Close-up photo of a 3.5-inch floppy disk

In the mid-90s, Darren landed his first corporate job at a company that sold IT systems to insurance brokers. Their software ran on servers about the size of small chest freezers—outdated by the 70s, let alone the 90s. Every month, they'd push out software fixes by sending each customer between 3 and 15 numbered floppy disks. The customers would have to insert the first disk, type UPDATE into the console, and wait for "Insert Disk Number X" prompts to appear on screen.

It wasn't slick, but it worked. The firm even offered a recycling service for the hundreds of disks that eventually built up at customer sites.

While working there, Darren became unfortunately well acquainted with one particular insurance broker, Mr. Lasco. The man refused all offers of training ("Too expensive!") and paid support ("You don't know enough!"), and was too good to read instructions, but could always be counted on to tie up some poor tech support rep's phone every time a new update went out. He never let them charge the call against his company's account, or even thanked anybody for the help. When told about it, management just shrugged their shoulders. Mr. Lasco's firm did have a big contract with them, after all.

Early one Monday morning, Darren answered his phone, only to receive an ear-splitting tirade. As Mr. Lasco ranted, Darren held in a sigh and used the time to start filing a support ticket.

"What's the nature of your problem, sir?" he asked during the gap in which Mr. Lasco paused to breathe.

"I—it's—your damn update won't work! Again!" Mr. Lasco sputtered. "My machine is full!"

Darren frowned. That wasn't an error message that the update process would ever throw. "'Full?' Hmm, maybe one of the server's hard drives is out of disk space? Maybe you need to—"

"No, you fool, it's full! It's FULL!" Mr. Lasco snapped. "I KNEW this would happen eventually! Do you know how much money I'm losing right now with this thing down? I want one of your people to come out here and fix this immediately!"

The demand prompted an eyeroll from Darren, who already knew Mr. Lasco would never pay for a consultant's time. Still, this was a perfect way to get him off the phone. "Why don't I forward you to your sales rep?"

To Darren's amazement—and pity—a software engineer was dispatched within the hour to drive several hundred miles to Mr. Lasco's site, with instructions to call Darren with updates.

By late afternoon, the call came. The engineer was laughing so hard, he couldn't talk.

"Is everything OK?" prompted Darren.

"Wait'll you hear this." The engineer struggled to breathe. "There's a gap in the server casing. All this time, Lasco's been inserting update disks into the server, and couldn't force any more in. I popped the case open, and swear to God, there must be a few hundred disks crammed in there, easy. Years of updates!"

Darren joined in the mirth, but it was short-lived. The poor engineer had to spend 7 hours onsite carefully extracting floppy disks wedged between drives and memory cards, sorting them, then applying the updates in order.

The one silver lining to the whole affair was that Mr. Lasco never called them again.

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