The Day I Feared for a Long Time: When Our Room Booking System Finally Broke

There is a specific kind of failure you carry with you long before it happens.

Not a dramatic failure.
Not a public one.

It is the system you know is fragile. The one that mostly works, but never confidently. The one you avoid touching because you are not sure what will happen if you do.

For me, that system was Evoko.

For years, our meeting rooms ran on a setup that felt increasingly brittle. Aging devices. Thin documentation. A vendor roadmap that did not inspire much confidence. It worked well enough that people tolerated it, but not well enough that I ever trusted it.

Every time a room panel froze.
Every time a calendar did not sync.
Every time someone asked why a room showed as available when it was not.

I felt it.

And I knew the day would come when it would not be a small issue. It would be a real failure.

That day finally arrived.

When “Mostly Working” Stops Working

The failure itself was not dramatic.

No alarms. No obvious crash.

Just the realization that rooms were not updating, panels were not syncing, and the usual restarts were not helping. It became clear that this was not a one off issue.

This was accumulated technical debt finally surfacing.

The hardest part was not the outage.

It was the confirmation.

I had known this was coming.

The Risk Was Not the Technology

The real concern was never just Evoko failing.

Room booking systems are trust infrastructure. When they fail, people do not think about software limitations. They question operations. They question reliability. They question whether the space is being run well.

In a flexible workspace, the basics matter. If the rooms do not work, nothing else really matters.

Choosing to Fix the Root Problem

When it broke, there were two options.

Patch it and buy time.
Or finally understand it end to end.

I chose the harder option.

Instead of treating it as a vendor support problem, I treated it as an architectural one. I rebuilt Evoko Home from scratch. I self hosted it. I reconnected it directly to Google Workspace. I traced errors through logs, permissions, and configurations until they made sense.

What became clear quickly was that Evoko does not fail loudly. It fails in small, specific ways. Missing permissions. Incomplete scopes. Assumptions that are not documented anywhere.

Each fix uncovered the next issue.

Accepting the EULA triggered authorization errors.
Adding rooms failed even with correct addresses.
Importing rooms required permissions that were never mentioned.
User sync exposed another missing scope.

None of these were obvious until you hit them.

What Really Broke

At some point in the process, it became clear that this was not just a technical problem.

I had known this system was fragile.
I had known it was under documented.
I had known that very few people actually understood it.

And I let it run anyway because it had not forced the issue yet.

This time, it did.

Rebuilding With Clarity

Eventually, it stabilized.

The server held.
Rooms imported correctly.
Devices began reconnecting one by one.

Some came online immediately. Others took more time and manual attention. But the system worked.

More importantly, it was no longer a black box. I understood how it worked, how it failed, and how to fix it.

That changed everything.

The Real Takeaway

This was not really about Evoko.

It was about the cost of carrying quiet risk in critical systems.

Anything you hope will keep working eventually stops doing so.
Anything you do not fully understand becomes a liability.
Anything fragile will eventually demand attention.

The day I had worried about for a long time finally arrived.

And once it did, it stopped being something to fear.

Kenny Kane

Kenny Kane is an entrepreneur, writer, and nonprofit innovator with 15+ years of experience leading organizations at the intersection of business, technology, and social impact. He is the CEO of Firmspace, CEO of the Testicular Cancer Foundation, and CTO/co-founder of Gryt Health.

A co-founder of Stupid Cancer, Kenny has built national awareness campaigns and scaled teams across nonprofits, health tech, and real estate. As an author, he writes about leadership, resilience, and building mission-driven organizations.

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