When Windows Quietly Changes, RMM Breaks on the Frontline

Keith Szot
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There's a particular moment in technology when things shift quietly. You don't hear an alarm. Gartner doesn't send you a postcard. It just happens in the background, and only later do you look up and realize the world is now running on slightly different rules. Windows is going through one of those moments right now, almost in stealth mode.

For most of its long, complicated life, Windows devices were built for people. They lived on desks, or in cubicles, or in back offices. Someone logged in. Someone typed things. Someone complained when something broke. The tools we built around them reflected that reality. They were all about profiles and policies and patches and the gentle art of remote access and control.

If you grew up in IT, you learned that pattern the same way a kid learns the neighborhood streets.

But if you walk into a store or restaurant today, you see something different. Windows is still there, but it's living a very different kind of life. It's tucked under counters, behind menu boards, inside kiosks, on small industrial terminals. These devices serve hundreds or thousands of people a day without ever shaking hands with a single “user.”

They don't ask questions. They don't care about personalization. They don't take coffee breaks. Their entire purpose is to do a specific job, reliably, for years at a time.

And that's where you start to feel the gap.

New Realities for the Frontline, The Same RMM Tools 

Most companies still use the same remote monitoring and management (RMM) tools for these frontline machines that they use for employee laptops and workstations. It's the only option anyone ever gave them. It feels sensible because it's familiar. You put an agent on the device and off you go. If something drifts, you fix it. If something breaks, you remote in. If you need to schedule updates, you cross your fingers and hope Windows cooperates.

This worked when the stakes were lower. It worked when the device had a human sitting next to it. It worked when downtime meant someone’s afternoon was slightly less productive.

But somewhere in the middle of the last decade, the stakes changed. A POS terminal going down today doesn't inconvenience a person. It halts revenue. A digital menu board freezing during a promotion doesn't irritate an employee. It confuses two hundred hungry customers. A kiosk glitch isn't a support ticket. It's an interruption of an entire service lane.

The frontline moved the goalposts, but the tooling stayed where it was.

People who have spent their careers in RMM land feel this tension most of all. They know their tools inside and out. They know how to script their way out of trouble. They have built entire mental models around fixing issues reactively. And they can do incredible things with the tools they have. You have to respect that.

But even they will admit, usually after a deep sigh, that something about this old approach feels a little too much like fighting the tide.

A dedicated device wants a known state, not a fixable one. It wants predictability, not flexibility. It wants to recover on its own, not wait for a human to remote in. It wants to behave like an appliance, not a workstation.

Once you see these machines for what they have become, the traditional approach starts to look slightly out of place. Not wrong exactly. Just misaligned with the physics of the job.

If you have ever sat with a restaurant IT team during a Saturday lunch rush, you know exactly what I mean. They're not interested in registry keys or group policy nuance. They want to know that every device on the floor will hold steady for the next ninety minutes. Reliability is not an aspiration in that moment. It's a necessity.

The Shift in Windows Management Infrastructure

What makes this even more interesting is that no one in the industry has named this shift yet. There is no “dedicated Windows fleet management” category. There is no set of tools purpose-built for how these devices actually live. The RMM vendors gesture toward it and say they support kiosks and POS and signage. And they do. But they support them the same way you can technically tow a boat with a Yugo. It works right up until the moment it doesn't, and then you learn something important about torque.

I don't think we're looking at a rebellion here. This isn't about throwing out the past. The past served us well. But there is a quiet evolution underway in how Windows is used in the physical world. These devices are no longer sidekicks to humans. They're becoming infrastructure in their own right.

And infrastructure needs a different kind of care.

The reason we're talking about this now: The shift is already happening out in the field. The frontline tells the truth before the tooling does. And if you listen to the people who keep these devices running, you hear the same thing again and again. They need something built for the world they're actually operating in, not the world Windows grew up in.

It's a good time to rethink some assumptions. It's a good time to question the default tools.

And it's a good time to pay attention to the edge, because the edge is where Windows is being reinvented quietly, steadily, and in plain sight.

We'll share more soon.

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Keith Szot
Keith Szot
Keith is the geek-in-residence behind Esper’s platform evangelism, bringing clarity, curiosity, and deep technical chops to the world of dedicated device management. He’s on a mission to help OEMs, developers, and enterprise IT teams rethink what’s possible at scale — whether that means migrating from legacy platforms, flipping fleets, or building something completely bespoke. Keith’s journey spans decades of platform innovation. Before joining Esper, he led product at a developer tools startup acquired by Symantec, then spent years at Microsoft working on MSDN, CryptoAPI, Windows CE, and Windows Mobile. He’s coded for everything from PDP-11s to TRS-80s, but he’s still happiest when staging an OTA that Just Works™
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