What is penetration testing?

Penetration testing is a security process that simulates real-life attacks on your IT systems to find weaknesses that could be exploited by hackers.

Whether you’re trying to comply with regulations like ISO 27001, build trust with customers and suppliers, or just want to be sure your IT infrastructure is secure, penetration testing is a proven method to strengthen your cyber security posture and prevent data breaches.  

Why would you use a penetration test?

There are several reasons why you could or should use penetration tests to evaluate your security, but here are some of the most common:

• Customers need proof of your security posture or accreditation with SOC 2 or ISO 27001
• You’re operating in a regulated industry such as finance or energy that require regular audits
• You want to reassure stakeholders that you’re secure from a specific attack 
• You’re responsible for the security of your organization, and you want to prove that an attacker can’t bypass current controls
• You’ve been breached and want to check the access vector has been closed
• You’ve implemented new security controls and want to check they’re working

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What are the different types of penetration test?

While penetration tests often use the same methodology, they vary according to the IT environment you’re trying to secure._‍

1. Network penetration testing

As the name suggests, a network penetration test identifies any weaknesses in your on-premises or cloud network infrastructure such as insecure configurations, encryption vulnerabilities, and missing security patches. It’s a very broad term that can cover:

• Internal infrastructure assessments 
• External (internet-facing) infrastructure assessments
• Web application testing
• API testing
• Bespoke-protocol assessments
• Man-in-the-middle assessments
• SIP testing 

It’s often simplified into external and internal tests. External penetration testing searches for vulnerabilities that could be exploited by an attacker via the internet. Think of it from the perspective of an "outsider". Internal penetration testing checks your internal environment and looks at how an attacker can gain a foothold into your corporate network, for example by exploiting a vulnerability in one of your internet-facing systems using social engineering (more on this later).

Generally speaking, external weaknesses pose a more serious threat. For one thing, a hacker must overcome an external security barrier before accessing your internal networks to access other systems. If you haven’t run any penetration testing before, an external test is often the best place to start, as the perimeter is the easiest thing for attackers to target. If you have trivial vulnerabilities in your internet-facing infrastructure, that’s where the hackers will start. You can read more in our guide to network penetration testing.

2. Web application penetration testing

Web application penetration testing uncovers vulnerabilities across websites and web applications, such as e-commerce platforms, content management systems, and CRM software. This reviews your entire web app security, including underlying logic and custom functionalities, to prevent data breaches.

Common vulnerabilities include database injections, cross-site scripting (XSS), and broken authentication. If you’re interested in learning more about the different types of web application weaknesses, their severity and how you can prevent them, the Open Web Application Security Project (OWASP) Top 10 is a great place to start.

Considering how many businesses now use web applications, and the valuable information they transmit and store, it is unsurprising that they are an attractive target for cyber criminals. Almost one-in-ten vulnerabilities in internet-facing applications are considered high or critical risk. For this reason alone, organizations that develop or use their own web applications should consider web application security testing. Learn more about our range of web application penetration testing services.

3. Cloud penetration testing

Cloud penetration testing is designed to find security issues in your cloud services, but since you don’t actually own the cloud infrastructure, platform or software as an entity but rather as a service, there are legal and technical restrictions on what you can actually test. Certain aspects of cloud security are controlled and handled by the cloud provider and the customer is responsible for the others, based on the Service Level Agreement (SLA) between you and your cloud service provider (CSP).

For instance, the cloud provider is not responsible for custom policies you’ve configured in your cloud account. Similarly, you're not responsible for patching the underlying infrastructure used by serverless functions, or the physical security of the data centers managed by the cloud providers. As a cloud user, your focus is on ‘security in the cloud’ and not ‘security of the cloud’. What you are responsible for, and therefore what can be included in the scope of a pentest, is dictated by the shared responsibility model.

News headlines are littered with examples of large companies leaking large amounts of data, so cloud pentesting aims to identify improper storage and handling of data in the cloud. Databases, object stores, logs and repositories can all be made public inadvertently, and attackers are continually scanning the entire internet for these sorts of exposures. Our research has shown how quickly data exposed to the internet gets accessed.

Using passwords that are weak or reused frequently can make cloud accounts vulnerable to password-guessing attacks, so pentesters will check for weak credentials. Unpatched vulnerabilities are an easy point of entry for hackers, and many use automated tools to find them, so penetration testers will also check for any out-of-date, third-party software. Read more in our dedicated cloud penetration testing guide.

4. Red teaming

Red team testing and penetration tests have different objectives and outcomes – they shouldn’t be confused or combined. Penetration tests aim to identify all vulnerabilities (or as many as possible within the engagement timeframe) that exist within the systems in scope.

Conversely, a Red Team acts offensively, imitating a specific threat actor, starting with minimal internal knowledge about the target organization, with the goal of achieving a mutually agreed objective. This could be compromising a specific system on the network, carrying out a specific action on a target system, or gaining access to a specific email inbox.

The goal is not to identify every vulnerability, but to see whether a specific attack is possible, and whether the internal Blue (defensive) Team or security controls can detect, disrupt and prevent the attack.

5. Social engineering

While not a test as such, it’s worth mentioning social engineering as it is sometimes included as part of the more comprehensive penetration tests. Social engineering is designed to see if employees stick to security policies and practices. It can show how easily a hacker could convince them to break security rules to provide access to sensitive information, or by using publicly accessible open-source intelligence (as detailed in the OSINT framework). The customer should also get a better understanding of how successful their security training is, and how the organization stacks up, security-wise, compared to their peers. You can read about some infamous examples here.

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Ask the expert: What does a penetration test involve?

With Intruder Security Expert, Ben Marr

How are point-in-time and continuous scans carried out?

Point-in-time assessments are set for a fixed period, determined in the initial scoping of works. This will ascertain the size of the application and complexity, and provide an estimate of the time and effort required to give complete coverage of the application. When it comes to the engagement itself, the test will go through a series of phases. At a basic level, these include information gathering, enumeration, active testing, exploitation of identified issues, and reporting.

Continuous testing is done cyclically throughout the year, rather than just once. This, in my opinion, gives a much better representation of the target’s security posture as your business operates and grows. The engagement will follow the same phases and perform the same level of testing, but importantly will also include those new features and/or systems which have been created. With a point-in-time assessment, these wouldn’t get tested until the next annual test, potentially leaving you vulnerable to weaknesses for a very long time.

What’s the difference between black, gray or white box testing?

These refer to the amount of information shared with the tester before the engagement. In a white-box assessment, the tester will be given enough information to help them perform the test as thoroughly as possible, such as source code, schematics of the systems, and so forth.  

A black box assessment is where no information is shared prior to the test beyond the scope and anything needed for authorization. This most accurately simulates what an attacker will be facing. In my opinion, for a penetration test where the testing window is finite and short, this isn’t the best way to go. It restricts the value of the pentest by arbitrarily making it more difficult for the tester to ensure that they have given the target adequate coverage.

Gray box assessments are where most penetration tests fall. Here, some information is shared before the engagement that will help the test to run smoothly. This could be the tester being walked through the capabilities of the application or given a demo, accounts to authenticate, or some system schematics.

The most important thing, regardless of the level of information given, is that the tester has a point of contact who knows the project well and has technical knowledge of the target. This means problems and issues can be resolved quickly, resulting in a more accurate and thorough test, and ultimately a more useful report.

What do testers look for?

While the tester is running through the phases of the engagement, they will be looking for anything present within the target(s) that can be a tangible risk. Where that risk could affect either the confidentiality, integrity or availability of the target. This could be as simple as a identifying an exposed development API which lacks authentication that's exposed to the internet, or as involved as extracting data from an uploaded Git repository and identifying vulnerabilities within the extracted code that may not have been identified through normal testing. The most important thing is that any risk that's identified is relevant to the target and to the client’s business.

How can you be sure there's no risk to my environment?

During a penetration test, there will always be some level of risk to the environment. However, it's important that the risk is managed throughout the engagement cycle. Firstly, by agreeing what types of testing are included/excluded within the rules of engagement, agreeing the target(s) which are in scope, and maintaining an open dialogue throughout the engagement so that everyone is clear and voices any concerns. Where possible, testing should be conducted in an environment that mirrors the live environment but is segregated to prevent putting users at risk.

Even with the best intentions, the worst can still happen. For example, while testing a banking app in a staging environment, I inadvertently took down the production banking system by inputting the characters “AAAA”. An oversight by the developers missed key validations on their API, and the back end wasn’t sandboxed sufficiently. This meant testing data could reach production without the testers and application owner knowing. As soon as the app owner noticed, we agreed to immediately de-scope the affected area to prevent further availability issues. This meant we could continue testing and eliminate any further outages.

This shows why it’s so important to have an open dialogue and do as much as you can to manage any risk to the business, so that when issues like this occur, they can be dealt with immediately.

‍What do pen testers find that an automated web app scanner could miss?

Broadly speaking, no two web applications are the same because they can be built entirely differently. This means that a risk for one application may not be a risk for another, and this makes it incredibly difficult to automate effectively. Humans understand nuance, and are also very good at identifying abnormalities that would get ignored by tooling which mostly relies on binary yes/no observations.

A simple example would be an exposed API endpoint. A scanner would see that there is an endpoint which is available and attempt to test for various vulnerabilities, but it misses the important context of: should it be available? A human would look at this, and then figure out if it affects the target’s security posture, or if this information could be used elsewhere for a more targeted and effective attack.

‍What kind of report can I expect?

Reports are traditionally created as a standalone document and distributed as a PDF after the engagement. Each company has their own reporting style dictating the flow and look of a document. However, they will all include key information, such as the agreed scope, methodologies used, a high-level summary of the target’s posture, and an itemised list of identified security shortfalls.

This will include a rating of the vulnerabilities, a description of what was identified including evidence where appropriate, and most importantly – remediation advice. Pentesting vendors should have a sample report so you can check that it meets your reporting needs.

What’s next for penetration testing?

By Product Lead, Andy Hornegold

Automation will continue to improve and enhance penetration testing as cyber security becomes more complex, and there’s a big shift towards application-layer security testing as people hand responsibility for underlying infrastructure to cloud-providers.

The big question is how AI will impact penetration testing, but it’s hard to say for sure at this point. Cyber security vendors have been using machine learning for some time now, but haven’t been able to produce positive use cases in penetration testing (although it has been useful for Blue Team activities).

In general, the training data hasn’t been available for penetration testing to build a good
model to conduct a full penetration test, since the environments are often very different. Whether AI is applied also raises ethical questions – penetration testing is an offensive security function and handing decision making over to an automated process should be considered carefully and treated with caution.

Like a golf caddy helping a player choose the right clubs and offering his or her expertise and wisdom, hopefully AI will complement rather than replace consultants, and help those responsible for cyber security to react more quickly to changing environments. Time will tell.

How Intruder can help  

Pentesting encompasses so many different techniques, it’s important to understand what risks you’re facing and what you hope to achieve before you choose the most appropriate type, tool and tester. If you need more help to get started, we’ve also got handy guides on how to choose the right pentesting company and the best penetration testing tools.

Penetration tests can seem expensive even if they’re only done once or twice a year, so you may wonder if they’re worth the cost, or if there are cheaper ways of doing them – including if they can be automated. While it’s not possible to fully automate a penetration test yet (some manual tasks will always need to be done by skilled professionals with expert knowledge and intuition), it’s also impossible for humans to manually check for every vulnerability – there are simply too many.

This is where continuous vulnerability scanning can help. These automated tools schedule regular scans, rapidly test for many thousands of weaknesses, and notify you of any issues – which is why scanners are a critical tool in the pentesters armory.

Intruder offers a combination of penetration testing and automated vulnerability scanning so you can protect your digital systems with proven, comprehensive security solutions.

If you’d like to see Intruder in action, take our Pro plan for a spin with a free 14-day trial or get a demo of our Premium plan. With Premium, your attack surface is scanned every day to check if new services have gone live or offline. If the scan identifies a new target, a licence will be assigned (if available) and the target will automatically be scanned for vulnerabilities. If you don’t have a licence, we’ll let you know. After every scan, your dashboard will be updated with a summary and any new results. You can also add bug hunting to your plan to pit your external targets against our team of penetration testers. Pro or Premium – we’ve got you covered.

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