Looking to pen test your website? Follow this five-step plan for a successful exercise:
- Prepare your defenses to ensure simulated attacks provide the deepest insights
- Negotiate with the testing team to establish scope, targets, and starting positions
- Gather information on your website and web assets to facilitate simulated attacks
- Conduct the agreed-upon penetration testing techniques and escalate, as needed
- Report on findings and use results to optimize defenses, training, and compliance
Step 1: Prepare for Simulated Attacks
Penetration testing is an advanced cybersecurity tactic that operationalizes attackers’ offenses to bolster your defenses. To get the most out of it, your defenses should already be as effective as they can be. In the run-up to a pen testing exercise, you should optimize patch management, threat and vulnerability scanning, firewalls and web filters, and other baseline security hygiene.
Then, you should also optimize defenses on specific parts of your web presence you’ll target, per Step 2 below. For example, if you know you’ll be running pen tests on your web apps, you should first conduct other forms of security testing for web applications to ensure that any controls you’ve installed are functioning as protected. The idea for a pen test is to study whether, when they are working as best they can, they are able to keep you protected.
Step 2: Negotiate Scope and Starting Positions
Next, you’ll need to make some decisions together with the penetration testing team, like whether you’ll pentest websites online or offline, which specific parts you’re testing, and how.
On one level, this means determining the specific virtual locations that the pen testers will target. You’ll need to decide if they’re focusing on your entire web presence, a specific set of pages or web apps, databases, and backend assets connected to the website—or all of them.
On another level, you need to decide whether you’re testing externally or internally:
- External tests begin from a position unknown to the organization, and the simulated attackers likewise operate with no special foreknowledge of the organization’s systems.
- Internal tests begin from within the organization, and the simulated attackers operate on some pre-negotiated amount of foreknowledge of or access to organizational systems.
These decisions will allow testers to begin reconnaissance and simulated attack preparation.
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Step 3: Gather Information about Testing Targets
After organizational preparation and negotiation with the pen test team, the simulated attackers need to do their own prep. In this stage, the testers conduct reconnaissance to identify specific vulnerabilities in your web assets that they’ll attempt to exploit. The specific weaknesses they look for will vary both based on the kind of attack (external or internal) and its intended targets.
For example, in more general pen testing targeting your website, testers may prioritize recon on your web hosting and network infrastructure. But in web application penetration testing, they may also dig into the specific devices from which staff are accessing the web apps to identify weak points, such as oversights related to personal devices or unaccounted-for networks.
Step 4: Conduct and Escalate Pen Test Exercises
In this stage, you’ll bring your website penetration testing online. Testers will initiate their attack sequences, with differences in tactics depending on if the test is internal or external in nature:
- In an external test, testers will attempt to breach through the perimeter defenses and take up a position within your website’s control systems and/or network assets that are connected to them. Tactics include cross-site scripting, network scanning, and more.
- In an internal test, testers are already within your system or have insider intelligence about it. Their goal is to seize central control of websites and web apps by exploiting access restrictions and network connections, employing social engineering, and more.
Additionally, if you’ve elected to conduct hybrid testing using elements of both, your testers may begin externally and then continue on internally once they’ve breached your website or systems.
And, in any case, attackers will continue to escalate tactics until an end condition is met. They may conclude once they’ve breached (external), once they’ve seized complete control (internal or hybrid), or once they’ve been caught and/or stopped by your organizational defenses (any).
Step 5: Report and Remediate Identified Weaknesses
Even after testers have completed their simulated attacks, the pen testing exercise is far from over. The final and arguably most important step involves reporting on what happened and using the intelligence generated to prevent a similar real-world attack from happening. That means optimizing your threat and vulnerability management and incident management suites.
The same threat intelligence should also inform ongoing staff security awareness training.
Another way that you can operationalize pen test intelligence is for regulatory compliance. If you’re subject to a regulation like PCI DSS, which explicitly requires pen testing, this will be a standard part of your compliance management. And if you’re subject to a regulation like HIPAA, which mandates vulnerability testing, pen tests are one of the best ways to satisfy its rules.
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Pen testing your website helps ensure that real-world attackers can’t seize control of it and cause harm to your organization. It’s an especially effective tactic when you prepare for it, negotiate the terms carefully, allow testers space for recon and simulation, and then reflect.
At RSI Security, we believe that discipline upfront—testing your systems in the most intensive way possible—is the best way to secure greater freedom down the road. We’ve conducted pen tests on websites, web apps, and overall cybersecurity deployments for countless organizations.
To learn more about our website penetration testing services, contact RSI Security today!