The other day, I overheard one of our engineers on a call with a customer. The frustration was palpable:
“STOP TRYING TO UPGADE MY COMPUTER! I’M SICK OF IT. EVERY DAMN DAY!!”
We exchanged knowing looks across the office. The engineer hit the mute button, and we laughed—because we get it.
But here’s the thing: computer upgrades are as much a pain for IT teams as they are for end users. What you might not realize is the chaos, strategizing, and occasional existential dread that goes on behind the scenes when it comes to updates.
Why IT Has a Love-Hate Relationship with Updates
For us, computer upgrades are a lot like prescribing pills is for doctors: absolutely necessary, but nobody wants them.
Our department is constantly stuck between two competing goals:
- Keep systems secure – Preventing data breaches and vulnerabilities.
- Minimize disruptions – Keeping the daily workflow as smooth as possible.
And believe me, we hate the fact that an entire industry—cybersecurity—exists because bad actors are always finding new ways to exploit old software.
Sometimes, we long for the “good old days” of upgrades, back when they actually felt exciting. I still remember the buzz around the launch of iChat AV, Boot Camp, and the Mac App Store. Those upgrades brought meaningful new features that made work more efficient or enjoyable. People wanted them because they added value to their day.
These days? Updates are more like the Netflix subscription you begrudgingly pay for but can’t escape. And don’t even get me started on its relatives—Disney+, Hulu, Apple TV, Max…
What Happens When You Dismiss the Upgrade Button
We know why you don’t want to update. It’s inconvenient. It interrupts your flow. It makes you save that half-finished document you’re still debating.
There’s also the mindset of “If it ain’t broke, don’t fix it.” And honestly, we get it. From where you sit, the old software might seem perfectly fine. What you don’t see are the vulnerabilities lurking under the surface—issues that could expose your entire company to a cyberattack.
But here’s what happens on our side every time you click “Remind Me Later”:
- We track it. Yes, we know exactly how many times that button’s been dismissed.
- We analyze patterns. Who’s holding up the fleet update? Who’s the “most improved” in getting updates done on time?
- We escalate when necessary. For the rare few who click “Remind Me Later” hundreds of times, let’s just say there’s a reason we call it the “Wall of Shame.”
The IT Balancing Act
Here’s where the real challenge lies for IT:
- If we delay updates, we’re leaving your systems open to real threats.
- If we rush updates, you risk downtime, compatibility issues, and workflow disruptions.
The reality is, IT departments are constantly walking this tightrope. We do our best to test updates in controlled environments and roll them out at times that cause minimal disruption.
For most customers, this approach works. Typically:
- 75% of users update without a problem.
- 10% need a little extra nudge.
- 5%… well, they become legends on our Wall of Shame.
The Forces Driving Updates
So, why do we push updates so hard if we hate them just as much as you?
It boils down to three key drivers:
- The Threat of Breaches: We know what happens when vulnerabilities are exploited—it’s never pretty.
- The Business Owner’s Bottom Line: They’re the ones paying for downtime, security incidents, and damaged reputations.
- Insurance Companies: Believe it or not, insurers check if your IT environment is secure. If it’s not, they’ll hike your premiums faster than you can say “patch Tuesday.”
These forces are the guardrails that keep us focused on what matters most: protecting your systems while doing our best to keep you happy.
Behind the Scenes: What IT Really Thinks
Here’s the truth: if IT could avoid pushing updates altogether, we probably would. We don’t enjoy hearing groans about downtime or interruptions. We’d rather spend our days solving real problems, building new systems, and finding ways to make your life easier.
But the alternative—letting systems go unpatched—is far worse. It’s a little like letting the inmates run the asylum. Sure, things might seem fine for a while, but when it falls apart, it’s a disaster.
So the next time you see that update prompt, just know:
- It’s not there to ruin your day.
- We’re not thrilled about it either.
- And yes, we’ll probably know if you click “Remind Me Later.”
Inside the IT department, updates are just one of many necessary evils. They’re a hassle for everyone, but they’re also how we keep your business secure and running smoothly. So when you think about dismissing that upgrade button one more time, maybe ask yourself: Do I really need another award? #wallofshame.
Scott Morabito is a technologist and founder of TechTonic. He was trained as a computer scientist and resides in Concord MA
