The Why and How of Using a Penetration Testing Strategy

Talks of security vulnerabilities, such as ransomware, social engineering, SQL injections, breaches, hacking, etc., are on the rise. As these attacks become sophisticated, identifying these easily is becoming increasingly difficult.  

In a software-defined world, there is no place for applications and systems that perform poorly or are open to vulnerabilities. Therefore, removing the weak links from applications and systems is a cybersecurity priority, especially as  hybrid work, remote work  and geographically displaced teams further dilute the enterprises' security perimeter. 

Identifying vulnerabilities in systems and applications with robust penetration testing strategies thus becomes crucial as cyber-attacks and threats become more frequent, severe, and sophisticated. 

An Introduction to Penetration Testing 

Penetration testing is an invaluable process that helps in identifying vulnerabilities and issues that traditional IT security tools may not pick up. Penetration or pen tests evaluate the security of an IT infrastructure by consciously and securely trying to exploit vulnerabilities that could exist in public or private networks, operating systems, services, and applications. Improper configurations or risky end-user behavior also contribute to increasing vulnerability risks, and can get exposed early on, only through a proper penetration testing strategy. 

Penetration tests validate the efficiency of the defensive mechanisms at work, as well as end-user adherence to security policies. These tests are conducted to identify potential points of exposure from public and private servers, endpoints, web applications, wireless networks, network devices, mobile devices, etc. 

The testers also attempt to employ the compromised system to launch subsequent exploits on other internal resources. They do this to incrementally exploit and achieve higher levels of security clearance. They also get deeper access to electronic assets and information via privilege escalation and gain greater clarity over security vulnerabilities at play. 

Penetration testing is often carried out by ethical hackers. They evaluate the security of IT infrastructures using a controlled environment and process to safely attack the resources under the identified scope, to identify and report on the discovered vulnerabilities. They apply different methodologies, tools, and approaches and conduct simulated cyber-attacks to test the strengths and weaknesses of the existing security systems. 

As rightly said by Najla Al Mazyad from Saudi Arabia’s technology giant STC’s elite Cybersecurity team: what separates a penetration tester from an  attacker  is 'permission'. 

The Importance of Penetration Testing 

The accelerating pace of digital transformation to run business operations and processes expose us to new technology risks. To that end, penetration tests become essential to help organizations: 

• Identify and fix vulnerabilities and bugs that hackers can exploit for a complete network takeover or bypassing security mechanisms to access administrative features in an application. 
• Drive compliance with regulatory standards while identifying vulnerabilities that could impact business operations, customers, or assets. The payments card industry, for example, mandates organizations to follow the PCI-DSS regulations for annual and ongoing penetration testing. The tests allow enterprises to mitigate the real risks associated with the network. 
• Protect the confidentiality of data, and maintain revenue and goodwill by keeping systems secure from external attacks and vulnerabilities. 
• Save remediation costs, reduce network downtime, and ensure business continuity by keeping the application, system, and network secure by identifying high-risk exploitable vulnerabilities in the system. 
• Verify security configurations to ensure a robust security posture. 
• Deliver ways to enable in-house security personnel to recognize and respond to cyber-attack types properly. 
• Fix vulnerabilities and gaps before they go into the production stage and save time and money. 
• Identify vulnerabilities in new IT networks during new acquisitions, merging of systems, and transfer of data and create a road map of improvements with clear timelines. 

How to Get Penetration Testing Right – Best Practices 

Penetration tests are most effective when performed by an experienced external service or contractor, or an internal team with a grey box or black box approach to the overall testing cycle. Sometimes, External resources with little knowledge of internal systems ensure objectivity while exposing vulnerable areas missed by internal developers or testing teams. 

Here are some of the best practices to follow to get penetration testing right: 

Clearly Define the Scope and Budget 

While organizations might want to test the entire environment, the costs might seem prohibitive. As such, identifying high-priority and low-priority areas that need penetration testing is the right approach. 

High-priority areas are where the biggest vulnerabilities live. Testers identify the highest risk points in the application code, configuration files, and operating systems, especially in software development projects. Low-code or no-code applications for internal business operations fall under the lower priority area. 

Take a Deep Dive into Data Sources 

Since data is an organization's biggest asset (including financial, transactional, and customer data sources), it enables full-scale and comprehensive penetration testing. This is important to meet industry and security regulations, especially for retail, financial, government, and healthcare industries. 

However, along with the data sources, it is also essential to test the software that connects to them and its supporting infrastructure. 

Consider Remote Resources 

Implementation and Execution of Remote resources, be it employees, automation systems, or resources that have remote access, needs to be supplemented by penetration testing to factor each remote endpoint into the test strategy. The tests identify the exposure to external attacks by finding and assessing your publicly accessible assets. 

Following this, it is important to adhere to a robust penetration testing methodology and standards such as Penetration Testing Execution Standard (PTES), Payment Card Industry Data Security Standard (PCI-DSS), National Institute of Standards and Technology (NIST) Special Publication 800-115, etc. 

It is also essential to prepare for the test, assess which tests the hosting or cloud provider allows, and get proper authorizations to conduct these. Moreover, it's vital to identify the team members who will review the test report, fix issues, and schedule the patching activities after testing is completed and the results have been reviewed. 

Here, establishing clear communication protocols between the organization, the test and development team, and the penetration testing team is critical. Along those lines, regular meetings to monitor progress for timely information exchange are also important considerations. 

Further, automating tests is essential for penetration testing to increase the testing footprint. However, automation on this would need highly intelligent AI and ML, since it needs human expertise to creatively exploit the system. Manually reviewing the results of automated scans can always help implement a robust and successful penetration testing plan. 

Why are the various steps involved in Penetration Testing? 

Reconnaissance, scanning, vulnerability assessment, exploitation, and reporting are the five main stages of penetration testing. 

• Reconnaissance: This stage is about gathering all the information about the network topology, operating systems, applications, and user accounts to help the tester plan an effective attack strategy. Reconnaissance can be categorized as either active or passive, depending on what methods are used to gather information. 
• Scanning: This evaluates open ports and checks network traffic on the target system. 
• Vulnerability assessment: This stage uses all the data gathered in the reconnaissance and scanning phases to identify potential vulnerabilities and determine the risk associated with them. 
• Exploitation: This is the most delicate penetration testing phase as it accesses the target system and requires bypassing security restrictions. The testers try to safely exploit the identified vulnerabilities simulating real-world attacks, while ensuring that the system isn't compromised or damaged.  
• Reporting: This stage documents the findings of the penetration tests. Clearly documenting vulnerabilities and putting them into context allows the organization to remediate security risks faster and with greater confidence. 

Why Do Enterprises Need Penetration Testing? 

Considering how reliant businesses have become on technology, continuous, proactive penetration testing has become strategically important. It's a proactive cybersecurity measure involving consistent, self-initiated improvements based on the reports generated by the tests. It successfully minimizes the number of retroactive upgrades and maximizes organizational security. 

The consequences of a  cybersecurity attack  are now more severe than ever before and can lead to substantial losses. With technology evolving continuously, organizations need to protect themselves and their assets from attacks more confidently, especially because of the growing sophistication of cyberattacks.  

Identifying and fixing vulnerabilities improves the security of organizational systems and protects their data from hackers. Using skilled ethical hackers, organizations can effectively identify, update and replace the parts of their system that are susceptible to modern hacking techniques before they prove detrimental.