Thinking Like an Adversary: What is Offensive Cybersecurity? 

What are the differences between pentesting, red teaming and bug bounties?

Offensive cybersecurity is the practice of using the same tools and techniques as cybercriminals to identify and exploit vulnerabilities in systems and networks. It is a proactive approach to cybersecurity that can help organisations understand their security posture and identify vulnerabilities before attackers can exploit them.

The importance of offensive cybersecurity is underscored by the increasing frequency and sophistication of cyberattacks. In 2022, there were an estimated 395 data breaches per day, and the average cost of a data breach was $9.44 million, according to IBM's Cost of a Data Breach 2022 report. Offensive cybersecurity can help organisations to reduce their risk of becoming a victim of a cyber-attack.

Many of the Big Tech companies have fully embraced elements offensive cybersecurity including bug bounty programmes. Google, Apple and Microsoft awarded record-breaking prizes to bug hunters in 2022, with Google alone delivering $12m in bug bounties. Now, in 2023, even OpenAI is betting big on bug bounties, offering up to $20,000 for ChatGPT users reporting vulnerabilities.

During 2022, the penetration testing industry disclosed over 25,100 vulnerabilities – a 4000 spike compared with the previous year.

This blog post will discuss the different types of offensive cybersecurity, the tools and techniques used by offensive cybersecurity teams, and the common mistakes to avoid. 

Vulnerability assessment refers to the process of identifying, assessing, and prioritising vulnerabilities in a system, network, or application using a combination of defensive and offensive processes, including vulnerability scanning, threat intelligence analysis, and risk assessment. Vulnerability assessments help organisations reduce the risk of a security breach by identifying vulnerabilities before attackers can exploit them.

Penetration testing (also known as pen testing and pentesting) is a security exercise where a person performs an authorised simulated cyber-attack on a computer system to find vulnerabilities, security failures or evaluate the general security level of the system. A pentesting team can perform white, grey or black-box exercises, depending on the level of access the organisation grants them.

How is pen testing different from vulnerability scanning? A penetration test is a detailed, hands-on examination by a real person that tries to detect and exploit weaknesses in your system. In contrast, a vulnerability scan is an automated, high-level test that looks for and reports potential vulnerabilities. Additionally, vulnerability assessment is usually performed by an insider, whereas penetration testing typically comes from a person or a team outside the organisation hired, usually on a temporary contract, for this task – or sometimes from the red team.

Red/blue/purple teaming: Red team assessments are intended to imitate real-world attacks, often with a particular goal, such as data breach or ransomware delivery. They are performed by an internal or external group of security researchers and/or ethical hackers, called the red team.

How is read teaming different from pentesting? Red team exercises are like penetration tests in that they are performed by humans, not fully automated. A significant difference is that red team engagements test an organisation’s defences against a particular threat, while a pentest is designed to identify as many vulnerabilities as possible. Red teams can also perform against defenders – the blue team – while either sharing information – in what is called a purple team – or not.

Bug bounty: Bug bounty programs are deals offered by many websites, organisations and software developers by which individuals can receive recognition and compensation for reporting software vulnerabilities and exploits. Participants access the system through pre-determined avenues or methods.

How is it different from pentesting and red teaming? While pentesting and red teaming are exercises performed by internal or external teams hired by the organisation, anyone with appropriate skills can participate in bug bounties. Bug bounty programs aim to identify vulnerabilities not detected through standard penetration testing procedures. This practice incentivises individuals, usually financially, to report discovered vulnerabilities, enabling organisations to fix and improve their security measures. Bug bounties are a way for defenders to incentivise security researchers to choose to disclose vulnerabilities ethically – and make money out of their activity – rather than illegally breaching their systems.

Network scanning is the process of identifying and enumerating devices and services on a network. Network scanners typically send out packets to different IP addresses and ports to see what responds. This information can then be used to identify potential targets for attack.

Some of the most common network scanning tools include Shodan, Nmap, Nessus, OpenVAS, Wireshark and Angry IP Scanner.

Malware analysis is the process of examining malware to understand its behaviour and how it can be detected and removed. Malware analysts use various tools and techniques to analyse malware, including disassemblers, debuggers, and sandboxes.

Reverse engineering is the process of taking apart software to understand how it works. Reverse engineers can use this information to identify security vulnerabilities and exploits.

Some of the most common malware analysis and reverse engineering tools include IDA Pro, Ghidra, Hex Rays, VirusTotal, Cuckoo Sandbox and Joe Sandbox.

Social engineering refers to a set of techniques and tactics intended to manipulate people into revealing confidential information or performing actions that compromise security. Social engineering attacks can be carried out over the phone, email, social media, or in person.

However valuable, offensive cybersecurity exercises also come with a lot of risks. If they make a mistake, security researchers can quickly shift from being white hats – another name for ethical hackers – to being black hats – cyber-attackers. Here are some common mistakes to avoid for those practicing offensive cybersecurity:

• Not understanding the scope of your engagement: It is important to clearly define the scope of your engagement with the organisation you are working for before you begin any offensive cybersecurity activities. This includes understanding what systems and data you are authorised to target, and what techniques you are allowed to use.
• Not following best practices: Offensive cybersecurity should always be conducted responsibly and ethically. This means following best practices such as not harming production systems or data, and not disclosing any vulnerabilities that you find to the public without the organisation's permission.
• Not leaving a clean slate: When you are finished with your engagement, you should remove all of your tools and files from the organisation's systems. You should also document any changes you made to the systems so they can be restored to their original state if necessary.

In addition to these general mistakes, there are a number of specific mistakes that offensive cybersecurity professionals can make when using some tools and techniques.

For example, when using a network scanner, it is important to configure it to scan only the authorised targets and to use non-intrusive scanning techniques.

Similarly, when analysing malware, it is important to use a sandbox environment to avoid accidentally infecting your own system.

By avoiding these common mistakes, offensive cybersecurity professionals can help ensure that their engagements are successful, and they are not putting the organisation they are working for at risk.

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