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Lessons from MSP Hell: Contracts Don't Mean Victory

Written by Dustin Puryear | Aug 5, 2025 1:15:00 PM

Contracts are great, until you realize you’ll rarely enforce them in court. For small MSPs, the real power isn’t in the paperwork. It’s in clear boundaries, cash flow, and communication.

One of the most brutally honest comments from the r/msp community nailed it:

“Contracts are only of value if you're willing to take someone to court to enforce it, which means they're worthless.”

And they’re right.

For small MSPs, the idea of spending tens of thousands on litigation just to recover a few months of unpaid invoices or to defend your service terms? It’s not realistic.

Even OP followed up:

“Taking a client to court just isn’t worth the time or money for a small MSP or SMB of any kind really.”

So where does that leave you?

The Shift: From Legal Enforcement to Practical Protection

If enforcement isn’t viable, then the game becomes prevention. That means:

1. Require Deposits Up Front

Before any onboarding, configuration, or hours of work: get paid. Not just a “trust me” nod. Get a real deposit.

“These days we focus more on clear communication and deposits up front.”

Deposits protect you from:

  • Scope creep

  • Disappearing clients

  • Delayed or disputed payments

  • Unbalanced risk

2. Prioritize Written Communication

Instead of trying to enforce contracts post-disaster, build alignment pre-emptively:

  • Outline expectations in plain English

  • Confirm scope and change requests via email

  • Send summaries after every meeting or decision

3. Align on Values—Not Just Services

Another Reddit insight hit the nerve MSPs feel too often:

“Never assume someone has the same intentions as you.”

You may think you’re solving business problems. They may just be looking for the cheapest tech monkey.

That mismatch can destroy relationships—and make contracts useless. The solution? Qualify clients not just by budget, but by mindset.

Why Litigation Isn’t Worth It for Most MSPs

Let’s do the math:

  • Legal fees: $5K–$20K minimum

  • Time lost: weeks of prep, court, and follow-up

  • Stress: sky high

  • Reputation risk: elevated

  • Actual payout (if you win): maybe $3K–$10K

Most MSPs simply can’t justify it. The ROI isn’t there. Worse, it distracts you from your real clients and growth.

Contracts Still Matter—But in the Right Way

This isn’t an anti-contract post. In fact, contracts are essential:

  • They outline expectations

  • They define deliverables and payment

  • They help set professional tone

  • They serve as internal documentation

But they are only one part of a healthy business structure. Their power lies in what they prevent—not what they enforce.

Learn from Others, But Build Your Own Guardrails

Here’s the last gem from the thread:

“Learn from other people but don’t follow them.”

Translation? Don’t blindly adopt someone else’s stack, pricing, onboarding, or legal strategy. Learn the “why” behind each move, and build a system that fits your size, market, and risk appetite.

Just because another MSP went all-in on long-term contracts doesn’t mean it’s right for you. Just because someone swears by prepaid blocks doesn’t mean it’ll fit your monthly recurring model.

Design for your reality. Optimize around your capacity. And build for sustainability, not assumptions.