Pentesting is Transforming: 8 Steps to a Successful Pentest Operation in 2025!
Pentesting isn’t what it used to be, folks. Gone are the days of single checklist exercises and surface-level scans. In 2025, we’re transforming the way we think about pentesting—making it a dynamic, intelligence-driven, and collaborative practice that does more than just “find vulnerabilities.” We’re taking a proactive, adversary-informed approach that considers not only what’s in your environment but how attackers are thinking about exploiting it.
Continuity in penetration testing is often overlooked, yet it’s a crucial element for maintaining a robust security posture. Bug bounty hunting comes closest to addressing this need, as it focuses on finding deltas — the incremental changes in code, configurations, or patches — before anyone else. Testers must track these changes over time, identifying new vulnerabilities that arise from shifts in the system. The ability to spot and exploit these deltas requires a deep understanding of a targets evolution.
Let’s dive into eight steps that can drive this transformation in your own pentest operations.
1. Start by Knowing Yourself: Your Digital Footprint
If you don’t know what you look like from the outside, you’re already missing key pieces of the puzzle. Your digital footprint—the combination of all your public-facing assets, IPs, domains, cloud resources, and services—is what attackers are scanning day in and day out.
Building a digital footprint gives you the eyes of an attacker. This first step means cataloging every piece of exposed infrastructure, application, and service. It’s a constantly evolving picture, and for pentesters, this is foundational. After all, how can you secure what you don’t know you own?
Automation does a decent job in finding some of your attack surface, but by utilizing penetration testers to properly do reconaissance, discovery and scanning will help find shadow IT and other important facets.
2. Keep Your Asset Inventory Up-to-Date with Attack Surface Management
Attack Surface Management (ASM) is not a buzzword; it’s a necessity. With organizations adopting more cloud resources and third-party services, assets appear and disappear at unprecedented rates. The ASM solution becomes your live radar, mapping out the assets that you might be missing—and as a result, increasing your attack surface.
Keeping this inventory fresh is crucial because it guides where your pentesters should focus their efforts. Outdated or incomplete information leads to pentests that miss critical vulnerabilities in newly added or overlooked assets.
3. Test Everything as You Change
The speed at which companies innovate and push code today can be daunting, but it’s essential that penetration testing evolves alongside these changes. Every new deployment or infrastructure change can be an open door if not vetted properly. Make sure to conduct regular pentests that cover the full spectrum—testing everything from configuration and code to cloud resources.
Think of it this way: if your environment changes but your pentesting lags, you’re putting yourself at risk. Incorporate pentesting into your CI/CD pipelines where possible, ensuring vulnerabilities are caught early and often.
IT is a moving target, and cybersecurity flows like a river—constantly evolving. To stay effective, pentesters must continuously adapt to these shifting currents.
4. Know the Attacker: Stay Informed with Cyber Threat Intelligence (CTI)
In 2024, Cyber Threat Intelligence (CTI) is non-negotiable for an effective pentest. Today’s attackers don’t operate in isolation—they’re tapping into resources, sharing techniques, and deploying new tactics. Pentesters need CTI to keep up.
Knowing the current threats that target your sector, your software stack, or your geographical region makes your pentest sharper and more focused. Ensure your team is actively monitoring CTI feeds and adjusting methodologies to simulate the tactics that matter most to your specific risk landscape. As you know, this should not happen once a year, but throughout the year.
5. Integrate Vulnerability Management with Pentesting
Vulnerability Management and Pentesting are two sides of the same coin. Vuln scanners and automated tools are great at identifying known weaknesses, but the real magic happens when this data feeds directly into the pentest workflow. The goal is simple: give pentesters a head start by equipping them with intel on existing vulnerabilities, so they can dig deeper and exploit the findings more effectively.
When a pentesting team can see the bigger picture from vuln scan data, they can prioritize critical flaws and demonstrate real-world impact, which is infinitely more valuable than isolated scan reports. Vuln scanning is just a small facet in continuous pen testing efforts, but still an important one. The pen test team is typcally the team most capable of prioritizing output of vuln scans, and the delta between scans is what should be continuously followed up on.
6. Report What Matters: Demonstrable Effects on Confidentiality, Integrity, and Availability (CIA)
Not every vulnerability needs to be fixed—but the ones that could compromise Confidentiality, Integrity, or Availability (CIA) absolutely should be. Reporting should focus on these principles, making it clear to stakeholders what’s at risk and why it matters.
Pentesters need to craft reports that convey not just “what’s wrong,” but “why this matters” in the context of the organization’s critical assets and functions. This approach helps teams prioritize and align with business goals, not just technical goals. Risk from pen testing and similar services is often over-reported where many of the items reported on are simply hygienic issues that testers are not capable of exploiting. Report on exactly this, impactful issues vs. hygienic issues.
7. Leverage Leaked Credentials and Assess MFA Effectiveness
This is one of the hottest trends in cyber crime today—taking leaked credentials into account, often referred to as Credential Stuffing. Using leaked credentials is not about hacking for hacking’s sake; it’s a method to identify weaknesses in user account management and MFA protections. A weak password paired with ineffective MFA implementation is a risk worth flagging.
Pentesters should analyze where these credentials provide access and assess whether critical accounts are truly protected by MFA. This is actionable intelligence that can guide password policy adjustments, MFA enforcement, and credential hygiene. If pentesters can log on with leaked credentials, so can the rest of the world.
8. Don’t Handicap Your Pentesters: Allow Free Reign with Stakeholder Collaboration
One of the biggest pitfalls in pentesting is limiting the tester’s scope or access. In 2024, give your pentesters the freedom to operate across the attack surface. However, this freedom should come with ongoing collaboration with stakeholders—clear communication ensures that tests are valuable, relevant, and aligned with real-world risks.
Pentesters should not be limited by arbitrary restrictions but should work closely with stakeholders to ensure that findings are prioritized and that actionable recommendations can be implemented efficiently. Too many times do we see companies being impacted due to shadow IT and other unmanaged assets, but no more.
These eight steps aren’t just a checklist—they represent a shift in how we think about pentesting. By embracing ASM, integrating CTI, leveraging vulnerability data, and fostering an environment of collaboration, we’re turning pentesting into a proactive, continuous, and intelligence-driven process. If we can adopt this mindset across our operations, we’re not just keeping up with attackers; we’re outpacing them. So let’s bring some real innovation back into cybersecurity—because in 2025 we’re not settling for anything less.
