Internal Pen Test Checklist | Network Penetration Testing

Every year, leaders sit in budget and planning meetings and ask the same questions:
What did we spend? What did we get for it? Where are we exposed?

One question rarely makes it onto the slide deck, even though regulators, auditors, and cyber insurers are all looking for the answer:

When was the last time we ran a real penetration test on our internal network?

If your answer is, “I think we did one a few years ago,” you’re not alone. But, you’re also betting your business on guesswork.

This article will show you why an annual internal penetration test is now the minimum standard, what a good test should deliver, and how to use the results to make strategic cybersecurity decisions.

Pen Test vs Vulnerability Scan: Why The Difference Matters

A vulnerability scan is an automated sweep. It looks for known issues, missing patches, and misconfigurations and then hands you a list.

A penetration test asks a different question: Given those weaknesses, what could an attacker actually do?

Good penetration testing uses automation in addition to human problem solving. Tools surface likely issues, and then experienced engineers chain those issues together and map out realistic attack paths through your environment.

An extensive pen test results in a clear, honest picture of how a hacker could advance from “first foothold” to “serious incident” inside your world.

Why An Annual Pen Test Matters More Than Ever

Your environment today doesn’t look like it did twelve months ago. Especially if you work in agriculture or manufacturing, you’ve probably:

• Brought new plants, locations, or remote sites online
• Connected more operational technology to your business network
• Added seasonal staff or contractors who needed quick access
• Rushed changes to keep up with supply chain or market shifts

Each change creates opportunities for misconfigurations and forgotten systems. Even with a strong IT team, it’s impossible to manually track every permission, integration, and exception.

An annual internal penetration test brings that chaos into focus. It helps you:

• Verify that your controls actually work in the real world instead of just on paper
• Show due diligence to boards, customers, auditors, and cyber insurers
• Prioritize limited security budget by focusing on weaknesses that attackers can really use, not just long lists of theoretical risk

When you test every year and track your remediation, you build a story of progress and steadily tighten the bolts on the things that matter most.

Where Pen Tests Usually Go Wrong

Pen tests can be a waste of time and money when they’re:

• Scoped generically, with no connection to how your business actually runs
• Driven entirely by tools, with little human analysis
• Reported as a seventy-page export that no one has time to read

That type of work checks a box, but it doesn’t make your team’s lives better.

An effective pen test should save you time by telling you what not to worry about. In other words, it should reduce uncertainty, not create more of it.

Watch out for these red flags that a vendor is selling you a report instead of insight:

• They can’t explain the test scope without heavy jargon
• They focus on the size of the report, not the clarity of the findings
• They can’t connect technical issues to business impact in plain language
• There isn’t a plan for a guided review or follow-up

What A High-Value Internal Pen Test Should Deliver

When Koltiv runs an internal penetration test, our engineers act as curious and responsible attackers inside your network. The areas we typically uncover issues are:

• Identity and access. Weak passwords, passwords stored in plain text, overly privileged accounts, and ways to escalate from a basic user to domain admin.
• Insecure or obsolete protocols. Default configurations running at a domain level that could be leveraged for MitM attacks or account takeover.
• Legacy and “forgotten” systems. Old Windows or Linux servers that still hold critical data and have not seen a patch in years.
• File shares and application servers. Places where sensitive information is available far more widely than intended.
• Everyday devices. Printers, cameras, and other embedded devices that ship with default credentials or poor security.
• Pathways across environments. Ways attackers could pivot between your corporate network, production environments, and cloud services.
• The human factor. Email phishing to test current e-mail security and end-user policy and procedures.

More important than the list itself is the story it tells. A high-value pen test report should give you:

• A clear narrative of how an attacker could move through your environment
• A short list of issues that truly move the risk needle with recommendations and remediation advice
• A high-level executive summary written so non-technical leaders can understand them
• Concrete remediation steps your internal or external IT team can actually take

If you finish the review and feel more focused instead of overwhelmed, the test did its job.

How A "Temporary" Fix Became A Production Risk

In a recent internal test for a manufacturing client, our engineers discovered an older file server sitting under someone’s desk. It held archived engineering drawings and had not been patched in years. Through that server, they were able to:

1. Access sensitive design data
2. Use an unpatched vulnerability to elevate privileges
3. Move laterally to systems that tied directly into production scheduling

No one had intentionally left that door open. The server was “temporary,” then became permanent, then faded into the background as people changed roles. 

The test gave leadership a concrete story. They saw how one forgotten asset could lead to intellectual property theft and production disruption. Together, we helped them retire that system, move its data into a managed environment, and close off the entire attack path.

One thorough test, one old server, and one huge risk removed.

A Simple 12-Month Pen Test Self-Check

You don’t need a security certification to know if you are behind. Start with these questions:

1. When was our last internal penetration test completed?
2. What has materially changed in our environment since then? (New sites, major apps, cloud services, or OT connectivity).
3. Did we fully address the critical findings from that last test?
4. Can we show auditors or insurers clear evidence of that remediation?
5. If we were breached tomorrow, could we look our customers and board in the eye and say we tested our defenses in the last year?

If you can’t answer most of those confidently, you’re overdue.

How To Get The Most From Your Next Pen Test

To turn a pen test from a report into tangible solutions, treat it like a short project, not a one-off event.

Before the test

• Identify a small group of stakeholders from IT, security, and the business
• Decide which locations, systems, and data are most important to protect
• Clarify rules of engagement, including hours, notification thresholds, and any systems that are too fragile for active testing
• Gather network diagrams and any existing policies that the testers should understand

During the test

• Provide a clear technical contact who can answer questions quickly
• Agree on how critical issues will be communicated if something serious is discovered mid-test
• Encourage your internal team to treat the testers as partners, not adversaries

After the test

• Schedule a review session where both technical staff and leadership are present
• Prioritize findings by business impact, not just technical severity
• Assign owners and timelines for remediation
• Decide whether certain fixes should be tracked in your normal project queue, your ticketing system, or both
• Set a tentative date for your next annual test so the cycle continues

What To Look For In A Pen Testing Partner

When you evaluate providers, ask questions that reveal how they work:

• How will you tailor the test to our industry, environment, and risk tolerance?
• How do you blend automated tools with human analysis?
• What does your report look like and who is it written for?
• How will you help our team prioritize and act on the findings?
• Can you support an annual testing cadence so we can show progress over time?

You’re looking for a guide who respects that you know your business and is willing to stand behind their work, not just a vendor who runs tools and walks away.

How Koltiv Helps You Stop Guessing

Koltiv is a Midwest-based technology partner that works primarily with growth-minded agriculture and manufacturing organizations. Our internal penetration testing approach is built to fit that world.

We start with how you operate. We learn where your most important systems live, how your plants and offices connect, and which risks keep leadership up at night.

We test like a determined attacker, then report like a trusted advisor. Our engineers use proven tools and creative thinking to uncover real attack paths, then translate them into plain language and a prioritized punch list.

We stay with you through remediation. We review findings with your team, answer hard questions, and help you plan follow-up, including your next annual test.

The goal is simple: Give you a clear, honest view of your internal risk so that you can make better decisions for your people, your customers, and your future.

Ready To Put A Date On The Calendar?

If your last internal penetration test is more than a year old (or you can’t remember when it happened), now is the time to act.

In a short conversation, we can confirm:

• When you last tested
• What has changed since then
• The right scope and timing for your next internal pen test

Schedule your internal penetration test with Koltiv and step into the new year with fewer unknowns and a clear plan to strengthen your defenses.