Ride-Along Penetration Testing
Most penetration tests happen to your team. A ride along happens with them.
This is a guide to embedded, collaborative testing, how it differs from a traditional independent engagement, and what your team actually walks away with.
What is Ride-Along Penetration Testing?
Ride-along testing is a collaborative penetration test where our testers integrate directly with your internal security team, working side-by-side, either virtually or in person. Unlike a traditional penetration test, where the testing team is siloed away from the security team for two weeks, and then presents a report, the main difference is who is in the room while it happens.
The essence of a ride-along is knowledge and skill transfer through an interactive, engaged partnership. By embedding our consultants with your team instead of testing independently, you get a level of hands-on learning that a standard engagement structurally can’t provide. Your people watch, ask questions, and participate in testing in real time, rather than reading about what happened after the fact.
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Senior IT Auditor
Financial Services
1 Credit = Up to 1 Full Day of Expert Work
Purchase credits ahead of time, and arrange testing as you need it. Partnership-based security testing on your schedule. One credit gets you up to one full day of expert work from consultants who understand your business. Engage our team as needed with complete flexibility.
Ongoing advisory services included for no extra charge. No rigid scopes, real-time collaboration, and engagement tailored to your priorities.
Exclusively from Secure Ideas.
Ride-Along vs. Traditional, Independent Testing
| Traditional Independent Testing | Ride Along Testing |
|---|---|
| StructureTesters work separately from your team, then deliver a report | Testers work directly alongside your internal team throughout |
| LearningHappens by reading, after the engagement ends | Happens in real time, as techniques are actually used |
| VisibilityYour team's first look at methodology is the findings document | Your team sees the methodology, tooling, and reasoning as it happens |
| Best ForAn independent, arm's-length assessment | Building your team's own capability, not just getting a report |
Neither approach is strictly better. A traditional independent test is still the right call when you need a clean, arm’s-length assessment with no internal involvement. A ride along is the right call when the report alone isn’t the point, when you also want your team to walk away better at this than they were before the engagement started.
Looking for focused security testing?
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Why Ride-Along Testing Works
The main difference between a ride-along penetration test and a traditional one is who is present for the testing. While this may seem like a small change, the impacts can be significant, and include:
Skill Transfer
Where the final report tells your team what testers found, the ride-along allows them to see how it was found, in the moment. Your team can ask questions and learn directly, live from the experts doing the tests.
Deeper Context
Working closely with your team gives our consultants real-time insight into your actual infrastructure, processes, and the specific challenges you face. These are details that may not come up during a kick-off call, or things that haven’t made it into the documentation yet. At the same time, your team also gets to see exactly how an outside tester thinks about your environment, a perspective that can shift how they see it themselves going forward.
Process Improvements
The end result is more than findings recorded in a report document. Your internal team gains measurable experience, making your cybersecurity practices, testing techniques, and methodology all stronger than they were before the engagement. Lessons learned here can pay off long after the test itself has finished.
CONTINUOUS TESTING
See how PETaaS® supports continuous testing with flexible, credits-based penetration testing and built-in advisory services.
Who Needs Ride-Along Testing?
Not every organization needs to move away from standard, annual testing, but a ride along may be worth considering if your organization is…
How a Ride-Along Engagement Works
An evaluation of your security program against the PCI Data Security Standard, covering PCI security assessments, self-assessment support, and advising on scope, applicability, and controls. You get direct access to a Qualified Security Assessor who speaks plainly and knows the standard inside and out.
Led by the “PCI Guy” himself – Jeff Man.
How Secure Ideas Approaches Ride-Along Testing
Secure Ideas treats a ride-along as a genuine partnership, not a standard pentest with an extra observer. Our consultants work directly alongside your internal team for the full engagement window, sharing methodology and reasoning as it happens rather than saving it for the final report. Every ride-along still follows our published penetration testing methodology in full; the collaborative format changes who’s involved, not the rigor of the testing itself.
We tailor the balance of guidance and hands-on testing to where your team actually is: more mentorship-driven for a team just building out its function, more peer-to-peer for a team that already tests but wants outside perspective and technique.
Because the relationship is the point as much as the report, we treat a ride along as the start of an ongoing partnership, not a one-time engagement.
Beyond the Test
Keeping Your Team Practicing
A ride along engagement is a powerful way to build your team’s capability, but this learning happens during one defined testing window. The skills your team builds need room to keep growing after the engagement ends.
Building lasting capability requires ongoing testing and advisory support between ride-alongs. Regular penetration testing keeps your team’s hands-on experience current as your environment changes, rather than fading until the next scheduled engagement. Advisory services provide guidance on remediation priorities, architectural decisions, and the techniques your team is still working to master.
This is exactly what Secure Ideas’ PETaaS® (Professionally Evil Testing as a Service) is designed for. PETaaS® provides continuous, human-led penetration testing through a flexible credits-based model, with built-in advisory services and real-time communication. Between ride alongs, PETaaS® keeps your team practicing and your program active.
Think of a ride along as the driving lesson, learning alongside an expert behind the wheel. PETaaS® is what keeps them in practice.
Ride-Along
Testing
Frequently
Asked
Questions
Have a question that isn’t answered here?
See our full FAQ page.
Does a ride along cost more than a traditional penetration test?
Scoping follows the same effort-based model as our other engagements. A ride along isn’t inherently more expensive, although the collaborative format may impact the timeline and coordination compared to a fully independent test.
Can a ride along be done remotely?
Yes. Ride along engagements work virtually or in person, whichever fits your team and the environment being tested.
How is this different from purple teaming?
A ride along is a full penetration test with your team embedded throughout for broader skill transfer, not limited to a specific set of controls. Purple teaming is a targeted exercise validating specific detection and response controls with the offensive red team and defensive blue team working together.
Is a ride along less thorough than an independent test?
No. It follows the same full methodology as any other Secure Ideas penetration test. What changes is who’s involved and how the findings get communicated, not the rigor of the testing itself.
Who benefits most from this format?
Teams building out an internal security function, teams that want testing and training from the same engagement, and organizations planning to eventually bring testing capability in-house.
Do we need an existing security team to do a ride along?
Not necessarily a dedicated one. IT staff wearing a security hat can just as easily be the team embedded alongside our testers; the format adapts to whatever internal capability currently exists.
Can we see a sample report from a Penetration Test?
Absolutely. Any reputable penetration testing company should provide sample reports upon request. Reports are your primary deliverable and should include an executive summary, testing narrative, detailed findings with risk ratings, replication steps for verification, and actionable remediation recommendations. Not all reports are created equal, so reviewing samples helps ensure the format and content meet your needs. Most companies will accommodate reasonable modifications to reporting formats.
What is Professionally Evil Testing as a Service (PETaaS®)?
PETaaS® is on-demand pentesting services, which provides you with continuous access to our penetration testing expertise rather than a one-time assessment. This approach offers on-demand or scheduled testing, which integrates with your software development lifecycle, and delivers regular vulnerability analysis with ongoing support. While it may initially appear more expensive than traditional testing, PETaaS® is significantly more cost-effective than hiring full-time security staff and provides proactive, real-time vulnerability identification.
Note: The industry lacks a standard definition for penetration testing as a service, so verify that your provider’s approach aligns with your expectations.
Other Pentesting Approaches
Continuous Penetration Testing
Continuous Pentesting keeps testing running instead of leaving your network exposed between annual checkups. We pair ongoing vulnerability scanning with a real consultant reviewing the results, and catching new risks as they appear across web apps, APIs, and IoT ecosystems. Regular reporting means you always know what’s new, what has changed, and where to point the roadmap next.
Security that doesn’t wait for next year’s test.
Threat-Led Penetration Testing
Threat-Led Pentesting simulates the specific tactics, techniques, and procedures of the threat actors most likely to target your organization, instead of following a generic playbook. We work with you to identify relevant adversaries and scenarios, then build a bespoke test around them. It’s the approach DORA now mandates for certain financial entities, and happens to be a strong fit for any mature security program.
Tested against the threats actually coming for you.
Purple Team Penetration Testing
Purple Team Pentesting engagements put our red team and your blue team on the same call, testing and defending in real time. As we run attacks, your team watches, tunes detection, and learns what an actual intrusion might look like on your systems. It’s a faster way to validate specific controls and walk away with sharper monitoring.
Your defenders, tested and trained at the same time.
Red Team Penetration Testing
Red Team Pentesting engagements go beyond finding vulnerabilities. Our consultants simulate a determined adversary, and chain together recon, phishing, and physical access attempts to show how far a real attacker could get and what they could walk away with. Most engagements wrap up in a month or less, with reporting delivered within a week.
See your whole attack surface the way an attacker does.
Time-Boxed Penetration Testing
Time-Boxed Pentesting focuses effort on your highest-priority assets within a set window, instead of trying to cover everything at once. It’s a strong fit for large environments, budget-conscious teams, or anyone just getting started with testing. We work to set the scope through a quick scoping call, so the timeframe fits your risk profile, instead of a generic template.
Focused coverage, built to fit your timeline.
Recognized authority and trusted guidance built on years of uncovering risks for organizations like yours.
My Experience in the CISSP Mentorship Program
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