Dropbox: when I fail to upload plenty of files and want to retry…

A usability issue I found in Dropbox and how it could be fixed

I use Dropbox to backup my files. I have experienced the disaster of losing an important file without another backup stored in the cloud to save my life so I know the pain. You don’t want to find a 500MB JSON file which you wrote hundreds of lines of Python scripts to parse from the Internet disappear when you’re in an urgent need, just because of some unexpected, mysterious reasons that you never know… Anyway, just backup everything.


So I generate huge traffic everyday to my Dropbox account, with a huge bunch of files including a variety of formats. Here comes the problem: sometimes the files fail to be uploaded due to local location changes/large size/unknown reasons. Dropbox will give me a notification like this:

The notification bar on the bottom of the page

OK. Let’s go back to find the file and retry uploading.

After scrolling back and forth for a while, I finally found the file that failed to be uploaded. The scrolling bar is not displayed in this screenshot, but I can tell you that it’s short like a point… Just because I uploaded too many files at one time!

I found it by staring at the screen like (⊙_⊙). Had to upload it again. The hover bubble gave me a friendly but not that useful suggestion. Oh, I saw a “Try the basic uploader”.

Nice. Although it cost me a couple of extra clicks, it worked. “Choose a file, and then…” It ended up that the file was uploaded to the root directory in my Dropbox instead of the folder it should be located in.


I’ve also used Google Drive. Dropbox has better experience than Google Drive on merging the folders with duplicate contents. That’s why many people also choose Dropbox as a version control tool. However, Google Drive has a more intuitive way to solve the “fail to upload” problem: a Retry label right next to the item that needs to be re-uploaded.

I can’t find a file that can’t be actually uploaded… But the way that the Retry option is directly associated with the item is the same.

So I think Dropbox would need to fix two things:

  • How users can quickly locate the uploading errors without scrolling too much if they upload lots of files at one time;
  • How users can retry uploading more easily with fewer clicks.

Maybe simply aggregating all the errors on the top of other successfully uploaded files can help users shorten the scrolling distance. Of course a Retry label should be an inline element next to the relevant item.

But this idea may cause confusion: “Retry All”, does this “All” also include those files that were uploaded successfully? From the perspective of usability, it shouldn’t. But from the visual perception standpoint, it should.

Or, separate all the errors and successful uploaded files into two sections. The mockup I created looks a little bit off but it could help you understand what I mean by “separate”.

I may come up with better solutions later so let’s make it open-ended for now.

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