Penetration Tests- Full Guide to the #1 Cyber Defense

What is Pen Testing

What is Pen Testing?

For years, the war between black hats (a nickname for malicious hackers) and white hats (a nickname for ethical hackers) has been at the center of public attention. And as in any war,  adversaries are equipped with weapons.

One of the most significant defense tools we have is pen testing, which simulates a cyberattack only without the malicious intent behind it.


How do pen tests work?

Penetration Testing is a way of assessing the security level of systems, applications, mobile services and infrastructure. 

This assessment begins with mapping the organization’s digital assets, including integrated third-party tools, user behavior, etc. The purpose of the test is to identify the weaknesses and vulnerabilities in the defense systems and produce a report detailing the findings and recommendations. 

This method is a highly efficient way to test the organization’s defense grid, and the data speaks for itself – 45% of Canadian organizations performed penetration tests to reduce the risk of falling victim to cyber-attacks. 

Types of Pen Tests

Every pot has a lid, every pencil has a pencil case and every organization has a penetration test that suits it. The separation to different types of PTs is designed to maximize efficacy by focusing the test on the organization’s specific needs. 

  • Web application pen test
  • Network pen test
  • Mobile pen test

Web application tests

Goldilocks might have preferred the softest bed of the bunch, but others would not agree with her choice. Web application penetration testings are usually sorted into three categories, and with each test simulating different scenarios, you ought to know what your goal is when choosing one:

Gray Box

 A test that can be performed from an outsider’s point of view or an insider attacker. In some cases, the tester will receive limited information about the organization’s information systems, such as user per system. The tester will then use this information to scan for potential vulnerabilities that can be exploited for malicious purposes.

The Gray Box is the most common of Pen Tests, and its advantage is the thorough cover of vulnerabilities visible to an outsider and insider attacker.

White Box

Julius Caesar would argue that the most painful stabs are those that come from behind, and indeed information security breaches made by attackers from within the organization can lead to a huge loss in the company’s profits and customer credibility. Just ask the giant company CISCO, which is still in a legal battle against a former employee who intentionally damaged their cloud infrastructure by infecting malware with malicious intentions.

The white box pen testing simulates a cyber-attack conducted by a hacker from within the organization (for example, a resentful employee who wants revenge) that is already accessible to the network and the company’s resources.

This test requires the organization to provide the software’s source code, including characterization and detailed information. 

By providing this information, the white hat hackers can conduct a comprehensive and thorough penetration test to find as many vulnerabilities as possible, thus enabling maximum use of time and wider coverage of the security systems. 

Black Box

Nothing beats real-life experience, and authenticity is exactly what a Black Box penetration test simulates. 

Black box Penetration tests are similar to real cyber hacks. When performing black box, the pen tester does not receive any preliminary information about the organization or the existing systems in it. 

Black Box pen-testing begins as an external test, however, if a breach has been made the tester will continue as an inside intruder, in coordination with the boundaries that have been initially set. 

It should be mentioned that black box Penetration tests usually take longer, as a large part of the test focuses on collecting data that will assist the performance of the intrusion. In addition, it is likely that this test will not uncover all the vulnerabilities, but instead the ones that are most useable by malicious hackers. 

Network penetration testing

In infrastructure pen testing, we test the resilience of your organization’s devices, focusing on equipment connected to the internal network that does not have access from the outside (such as routers, printers, organization computers, etc.). In the world of infrastructure, the tests can be divided into 2:

  • Internal pen test
  • External pen test

Internal pen test

Organizations might not consider internal attacks as a major threat, however, the damage that can be done is enormous and should be taken very seriously. An internal pen test is an attempt to penetrate and gain access to enterprise information systems, and it is done from the perspective of an attacker who has access to the internal network or works with limited access to the network.

In computers where there is adequate hardening the actions that an attacker can do are limited. During an internal penetration test, the pen tester tries to raise their permissions (escalation) as much as possible, thereby gaining access to all the devices that are included in the test.

As proof for examination, evidence is usually sent to confirm the findings, such as:

  • Passwords for administrative access and databases
  • E-mails and confidential documents
  • Screenshots

External pen test

This test examines the ability of an organization’s security grid to withstand external attacks. This process involves scanning the information systems and network accessibility outside the organization, to try to locate existing vulnerabilities that can lead to intrusion or damage to the organization. 

Usually, these attacks occur without prior information on the inside of the organization, and this situation comes in the form of an intentional attack attempt by an external attacker or a “random” attack attempt that attacks the organization according to the following methodology:

  • Gathering external information about the organization and testing its relevance regarding the intrusion test.
  • Perform a vulnerability scan to identify existing vulnerabilities.
  • Conducting a risk survey based on the results of the scan to prioritize and relevance of the findings.
  • Performing a “safe hacking” process based on previous findings.
  • Testing network devices that are accessible outside the organization, such as FW, routers, mail servers, etc.



Mobile pen test

Penetration testing for mobile apps, or a specific mobile device, has become essential as work and home life blend with each other. Many employees use their smartphones for the day-to-day management of work, and it’s like the holiday season for hackers, as mobile has become an easy and popular target. App creators might request a penetration test to reduce the risk of a successful attack from an infected mobile, as well as to ensure the safety of the user device in case of an infected code.

Mobile pen testing is also relevant to any professional who has sensitive information concerning their clients and is defined as a target for hackers – lawyers, financial advisors, etc. 

The Importance of Pen Tests

No article is complete without data and graphs to instill fear in us and create a headache. However, being alert and aware of the cyber threats facing organizations is key in reducing cyber risks. Unfortunately, these threats are only becoming more sophisticated, and their frequency is increasing by the year.  An extensive survey conducted in England by the British government revealed alarming data on the frequency of cyber attacks – at least once a month in 50% of all private sector companies. 


Source: gov.UK

If you are a small business owner, this could very well be a breaking point. According to the NSA, about 60% of small businesses go bankrupt after six months of a successful cyber attack. For further reading about the unique predicament of small businesses and organizations, continue to the full article.

Even organizations whose immediate consequences are minor, such as temporary loss of access to documents and networks, experience long-term consequences following a successful attack. More than a third of these organizations, most often large firms, report increased financial investment in the implementation of defense systems, employee recruitment or transfer to manage the breach, and additional remediation costs. 


Source: gov.UK

It is crucial that S&M businesses consult with a cyber security firm, that will implement holistic cyber solutions and conduct pen tests, to prevent the next cyber attack

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