On November 7th, 2025, I lost a decade of my work and personal history in what should have been a routine restart.

I’ve been an Apple user since I was 12 years old. I’ve owned and operated my music school, ABC Academy of Music (music-lessons.ca), for 22 years. I’ve built my entire business and personal computing life on Apple’s ecosystem—Macs, iPhones, iPads, iCloud, the full productivity suite. I’ve had enough faith in Apple to be a shareholder.

In all those years, Apple has never let me down the way it has now.

What Happened

My Mac maxed out its RAM. The system generated low memory alerts. I did what anyone would do: I force quit applications, emptied the Trash, and restarted.

When the machine came back up, it appeared to be reinstalling macOS. When the process completed and I reached my desktop, everything was gone. Not just the files on my desktop. Everything in iCloud too.

At first I assumed the files simply hadn’t synced yet—that the machine needed to reconnect to iCloud. This was exactly why I used iCloud in the first place: not just as a backup, but so I could access my files anywhere, on any machine. That’s what Apple promises. That’s what I paid for.

But the files never came back. Whatever happened during that crash didn’t just affect my local machine. It wiped my iCloud storage too.

What I Lost

Custom CRMs I built over more than a decade to run my multi-location music school. Paid client lists and active student records. Student reporting systems and databases. Financial records spanning years of business operations. Our certificate of incorporation. Tax filings. Marketing materials, custom designs, logos, templates, and tools developed over 10+ years.

Personal files too. My taxes. My CV. University transcripts. Recipes that are deeply important to me as an amateur chef—some handed down, some developed through years of trial and error.

Strangely, some aspects of iCloud appear completely untouched. My Photos are fine. But Keynote, Pages, and Numbers have only limited files restored. The inconsistency is baffling, and no one has been able to explain it.

Three Weeks of Trying

It’s now been three weeks since the incident. I’ve spent countless hours on calls with Senior iCloud technicians. They’ve been professional. They’ve escalated my case. They’ve told me they’re doing everything they can.

But what they’ve restored amounts to a fraction of my actual data and files—and none of it is what I need to run my business or access my personal history.

Here’s what Apple support has refused to do:

  • Connect me with the iCloud engineers who actually understand the system architecture
  • Provide me with a disk image of my iCloud drive so I can work with independent specialists
  • Explain how a local system crash could propagate to cloud storage

Even the Experts Are Stumped

I’ve taken my computer to forensic data recovery specialists. Even they were unable to make sense of why this happened or offer a solution. The data was supposed to be living in Apple’s cloud—not dependent on my local machine. The experts I consulted could not explain how a local crash could wipe cloud storage, and they had no path forward for recovery.

This leaves Apple as the only entity that can investigate what happened and potentially recover my data. And Apple won’t connect me to anyone who can.

The Deadline

November 7th was the incident date. Cloud storage systems typically have a 30-day window before deleted data is permanently purged. That deadline is approximately December 7th—days away.

If Apple doesn’t act before that window closes, everything could be gone forever.

Why I’m Sharing This

I’ve reached out directly to Tim Cook, Eddy Cue (the SVP who oversees iCloud), and Apple’s PR team. I’ve outlined the situation and explained the steps I’m taking.

I don’t want to make noise about this. It’s time I don’t have, and it’s not in anyone’s interest. I just want my data back—what I paid for, what I spent years creating.

But three weeks of working through normal channels hasn’t connected me to anyone who can actually help. Time is running out. Regretfully, I feel I must escalate this publicly because I have no other options.

The Question

How does a local system crash wipe cloud storage? Isn’t the entire point of the cloud that it’s separate from your local machine? Isn’t that what we’re paying for?

Even forensic data experts couldn’t answer these questions. Only Apple can.

I’m sharing this because other people deserve to know: iCloud may not work the way you think it does. And if it fails, getting help may be harder than you expect—even if you’ve been a loyal customer for decades.

What I Want

I want engineering resources assigned to investigate this and attempt deep recovery. I want the disk image so independent specialists can work in parallel. I want to understand what happened.

Most of all, I just want what’s mine.

If you’ve experienced something similar, or if you have advice for getting engineering-level help at Apple, I’d appreciate hearing from you. And if you think this story is important, please share it.

Time is running out.