, they record what they’re able to exploit, how long the process takes, and any areas of concern that the client can learn from.

4. Reporting

At the reporting stage, testers share the weaknesses they find in the software and systems they test, and explore what the client needs to do to strengthen their security to avoid attacks in the future. For example, they might suggest using alternative software, or to focus on boosting password strength.

5. Remediation

Following penetration testing, the client takes data delivered in the report and implements changes. We recommend clients run penetration tests at least twice a year – if not continuously – and at the next test, they can review the steps taken with testers and explore any future changes needed.

Penetration Testing vs. Automated Testing

Penetration testing, in software or otherwise, relies on human expertise supported by manual checks and measures, as well as automated processes to scan for weaknesses. Automated testing alone is a hands-off process where clients can simply scan their software and systems for vulnerabilities and make their own fixes.

VikingCloud follows traditional, manual penetration testing services, though we run vulnerability scanning as part of the process. Manual testing is much more comprehensive than automated scanning, meaning there’s less chance of weaknesses going undiscovered, opening doors to hackers.

Automated testing is, however, preferred by businesses who prioritize efficiency and who want as simple a process as possible. That said, purely automating testing risks you missing crucial security flags.

Best Practices for Effective Software Penetration Testing

The best practices to follow in software penetration testing and generic analysis include being clear on scope and boundaries, following methodologies, responding to tester recommendations, and following up with regular tests with the same experts.

Here’s a quick breakdown.

• We always endeavor to set out a clear action plan at the start of every test process. Setting clear expectations, boundaries, scope, and budget ensures everyone is clear on what testing is likely to achieve, and what to expect from remediation advice. That means the client, too, must also be as clear and as transparent a possible on the processes they follow.
• It’s wise for penetration testers to follow frameworks, such as NIST, OWASP or PTES, to ensure all bases are covered. Frameworks are process templates agreed upon by experts to offer thorough, comprehensive penetration testing. Following frameworks can also reduce risks that might arise when using controlled attacks.
• Some clients may not follow the advice given by penetration testers at the end of analysis – their reasons may vary, but it’s always important to follow expert advice. Expert penetration testers understand software and network weaknesses and how to remedy them – it’s wise to respect their reports and to take steps to implement changes.
• As mentioned, we recommend that penetration tests should take place at least twice yearly to keep up with changes in the threat landscape. However, it’s also wise to run tests after you make significant changes to software or infrastructure, to ensure there are no security gaps in your new setup.

Conclusion

Software penetration testing is an effective way to learn more about your security posture and the potential risks that lie just beneath the surface. Ultimately, without penetration analysis, you may never know what’s at risk.

Therefore, it’s worth planning ahead to work with a seasoned team that can help you break down weaknesses and take steps to boost your security against rising threats. VikingCloud is here to help – contact us now to learn more, and to set up a free consultation when you’re ready.