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Pentesting Frequency: 5 Key Questions to Get You on the Right Schedule

In this modern age, with the ever-growing, permanent presence of online technology in every facet of our lives, the risk of hacking — and the number of vulnerable assets accessible to hackers — increases in tandem with growth. And these breaches are proving more costly to companies every year. IBM reported last year that data breaches were now costing companies an average of $4.24 million per incident, a 10 percent increase in costs from the year prior. 

Companies are keenly aware of the risks involved in a breach. Organizations want their apps, sites, and systems to be as protected as possible. And if you’re a security professional, it’s your job to make sure that happens. Of course, in an ideal world, you and your team would have all of the personnel, tools, and funds needed to provide round-the-clock checks and telemetry. But your reality is probably far from ideal. Between the never-ending talent shortage for cybersecurity workers and a recession that is squeezing businesses’ budgets, you will likely need to find the best possible balance between your organization’s needs and your resources.

PlexTrac empowers the efficient collaboration of your entire security team, saving you precious time and resources in the fight against adversaries. Click here to learn more about PlexTrac.

How Often Should You Perform a Pentest?

There are plenty of small, secondary steps your team can take to reduce the risk of a breach — vulnerability scans, education campaigns, etc. — but the best and most successful risk-reducing practice is full-on pentesting, where the results of the pentest drive mitigation activities. The research, testing, escalation, and reporting involved in a thorough pentest can help ensure that any weaknesses in your organization’s (or client’s, if you are part of a security service provider) assets are detected and addressed before they become a problem.

With that in mind, how often should you perform pentests? The short answer: probably more often than you think. According to Fortra’s 2022 Pentesting Report, 42 percent of cybersecurity professionals run pentests 1-2 times per year (per client). But most experts, and our pros here at PlexTrac, believe that this is not sufficient in most cases.

How Much Is Enough?

Determining “enough” heavily depends on the specific needs of your organization or clients and their assets, but if security is a priority, and if you have sufficient hackable assets, many security experts argue that a company should perform pentests at least once per week, either on a portion of a system or the entire asset.

“Are you crazy?!” you may be asking.

We get it. This may sound like an impossible goal, requiring resources that you can’t spare and time you don’t have. But with the help of our five key questions, you can analyze your organization’s or client’s assets, determine the needs, and create a pentesting routine that streamlines most of the process and provides the protection everyone truly needs.

The Optimal Pentesting Frequency: 5 Key Questions to Ask

So, how do you decide the pentesting needs of your organization or client? It’s a question that deserves careful thought and planning. Fail to test often enough, and you are left vulnerable to serious threats. Test too often, and your resources may be stretched to the point that your team is cutting corners and missing vulnerabilities in the rush to meet demanding deadlines. Here are some crucial questions to ask that will help you determine an optimal routine.

What is the Scope of the Pentest?

In order to start this process right, it’s best to determine the complete scope of the pentest. Asking this question lays the foundation for all of the other plans you make for scheduling. From the perspective of a service provider, unless the client is new, your team already has a good idea of the scope of the pentesting project, and how long a standard pentest on the assets should take. From the perspective of an internal team, you may need to work with your consultants if you are outsourcing your penetration testing to get a better sense of what frequency of testing is needed.

Scope includes more than just the size and number of assets. Throughout this process, you’ll need to take into consideration the program’s needs and preferences.

Even if your team feels that a complete asset discovery scan every week is necessary, if budget limitations are in play, or you need to avoid certain assets to prevent business interruptions, you may need to adjust your scope or work within the limitations applied by the business..

What Scale of Tests Do You Want To Run?

After determining the scope of the project, you can next decide the optimal scale of testing. Analyzing the types of assets that your team will be scanning, you will be able to determine which areas will need a full penetration test weekly, and which need less frequent or less intensive testing. As you discover the answers to the previous questions, you also need to determine the level of effort or necessity for manual testing.  While you want to ensure that no assets are left vulnerable, asking this question could save you unnecessary time and labor down the road. 

For internal teams, this is also a good time to decide what testing needs to be outsourced and what you might be able to handle internally to ensure you can achieve your optimal frequency and scale within the constraints. 

What is the Budget?

The  budget is a major constraint that will play a role in determining how you plan your pentesting or that of your clients. If they cannot (or do not) offer enough of a budget to cover the services you think are necessary, then it is up to you and your team to get creative, using the information you’ve gathered with the preceding questions to plan the best job possible within the limitations you’ve been given. 

What Resources Do You Want to Use?

With the scope, scale, and budget for your pentesting program now established, you can move on to determine what are the best resources for the job. 

Pentesting and Automated Vuln Scan Tools

Now that you’ve committed to a more effective pentesting frequency for your organization or clients, you need to determine what tools you need. Fortunately, there are a wide array of tools available to help every step of the process: project process, ticketing, information gathering, vulnerability scanning, pentesting, reporting, and remediation. The right tools will streamline your work, ease communications, and shorten your timeline.

Personnel

The tools you select are only as effective as the experienced professionals wielding them. Your team is your greatest asset, since they are the ones who will ultimately interpret the findings of the penetration test and help your organization or client correct the uncovered weaknesses. However, you should make sure that you are using this crucial resource carefully — your personnel have finite time and energy, so everyone would be best served if you apply your personnel’s labor efficiently. Where are your senior pentesters most needed? What tasks can be handled by the new hires? Distribute your labor effectively, and you can automatically improve the entire pentesting process.

Client and Administrative Goodwill

From the service provider perspective, keep in mind that a pentesting project will occasionally go south — more issues will be uncovered, you might lose some staff, a project unexpectedly goes over budget or needs more time to wrap up. In these times, you need to have a good idea of how much flexibility your clients and your bosses can offer you. If you have good rapport with your client, you might be able to reach out right away to ask for an extended deadline. But not every client can afford to offer that kind of flexibility, so knowing your options beforehand can help you determine how to most efficiently troubleshoot down the road. 

How Often are the Assets Modified?

The assets you test don’t remain in a static state, and with every change they undergo, more potential vulnerabilities are created. These changes, prompted by an organization’s internal operations or by a service provider’s suggested remediations, must be included in the pentesting plan. The retesting necessary after these changes might not need to be as thorough as a full pentest (especially if you know exactly what changes occurred), but will still require time and labor, so it’s best to adjust expectations and resources for this extra testing before the pentesting process begins.

The Best Pentesting Schedule Needs the Best Tools

A pentesting practice doesn’t become efficient overnight. And in addition to hiring the right people and developing the right processes, you also need to equip your team with the best tools for the job. Enter PlexTrac, The Premier Cybersecurity Reporting and Collaboration Platform.

With PlexTrac, your team will be able to work more efficiently and effectively in the fight against persistent threats. Book a demo of PlexTrac TODAY to learn how you can crush your pentesting goals with our platform.

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