The threat of cyberattacks is growing both in complexity and frequency, prompting many organizations to adopt a preventive approach to cyberdefense. Penetration testing provides your security personnel deep analytics on how attackers may target your systems, which empowers you to build commensurate protections. With the most advanced penetration testing techniques, you can optimize your security proactively rather than reactively.
Advanced Penetration Testing 101: Top Tactics
In a nutshell, all penetration testing involves using offense to strategize defensive. The target organization hires an individual or team of testers that simulate an attack on your systems to understand, prepare for, and prevent—or swiftly recover from—a real attack in the future.
The greatest strength of penetration testing lies in its wide applicability across industries and cybersecurity architectures. Four of the most complex, impactful approaches to testing are:
- Focusing on networks specifically
- Testing web applications independently
- Emulating social engineering attacks
- Conducting tests on physical assets
Beyond these more advanced penetration testing strategies, more fundamental tactics in penetration testing can also provide powerful insights. We’ll review these, in turn, below.
#1: Network-Focused Pen-testing
Penetration tests can be conducted on an organization’s overall cybersecurity landscape, or they can be trained on any specific element therein. Network infrastructure and architecture are some of the most crucial elements of your entire security system. So, pen-testing your networks specifically can identify critical vulnerabilities latent within your various:
- Physical and virtual network and connectivity components
- Systems and accounts connected to these networks
- Individual endpoints connected to these networks
Network pen-testing can use a mix of black-box and white-box testing strategies (see below) to uncover exploitable flaws in your network configuration, firewalls, authentication protocols, and endpoints (e.g., printers, routers, workstations). It’s a roundabout way to cover all parts of your IT and security landscape through the vantage point of its main connective tissues.
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Wireless pen-testing
Some of the most critical kinds of networks to pen-test are wireless ones. Attackers can easily compromise your systems by taking advantage of vulnerable WiFi infrastructures, such as unsecured routers or access points. This usually begins with a discovery process.
Wireless pen-testing attempts to perform the same discovery tests on your organization’s wireless networks and all devices connected to them. Security personnel conducting the tests start with physical reconnaissance to identify the extent to which your WiFi networks are accessible in and around the premises. Then, they use techniques like packet capture or de-authenticating to identify wireless networks and exploit vulnerabilities, respectively.
#2: Web application pen-testing
With the widespread adoption of web applications by today’s organizations comes a new entryway for hackers to gain access to sensitive data. Therefore, pen-testing focused on web apps should demand a significant chunk of your bandwidth and resources to find and rectify vulnerabilities. Web application pen-testing usually tests for common issues such as:
- Security Misconfigurations
- Password Cracking
- SQL Injection
- Broken authentication and session management
- Cross-Site Request Forgery
- Caching Servers Attacks
Securing web apps checks against user error, internally and across connected third parties.
#3: Social engineering pen-testing
One of the most easily exploitable components of any organization is its personnel. Social engineering attacks constitute almost 98% of all cyberattacks. Cybercriminals can easily bait users into compromising sensitive information by posing as a superior or trusted authority.
Hence the essential need for penetration tests simulating social engineering scams.
These pen-tests should take multiple forms, mirroring the often multi-faceted nature of social engineering scams. Assess your staff’s ability to recognize, appropriately respond to, and then report common cyberattacks like phishing, USB drops, tailgating, impersonation.
#4: Physical pen-testing
Finally, hackers will often try to gain access to sensitive virtual assets via physical exploits. This usually includes bypassing physical security controls like cameras, barriers, locks, alarms, and security guards. If they gain entry to secure buildings, server rooms, or other security systems, they can easily execute deadly cyberattacks from within.
Your pen-testing plan should include periodic physical pen-testing. In these tests, personnel should attempt to gain illegitimate areas and assess the relative effectiveness of physical or proximal controls. Ideally, these should branch out into multi-layered attacks on software.
Other Considerations for Penetration Testing
Penetration testing assesses an organization’s security infrastructure by “penetrating” its exterior with simulated attacks or capitalizing on that entry with targeted internal movements.
By exploiting an organization’s security systems and demonstrating the potential damage that can be caused, pen-testing can help security professionals improve their defenses and adequately prepare against real-world cyberattacks. Other benefits of pen-testing include:
- Revealing hidden or obscure risks of a successful security breach
- Assessing your cyberdefense readiness and ability to respond to threats
- Ensuring your business operations are protected against unexpected downtime
- Providing unbiased, objective evaluation of your cybersecurity systems
- Maintaining compliance with regulatory standards like PCI or ISO
Penetration tests assess hardware and software, but also the security awareness of your employees and their preparedness against physical and social engineering attacks. The tests are often outsourced to security services providers for deep, unbiased insights.
Pen-testing is usually conducted in a structured manner by following a set of phases, from information gathering and threat modeling to vulnerability exploitation and reporting. No two tests are the same, but there are three common formats that most fall into. There are also some widely-followed standards like the Penetration Testing Execution Standard (PTES) that provide baseline expectations from pen-testing that organizations can leverage—see below.
Three Ways To Conduct a Pen-test
Penetration testing can be used to simulate both external and internal threats to an organization’s security systems. Depending on the amount of information available to the personnel conducting the tests, pen-testing can be classified into three primary types:
- Black-box testing – A “black-box” or external test begins with the tester assuming little to no information about the organization’s security infrastructure, web apps, or source code. Hence, a black-box test simulates an attack from an external hacker.
- White-box testing – A “white-box” or internal test begins with the tester assuming some pre-negotiated amount of intelligence concerning the organization’s security environment or assets. This simulates an attack “from within,” such as from a disgruntled current or former employee that already has access to your systems.
- Gray-box testing – A “gray-box” or hybrid test typically involves elements of both prior types. It may begin as an external pen-test, then continue internally. Or, it may simulate a multi-pronged or longitudinal attack, focusing on long-term impacts.
Organizations have much to learn from each of these three methods due to their unique focus on attack vectors and their intensity and duration. Many organizations find the most beneficial approach is conducting pen-tests spanning all kinds and at regular intervals.
PTES guidelines for pen-testing
The Penetration Testing Execution Standard (PTES) is a set of guidelines and procedures that organizations can use to structure their pen-testing efforts. In early 2009, a group of cybersecurity experts got together to form the PTES. In practice, they put an end to the uncertainty that characterized much early pen-testing due to an absence of quality control.
The objective of PTES is to provide a set of baseline expectations that organizations should follow, whether they’re pen-testing themselves or taking help from outside experts. These norms are structured around seven successive stages of any pen-testing process:
- Pre-engagement Interactions
- Intelligence Gathering
- Threat Modeling
- Vulnerability Analysis
- Exploitation
- Post Exploitation
- Reporting
These norms aren’t rigid or comprehensive, and, as such, they do not cover every testing scenario. Instead,they aim to provide minimum necessary requirements each pen-test should have.
Get Pen-tested with RSI Security
Penetration testing, if done properly, requires best-in-class expertise and robust processes to yield the best results. RSI Security’s penetration testing services can help you evaluate your hardware, networks, web applications, and cloud environment with root cause analysis and minimal business disruption.
Contact RSI Security today to leverage the cutting-edge techniques of advanced penetration testing and rethink your overall cyberdefenses.