How do I upload really large files to Dropbox?

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How I Move Huge Files to Dropbox: Let Me Walk You Through It

So, here’s the thing about Dropbox and mega-sized files: there’s a trick to getting those bad boys uploaded without wanting to pull your hair out. I’ve played with various methods after running into that notorious web uploader limit (yeah, anything past 50GB gets you a “Nope!” banner). But I found a workflow that’s smooth — well, usually.

The Desktop App – For When the Web Hates Big Files

Honestly, the best way to get files somewhere between 50GB and 350GB into Dropbox is to just grab their desktop app. It turns your computer into a Dropbox deposit box.

Here’s how I do it (it’s basically idiot-proof):

  1. Download and install the Dropbox desktop software for your OS (Windows or macOS — doesn’t matter).
  2. That creates a Dropbox folder somewhere on your hard drive. Open it up. Toss your enormous file(s) in there. You can use drag and drop, or the old Ctrl+C/Ctrl+V magic.
  3. Dropbox takes it from there. It’ll start syncing your file, chunk by chunk, to the cloud. You can go grab a snack (or five, depending on your upload speed).

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No fussing with browser timeouts. No mystery progress bars that stick at 98% and then error out. The desktop app is your friend.

What If You’ve Got a File OVER 350GB? (‘Cause Life Happens.)

Ever try uploading a 400GB folder and watch the sync freak out? Yeah. Same. Dropbox flats out on files bigger than 350GB. Even the desktop app throws in the towel.

You’ve got a couple choices here:

  • Crush/compress/split the file: Yeah, age-old “.zip” or “.rar” methods. Not fun.
  • Level up with a cloud drive manager.

After flailing around for a while, I landed on CloudMounter. This tool lets you basically mount Dropbox as if it were another drive on your desktop. The point? You manage all your cloud files from Finder (or Explorer), just like your C: drive.

Once connected, you just move or copy over whatever files you want to stash away — doesn’t matter if they’re super-sized. CloudMounter handles the traffic, and Dropbox’s desktop sync swoops in for the finish.

It boils down to:

  • Install CloudMounter.
  • In Finder, pick the monster file or folder you need in Dropbox.
  • Use drag and drop, or the Apple-style copy-paste (Cmd+C, Cmd+V).
  • The app and Dropbox do their thing together; you can go binge-watch something in the meantime.

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I won’t claim it’s magic, but it does make cloud juggling a little less of a circus act.

TL;DR

  • Regular Dropbox webpage: Nope, won’t handle files over 50GB.
  • Desktop app: uploads files up to 350GB no sweat.
  • If you’ve somehow got files even fatter than that, try CloudMounter or something similar and treat Dropbox like a regular drive for monster moves.

That’s my go-to setup — keeps my sanity mostly intact. Questions? Nightmare stories? Share them below, we all suffer together.

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