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What Is Penetration Testing? How to Use It Against Hackers

September 25, 2020

penetration testing

Hackers are evolving continuously, and so are their methods. 

With the changing cybersecurity landscape, hackers have nudged their creativity to develop new strategies for cyber attacks. Security breaches are more frequent and technologically equipped now than they were a decade ago. 

The growing popularity of modern hacking tools is fueling such incidents. So when attackers are adopting cutting-edge technology to hamper your organization's reputation, you need to answer and act accordingly. 

You must identify and fix vulnerabilities in your network, system, and applications that may expose you to any cyber attack. You need to be proactive and consistent while doing it. It's better to use technology such as vulnerability scanners, pen testing tools, and others to manage the plethora of vulnerabilities you’ll deal with. 

The first step here is to scan for security vulnerabilities in your IT infrastructure. Once the vulnerability assessment is completed, you can leverage pen testing to identify ways a hacker can exploit your environment's weaknesses and build a robust vulnerability management program.

The penetration testing process helps you discover blind spots that hackers can use to breach your cybersecurity framework. 

Not only does it help you to improve your security posture, but it also allows you to prioritize the vulnerabilities based on the possible risks associated with them. Furthermore, it ensures that your testing framework measures with those required by different compliances. 

What are penetration testing tools?

Penetration testing tools are technological interventions that security professionals need to perform different types of penetration testing. These tools include vulnerability scanners, port scanners, application scanners, and others grouped in one entity to carry out a successful penetration test. 

Whether open-source or licensed, you can use these pentest tools according to the type of test you are conducting.  Here are the top five penetration testing tools available on the market. 

Types of penetration testing tools

Before diving deeper into understanding the penetration testing software, let’s learn more about the basics of penetration testing so that you could make a better decision in choosing your best fit. To begin with, let’s start with the types of penetration testing tools available.

Port scanners

Port scanners are security tools that are designed and equipped for probing a server or host for open ports. These can be used by administrators to identify and verify the network security policies. Besides, attackers can also use it to detect the type of network services running on the target and plan their attacks accordingly. 

Port scanners typically gather information and data about the host in the network environment remotely. This tool can detect both TCP (Transmission control protocol) and UDP (user datagram protocol) ports. 

It also gives you the freedom to conduct probing activities like the SYN, SYN-ACK, ACK sequence (three-way handshake in TCP ports), half scans, and more.

Port scanning techniques

  • Ping scan: This is the simplest of all port scanning techniques. It includes an automated blast of pings (ICMP - Internet Control Message Protocol) at different ports to identify those that respond. Admins usually disable ping on the firewall or the router, but then it makes it difficult for troubleshooting network problems.
  • TCP half-open scan: This technique is sometimes referred to as a SYN scan. Here the scan sends a SYN message and expects a SYN-ACK response from the open ports. But, the scanner doesn't complete the connection one it gets the response. This method is widely used by attackers to identify the targets.
  • TCP connect: This technique is similar to half-open, but the connection is completed once the scan gets a response from the open port. Since the connection is completed, you would be increasing the network's noise and may trip an alarm, unlike a half-open scan.
  • Stealth scan: This technique is even quieter than others. The scan sends data packets to ports with a FIN flag and expects a no-response (open port. If you get a RST, the port may be closed. Firewalls are looking for SYN packets, so FIN often goes undetected.

Vulnerability scanners

Vulnerability scanning tools detect and identify the known vulnerabilities present in your IT environment. They identify the CVEs (Common vulnerabilities and exposures) and cross-check with one or more vulnerability databases like the NVD (National vulnerability database) and so on.

Vulnerability scanning tools help you detect vulnerabilities with their risk measure quantified by the common vulnerability scoring system (CVSS), enabling you to prioritize remediation efficiently. The scan helps you ensure that your IT assets adhere to the compliances and the organization's latest security policies while helping you mitigate cyber attacks.

Application scanners

Application scanners evaluate security vulnerabilities across web applications. They help you identify cookie manipulation, cross-site scripting, SQL injections, and other backdoors and threats that an attacker can use to exploit your application vulnerability.

Web application assessment proxies

You can place this tool in between the penetration tester's browser and the target webserver to closely see and evaluate the exchange of information going on in real-time. With this, you can manipulate the hidden HTML fields to gain access to the system. 

Altogether, the tool allows you to keep and maintain the focus over information and data flow at a much closer level.

Why do you need penetration testing?

Pen testing involves examining all your possible attack surfaces before a real cyberattack. It's imperative to have it in continuous cycles as it shields your security framework from becoming a costly liability. You might have come across a popular saying:  the best defense is a good offense; pen-testing complements it in the cybersecurity landscape. 

Enables you to unveil critical security flaws

The best way to protect your IT environment from attackers is to detect your weaknesses before they can. Penetration testing does that by identifying the vulnerabilities first and then finding ways to exploit them just as a hacker would. This enables you to shield your IT assets from possible attacks.

As it involves scanning your network, systems, operating system (Mac OS, Microsoft Windows, Linux, etc.) and applications, it uncovers the critical vulnerabilities that could compromise your security. Not only does it empower you to detect security weaknesses better, but it also unveils the hidden ones like those in people by social engineering techniques. 

You can predict the extent to which your organization's vulnerabilities can be exploited and can take measures accordingly.

Allows you prioritize remediation of severe vulnerabilities

As penetration testing examines the extent of a possible attack, it helps you prioritize remediation and enables you to devise short term and long term plans. After a well-conducted penetration test, you won't be blind-sighted to the impact and ease of exploiting your organization's security weaknesses. This would enable you to remediate the most severe vulnerabilities strategically, and guide your team, empowering you to be a better leader in your organization.

Assists you in developing robust security measures

While testing your network, system, and applications, security researchers come across many gaps in your security measures and protocols. A summary of these helps you bridge these gaps proactively, and contribute to building cyber resilience.

Penetration testing experts will also provide you with actionable insights and recommendations on eliminating such security weaknesses, enabling you to revamp your existing security protocols and processes.

Helps you comply with security regulations

With data security being a prevalent concern, you must adhere to the security standards such as PCI, HIPAA, GDPR, ISO 27001, and others while serving end-users in their scope. The governing authorities expect you to conduct audits regularly to ensure compliance, and in case of non-compliance, you would be liable to pay hefty fines.

Penetration testing helps you comply with these regulations by evaluating your IT assets and safeguard the integrity of data stored within. It would debar hackers from scavenging the stored data and create an unbreachable security framework that adheres to compliance standards.

Major approaches to penetration testing

There are three major approaches to conduct penetration testing. These are as follows:

 penetration testing approach

White box penetration testing

White box tests are those where the organizations share the information of an application or system and ask security researchers to identify exploitable vulnerabilities. Here, the penetration tester has complete access to source code and the environment, which helps them conduct an in-depth analysis and produce detailed results. 

These tests usually take around two to three weeks, based on the width of your organization's IT infrastructure. Even though it produces detailed analysis, it sometimes gets complicated to identify the focus area, taking into account the given level of access.

Black box penetration testing

In black box tests, organizations do not share their security information with the security researchers and allow them to dig into their network and identify vulnerabilities independently. The main objective of this approach is to mimic a real-world cyber attack, where the ethical hacker assumes the role of an anonymous hacker.

Black box penetration testing demands a high technical expertise level and can normally take up to six weeks to complete. They are generally costly, as the security professional has to plan, execute, and report the test result with no starting point.

Grey box penetration testing

In grey box pen tests, the security professional has partial access to the network or web application. The primary benefit of conducting a grey box pen test is the focus and efficiency you get in the security assessments. It's targeted and more effective in filling the security gaps and prioritizing the imminent security remediation.

6 types of penetration tests

There are six types of penetration tests that would collaboratively provide 360-degree security to your organization's IT infrastructure. Let's dive deeper into understanding each one of them in detail. 

1. Network services penetration test

Network services penetration tests involve examining your network devices such as LAN, switches, and routers. It's possibly the most common penetration test in the industry. Experts recommend  conducting both internal and external network tests at least once annually.

2. Web application penetration test

The web application penetration test scrutinizes web-based applications for exposed weaknesses that can put your cybersecurity at risk. In addition to testing applications, the test also finds vulnerabilities in databases, browsers, and their components, such as plugins, java scriptlets, and more. These tests are targeted, detailed, and are carried out by identifying every touchpoint of the application with the user and examining it for flaws.

3. Client-side penetration test

You can conduct these tests to identify possible attacks on client-side applications or programs such as web browsers, email clients, multimedia flash players, and others. These detect attack vectors such as cross-site scripting, HTML injection, open redirections, and others.

4. Social engineering penetration test

You can conduct a social engineering penetration test by copying a hacker's act in retrieving sensitive information from the internal users through phishing, tailgating, or others. These tests allow you to train your internal team better and always keep an eye out for malwares and any fraudulent activity. 

5. Wireless penetration test

These tests involve examining your IT assets connected with one another and the internet. The scope of these tests include investigating your laptop, PCs and other IoT enabled devices in your IT infrastructure. You should perform these tests in the office so that you can have access to the WiFi network.

6. Physical penetration test

In such tests, the security professional attempts to overcome physical barriers to reach your organization's IT assets and employees. These tests expose flaws in the physical barriers (such as locks, sensors, etc.) and recommend proper measures to strengthen your business's security posture.

How is penetration testing done?

Performing a penetration test in an organization is a six-step process. You can execute these steps to build a scalable and repeatable penetration testing process in your company.

Penetration testing process

Plan the penetration test

Conducting a penetration test requires a great deal of preparation. It's advisable to call a kickoff meeting with the security professionals to decide the project's scope, objectives, and stakeholders. It would also help if you fixed a timeline of these tests as you don't want to disturb the company's everyday operations amid the testing.

During the tests, there is a possibility that some systems may crash due to inflated network traffic. You can exclude those systems out of the scope to prevent such incidents. In the planning phase, it is vital to decide whether the staff needs to be informed. 

A complete penetration testing involves breaching a network/system illegally. You must ensure that you have obtained legal clearance from the company before conducting the test, as it protects the company's interest and prevents the tester from legal actions.

Gather information

After planning the penetration test, the next step is to gather information. You can conduct network surveys and identify the number of reachable systems. Here, you can expect the domain names, database server names, ISP, host IP addresses, and a network map as a result of the survey.

Once you have completed the network survey, you can move on to port scanning. Now you have to detect the open and closed ports in the network. This is also the place where you exclude those ports which the organization doesn't want to test.

Scan for vulnerabilities

Now that you have gathered sufficient information about the systems, the next step is to identify the vulnerabilities that exist in those systems. You can use vulnerability scanning tools to automate this process and prepare a list of vulnerabilities to target closely.

Vulnerability scanners prepare the list of vulnerabilities automatically and prioritize them based on the risk score. This enables you to target those that can have a higher impact on your cybersecurity or those that are easier to exploit. 

Attempt the penetration

Once you have identified the vulnerabilities, the next step is to attempt the penetration test. Now before moving ahead with it you must estimate how long a particular pen test will take and what will be the targets. 

Even if vulnerabilities exist, it does not imply that they can be exploited easily. It might take a lot of effort and time to yield benefits for the attacker. So you can manage them in the long-term plan, whereas vulnerabilities that are easy to exploit and pose a considerable risk should be taken up in priority.

These days password cracking in normal practice in penetration tests. You have services like telnet and FTP running on systems, making it a good place to start and use a password cracker. You can use dictionary attack (using a word list of dictionary file), hybrid crack (using variation of words in a dictionary file), or brute force (testing passwords made up of characters going through all the combinations possible).

It doesn’t end here. You have two more areas with which you can penetrate the company's security. You can do it by social engineering or by bypassing physical security. You have to check these as well to conduct a comprehensive penetration test.

Analyze and report

Once you have completed all the steps mentioned above, the subsequent step is reporting. Your report starts with an overview of penetration testing. Moving forward, you can highlight the most critical vulnerabilities that could substantially impact the company. Then, you state the less critical ones. 

The sole reason for separating the vulnerabilities into critical and less critical is to help organizations make decisions. Altogether, your report should cover a summary of the process, a comprehensive list of information gathered, a list of vulnerabilities, their description and suggestions, and recommendations for the remediation process.

Clean up

The last step of the penetration testing process is cleaning up. You have to clear the mess that might have come up during the pen test. Then, you should execute the cleaning up of compromised hosts securely so that you don't affect the organization's normal operations. It's the penetration tester's responsibility to inform the organization about the changes that were created during the penetration test and revise them back to normal. 

Top 5 penetration testing tools

Penetration testing tools help you mimic a cyberattack by exploiting vulnerabilities and security gaps in your IT infrastructure. They allow you to explore different ways a hacker can take advantage of flaws in your network or system, and empowers you to fix them before they can be of illicit use. 

The list below contains real user reviews from the best penetration testing tools on the market. To be included in this list, a product must:

  • Simulate cyberattacks on computer systems or applications
  • Gather intelligence on potential known vulnerabilities
  • Analyze exploits and report on test outcomes

* Below are the five leading penetration testing tools from G2's Summer 2020 Grid® Report. Some reviews may be edited for clarity.

1. Acunetix Vulnerability Scanner

Acunetix Vulnerability Scanner can be used by both standalone and complex environments. Its vulnerability scanning engine is written in C++, making it one of the industry's fastest web security applications. The software is known to furnish less false positives, saving resources during penetration testing and allowing your analyst to focus on new vulnerabilities. 

What users like:

"I love the graphical interface as it is very user friendly and anyone can operate it without prior knowledge on information security. It's scan results accuracy is 99%, so we don't need to spend a lot of time finding false-positive results."

- Acunetix Vulnerability Scanner Review, Anshajanth Y.

What users dislike:

"Downloading scan-data in CSV form is currently not possible, but the people at Acunetix told me this feature is heavily requested and worked on for a next update/upgrade. Manipulating over 200 targets via the web interface is currently also a little cumbersome, but that CSV download should resolve that issue."

Acunetix Vulnerability Scanner Review, Steven R.

2. Appknox

Appknox's on-demand mobile application security platform empowers businesses to identify and fix vulnerabilities using an Automated Security Testing suite. The software platform has reduced delivery timelines, manpower costs and is mitigating security threats for global banks and enterprises in more than ten countries. It is a powerful plug and play VAPT platform that enables businesses to build a secure mobile ecosystem.

What users like:

"The team takes care of all our needs for web, mobile web and native apps. Furthermore, not many companies out there can do scans and pen-tests for SDKs, Appknox does it all. From the initial scan to the mitigation approaches and re-scan, they are a one stop shop. They also help answer any follow-ups from folks who request more details. This has been very valuable to us."

- Appknox Review, Amod S.

What users dislike: 

"The only thing I dislike about the solution is relying on the Appknox team only for manual testing. I would appreciate it if I could simulate manual testing using a mobile simulator combined with Appknox Suite. But overall, the solution meets my expectations, and there is always room for improvement."

- Appknox Review, Zechariah A.

3. Netsparker

Netsparker is a web application security solution that can identify vulnerabilities in all types of modern web applications, regardless of the underlying architecture or platform. Once the software identifies exploitable vulnerabilities, it uses the unique Proof-Based Scanning technology to generate a proof of exploitation and eliminate the chances of false positives. The software is available in several variations, depending on the customers' requirements. 

What users like:

"I like its ability to have continuous vulnerability scanning bundled into a single reliable web app and track the progress of various vulnerabilities over time. NetSparker analysis and reporting are on point. It's quite nice having the ability to generate different types of reports, integrate with issue trackers (GitHub), and receive alerts (via email and Slack)."

- Netsparker Review, Patrick H.

What users dislike: 

"Netsparker becomes slow when running extended scans, even though they are always in-depth. The software is a bit heavy to run and can take up a lot of processing power."

- Netsparker Review, Aanu B.

4. Intruder

Intruder is a cloud-based vulnerability scanner that enables you to avoid costly data breaches by finding cybersecurity weaknesses in your most exposed systems. The software helps you build a robust cybersecurity framework by allowing you to focus on critical vulnerabilities instead of those which can be managed easily.

What users like: 

"We have learned so much from our work with Intruder. The software understands the challenges that normal people face daily in offering secure products and services to their customers. They provide a service that not only protects us but helps us make difficult decisions and tradeoffs about what to do when faced with a security challenge.

Beyond that, they are very easy and friendly to work with. Straightforward, transparent partners are hard to find in the security space where so much is opaque and complicated."

- Intruder Review, Timothy K.

What users dislike:

"The way the licensing works makes you get locked in after you scanned a single endpoint. It would be cool if a license could "float" for the first few days as you are figuring the tool out, and then once you get locked in, it can't be changed. Also, sometimes when I log in, it downloads the most recent PDF report instead of taking me to the dashboard."

- Intruder Review, Zach R.

5. SQLmap

SQLmap is an open-source penetration testing tool that uses a powerful detection engine and automates the process of identifying and exploiting SQL injection flaws. It’s one of the leaders in penetration testing software with a broad range of switches lasting from database fingerprinting, over data fetching from the data, to accessing the underlying file system and executing commands on the operating system via out-of-band connections.

What users like:

“SQLmap supports different SQL injections, such as injections, command injections, and many more. SQLmap is developed in Python, and it comes free with the Kali, or you can download the repository from the internet and use it in a Linux operating system. Most of the SQL injection vulnerabilities can be exploited using this software, making it an essential tool penetration test.”

- SQLmap Review, Medhavi W.

What users dislike:

“It does not have a graphical user interface. It may prove to be a little bit difficult for some users because of this. Even with the command-line interface, the learning curve is small, with all the help and tutorials available online. Another thing to dislike is the generation of false -positives in vulnerability scanning. Even though this is true with any vulnerability scanning software, if the number of false positives can be limited to a minimum, SQLmap would be a preferred choice. Anyways, the tester needs to double-check the reported vulnerability by manually testing it.”

- SQLmap Review, Isuru S.

Shield your cybersecurity now 

Penetration tests emulate a 'real-work' cyber attack, thus providing the extent to which a hacker could exploit vulnerabilities. It would make you aware of the security gaps that need to be bridged to shield your cybersecurity, provided that you are regular and proactive in it.

Hackers need only one gap to fulfill their shallow motives; make sure you don't leave them uncovered. You should take action to address those vulnerabilities and manage your security posture effectively. 

Want to take your security standards to the next level? Learn more about the role of AI in cybersecurity and how it can help you improve your security posture.

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