What Is a Penetration Test?

Penetration testing is a technique used in cybersecurity to test vulnerabilities and threats in an application or network. Here, the penetration professionals think from the attacker’s point of view and evaluate the effectiveness of security measures. If the flaw is found, they modify it before the hacker attacks. And safeguards the security controls. Most ethical hackers perform penetration tests to check the exploitable vulnerabilities. Many organizations are also using pen testing before the release of a product to test it.

What Is the Primary Purpose of Penetration Testing?

The purpose of penetration testing is to detect security weaknesses and issues. This testing can also be used to test an organization’s security policy, its attachment to compliance requirements, its employee’s security awareness, and the company’s capability to pick up and react to security incidents. The final goal is to detect security problems and vulnerabilities. In addition, we have many side goals that Pen testing activities can do:

• Test the compliance of security policies.
• Verify the awareness of the staff in terms of security.
• Check if and how an organization can face a security breach.

Penetration Testing Strategic Approaches

There are a few ways where cybersecurity experts can take while executing a penetration test. The key difference tells how much knowledge that the theoretical attacker thinks to have.

1.  Gray Box Penetration Test

This type of penetration testing will have the tester possess some basic knowledge about the system. It could be initial credentials, a network infrastructure map, or application logic flow charts. The test will give away a very realistic outcome because many cyber attackers will not even attempt to attack without a small amount of information about the target. This way essentially skips over the “reconnaissance” step and first gets to the actual pen test. It can be done more quickly and focus exactly on systems that are already known to be risky.

2. Black Box Penetration Test

This type of test was performed without any idea of the earmarked network or the systems running on it. The tester does not have any idea about the internal code or software and has no access to any credentials or sensitive data. This form of testing is realistic because it enables the tester to think like a potential hacker when searching for vulnerabilities. While it may seem like the exact form of testing, black box tests are restricted by time limits. The tester usually has a certain time to check on the system and try to earn access, while a hacker does not have similar restrictions and could detect weaknesses that are not obvious.

3. White Box Penetration Test

The last penetration testing approach is a less simulated cyberattack than a complete scanning of a system at the source code level. Testers are given the highest access privilege level, allowing them to break through the system completely for logic vulnerabilities, misconfigurations, poorly written code, and deficient security measures. While very comprehensive, it may not identify the gaps that an attacker would exploit from the outside using unconventional procedures. For this reason, it is often helpful to do a white box test in co-existence with black or gray box testing.

Types of Penetration Testing

To begin with, there are five types of penetration testing, with each having to resolve different types of security problems. For the company to perform a Pen test on their system, it is necessary to understand the differences to know which type of test will meet the need.

1. Network Penetration Test

In a network penetration test, you would be testing a network environment for potential security vulnerabilities and threats. This test was divided into two categories: external and internal penetration tests. An external penetration test would involve testing the public IP addresses, whereas, in an internal test, you can become part of an internal network and test that network.

The test generally aims at the following network areas in their penetration tests.

• Firewall configuration
• Firewall bypass testing
• Stateful analysis testing.
• IPS deception
• DNS level attacks

2. Web application penetration test

A web application penetration testing examines the potential security problems or problems that occurred due to insecure design, development, or coding. This test detects the potential vulnerabilities in the websites and web applications with CRN and externally or internally developed programs, leading to exposing or leaking important data and personal confidential data. This test is designed to focus mainly on browsers, websites and web applications, and other components like plug-in, procedures, Applets, etc.

2.  Client-side test

The client-side test can also be called an internal test run to identify potential security threats that could emerge from within the organization. It could be a disadvantage in software applications running in the user’s workplace where a hacker can easily utilize it. The theme of utilizing can be exploiting vulnerabilities in client-side applications like through emails, web browsers, Macromedia Flash, Adobe Acrobat, and other modes. A hacker can use a vulnerable application through a smartly crafted email or by attracting the employee to visit a malicious web page or by malware loaded on USB sticks that are automatically executed once kept in the user’s workplace. Though running the client-side test can identify the disadvantages and reduce data breach and system vulnerability.

3.  Wireless network test

Wireless network test is about dealing with wireless devices like tablets, laptops, notebooks, iPods drives, smartphones, etc. As the name itself says that the test has to examine all the wireless devices to detect any security loopholes and identify the devices that are deemed to be weak or rogue. Besides the gadgets, the penetration test considers testing administration credentials to determine crossing access rights.

Social engineering pen test

Social engineering acts as a crucial play in penetration testing. It is such a test that proves the Human Network of an organization. This test helps secure an attempt of a potential attack from within the organization by an employee looking to start a breach or an employee being cheated in sharing data. This kind of test has both remote penetration test and physical penetration test, which aims at most common social engineering tactics used by ethical hackers like phishing attacks, imposters, tailgating, pre-texting, gifts, dumpster diving, eavesdropping, to name a few.

Mainly organizations need penetration testing professionals and need minimum knowledge about it to secure the organization from cyberattacks. They use different approaches to find the attacks and defend them. And they are five types of penetration testing: network, web application, client-side, wireless network, and social engineering penetration tests. One of the best ways to learn penetration testing certifications is EC-Council Certified Penetration Testing Professional or CPENT is one of the best courses to learn penetration testing. In working in flat networks, this course boosts your understanding by teaching how to pen test OT and IoT systems, write and build your exploits and tools with advanced binaries exploitation conduction, access hidden networks, and exploit customization to get into a most profound segment of the network. There are two ways to get certified, and you can choose in which way. The first one is by joining the CPENT Training Course. Learners will get the full knowledge of pen testing methodology. Another one is CPENT Challenge Edition. The learner has to tackle the pen testing challenges and earn your certification.

Vulnerability Analysis

Testing

Vulnerability testing is the process of discovering flaws in systems and applications which can be leveraged by an attacker. These flaws can range anywhere from host and service misconfiguration, or insecure application design. Although the process used to look for flaws varies and is highly dependent on the particular component being tested, some key principals apply to the process.

When conducting vulnerability analysis of any type the tester should properly scope the testing for applicable depth and breadth to meet the goals and/or requirements of the desired outcome. Depth values can include such things as the location of an assessment tool, authentication requirements, etc. For example; in some cases it maybe the goal of the test to validate mitigation is in place and working and the vulnerability is not accessible; while in other instances the goal maybe to test every applicable variable with authenticated access in an effort to discover all applicable vulnerabilities. Whatever your scope, the testing should be tailored to meet the depth requirements to reach your goals. Depth of testing should always be validated to ensure the results of the assessment meet the expectation (i.e. did all the machines authenticate, etc.). In addition to depth, breadth must also be taken into consideration when conducting vulnerability testing. Breadth values can include things such as target networks, segments, hosts, application, inventories, etc. At its simplest element, your testing may be to find all the vulnerabilities on a host system; while in other instances you may need to find all the vulnerabilities on hosts with in a given inventory or boundary. Additionally breadth of testing should always be validated to ensure you have met your testing scope (i.e. was every machine in the inventory alive at the time of scanning? If not, why).

Active

Active testing involves direct interaction with the component being tested for security vulnerabilities. This could be low level components such as the TCP stack on a network device, or it could be components higher up on the stack such as the web based interface used to administer such a device. There are two distinct ways to interact with the target component: automated, and manual.

Automated

Automated testing utilizes software to interact with a target, examine responses, and determine whether a vulnerability exists based on those responses. An automated process can help reduce time and labor requirements. For example, while it is simple to connect to a single TCP port on a system to determine whether it is open to receive incoming data, performing this step once for each of the available 65,535 possible ports requires a significant amount of time if done manually. When such a test must be repeated on multiple network addresses, the time required may simply be too great to allow testing to be completed without some form of automation. Using software to perform these functions allows the tester to accomplish the task at hand, and focus their attention on processing data and performing tasks which are better suited to manual testing.

Network/General Vulnerability Scanners

Port Based

An automated port based scan is generally one of the first steps in a traditional penetration test because it helps obtain a basic overview of what may be available on the target network or host. Port based scanners check to determine whether a port on a remote host is able to receive a connection. Generally, this will involve the protocols which utilize IP (such as TCP, UDP, ICMP, etc.), However, ports on other network protocols could be present as well dependent on the environment (for example, it’s quite common in large mainframe environments for SNA to be in use). Typically, a port can have one of two possible states:

    Open – the port is able to receive data

    Closed – the port is not able to receive data

A scanner may list other states, such as “filtered”, if it is unable to accurately determine whether a given port is open or closed.

When the scanner determines that a port is open, a presumption is made by the scanner as to whether a vulnerability is present or not. For example, if a port based scanner connects to TCP port 23, and that port is listening, the scanner is likely to report that the telnet service is available on the remote host, and flag it as having a clear text authentication protocol enabled.

Service Based

A service based vulnerability scanner is one which utilizes specific protocols to communicate with open ports on a remote host, to determine more about the service that is running on that port. This is more precise than a port scan, because it does not rely on the port alone to determine what service is running. For example, a port scan may be able to identify that TCP port 8000 is open on a host, but it will not know based on that information alone what service is running there. A service scanner would attempt to communicate with the port using different protocols. If the service running on port 8000 is able to correctly communicate using HTTP, then it will be identified as a web server.

Banner Grabbing

Banner grabbing is the process of connecting to a specific port and examining data returned from the remote host to identify the service/application bound to that port. Often in the connection process, software will provide an identification string which may include information such as the name of the application, or information about which specific version of the software is running.

Web Application Scanners

General application flaw scanners

Most web application scans start with the address of a website, web application, or web service. The scanner then crawls the site by following links and directory structures. After compiling a list of webpages, resources, services and/or other media offered, the scanner will perform tests, or audits against the results of the crawl. For example, if a webpage discovered in the crawl has form fields, the scanner might attempt SQL injection or cross-site scripting. If the crawled page contained errors, the scanner might look for sensitive information displayed in the error detail, and so on.

It should be noted that crawling and testing phases can be staggered and performed at the same time to reduce overall scanning time. This is the default behavior for many web application scanners.

Directory Listing/Brute Forcing

Suppose there are directories available on the website that the crawler won’t find by following links. Without prior knowledge of these directories, provided by the user, the scanner has at least two additional options.

The scanner/crawler can search for “common” directories. These are directories with names and variants of names that are commonly found, and are included in a list that has been compiled as the result of years of experience and scanning. Most web applications have a “built-in” list of this sort, while some penetration testers maintain their own custom lists. Sometimes directory names are unique enough that they can be used to identify a 3rd party web application with reasonably high accuracy. An accurate directory list can often be the key to finding the “administrative” portion of a website – a portion most penetration testers should be highly interested in discovering.

Brute forcing directories is a similar approach, though instead of using a static list, a tool is used to enumerate every possibility a directory name could have. The downside of using this approach is that it has the potential to crash or inundate the web server with requests and thus cause a denial-of-service condition. Care should be taken to perform directory brute forcing while someone is keeping a close watch on the condition of the web server, especially in a production setting.

The reason you as the penetration tester would want to perform directory listing is to extend your attack field or to find directories that could contain sensitive information (which depending on the goal of the penetration test, may lead to a major finding within it).

Web Server Version/Vulnerability Identification

Many web application scanners will attempt to compare the version of the web server with known vulnerable versions in security advisories. This approach can sometimes lead to false positives; as there are some cases where open-source web servers are forked or copied and given new names, banners, and assigned different version numbers. Additional steps should be taken to verify that the web server is, in fact, running what the banner, or web scanner reports.

Methods

Several web server methods are considered insecure, and can allow attackers to gain varying levels of access to web server content. The fact that these methods are part of the web server software, and not web site content differentiates it from other vulnerabilities discussed thus far. Some insecure methods include:

OPTIONS

While the HTTP OPTIONS method is not insecure by itself, it can allow an attacker to easily enumerate the kinds of HTTP methods accepted by the target server. Note, the OPTIONS method is not always accurate and each of the methods below should be validated individually.

PUT/DELETE

Using the PUT method, an attacker can upload malicious content such as HTML pages that could be used to transfer information, alter web content or install malicious software on the web server. Using the DELETE method an attacker could remove content or deface a site causing a disruption of service.

Additionally, modern REST applications use PUT in a different manner:

Create->POST Read->GET Update->PUT Delete->DELETE

WebDAV

WebDAV is a component of the Microsoft Internet Information Server (IIS). WebDAV stands for “Web-based Distributed Authoring and Versioning” and is used for editing and file management. WebDAV extensions are used by administrators to manage and edit Web content remotely on IIS Web servers and can include PROPFIND, COPY, MOVE, PROPPATCH, MKCOL, LOCK, and UNLOCK .WebDAV interacts with core operating system components, which can expose a system to several possible vulnerabilities. Some of these potential risks include:

    Buffer overflow conditions due to improper handling of user requests

    Denial-of-service conditions from malformed requests

    Domain based scripting attacks

    Privilege escalation

    Execution of arbitrary code

TRACE/TRACK

Modern web servers support the TRACE HTTP method, which contains a flaw that can lead to unauthorized information disclosure. The TRACE method is used to debug web server connections and can allow the client to see what is being received at the other end of the request chain. Enabled by default in all major web servers, a remote attacker may abuse the HTTP TRACE functionality to disclose sensitive information resulting in a loss of confidentiality.

Network Vulnerability Scanners/Specific Protocols

VPN

Conventional vulnerability assessment tools are not capable of performing the correct protocol negotiations with VPN devices that service Internet Key Exchange (IKE). In situations where IKE is in use, it will be necessary to use additional toolkits that can perform functions such as accurate fingerprinting, back off patterns and identify authentication mechanisms that are in use. By identifying these attributes of a VPN device, weaknesses can be identified in running code versions as well as authentication types such as static preshared keys.

Voice Network Scanners

War Dialing

Many organizations still utilize out of band access over telephone lines. Using vulnerability assessment tools that are designed to conduct war-dialing can determine weaknesses in authentication and network architecture.

VoIP

Voice over IP technologies are now abundant within most organizations. Many tools have been developed to conduct vulnerability analysis of VoIP infrastructures. Using these tools, one can identify if VoIP networks are properly segmented and potentials for leveraging these networks to access core infrastructure systems or record phone conversations on a target network may exist.

Manual Direct Connections

As with any automated process or technology, the margin for error always exists. Instabilities in systems, network devices and network connectivity may introduce inaccurate results during testing. It is always recommended to execute manual direct connections to each protocol or service available on a target system to validate the results of automated testing as well as identifying all potential attack vectors and previously unidentified weaknesses.

Traffic Monitoring

Traffic monitoring is the concept of connecting to an internal network and capturing data for offline analysis. Route poisoning is excluded from this phase as these create “noise” on the network and can easily be detected. It is often surprising how much sensitive data can be gleaned from a “switched” network. This “leaking of data” onto a switched network can be categorized as follows:

ARP/MAC cache overflow, causing switched packets to be broadcast – this is common on Cisco switches that have improper ARP/MAC cache timing configurations.

Etherleak – some older network drivers and some embedded drivers will use data from system memory to pad ARP packets. If enough ARP packets can be collected, sensitive information from internal memory can be captured

Misconfigured clusters or load balancers

Hubs plugged into the network Note that some of these categories only result in data leakage to a single subnet, while others can result in leakage to much larger network segments.

Validation

Correlation between Tools

When working with multiple tools the need for correlation of findings can become complicated. Correlation can be broken down into two distinct styles, specific and categorical correlation of items, both are useful based on the type of information, metrics and statistics you are trying to gather on a given target.

Specific correlation relates to a specific definable issue such as vulnerability ID, CVE, OSVDB, vendor indexing numbers, known issue with a software product, etc. and can be grouped with micro factors such as hostname, IP, FQDN, MAC Address etc. An example of this would be grouping the findings for host x by CVE number as they would index the same issue in multiple tools.

Categorical correlation relates to a categorical structure for issues such as in compliance frameworks (i.e. NIST SP 800-53, DoD 5300 Series, PCI, HIPPA, OWASP List, etc.) that allow you to group items by macro factors such as vulnerability types, configuration issues, etc. An example of this would be grouping all the findings for hosts with default passwords into a group for password complexity within NIST 800-53 (IA-5).

In most cases penetration testers are going to focus on the micro issues of specific vulnerabilities found in redundancy between multiple tools on the same host. This redundancy can skew the statistical results in the test output leading to a false increased risk profile.

The inverse of this is with an over reduction or simplification in macro correlation (i.e. top 10/20 lists) as the results can skew the output resulting in a false reduced risk profile.

Attack Avenues

Creation of attack trees

During a security assessment, it is crucial to the accuracy of the final report to develop an attack tree as testing progresses throughout the engagement. As new systems, services and potential vulnerabilities are identified; an attack tree should be developed and regularly updated. This is especially important during the exploitation phases of the engagement as one point of entry that materializes could be repeated across other vectors mapped out during the development of the attack tree.

Isolated Lab Testing

The accuracy of vulnerability analysis and exploitation is substantially greater when replicated environments are setup in an isolated lab. Often times, systems may be hardened with specific control sets or additional protection mechanisms. By designing a lab that mimics that of the target organization, the consultant can ensure that the vulnerabilities identified and exploits attempted against the desired targets are reliable and lessen the opportunity for inaccurate results or system inoperability.

Visual Confirmation

Manual Connection with Review

While proper correlation can help reduce false findings and increase overall accuracy, there is no substitute for visually inspecting a target system. Assessment tools are designed to review the results of a protocol/service connection or the response and compare to known signatures of vulnerabilities. However, tools are not always accurate in identifying services on uncommon ports or custom logic that may be built into an application. By manually assessing a target system, its services available and the applications that provide functionality for those services, a tester can ensure that proper validation and vulnerability identification have been completed.

Common/default Passwords

Frequently, administrators and technicians choose weak passwords, never change the default or do not set any password at all. Manuals for most software and hardware can be easily found online, and will provide the default credentials. Internet forums and official vendor mailing lists can provide information on undocumented accounts, commonly-used passwords and frequently misconfigured accounts. Finally, many web sites document default/backdoor passwords and should be checked for every identified system.

Hardening Guides/Common Misconfigurations

One of the primary goals of penetration testing is to simulate the tactics and behavior of an actual attacker. While automated scanning can reduce the time window of a test, no scanner can behave like a human being. Hardening guides can be an invaluable reference for a penetration tester. They not only highlight the weakest parts of a system, but you can gain a sense of the diligence of an administrator by validating how many recommendations have been implemented. During every penetration test, time should be taken to review every major system and its recommended hardening settings, in order to discover vulnerabilities left in place by the administrator.

User forums and mailing lists can provide valuable information about systems and the various issues administrators have in configuring and securing them. A tester should research target systems as if he were installing one himself, and discover where the pain points and probable configuration errors will lie.

Private Research

Setting up a replica environment

Virtualization technologies allow a security researcher to run a wide variety of operating systems and applications, without requiring dedicated hardware. When a target operating system or application has been identified, a virtual machine (VM) environment can be quickly created to mimic the target. The tester can use this VM to explore to configuration parameters and behaviors of the application, without directly connecting to the target.

Testing Configurations

A testing VM lab should contain base images for all common operating systems, including Windows XP, Vista, 7, Server 2003 and Server 2008, Debian, Ubuntu, Red Hat and Mac OS X, where possible. Maintaining separate images for each service pack level will streamline the process of recreating the target’s environment. A complete VM library in combination with a VM environment that supports cloning will allow a tester to bring up a new target VM in minutes. Additionally, using a snapshot feature will allow to work more efficiently and to reproduce bugs.

Fuzzing

Fuzzing, or fault injection, is a brute-force technique for finding application flaws by programmatically submitting valid, random or unexpected input to the application. The basic process involves attaching a debugger to the target application, and then running the fuzzing routine against specific areas of input and then analyzing the program state following any crashes. Many fuzzing applications are available, although some testers write their own fuzzers for specific targets.

Identifying potential avenues/vectors

Log in or connect to a target network application to identify commands and other areas of input. If the target is a desktop application that reads files and/or web pages, analyze the accepted file formats for avenues of data input. Some simple tests involve submitting invalid characters, or very long strings of characters to cause a crash. Attach a debugger to analyze the program state in the event of a successful crash.

Disassembly and code analysis

Some programming languages allow for decompilation, and some specific applications are compiled with symbols for debugging. A tester can take advantage of these features to analyze program flow and identify potential vulnerabilities. Source code for open source applications should be analyzed for flaws. Web applications written in PHP share many of the same vulnerabilities, and their source code should be examined as part of any test.

5 Tips to Prevent and Mitigate Ransomware Attacks

Ransomware attacks are increasing in frequency, and the repercussions are growing more severe than ever. Here are 5 ways to prevent your company from becoming the next headline.

Ransomware attacks cost companies over $100 billion a year. Making matters worse, the overwhelming majority of ransomware attacks now include a threat to leak stolen data if the ransom isn’t paid, a technique called “double extortion.”

Cybercriminals like ransomware because the entry barrier is exceedingly low — if you don’t know what you’re doing, you can always buy a “ransomware-as-a-service” solution off the Dark Web — and the paydays are lucrative.

Preventing ransomware attacks requires a layered approach that combines security defenses with proactive measures to prevent ransomware from taking hold in the first place. Here are 5 tips.

1.    Perform regular system backups

Long the gold standard of ransomware recovery, systems backups don’t provide as much protection as they once did due to double extortion. Additionally, many next-gen ransomware strains seek out and destroy backups. However, secure backups still play a vital role in restoring systems after a ransomware attack, as well as hardware failures and natural disasters. Utilize at least two different backup methods, each stored at a different location.

2.    Segment your network

Network segmentation, which involves parceling off a larger network into smaller segments using firewalls, virtual LANs, and other techniques, doesn’t prevent cyberattacks from happening. However, it does stop malware or human intruders from moving laterally within your network — a key factor in double extortion ransomware attacks. Cybercriminals can’t exfiltrate what they can’t access. Segmenting is typically done by function, such as separating customer-facing services from internal apps, or by data type, such as separating regulated data from non-regulated data.

3.    Conduct regular network security assessments

Most compliance standards, including NIST, HIPAA, and PCI DSS, mandate that organizations perform penetration tests and vulnerability scans at certain intervals. Typically, they require organizations to run vulnerability scans quarterly and perform penetration tests annually. However, these are the bare minimum requirements. There are many circumstances under which more frequent scans or pen testing are warranted, such as whenever organizations make a major change to their data environment.

4.    Conduct employee security training

It happens every day: Millions of dollars worth of security technologies are defeated because an employee clicked on a phishing link. Just as employees who work in industrial environments must undergo safety training to operate machinery, knowledge workers must be trained to operate computers safely. Because the cybersecurity threat environment is always changing, employee cybersecurity training is a process of continuing education. Among other things, organizations need to regularly conduct simulated “phishing attacks” to gauge employee awareness and knowledge. Employees also need to know who to contact, and how to get in touch with them, if they encounter a security issue or have a question.

5.    Get your password security under control

Even before remote work became widespread, over 80% of data breaches were due to compromised passwords. As remote work exploded in popularity, brute-force attacks targeting remote desktop protocol (RDP) connection credentials rose exponentially. The majority of ransomware attacks now involve either RDP credential compromise or phishing — in other words, compromised passwords. Organizations need to implement robust password security protocols, including requiring employees to use strong, unique passwords for every account and enable multi-factor authentication (2FA) whenever it’s supported.

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General Findings:

The general findings will provide a synopsis of the issues found during the penetration test in a basic and statistical format. Graphic representations of the targets tested, testing results, processes, attack scenarios, success rates, and other trendable metrics as defined within the pre engagement meeting should be present. In addition, the cause of the issues should be presented in an easy to read format. (ex. A graph showing the root cause of issues exploited)

What is Penetration Testing

Penetration testing, or pen testing, is a form of ethical hacking where computer systems or a network of web applications are attacked by highly skilled security professionals to find vulnerabilities. The test can be automated, carried out manually, or even be a mix of both depending on the requirements. 

The idea behind penetration testing is to identify possible entry points in the organization’s network and breach the defense mechanism of the target. Once the system is hacked, the security professionals gather as much information as possible and prepare a report that helps the company to take corrective measures and fortify their walls. Since the testing is carried out by people trying to help the organization, it is also known as the white-hat attack. 

Why Penetration Testing is Important

No organization’s default security system is watertight. There are always tiny holes that need to be found and plugged. The importance of this method of cybersecurity can be gauged from the fact that in 2016, The Pentagon opened its doors to outsiders to test the defense of their unclassified computer systems. The 1,400 hackers who registered for the “Hack the Pentagon” program exposed 100 security threats that even an organization like the United States Department of Defense was not aware of earlier.

Here are a few reasons why organizations must employ pen testing professionals from time to time:

Discovering Vulnerabilities Before Attackers

A pen tester, under a controlled environment, carries out attacks the very same way hackers with malicious intent would do. They break their heads to find out vulnerabilities that could potentially cause damage to the organization. They filter issues like software errors, poor configurations, inaccurate system settings, and other shortfalls. This helps organizations to understand vulnerabilities and correct them as soon as possible to avert any major attacks.

Reducing Network Downtime

IT system downtime can burn a hole in the pockets of business organizations. According to a Gartner report, organizations lose up to USD 5,600 on an average per minute due to this reason. A regular pen test reduces the downtime drastically, thus keeping the organization’s engine running smoothly.

Building a Safer Ecosystem

Pen testers not only find faults in the organization’s system but also suggest ways to tackle them. Experienced testers help their clients to understand their flaws and engage with the firm’s technical experts to build better defense mechanisms to avert potential attacks.

Protecting Reputation

Several factors go into building brand value and consumer trust. Every security mishap involving customers’ data directly affects the brand value and sales and even brings bad repute for the company, which big organizations cannot afford.

Penetration Testing Parameters

Organizations that operate through robust IT infrastructure are always vulnerable to organized system attacks from hackers, attackers, unscrupulous rivals, political dissenters, etc. and are perpetually in search of vulnerabilities in security systems of an organization. These vulnerabilities eventually become parameters on which organizations test their preparedness to ward off future attacks.

There are various kinds of vulnerabilities that attackers exploit to run malicious codes, access drives of computers in their target servers or personal computers, modify data, and even inject viruses. 

Weak Passwords

Weak passwords are the lowest-hanging fruit for any potential attacker who wants to breach the target organization’s defense system and exploit it. 

Outdated Applications

Hackers often use outdated applications and systems as easy entry points. It is imperative to keep applications and operating systems constantly updated, as they contain important patches that safeguard systems. 

Injection Vulnerabilities

Attackers aim to gain database and server access by pushing in the malicious payload in the form of codes and scripts. Payloads are the part of the attack which inflicts the target. All attack vectors, like viruses and malware, contain at least one payload. The most widely exploited vulnerabilities are authorization for invalid inputs in submission forms, contact forms, and other input-based fields.

Encryption, Authentication, and Authorization

Encrypting data is needed to ensure there are no leaks during data storage and transmission. When organizations do not adhere to proper encryption protocols, such as TLS, SSL, etc., they become sitting ducks for attackers. 

Authentication shortfalls, such as weak, default passwords, and broken access control, are exploited by attackers to extract sensitive information.

Vulnerable Components

There are certain applications, frameworks, and software that are repeat offenders when it comes to compromising data. Such frameworks that are prone to exploitation are detected during a pen test.

Misconfiguration Issues

According to Cobalt’s “Pen Test Metrics 2018” report, misconfiguration is the most common vulnerability detected during pen tests.

Attackers can wreak havoc on an organization’s system if they discover open ports, overexposed services, or network misconfigurations. Any such attack can cause harm to the integrity of the company and force users to quit using its applications.

Business Logic Vulnerabilities

It is an application vulnerability that surfaces due to security loopholes. Attackers target those areas of the application where developers are prone to make errors. This class of flaw is very difficult to detect through automated scans. A thorough pen testing by seasoned professionals is the company’s best bet of finding such loopholes.

Penetration Testing Teams

Pen testing is an elaborate and detailed process and is not carried out by just one person or team alone. Testers are broadly categorized into three teams: Red, blue, and purple. 

Although they are interconnected, each team has a distinctive and equally important role to play in the whole process. We define their roles below:

Red Team 

This is the team directly tasked with penetrating the organization’s defense barrier and gaining access to the systems. It can be compared to the stealth team in armed security forces. The team consists of highly skilled ethical hackers who are not associated with the target company in any way. The red team utilizes the latest hacking techniques and may even write their scripts to develop a virus to attack targets, much like how a hacker with malicious intentions does. They infiltrate the systems using both physical and virtual techniques while trying their best to evade detection. This team will go to any length, within the legal framework, to find an entry point to accomplish its task. 

This team generally utilizes open-source intelligence to carry out reconnaissance and gathers information on the target organization and its systems. On occasions, the red team may also carry out fake attacks to mislead the security system. Its members are trained to attack quickly and when they are least expected to do so, thus effectively mimicking a real-life attack. 

Blue Team

This team comprises highly skilled analysts form within the organization whose main role is to neutralize any attack to the company security system. This process shows how well the blue team is equipped to handle similar situations if and when they arise in a real-life scenario. They are tasked with the duty of finding out, handling, and weakening attacks orchestrated by the red team. It has to be on its toes all the time, foresee any emerging attack, and take necessary precautions to avert or minimize the damage. It needs to actively monitor traffic on the organization’s network and be ready to jump into action in the shortest possible time. 

Purple Team

The target organization’s top security professionals make up this team. Its primary task is to observe how effectively the red and blue teams are working with each other. If the purple team observes any issues with the functioning of either of the teams, it can provide suggestions for course correction. At times, it can support the blue team to beef up security and help it chalk out recovery plans in the case of attacks which can be utilized later. Eventually, the goal of the purple team is to learn about the vulnerabilities in the organization’s system and prepare a road map, which includes educating the current employees about security threats and reinforcing the security wall of the network.

Penetration Testing Method

Organizations employ different types of strategies to safeguard their networks, applications, and computers against cyberattacks. They involve using in-house and external professionals and agencies to mimic attacks as if they were taking place in a real-life scenario. Below are some strategies organizations employ to preempt hacking attempts:

Targeted Penetration Testing

In this type of testing, the organization’s IT professionals coordinate with pen testers and keep each other informed at all stages of the process. The tests are carried out on an open server so that all developments can be monitored, recorded, and analyzed by both parties.

External Penetration Testing

It is a very conventional approach to pen testing, where ethical hackers try to breach internal networks through external servers, clients, and people. The pen tester’s main objective is to gain access to a particular server through whatever means it can be done within legal limits. Testers may take advantage of a weak web application or even coax a user to divulge sensitive information, like passwords, over a phone call.

Internal Penetration Testing

The primary objective of internal pen testing is to analyze the company’s defense mechanism in case of an attack where the hacker has breached the initial network. The pen tester mimics internal attacks that often target the lesser important systems. Then, they launch an attack on the primary target with the help of the information gained earlier.

Blind Penetration Testing

Testers carry out an attack using publicly available information. It is as close it gets to a real attack, where ethical hackers have to work their way in taking cues from the information already at hand and not depend on any help from the organization even when it has authorized this type of testing.

Double-Blind Penetration Testing

This process, also known as zero-knowledge testing, is even more covert than blind testing. Testers have little or no knowledge about their target’s defense systems, and, likewise, the target company has no clue what approach, scale, and duration attackers will adopt to harm its systems. This approach needs highly skilled pen testers, as they have to rely on their experience to choose appropriate tools and methods to break into a company’s defenses.

Types of Penetration Testing

To expose loopholes in a company’s security system, there are three types of pen testing models which can be employed: black-box testing, white-box testing, and gray-box testing, which are described below:

Black-Box Testing

This is also known as the trial-and-error method in which security experts are not provided any details on the company’s network, software, or source code. In such a case, the hacker goes for a full attack against the network to find an entry point that can be exploited. This method requires a lot of effort and is time-consuming. Attackers have the luxury of time on their hands in real-life scenarios. Miscreants can devise a complex attack plan over several months and attack when it is least expected. Testers often rely on automated processes to ease their burden while carrying out this testing process.

White-Box Testing

It is the exact opposite of black-box testing. This method, also known as clear-box testing, grants complete access of the network to the tester. The security expert is provided with vital information about the company’s internal workings, software, and source code. Since the tester is loaded with information, the process becomes less tedious when compared to the previous method. Despite being a more comprehensive method, white-box testing has its drawbacks. Give the information overload, choosing a core area to focus on can be a huge task. The tester has to narrow down on the specific components that need to be analyzed against hacking attempts. This method requires more advanced software tools and analyzers.

Gray-Box Testing 

As the name suggests, this method employs principles of both black- and white-box testing. Neither complete details about the company’s system are divulged, nor is the tester kept in complete oblivion. Basic details, such as software code and other information that grants the tester access to the system, are provided. This method provides greater freedom to the tester who can choose to employ both manual and automated processes to find loopholes. It can recreate a scenario where a hacker has already gained internal access to the network. It helps the organization understand complex vulnerabilities and develop a more streamlined security plan. This is by far the most effective method and improves the chances of zeroing in on possible vulnerabilities that are a little harder to detect.

These types of pen testing can be further divided into more specific groups, such as:

Social-Engineering Tests 

In this pen-testing method, the tester encourages an employee or a third party to reveal sensitive information, like passwords, which can be used to break into the network. Even a tiny hint provided by an employee can go a long way in compromising the system. This has proven to be an efficient hacking technique that takes advantage of human weaknesses. Social-engineering tests can be carried out in two ways – remote and physical. In remote testing, the hacker uses technology like phone or phishing emails to gather information. In physical testing, the pen tester comes in actual contact with the person. A tester can disguise themselves as a company employee and extract vital information. Either way, the target company should provide the requisite permission before such tests are conducted.

Web-Application Tests

This is a far more complex test and requires thorough planning before implementation. Areas like web applications, browsers, and their plug-ins are put to test in this process.

Client-Side Tests 

The objective of these tests is to find out local threats. Miscreants exploit glitches in applications running in the system. Apart from third-party applications, threats can arise from careless practices used within the organization. Running uncertified operating systems is one such loophole. Therefore, comprehensive testing of the local system and network is very important.

Wireless-Network Tests 

As the name suggests, this process is carried out to analyze all wireless devices, such as smartphones, tablets, laptops, etc. which are connected to the organization’s server. Configuration protocols of wireless devices and access points should be tested and any violation should be detected.

Penetration Testing Phases

Pen-test is a comprehensive and meticulous process that varies with the kind of testing – whether it is internal or external. The testing process can be broadly broken into four phases: Planning, discovery, attack, and reporting.

Planning or Agreement Phase 

All activities conducted before the actual test take place during this phase. This is the stage where the tester and the company decide on the scale of operation and complete all the paperwork. Approvals, documents, and agreements, such as the non-disclosure agreement, are inked at this stage. Unlike a hacker, a tester is bound by legalities, timelines, and agreements. Several factors need to be taken into consideration at this stage while developing a sound course of action. An attacker in a real-life scenario would have ample time in their hands to find an entry point and exploit the vulnerabilities, but a tester has a limited period available – also taking into consideration the working hours of the business to carry out the process. The company may also limit the scope of the test fearing the financial impact on the business due to information leaks. The tester also has to work within the legal framework and strictly adhere to the conditions mentioned in the agreement signed by both parties.

Discovery Phase

This is the stage where the actual testing and information gathering takes place. This phase can be further divided into three parts: footprinting, scanning, and enumeration phases, followed by vulnerability analysis.

Footprinting is gathering information about the target involving non-invasive processes. Scanning the internet for information on the organization is often an overlooked process but can lead to a goldmine of relevant information. Since no attempt is made to break into the system, the tester remains undetected. If the tester puts in a concentrated effort, useful information like IT setup details and device configurations can be dug up, which can come in handy while carrying out the actual break-in.

Then come the scanning and enumeration stage in which the tester invades the security system of the target to gather information like operating system details, network paths, live ports, and the services operating in them. The tester has to smartly break into the system while ensuring the traffic on the network does not spike up and alert the system administrator. Only those tools that have been tried and tested before should be employed by the tester. To minimize the possibility of false positives in the later stages, the tester has to find out the precise details about the operations system and services running on the system and record them in the reports.

Once adequate information is gathered, the pen tester should try to identify loopholes in the defense mechanism of the target. This component is called vulnerability analysis. The efficacy of this process largely depends on the knowledge and skill levels of the tester. Keeping up with the latest trends and developments is essential for any tester to be successful. A tester may use automated processes to find out an entry point and exploit it. The pen tester may also try to use random inputs to check for discrepancies in the system output. It should be kept in mind that the whole process of pen testing is not solely tool reliant, so the testers have to be on top of their game to make the operation successful.

Attacking phase

This is the make or break phase of the pen testing process. It is intriguing and challenging in equal parts. This phase can be broadly classified into the exploitation part and the privilege escalation part.

In the exploitation part, the tester tries to find ways to take advantage of loopholes in the security system found out in the previous phase. The tester must have prior knowledge of C or other scripting languages, such as Python or Ruby. This phase must be carried out tactfully as even one misstep can bring the whole production system crashing. The exploits must be first carried out in a controlled environment before attacking the system. Organizations may not want certain sensitive areas of their systems exploited at all. The tester has to tread carefully and provide sufficient information while explaining the impact of the vulnerability on the network. There are proficient exploitation frameworks available commercially that the tester can make use of. A pen tester should try to make the most of these frameworks and not use them merely for carrying out exploits. In some cases, an exploit may not lead to root access, pushing the tester to analyze further to reach the threat.

As mentioned earlier, on certain occasions the exploit does not lead to root access. In such cases, the tester is required to carry out deeper analysis and gain information that grants them administrative privileges. The tester could be required to take the aid of additional software to attain special privileges. This is what is known as privilege escalation. Pen testers should also consider targeting other systems in the network once access is gained. This process is called pivoting and helps in understanding the real impact of an exploit on a company’s security mechanism. However, it requires prior permission and clearance from the target organization, and the tester needs to keep a record of all the exploits carried out.

Reporting Phase

This is the final stage in the pen testing process and can be carried out along with the other phases or completed at the very end. This is probably the most important phase of the whole process because the organization pays the tester precisely for this report.

The final report must be elaborate and prepared to keep in mind that all technical aspects are lucidly explained for the management. The technical details, including all the successful exploits carried out, must be mentioned with adequate evidence in the form of screenshots. A clear recovery path must be recommended as well. 

Penetration Testing Tools

Pen-testing tools are software applications used by testers to carry out their activities efficiently. Depending on their goals, testers opt for tools that they feel best suit their requirements. There are countless testing tools, both paid and free, available on the web. Given below is a list of some of the widely used pen-testing tools:

Metasploit

It is an open-source framework widely used by both the red and blue teams. As it is an open-source, Ruby-based framework, Metasploit can easily be tailored for almost all operating systems. The framework is powerful and can detect vulnerabilities in network servers with ease. Once the loophole is detected, the framework’s extensive database helps testers carry out the exploit. Metasploit has changed the landscape of pen-testing. Earlier, testers had to break in manually using various tools. They had to write their code and inject them into the network. This framework has eased the process and now is the go-to tool for most testers and even hackers. It has around 1,700 exploits over 25 platforms, that include Java, Android, PHP, and Cisco among others.

Visit Website: Metasploit

Wireshark

It is a packet sniffer/network protocol analyzer that lets the tester view the happenings in the network in real-time with the minutest of details. This open-source project, which has been developed through contributions over the last two decades, effectively deep-scans several web protocols with ease. It is part of the kit of most testers due to its protocol analysis features that make accessing traffic in real-time hassle-free. Wireshark can break down data packets and determine their characteristics and map their origin and destination. This helps in detecting loopholes within the system. It is adept in handling SQL injections and buffer overflows risks and is efficient in testing wireless networks. Its USP, however, remains the ability to break down traffic to the finest details.

Visit Website: Wireshark

Kali Linux

This Linux distribution contains a powerful set of tools for pen-testing, which has over 600 ethical hacking components. It is a highly advanced testing suite available on Linux machines. The tester needs to be well-versed in TCP/IP protocols to operate these tools effectively and carry out activities like code injection and password sniffing. This suite of tools is meant for brute force attacks. For many testers, it is a one-stop solution for all their needs. There are provisions for vulnerability analysis, wireless attacks, passwords cracking, spoofing, sniffing, and even hardware hacking in this versatile suite of tools. To make things better, other popular pen-testing tools, like Metasploit and Wireshark, can easily be run on Kali Linux.

Visit Website: Kali Linux

John the Ripper

It is a free testing tool used to crack passwords written mostly in C. John the Ripper auto-detects encryption, runs it through a plain-text file containing commonly used passwords, and comes to a halt after detecting a match. This tool can help organizations detect weak passwords and revamp their protection policies. The tool comes with an inbuilt list of common passwords in over 20 languages.

Visit Website: John the Ripper

Netsparker Security Scanner

It is one of the most popular pen-testing web applications. Testers can use Netspaker to detect anything from cross-site scripting to an SQL injection in websites and web applications. It can scan up to 1,000 applications in one go. It employs a proof-based scanning mechanism, guaranteeing maximum accuracy. This application is equipped to scan common modern web applications, including HTML5, Web 2.0, and even password-protected web assets. Once it detects vulnerabilities, the software assigns them a severity level to help the tester focus on areas that need immediate attention. The management system of the software gives testers greater freedom in creating and assigning roles, carrying out retests, and taking corrective measures. 

Visit Website: Netspark Security Scanner 

Aircrack-ng

This open-source tool is the first choice of the testers who want to break into a wireless network. Pen testers can use this tool to monitor and analyze the Wi-Fi security mechanism of a target, collect data packets, and convert them into text files for further study. Testers can easily break into WPA and WEP security protocols using this tool. Originally developed for Linux, Aircrack-ng now is compatible with operating systems like Windows, FreeBSD, OS X, Open BSD, Solaris, and eComStation. Although it is effective in cracking keys on the WEP and WPA-PSK networks, the tool loses its functionality when it comes to testing non-wireless networks.

Visit Website: Aircrack-ng

Acunetix Scanner

It is an automated pen-testing tool that is used to detect cross-site scripting and SQL injections. The framework is advanced and capable of digging out tough-to-detect vulnerabilities. Its sophisticated AcuSensor technology, manual penetration tool, and vulnerability management system ease black- and white-box testing and improve the correction process. Another advantage of using this tool is that it can scan thousands of web pages in an instant and also be operated locally or through a cloud network set-up.

Visit Website: Acunetix Scanner

Burp Suite

It is a Java-based web penetration testing system that acts as an interception proxy. The framework has become a go-to tool for the pen testers who want to identify vulnerabilities and detect attack vectors affecting an organization’s web applications. Testers can route their traffic through Burp Suit’s proxy server, which then acts as a gatekeeper recording each request relayed between the developer and the target web application. Testers, then, can pause and analyze every individual request and discover injection points. Its myriad features have made the framework increasingly popular.

Visit Website: Burp Suite

Nessus

It is a remote security-scanning tool that has been in existence for over two decades and used by scores of testers and companies for security purposes. The testing tool carries out over 1,200 checks on a single device in the network and checks if any vulnerabilities can be exploited by hackers to break in. It is one of the best vulnerability scanners out there and suited for experienced testers owing to its complex interface. The tool is adept in detecting software flaws, missing patches, and malware. It narrows down vulnerabilities but does not allow the tester to exploit them.

Visit Website: Nessus

Limitations of Penetration Testing 

Even if an organization regularly conducts pen tests, its system will not become foolproof due to certain limitations of the testing process. A pen test cannot eliminate all vulnerabilities, because, at the end of the day, the quality of the test depends on several factors, including the skill set of the testing team. Here are a few drawbacks in pen-testing processes that cast doubts over their overall effectiveness:

Skill and Experience of Testers

Penetration tests can be broadly divided into three sections: network, system, and web. It is highly unlikely that an objective result can be obtained if a tester specializes in one area and has only working knowledge of the other two. Since the dynamics of security structures keep changing at a rapid pace, it is difficult to find someone who is an expert in all three areas. 

Time Constraint

Testers have a given period within which they have to find vulnerabilities, breach the systems, and prepare reports. Attackers are not bound by a time frame. They can plan an attack in leisure and carry it out when the target least expects it. Testers are also burdened with the task of recording every step they take and gather evidence in the form of screenshots and documentation. An attacker, on the other hand, can carry out attacks without being bothered about making diary entries or similar laborious requirements.

Custom Exploits

Not all security systems can be breached using the standard pen-testing framework. Advanced systems need to be cracked by creating a custom attack plan with customized scripts. Writing a custom code is an advanced skill. To avail the services of such highly skilled testers, a company needs to allocate a substantial budget.

Access Limitations

Companies often draw lines that the testers cannot cross. Only certain servers and segments that the organization has allowed to be scrutinized can be attacked by testers. But, in a real-life scenario, attackers are not bound by any contract or restrictions. This limits the actual efficiency of the test and may give the organization a false feeling of the system being watertight.

How often Should Penetration Testing be Conducted

Since pen testing is a tedious process, there cannot be a one-size-fits-all approach, and organizations have to look into factors like size, budget, regulations/compliance, company policies, and infrastructure before calling in the “good guys” to hack their system.

Most companies wake up to its need when it is too late. Only after facing a major attack, companies realize the need for thorough system analysis. Post attack, they often burden their IT teams to trace the source, analyze the overall damage, and plug the leak. But, all this can probably be avoided if a pen test is conducted before an attack takes place, thus saving time, effort, and eventually money. 

As networks update their infrastructure, the complexity of threats rises as well. Therefore, a one-time penetration test is an exercise in futility. It is an ongoing process, and, depending on the factors mentioned earlier, organizations need to devise a testing plan that suits their requirements.

Penetration testing is also oftentimes confused with vulnerability scanning and some consider them to be the same concepts. However, the basic difference between the two is that vulnerability scan searches systems and reports on known vulnerabilities, whereas penetration testing is much more aggressive and attacks the organization’s systems and replicates real-life attacks. You may learn more about the differences between the two from our earlier post – vulnerability scanning vs penetration testing.

Conclusion

Security experts recommend that all organizations should undergo a penetration test ideally once a year to ensure that their network is in good health. Despite its limitations, pen-testing remains the most efficient way to mimic a real-life attack and test the defense mechanism of the target organization. However, given that it is carried out in a controlled environment and its efficiency is dependent on the testers’ skills, the results of this exercise should be taken with a pinch of salt. Organizations should also understand that pen testing is not an alternative to the existing application security testing system, but it is there to supplement it. The information thus gathered can help companies plan their security budget in a better manner and developers create software/applications that withstand similar attacks in the future.