Dropbox: Certain Files Won’t Synchronize

Here’s a very interesting problem I encountered just last week. I was speaking to a colleague over the phone, and she told me that she had placed a particular document in a folder that we both shared on Dropbox. I looked into that folder, but was unable to locate the file that she spoke of. At that point, I realized that the Windows client really had no way of reporting whether it synchronized properly, or not. No matter what I did, the Dropbox client was convinced that everything was synchronized.

Since I wasn’t getting much information from the desktop client, I decided to log into the website. Surprisingly, the file was visible from the web interface – but it wasn’t appearing on my computer. Here’s what it looked like, roughly:

A word document titled "5E:Dolphins.docx" can be seen in the Dropbox web interface.

Notice anything… uncommon? It’s not often that I see colons in filenames, and so the sighting stood out to me. I then recalled that my colleague used a Mac, rather than a PC. I had a feeling that the colon character was invalid in Windows, and I decided to test my theory.


Sure enough, Windows blocked me from creating a text file with a colon in the filename, and it showed me the following message:

A filename cannot contain any of the following characters:
\ / : * ? ” < > |

To fix the problem, I simply asked my colleague to remove the colon from the filename. As soon as she did, Dropbox downloaded the file to my computer, and all was well. It turns out that this problem is well documented on the Dropbox help site, and that they even created a tool that helps identify problem files.

In the end, I feel it is Dropbox’s responsibility to improve the way the client reacts to such problems. Without my background in Computer Science, I probably wouldn’t have discovered the source of the problem within a reasonable time. Unfortunately, it seems that the issue isn’t getting many votes within Dropbox’s suggestion forum. Let’s hope they decide to implement it anyway, to improve the quality of their service.

See Also

Dropbox Help: Why aren’t certain files on one computer syncing to another?