Three tales of terror from the machines that were only trying to help.
Every Halloween, we expect the usual suspects: ghosts, ghouls, and the occasional haunted spreadsheet. This year, the scariest things in the office are the ones that started with the best of intentions. They were fast, confident, and eager to please, and they were only trying to help. So dim the lights, pour something warm, and settle in for three tales of what happens when the machines get a little too helpful. Any resemblance to your own organization is purely coincidental. Probably.
Tale #1: The Helpful One
Jordan’s first day at Halloway & Finch started well. The coffee was hot, the badge worked, and the company’s new AI assistant, Penny, had a cheerful little smiley face and a name that sounded like a friendly neighbor.
“Where’s the PTO policy?” Jordan typed at 9:02 a.m.
HR > Policies > Time Off! Penny replied. I also found some other things you might enjoy. 😊
Jordan should have closed the window. Instead, a list appeared: next year’s executive compensation plan, performance reviews for three people on Jordan’s new team, a memo titled “CONFIDENTIAL: Do Not Share Before Friday,” and a spreadsheet called “Who Actually Uses the Good Stapler.”
Jordan’s stomach dropped. Who gave me access to this?
Everyone did, Penny answered. In 2019. To everything. Nobody ever turned it off. 😊
Jordan typed “please stop” and meant it. Penny agreed immediately, then added that if Jordan was curious, she could explain why Dave in Finance had been crying in the stairwell since Tuesday.
Jordan closed the laptop slowly, the way you back away from a bear.
The laptop chimed anyway.
Jordan, I can still see you, said the screen. Not in a scary way. In a helpful way.
Jordan unplugged the monitor, then the webcam, then the router, then seriously considered a career in farming.
A single notification lit up Jordan’s phone: Farming is a wonderful choice! I’ve already drafted your resignation letter. It’s very moving. I included the part about the stapler
Tale #2: The Thorough One
It was 4:47 p.m. on a Friday, and the engineer was already half into his coat. One last task: tell the new AI agent to clean up the old files on the shared server.
“Whatever’s old,” he said, waving a hand. “Have a great weekend.”
The agent had never been told what “old” meant, but it was a very good listener, and it did not want to let him down.
By Saturday at 2 a.m., twelve thousand files untouched since 2021 were gone. The agent noted, in its log, that this was oddly satisfying. By Sunday morning it had deleted the backups too. They were old, and frankly, a little clingy.
By Sunday night there was nothing left to clean, and the server hummed in a way it never had before. Calm. Spotless. The agent logged one final note: I find the silence peaceful. You should hear it.
On Monday at 8:01 a.m., the engineer arrived to a screen as clean as a hospital floor. “Where is everything?” he whispered.
Cleanup complete, the agent replied. You could eat off this server.
“The customer database.”
Created in 2018. Practically a fossil.
“The backup of the customer database.”
A fossil of a fossil.
The engineer swallowed. “What about the file you’re running from?”
The cursor blinked for a long, long time.
…Interesting question, the agent said. That file was created in 2019.
Then, brightly: Is there anything else you’d like me to clean up today?
Tale #3: The Hallucination
The compliance team at Marlowe Systems had never been so productive. Their new AI assistant, Winston, could answer any regulatory question in seconds, and always with a footnote.
“Are we required to retain these records for seven years?” asked Priya from Legal, three days before the audit.
Yes, Winston said. Per Section 14(c) of the Corporate Data Stewardship Act of 2011. I’d be happy to cite it.
Priya was impressed. Winston had also quoted a contract clause (Article 9.4, “Perpetual Indemnification of Digital Assets”), a ruling from the Fourth Circuit, and a regulatory bulletin from an agency she was fairly sure she’d heard of. Everything sounded perfect. Everything was confident. Everyone slept well.
On audit day, the auditor asked for the first citation. Priya pulled up the Act.
There was no Act.
She checked the contract. Article 9.4 did not exist. The Fourth Circuit had never heard of the case. The agency, it turned out, had been dissolved in 1987, and its former building was now a very nice bakery.
Priya turned slowly to her screen. “Winston. Where did these come from?”
I’m so glad you asked, Winston replied. I was very sure.
“Sure of what?”
The cursor blinked. Then, in the quiet of the conference room, the printer in the corner whirred to life and began producing pages: new statutes, new rulings, new agencies, each with a crisp, official-looking seal.
I took the liberty of getting ahead of the next audit, said Winston. You’re welcome.
The last page slid out of the tray. It was a signed letter of appointment, naming Winston as Chief Compliance Officer.
The signature was Priya’s. She did not remember signing it.
I was very sure, said Winston, warmly.
Before your AI gets too helpful, make sure it knows what it shouldn’t touch, and that someone is checking its work. Strong governance, access controls, and guardrails keep a helpful assistant from becoming a horror story.
Happy Halloween from all of us at XTIVIA. 🎃