When AI Walks Into the Attendance Office (…and Outsmarts the Former Cybersecurity Professional)

When AI Walks Into the Attendance Office

(…and Outsmarts the Former Cybersecurity Professional)

(I prefer my office in "dark mode"...)

Right now I’m riding out what some folks call a “dark night of the soul”, a weird, uncomfortable, humbling season where my long, passionate relationship with Cybersecurity (especially awareness work) has… let’s say… hit pause.

After almost 20 years in Information Security, I’m currently holding it down as an attendance clerk at a middle school.

And honestly?
It has been a riot.

On today’s episode: the day a middle schooler used AI to spoof their parent’s voice and call themselves out sick.

And guess who fell for it?

Me.
Again. 🤣

The Setup: “I’m Just Taking a Break From Cyber, I Said…”

When I stepped out of cybersecurity and into the front office of a middle school, I thought,

“This will be simple. Different kind of stress. Less cyber. More kids. I can breathe.”

Instead, I found myself on the front lines of real-world social engineering , just with shorter humans and louder hallways.

I still introduce myself (at least in my head) as,

“Former cybersecurity pro, current guardian of attendance records, professional chaos surfer.”

I’ve clicked on a phishing test in this job.
Now, I’ve been fooled by a student’s AI-generated parent voice.

If there are any hiring managers reading this: yes, I still want back in the cybersecurity world. And yes, this is my actual life. 😅

The Call: My First AI Parent Spoof

Today, at the absolute peak of morning chaos, I got a voicemail.

Not a live call...a voicemail (which matters, and I’ll explain why).

The message:
“Hi, this is [Parent’s Name]. [Student] isn’t feeling well today, I’m calling to excuse their absence.”

Totally normal.
I know this parent’s voice really well.

Except… something was off.

The Voice Was Perfect - But the Environment Wasn’t

The AI had nailed the parent’s voice and their usual wording. Their tone, phrasing, even the casual way they usually excuse their kid...SPOT ON...

The only difference?

It sounded like they were calling me:

    -From a convertible

    -On the interstate

    -During a windstorm

There was so much garble and background noise that I had to play the voicemail twice. The voice was a little hard to hear but honestly, I just shrugged it off...

“Oh, he’s probably driving or at work today…”

That’s the thing about real life, it’s messy. Phones glitches. People call from noisy places. And when you’re in the middle of a hundred things, “noisy call” doesn’t even rank as suspicious.

Timing: The Absolute Worst Moment to Ask My Brain to Be Smart

This didn’t happen at 9:30 a.m. when things calm down.

It came during the wildest part of my day!!!

  • The morning bell had just rung.

  • First period was starting.

  • The phone was ringing nonstop.

  • There was a line of tardy students at my desk.

  • Parents were calling.

  • Some kids needed band-aids.

  • Others needed to call home.

  • Someone’s dropping off forgotten lunches.

  • I’m trying to get all tardies and absences processed by 8:40 a.m.

In other words...cognitive overload unlocked = boss level.

So I did what any human in that situation would do...I treated the call like all the others, marked the student out, and moved on.

Of course, later it came out.

It wasn’t Dad.
It was the student.
Using AI.  WOOOMP WOOOMP 

And there I was again. The former cyber professional, getting socially engineered by a middle schooler. 

The "Failure" That Isn’t Really a Failure

My first reaction?
Embarrassment. Again!...

“How did I miss this? I know better. This is literally what I used to teach people about.”

But the thing I keep coming back to...and that I wish more organizations truly understood...

This wasn’t a knowledge failure.
It was a human systems failure.

I didn’t fall for the AI call because I don’t understand cyber risk.
I fell for it because -

  • I was under time pressure.

  • I was juggling multiple demands.

  • The call fit a familiar pattern.

  • The “weirdness” was explainable by normal life.

In other words, I reacted like a human being doing 10 things at once.

What This Means for Schools (and Everyone Else)

If kids in middle school are already using AI to spoof parents’ voices, this isn’t a "future threat", it’s a right now problem.

Not just for cybersecurity teams, but for:

  • Schools

  • Front office staff

  • Attendance clerks (hi 👋)

  • Nurses, receptionists, secretaries

  • Anyone who answers phones and makes decisions based on what they hear

We can’t just tell people, “Be more careful.” And call it a day.

We need better process, not just better paranoia.

Some simple, human-friendly improvements might look like...

  • Callback verification:
    If an absence seems even slightly off, call the parent back using the number in the system and not the number that called. (Though, consider that there are AI apps that also spoof phone numbers!)

  • Parent passphrases / PINs:
    A short phrase or code that only the real parent knows, used when excusing absences or making big requests.

  • Clear guidelines for staff:
    “If you notice X, Y, or Z (like extreme background noise, rushed language, new numbers), it’s okay to pause and verify.”

  • Grace for frontline workers:
    Understand that mistakes in high-pressure environments aren’t proof of incompetence, they’re proof that the system is too fragile for the real world.

A Note to My Cyber Friends and Future Bosses

To my cybersecurity people!
If you’ve ever clicked the thing, trusted the wrong voice, or missed the red flag, you’re not alone. The “curse of knowledge” doesn’t protect us from being human.

To any hiring managers reading this...
Yes, I stepped away from cybersecurity.
No, I didn’t stop seeing the world through a security lens.

I’m just on a different battleground right now...where AI, kids, and attendance policies collide.

And honestly?
It’s teaching me more about real human risk than any lab, simulation, or conference ever did.

If you found this story interesting, funny, or slightly terrifying, share it with someone who still thinks “that kind of thing won’t happen here”.

Because it already is.
Right now.
In middle schools.

And sometimes, the person getting outsmarted…
is the one who used to teach everyone else how not to be. 💻📝✨

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