The Pen Test You Keep Postponing: When to Schedule (and When Not To)

TL;DR: How do you know when to schedule a pen test? Well, most organizations push them to Q4 because it feels like a “year-end” task, but then they’re scrambling during the busiest, highest-stakes quarter of the year. The truth is that pen testing should be driven by both events and the calendar, and we strongly recommend all organizations practice continuous and intentional security monitoring year-round. The key difference is finding and responding to the gaps before they matter, rather than putting out a fire after it’s already burning.

The Q4 Scramble Nobody Plans For

Ask any CEO,

“What’s the busiest time of year for the leadership team, if you had to pick one?”

Many will confidently respond: Q4. It has a way of sneaking up on everyone.

And we get it. No one plans to scramble; it just kind of happens. The tasks you said were a “future problem to worry about?” Well, they’re here now. There’s no more running from those last projects, “use it or lose it” funding is about to hit their deadlines, and annual compliance requirements are knocking at the front door, loudly.

The same procrastination often gets applied to security. Too often, Penetration Testing, also known as pen tests or pen testing, gets put on the backburner. And when it does, your IT team loses the chance to find and fix gaps proactively, the right way.

What Is a Pen Test?

Penetration testing (or pen testing) is a security exercise where a qualified (and ideally, certified) expert attempts to ethically hack into your computer system, network, or application with the goal of finding and safely exploiting vulnerabilities before a real threat does. What’s found can then be addressed safely and confidently.

“Think of a penetration test as a fire drill for cybersecurity. We safely test your defenses, find the gaps, and help you fix them before a real attacker comes knocking.”

– Lynn Soeth, High Point Networks Security and Sales Engineering Service Manager

So, When Should You Schedule a Pen Test?

Of course, it depends. It depends on your business cycle and what you’re aiming to accomplish.

If your company is making major changes to the network, deploying new applications or software, handling M&A integrations, or even migrating to the cloud, you’ll want a pen test before anything goes live. Security gaps occur over time even for the best IT teams. In cases of mergers and acquisitions, it’s not uncommon to inherit that other company’s unattended risks. You’ll want to know where those gaps lie so they can be addressed, and you can sleep better at night.

Another clear time to schedule a pen test is after a security incident. When one occurs—yes, it’s often a matter of when, not if—you’ll want to confirm that the issue has been fully resolved, and no other gaps exist.

And of course, if your company is under CMMC, NIST CSF, PCI DSS, HIPAA, SOC 2, or similar compliance frameworks, ensure you schedule with enough buffer time to remediate the findings well before the audit, not right before it.

Is There a Time to Avoid Pen Tests?

There certainly can be! And that’s unique to your business and industry.

Know you have a specific period that’s especially busy for your business? Avoid that time to ensure nothing is disrupted (pen tests won’t typically disrupt operations, but we like to plan for every scenario).

For education, that might be during school enrollment. Agriculture? Perhaps it’s peak planting and harvest when stress can be high. Retail? Avoid any big annual sales or holiday shopping surges. Tax firm? Avoid Q1. You get the picture!

How Often Should You Run a Pen Test?

Once per year should be the absolute baseline for standard compliance. For today’s businesses, though, we strongly recommend a more regular cadence.

High-risk, high-regulatory industries like finance, healthcare, and e-commerce should consider quarterly testing to proactively manage threats. In these industries, sensitive data is processed and stored on a regular basis. Those proactive efforts are vital to the security of your people’s data and business’s uptime.

Larger enterprises with complex infrastructures can also benefit from more frequent testing. For environments with a larger attack surface, or those that undergo frequent infrastructure changes, testing once a year — or even twice a year — often isn’t enough to keep pace with threats.

For mid-sized organizations and small businesses with moderate to low risk, less complexity, and fewer system changes, bi-annual pen testing may suffice. Even so, we recommend complementing the pen tests with other security measures.

The Importance of Continuous Security in Layers

A pen test is a snapshot. It tells you where your defenses stand on the day it’s run —valuable, but a single frame, not the whole picture. The environment you tested in July isn’t the one you’re running in October. New users, new applications, new vulnerabilities, and new attacker tactics all show up in between.

That’s why we treat pen testing as one layer of a continuous strategy, not the strategy itself. A point-in-time test confirms your defenses are working. The layers around it are what keep them working between tests:

• Continuous monitoring to catch anomalies as they happen, not months later
• Regular patching and updates to close known gaps before someone else finds them
• Endpoint and identity protection that holds up as your environment changes
• Ongoing education so your people stay your strongest layer, not your weakest

Think of the pen test as the checkup and continuous security as the daily habits that keep you healthy between visits. One tells you where you stand. The other is what keeps you standing.

Not Sure Where to Start? We’re Happy to Help.

Proactive steps include knowing your audit cycle, getting on the books before everyone else does, and giving your team enough runway to act on what they find. And the businesses that avoid that mad rush aren’t doing anything groundbreaking. They’re just starting the conversations earlier.

Not sure where your business stands heading into Q4? We put together a quick self-assessment to help you find out.

→ Download the checklist 📋

This is what we do, and we love to do it. Our mission is to keep businesses like yours safe, happy, and growing. Our cyber team proactively works with customers to plan ahead, so that cybersecurity fits their calendars, instead of owning it.

Talk to a cybersecurity expert today.

Because a conversation now is so much easier than a scramble later.