Dropbox keeps threatening to delete my files

For the past two years, I’ve been on the receiving end of a passive aggressive win-back campaign from Dropbox. The feud originally started when I migrated away from Dropbox and hence canceled my subscription while leaving them saddled with over a terabyte of my data to carry forever, like a camel in the digital desert. After all, why wouldn’t I? I was assured by their help forums that my files would not be deleted, no matter what:

However, this hasn’t prevented Dropbox from trying to get me back. It all started innocently enough:

Thanks Dropbox, for letting me know and being there to help! Unfortunately, I had no desire to reactivate my account. Over the next couple of years, Dropbox has tried every trick in the book to get me back – they’ve tried letting me know I’m “100x over the limit”, stating things are “pretty urgent” and that I have to “Open ASAP”. I also appreciate the haphazard use of punctuation and emojis in this email chain. So far I’ve received over 50 emails. I’m honestly a bit sad about the person who has to presumably sit and come up with a new email title every week to keep cranking up the tension. At this point, I’m half expecting them to show up at my doorstep with a pleading look.

Seeing as I was not impressed by being 100x over my limit, Dropbox tried 500x next. Surely this would get my attention!

When that didn’t help either, Dropbox went back on its promise and finally threatened to delete my files in a series of countdown emails culminating with this 15 day reminder:

They even tried setting a date!

The date came and went, but conspicuously, my files were not deleted, although the email linked to a more sternly worded support article saying they would eventually delete data if over quota. Clearly the policy had shifted, although the now incorrect answer is still the top search result. So far though, Dropbox decided to just pretend they never sent the previous email chain and went right back to their previous tactic of strongly suggesting an upgrade.

Logging into the web portal, Dropbox gleefully told me I can “Upload anything”, in a bright red alert box, ending with a “Upgrade for more” button. But my files are still there, possibly waiting for when the emails finally get to me and make me resubscribe again.

What’s the lesson here? Perhaps it’s that we shouldn’t trust corporations to keep their word. Or maybe that promising to host files in perpetuity for non-paying customers is a business model with some obvious flaws. Regardless, I’m curious to see how long this digital standoff will last. Will they eventually delete my files, or will I be receiving increasingly desperate emails well into my retirement years? Only time will tell!

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