Dropbox Cautionary Tale


This is my first post in a long time. You know, pandemic, elections, world falling apart distractions. Will be prepping for my next AWS cert soon. But in the meantime, I have a cautionary tale about Dropbox.

I love Dropbox. It has saved me so much time. It’s the most reliable synchronizing software I’ve used. But beware of a fatal flaw I came across last week, which was almost a disaster.

I’m a backup fanatic. I have four copies of everything locally, and three more copies of everything in cloud services.

But I did not include my Dropbox folder in that set of backups. Because, you know, Dropbox.

On my 8-year-old MacBook Air (my traveling Mac machine), I have my Dropbox folder on an external drive. The internal drive is simply too small. If I restart the system without the drive connected, I properly get a simple warning, and I temporarily disable it. But last week the machine was already booted up, and the drive was connected. While moving things around to clean the room it was in, the drive got disconnected. I was unaware that this happened, so I did not yet reconnect it.

But Dropbox considered that to mean “delete all Dropbox files.”

All my files were disappearing on all the machines where I had Dropbox installed. I mean like five different machines. I noticed this when a development project I was working on started failing. I saw it was due to files disappearing. Panicked, I scrambled to turn off the automatic start setting of Dropbox on each machine and shut it down.

Too late.

But then I remembered I have the 30 day deletion recovery feature on Dropbox, so I desperately tried restoring. Over a million files. The site could not handle it. Spinning cursor. Spinning. Spinning. Canceling, I then tried restoring subfolders piecemeal. Spinning. Spinning. Error message.

I started digging through the site looking for a number to call to ask if I could get a physical hard drive sent to me with all my deleted files. I never found such an option (still don’t know if that’s available).

More panic.

Had lunch to take a breath. Then I realized, luckily, because the drive was never reconnected all the files were still on that drive! Saved! It took me several days, but now all my files are restored.

And now my Dropbox folder is part of my regular backup process.

I hope this helps others avoid this situation. We already have enough to worry about these days. Stay safe, everyone.


  1. I learned this the hard way as well. I still don’t include my dropbox in my backups, but I just NEVER put my dropbox on an external drive. great post.


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