Most MSPs are terrified to bring in pen testers.
Let’s just say it out loud.
You’ve spent years building trust with your clients. You’re their go-to for IT problems. They rely on you. They trust your judgment. And then someone suggests bringing in a penetration tester, and your stomach drops.
The fear makes complete sense.
What if the pen tester finds a bunch of vulnerabilities that make your team look incompetent? What if they talk directly to your client and position themselves as the “real” security experts while you’re just the “IT person”? What if they trash your infrastructure decisions in front of the CEO? What if this one engagement damages a relationship that took years to build?
It happens. Partners get burned by pen testers who treat findings as gotcha moments rather than opportunities for collaboration. Pen testers who write reports that read like indictments. Who bypasses the MSP entirely and builds rapport directly with the client. Who positions every vulnerability as evidence of negligence.
No wonder you’re hesitant.
But here’s the thing: that fear is keeping your clients less secure than they should be. And eventually, it’s going to cost you the relationship anyway.
The Real Risk Isn’t the Pen Test
Let’s talk about what you’re actually afraid of.
You’re not afraid of vulnerabilities existing. You know they exist. Every environment has them. You’re afraid of how those vulnerabilities will be presented and who will look bad when they’re discovered.
You’re imagining the pen tester sitting across from your client, saying, “Well, your MSP should have caught this. This is pretty basic stuff.”
You’re picturing a report that makes it sound like your team has been asleep at the wheel for years.
You’re worried the client will start questioning everything you’ve done and whether they should find a new MSP who “actually understands security.”
These fears are legitimate because they’re based on real experiences. Some pen testing companies absolutely do this. They use findings as leverage to upsell their own services. They undermine existing relationships to create new ones. They act like security rockstars who’ve swooped in to save the day from the “incompetent” IT people.
But consider the actual danger here: The real risk is NOT bringing in a pen tester, and then your client gets breached.
When the Breach Happens Anyway
Picture this scenario:
You’ve been managing a client’s IT for five years. Good relationship. They trust you. You’ve been hesitant about penetration testing because, honestly, you’re worried about what it might find and how it might reflect on you.
Then they get hit with ransomware.
Everything’s encrypted. Operations stop. Customer data is compromised. The client is furious, panicking, facing regulatory fines and reputational damage.
And the first question they ask is: “How did this happen? Why weren’t we protected?”
Now you’re in a position where you have to explain why comprehensive security testing wasn’t part of your service offering. Why were vulnerabilities that could have been identified and fixed months ago exploited by attackers instead?
The relationship you were trying to protect by avoiding pen testing? It’s probably over anyway. But now it’s ending with a breach, finger-pointing, potential lawsuits, and a client who feels betrayed.
Compare that to the scenario where you proactively brought in pen testing, vulnerabilities were discovered, you collaborated on remediation, and the client saw you as forward-thinking and security-conscious. Even if the pen test found some uncomfortable things, you controlled the narrative and demonstrated commitment to their security.
Which scenario actually protects the relationship?
Finding Vulnerabilities Is the Good News
Here’s a mindset shift that changes everything:
Finding vulnerabilities during a pen test is supposed to be the good news.
Vulnerabilities exist everywhere. They always will. Software has bugs. Configurations drift. People make mistakes. New attack techniques emerge. The idea that any environment could be completely free of vulnerabilities is a fantasy.
The question isn’t whether vulnerabilities exist. The question is whether your team finds them first or an attacker does.
A pen test that identifies security gaps is a win. It means the problem gets fixed before it becomes a breach. Before customer data gets compromised. Before regulatory fines hit. Before the client loses trust in their entire IT infrastructure. Before you’re dealing with an actual incident instead of a report.
Think about it this way: would you rather get a phone call saying “we found some vulnerabilities in the pen test that need attention” or “your client’s entire database just got dumped on the dark web”?
Every vulnerability found in testing is a bullet dodged. Every gap identified is an opportunity to strengthen security before attackers exploit it. Every finding is a chance to demonstrate proactive risk management rather than reactive crisis response.
But that only works if the pen testing is positioned as collaboration rather than criticism.
Why the Wrong Pen Testing Partner Destroys Trust
Not all pen testing providers understand the MSP relationship. Some actively work against it.
Here’s what happens with the wrong partner:
- They bypass you entirely. All communication goes directly to your client. You’re finding out about findings and recommendations at the same time as everyone else—or worse, after your client has already heard them. You look out of the loop on your own client’s security.
- They position themselves as the experts and you as the problem. The subtext of every conversation is “your MSP should have known this.” They’re not explicitly saying you’re incompetent, but the implication is clear. Your client starts wondering what else you’ve missed.
- Their report reads like an indictment. Instead of “here are some gaps we found that should be addressed,” it’s written like “here’s a comprehensive list of everything wrong with this environment.” Every finding feels like an accusation.
- They use findings as a sales pitch. “We found all these problems, and coincidentally, we offer managed security services that could fix them for you.” They’re not there to support your relationship; they’re there to replace you.
- They don’t understand operational reality. Their recommendations are technically correct but operationally impossible. “Just rebuild your entire network with micro-segmentation” sounds great until you consider the budget, downtime, and business impact. You’re left explaining why their “obvious” solutions aren’t feasible.
- They make you look reactive instead of proactive. Because they’ve structured the engagement adversarially, even though YOU brought them in, it looks like problems were discovered despite you, rather than because you were proactive about security.
This is the nightmare scenario that makes MSPs avoid pen testing entirely. And it’s a completely valid fear when you’re working with the wrong provider.
The Partnership Model That Actually Works
Here’s how pen testing should work when the provider actually understands channel partnerships:
Partners stay in the loop on every communication. Nothing goes to the client without you knowing about it first. You’re not surprised by the findings. You’re not left out of conversations. You’re positioned as the one who brought in expertise to strengthen security, not the one who needed to be worked around.
Technical questions get answered collaboratively. When the client has questions about findings, you’re part of the conversation. The pen tester isn’t positioning themselves as replacing you; they’re supporting your relationship by providing specialized expertise while you remain the trusted advisor.
Reports get structured for different audiences. Technical folks need detailed remediation steps they can actually implement. Executives need to understand business risk without getting lost in CVSS scores and CVE numbers. The report should make you look good for bringing in this expertise, not bad for needing it.
Findings are framed as opportunities, not failures. Instead of “your MSP misconfigured this,” it’s “here’s a gap that should be addressed.” The focus is on fixing problems, not assigning blame. Vulnerabilities are presented as the normal result of complex environments, not evidence of incompetence.
Remediation is practical. Recommendations consider budget, operational constraints, and business needs. “Replace your entire infrastructure” isn’t helpful. “Here are three options ranging from quick wins to comprehensive solutions” actually is.
The goal is to make you look better. The pen testing provider understands their job is to support your client relationship, not compete with it. Every interaction should reinforce that you’re the one who’s security-conscious enough to bring in specialists. You’re proactive. You’re thorough. You’re looking out for the client’s best interests.
This isn’t some theoretical ideal. This is how it should work every single time. And when it does work this way, pen testing becomes a relationship strengthener rather than a threat.
What This Looks Like in Practice
Let me paint a picture of how collaborative pen testing actually plays out:
Pre-engagement: You have a conversation with the pen testing provider about your client, their environment, their concerns, and your relationship. The provider understands that their job is to support you, not replace you. You’re all on the same team.
During testing: As findings emerge, you’re kept in the loop. No surprises. If the tester discovers something significant, you know about it before your client does. You have time to understand the issue, consider remediation options, and prepare for the conversation.
Client communication: When the pen tester talks to your client (with your involvement), they’re clear that you brought them in and that you’re collaborating on security. They defer to you on operational questions. They reinforce your expertise rather than undermining it.
Reporting: You review the draft report before the client sees it. If something is framed in a way that doesn’t reflect the full context, you can discuss it. The final report positions findings as actionable intelligence, not accusations. It acknowledges the complexity of managing security in real-world environments.
Debrief: The findings presentation is a collaborative discussion, not a lecture. The pen tester walks through what they found. You contribute context about why certain things are configured the way they are. Together, you discuss prioritization and remediation approaches. Your client sees a unified team working on their behalf.
Follow-up: After remediation, retesting is available to confirm that fixes were effective. You’re not left wondering if you addressed issues correctly. The pen tester validates your work, giving your client confidence that gaps have been properly closed.
Throughout the entire process, you look like the security-minded professional who brought in specialized expertise to ensure comprehensive protection. Your client’s confidence in you increases rather than decreases.
That’s what good looks like.
The Size of the Engagement Doesn’t Matter
Here’s something important: this collaborative approach should be consistent regardless of project size.
Some pen testing providers are great on large engagements but treat smaller projects as checklist exercises. You get the partnership treatment on a $50,000 assessment, but not on a $4,000 external network test.
That’s backwards.
Your small clients, the ones with modest budgets who can only afford basic testing, need the collaborative approach even more. They’re more vulnerable. They have less security expertise in-house. They’re more dependent on you as their trusted advisor. If the pen testing provider treats them like a commodity engagement and makes you look bad, you lose the relationship, and they lose protection.
The right pen testing partner treats every engagement the same way. Whether it’s a comprehensive assessment or a focused test, the approach stays consistent:
- Partners stay in the loop
- Communication is collaborative
- Reports are structured for action
- Findings are framed constructively
- The goal is to support the relationship
This consistency means you can confidently bring in pen testing for any client at any budget level without worrying about being undermined.
When Trust Breaks Down, Everyone Loses
Let’s be clear about what happens when the pen testing relationship goes wrong:
You lose the client relationship. Either immediately because the pen tester made you look incompetent, or eventually, when a breach happens and you’re blamed for not being proactive about security.
Your client stays less secure. Because you’re afraid to bring in pen testing, vulnerabilities that could have been found and fixed remain exploitable. Your client faces more risk because the trust model is broken.
The pen testing provider loses repeat business. If they’re burning partner relationships, they’re not getting referrals or follow-on work. They might win a one-time client, but they’ve lost an entire channel.
The industry becomes more adversarial. When MSPs and pen testers don’t trust each other, security suffers. Collaboration breaks down. Clients get caught in the middle.
Nobody wins in this scenario.
On the other hand, when the partnership works:
Your client gets better security. Specialized expertise complements your general IT knowledge. Vulnerabilities get found and fixed. Risk decreases.
Your relationship strengthens. You’re positioned as the forward-thinking advisor who brings in experts when needed. Your client trusts you more, not less.
You expand your service offering. Security testing becomes part of your value proposition. You can confidently recommend it without fear of losing control.
The pen testing provider establishes a reliable channel. Happy partners mean steady referrals and long-term relationships. It’s a sustainable business built on trust.
Everyone wins.
What to Look For in a Pen Testing Partner
If you’re an MSP considering bringing in pen testing, here’s what to look for:
They ask about your relationship with the client. Not just technical questions, they want to understand the dynamics, the sensitivities, and how to support rather than disrupt.
They’re explicit about communication protocols. They clarify upfront how client communication will work, who’s in the loop, and how to avoid surprises.
They show sample reports before engagement. You see what your client will see. No surprises about tone or framing.
They have other MSP partners who vouch for them. Ask for references from other partners. Find out if they actually deliver on the collaborative promise.
They’re clear about their role. They position themselves as technical specialists supporting your client relationship, not as competitors trying to replace you.
They’re flexible on engagement structure. They work with your process, your client communication style, and your relationship dynamics.
They understand operational reality. Their recommendations are practical, not purely theoretical. They get that “just rebuild everything” isn’t an option.
They offer you control over the narrative. You’re involved in how findings are presented and discussed. You’re not a bystander in your own client relationship.
If a pen testing provider can’t clearly articulate how they’ll support rather than threaten your partnerships, keep looking.
The Bottom Line
MSPs are terrified of pen testers for legitimate reasons. Bad experiences happen. Relationships get damaged. Trust gets broken.
But avoiding pen testing because you’re afraid of how it might reflect on you is a losing strategy. Eventually, your clients will either get breached (and blame you for not being proactive) or they’ll hear about pen testing from someone else and wonder why you never recommended it.
The solution isn’t avoiding pen testing. It’s finding a partner who actually understands collaboration.
Pen testing should strengthen client relationships, not threaten them. When you can confidently bring in security specialists without worrying about being undermined, everyone wins.
Your clients get better security. You look like the forward-thinking advisor who brings in experts when needed. The pen testing provider builds a sustainable channel based on trust. And most importantly, vulnerabilities get found and fixed before attackers exploit them.
That’s how it should work. That’s how it can work. But only if you’re working with the right partner.
Partner with MainNerve: Collaboration Over Competition
MainNerve treats every partner engagement the same way, regardless of project size. Whether it’s a $4,000 pen test or a $50,000 assessment, the approach stays consistent.
Partners stay in the loop on every communication. Nothing goes to your client without you knowing about it first. Technical questions get answered collaboratively, with you as part of the conversation. Reports get structured so IT teams have actionable remediation steps while executives understand business risk.
Our goal is to make you look better to your clients by providing expertise you can rely on. Not replacing you. Not going around you. Supporting you.
We understand that you’ve spent years building trust with your clients. We’re not here to damage that—we’re here to strengthen it by providing specialized security expertise that complements your IT services.
Need a pen testing partner who understands collaboration? Let’s talk about how we can support your client relationships without threatening them.
Contact MainNerve today because security testing should make you look good, not put you at risk.
