Stop Waiting to Schedule Your Pen Test

A compliance manager called me a few weeks ago. She was three weeks into a new job and had just learned a pen test report was due by the end of the quarter. She didn't know when the last test ran, what had changed since, or who had to sign off before testing could start. 

She is not alone. I see this all the time. 

More and more, the person responsible for scheduling a pen test is not in security or IT. It may be someone in product, procurement, or compliance who inherited the task alongside a long list of other work to accomplish. They know a deadline exists, but they don't have visibility into every step that has to happen before it. 

Still, timing is the single biggest aspect that can cause challenges during a pen test, and most of it is avoidable if you get in front of it early. 

Best Practices for an Effective Penetration Test 

Start Your Pen Test with The Basic Facts 

If you're new to the role, find out when the last pen test happened and what the scope covered. Ask whether the requirement is annual or quarterly, because it's not the same across every organization, and it can change over time. Requirements, scope, and frequency changes. What worked for your audit two years ago might not be enough now. 

Know Your Pen Test Deadline and Every Date That Matters In Between

Your ATO date, ROC date, and SOC review window are fixed dates and there's not much flexibility with them. But they are rarely the only dates that matter most. A big client may be waiting for a clean report before they'll sign a contract. Your dev team's release schedule might determine when the environment is even testable. Some teams also have blackout periods where testing isn't allowed at all. 

Treat The Pen Test Itself as One piece of The Job 

The actual testing window gets most of the attention, but it's only one link in a longer chain: 

Legal alone can eat weeks redlining a contract back and forth. And if you need sign-off from procurement, security, and the dev team before you can even kick things off, that's real time on the calendar, not paperwork you can skip. 

How Long Does a Penetration Test Take? 

Say the requirement is a clean report by September 30th. Here's roughly what the path can look like, working backwards: 

That's a six-week testing and remediation cycle sitting on top of about four months of planning, contracting, and prep work. And that's a fairly clean scenario. Bigger tests take longer. Some organizations need 60 or 90 days just for remediation. Factor in holidays, PTO, or a busy pen test provider that needs more lead time to staff the right people, and the timeline stretches even further. 

Why Early Planning Results in a Smoother Pen Test 

A pen test crammed into the last two weeks of a quarter is like trying to renovate a kitchen the week before hosting Thanksgiving. Everything gets rushed and corners get cut. No one is happy with the results. 

Early planning helps in other ways too. You can bundle the test with other projects instead of running everything separately. You can make sure your environment is actually ready before the tester shows up, instead of burning testing days on access issues and broken accounts. You give remediation the real time it requires instead of a last-minute scramble. 

Sometimes last-minute planning and testing are inevitable. A new requirement might drop suddenly. A client may move up a deadline. Unavoidable things happen. But most of the time, the pressure is self-inflicted, and it doesn't have to be. Either way, the goal is to reduce the damage by getting the facts, lining up the dates, and making the next move as early as you can. 

When was your last pen test? If you don't know the answer off the top of your head, that's the first thing to go find out. Bonus tip: if you don’t want to scramble to do this next year, Schellman offers multi-year agreements, and we’ll be there to make sure your next assessment (or consolidated audit with PCI, SOC, FedRAMP, HIPAA, etc.) runs smoothly and on time. Contact us today or fill in our Penetration Testing Scoping Questionnaire to learn more about how to better plan for your next penetration test.