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Why Most MSP Security Incidents Start with “We Thought We Were Covered”

January 1, 2026 by
Jaspreet Singh


(A Real MSP Owner’s Perspective)

As an MSP owner, I’ve learned something the hard way:

Most security incidents don’t start with sophisticated hackers or zero-day exploits.

They start with assumptions.

“We already have MFA.”

“The firewall is in place.”

“Microsoft handles security.”

“The client is too small to be targeted.”

I’ve heard all of these — and at some point, I believed a few of them myself.

Security incidents usually happen not because tools are missing, but because responsibility is unclear and basics are quietly ignored.

The MSP Security Reality No One Likes to Admit

In most SMB environments, security is spread across:

  • Microsoft 365

  • Endpoint protection

  • Firewalls

  • Email filtering

  • Backups

Each solution works — on its own.

But attackers don’t attack tools individually.

They attack the gaps between them.

And when something goes wrong, the question always comes back to the MSP:

“Why wasn’t this prevented?”

Assumptions I See Cause Real Incidents

1️⃣ “Microsoft 365 Is Secure by Default”

This is one of the most dangerous assumptions.

Microsoft provides a powerful platform, not a secure configuration.

In real environments, I still see:

  • Legacy authentication left enabled

  • MFA exclusions added “temporarily” and forgotten

  • Global admin accounts without proper monitoring

  • Conditional Access not enforced consistently

Nothing here is advanced — but every item is exploitable.

2️⃣ “Endpoints Are Protected, So We’re Safe”

Endpoint protection is important, but it’s not the primary attack path anymore.

Most modern incidents involve:

  • Stolen credentials

  • Token theft

  • MFA fatigue

  • OAuth abuse

No malware.

No alerts.

Just valid sign-ins.

If identity isn’t protected properly, endpoint security won’t save you.

3️⃣ “The Client Is Too Small to Be Targeted”

SMBs are targeted because they’re smaller, not despite it.

From what I see:

  • Less monitoring

  • Fewer security policies

  • More trust-based access

  • Slower detection

Attackers automate everything. They don’t care about company size — only ease of entry.

Where MSPs Usually Get Caught

Most MSP security issues come from:

  • Inherited legacy setups

  • “Temporary” exceptions that became permanent

  • Security handled reactively, not proactively

  • No clear ownership between MSP and client

When a breach happens, the tools get blamed — but the real issue is usually design and discipline.

What I’ve Changed as an MSP Owner

Over time, I’ve adjusted how I approach security for clients:

  • I assume defaults are insecure

  • I treat identity as the primary security boundary

  • I document responsibility clearly

  • I remove exceptions aggressively

  • I focus on fundamentals before adding more tools

Security improves not when you buy more products, but when you reduce assumptions.

Final Thought

Every serious incident I’ve reviewed had the same root cause:

“We thought we were covered.”

Security isn’t about feeling protected — it’s about verifying that you actually are.

As an MSP owner, my goal isn’t to sell fear.

It’s to remove blind spots before attackers find them first.

About MSPinsights.ca

MSPinsights.ca shares real-world MSP lessons around cybersecurity, Microsoft 365, and SMB IT — written from hands-on experience, not theory.

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