Set it, Forget it, Regret it: Where MSP Automation Falls Apart and How to Fix It

Automation is meant to make things easier.

Fewer repetitive tasks. Cleaner workflows. More time for higher-value work. But without the right MSP automation strategy, most MSPs struggle to see real operational impact. Instead of saving time, they’re burning it: grappling with clunky setups, half-built automations, and tools that never quite delivered.

The issue isn’t bad tech. It’s bad assumptions.

Too often, automation gets treated like a one-time project: they flip the switch and forget it. But real impact takes structure, strategy, and follow-through. Without that, what should be a force multiplier becomes a sunk cost.

So why do so many MSPs miss the mark, and what does it take to finally make automation deliver?

Automation LookS Easy, Until It Isn’t

It starts with a promising investment: a powerful RMM, a new PSA platform, maybe even a dedicated automation engine. You picture a future where customers are automatically onboarded, tickets sort themselves, patches apply without a hitch, and reports land in your inbox without asking. Less manual work, happier clients, stronger margins, all driven by standardized workflows.

The promise is real. And the tools are capable.

But most MSPs run into trouble when they overlook the operational complexity behind the scenes.

Take automated ticket routing. It sounds simple. But if your team uses different tags, your clients submit unclear requests, and your workflows don't account for all scenarios, the result is misrouted tickets and missed SLAs. Instead of saving time, your team ends up fixing what automation broke.

It’s a familiar pattern: automation runs ahead of oversight, and the very tools meant to reduce effort end up creating more of it. We’ve seen this play out in MSP environments where automation is implemented without the operational structure to support it, leading to breakdowns that erode confidence rather than build efficiency.

And this isn’t rare. While 95% of MSPs say automation is essential to scale, fewer than 22% believe they’re using their tools effectively or seeing meaningful ROI. That gap between potential and performance is where most automations start to fall apart.

Here’s why that happens: automation doesn’t fix broken processes. It makes them faster and louder.

From our experience, and as we noted in a previous article on workflow and tool missteps, the usual culprits are:

• Process standardization– If your workflows are inconsistent or undocumented, automation will only replicate the chaos faster.
• Staff training and buy-in – If your team doesn’t trust or understand the automation, they’ll bypass it, creating shadow processes that break the system.
• Ongoing iteration – Automation isn’t “set and forget.” It’s “set, test, refine, repeat.” Without continuous improvement, even the best workflows become outdated.

The good news is these problems are solvable. But only if you approach automation with the right plan and discipline.

When Automation Becomes an Assumption Instead of a Strategy 

The gap between belief and execution is often driven by a misunderstanding of what automation is meant to do.

When MSPs invest in automation, they usually believe in the outcome: scale, efficiency, and consistency. But too often, they treat the tool as the solution, not part of a broader strategy. That’s where execution breaks down.

Instead of asking how automation fits into their processes, many teams assume it will simply replace them. That assumption sets the stage for misalignment, wasted effort, and missed ROI.

Here are the most common misconceptions that hold automation back:

Automation is instant

The idea of quick results sounds appealing, but in practice, automation needs time: time to map the process, test logic, and adjust based on real-world feedback.

Automation is automatically a fit

Just because a platform works for one MSP doesn’t mean it works for yours. Unless it's built around your actual workflows, it won’t deliver consistent results or meaningful automation ROI in MSPs.

Automation is one-size-fits-all

Platforms like Rewst provide the framework. But unless they’re configured around your actual workflows, they won’t produce consistent results.

When these assumptions go unchecked, it leads to a pattern we’ve seen far too often:

• Tools go underused because no one knows how to apply them to real scenarios.
• Processes break down as disconnected automations create more complexity, not less.
• Teams lose clarity on what’s automated, what isn’t, and what they’re accountable for.

Treating automation like a switch you flip undermines its real potential. The shift happens when you start viewing it as part of your operating model, not a shortcut.

And that starts with better questions. Not “What can we automate?” but “Where does automation support our goals, and how do we build around that?”

What Successful Automation Actually Looks Like

The MSPs who succeed with automation are the ones who move with intent. They don’t chase every new platform or try to automate everything at once. Instead, they approach automation as an ongoing practice that supports operations, not shortcuts them.

Here’s what sets their approach apart:

They map the process before they automate it

They begin by understanding the workflow. By documenting how tasks are currently done, identifying inefficiencies, and validating the process, they avoid automating what’s already broken or inconsistent.

They involve the team

Automation decisions don’t happen in a vacuum. High-performing MSPs engage frontline staff, service leads, and even non-technical roles to shape automation around real-world usage. This results in smoother adoption and fewer breakdowns.

They iterate, not overhaul

Successful MSPs don’t expect perfection on day one. A previous article on smaller, iterative fixes shows how building gradually, especially within platforms like Rewst or ConnectWise RPA, often delivers more value than trying to launch everything at once.

To apply this mindset, consider using a practical automation review framework—a simple way to assess what’s working, what’s not, and where to optimize.

Audit → Align → Adjust

• Audit – What’s currently automated? What’s effective? What’s being bypassed or causing friction?
• Align – Are your workflows and tools supporting your business goals? Is your team trained and your stack integrated?
• Adjust – What small improvement can you make this quarter? What process is close to working but needs refinement?

You don’t need to rip out what you’ve built. Real progress often comes from tightening what’s already there.

For example, our consultants start with the tools you already use. They help optimize what’s under the hood, align it to how your business actually operates, and give your team the structure they need to scale without the chaos.

Imagine What You Could Do With Fewer Fires to Put Out 

Let’s go back to that ideal day: the one where your systems run quietly in the background, your team knows exactly what to expect, and you’re not waking up to another mess waiting in the queue.

That version of your business isn’t just possible. It’s what automation was always meant to deliver. Fewer breakdowns. Fewer workarounds. Less guesswork.

But getting there doesn’t happen by chance. It happens when automation is aligned to real processes, owned by your team, and refined with purpose, not pressure.

At MSP+, we help MSPs turn automation into a true operational asset. Our team works within your existing stack, aligning tools, structure, and processes to support scalable, efficient delivery.  We become your Rewst consultants and  advise on several other platforms.

If you're looking to optimize what you already have, our MSP automation services provide a structured path to improve system performance without starting from scratch.  You can even take our Automation Readiness Assessment to see your potential ROI from improving your processes.

Because when your automation works the way it should, you gain something most MSPs rarely have: time. Time to think. Time to lead. Time to grow.