For months, I've been fighting one Mac machine that syncs with my dropbox account. I have sync to several Windows, Linux and OSX clients, and only one of them exhibits this problem.

Basically, it randomly deletes files. Seriously. Some days I will turn on another machine and be notified that x, x and z files have been deleted. A check online at the event log shows that it was my user from the mac machine that initiated the deletes. At first I thought somebody was playing with that machine, but I've since duplicated the behavior while I was watching. When it syncs, it frequently marks a few (or even hundreds) of files as deleted.

  • The files still exist and are marked with green X's on the Mac in question.
  • They can be undeleted from the dropbox website and they will show back up on all the clients. The next time the trouble mac syncs, they will be deleted again.
  • Usually the same files, but the fileset sometimes changes. Troublesome filesets persist at being trouble until they are undeleted a few dozen times and eventually something happens that it sticks.
  • It's usually in the most recently used folder, but not always the most recently touched files. Sometimes it's untouched files from months back.
  • Dropbox has been uninstalled / re-installed with the latest (1.1.35 at the moment) version, but this has persisted across a dozen upgrades.
  • I have unlinked the box, deleted the dropbox files and started over with a freshly linked and synced dropbox folder. The problem shows up immediately with a random batch of files deleted during the first sync.
  • One other Mac client has exhibited this problem once, but I've been unable to reproduce it there.
  • One other time a folder got stuck marked as syncing and would never finish 3 files. Deleting the folder with dropbox off, then starting dropbox and asking it to sync it again cleared that up.
  • The files in question have no special flags and are of varying file types (pdf, odt, mp3, etc). Some of the files originate from the trouble machine, others were created on other machines. The source doesn't seem to be a defining issue.

Any suggestions? I have to watch the event log every day that that machine gets turned on to see what gets deleted and manually restore them using the website.

  • 1
    Has the troublesome OSX machine got the latest version of Dropbox? - it does not seem to upgrade automatically
    – mmmmmm
    Commented Jun 7, 2011 at 11:06
  • Yes. It has been upgraded manually through several versions of Dropbox and is running the most current (1.1.35) version. See existing bullet points.
    – Caleb
    Commented Jun 7, 2011 at 11:14
  • Remove dropbox from the troublesome mac. Though that is very strange, i have yet to encounter that problem. The drive wouldn't by chance have any bad blocks (sectors) there?
    – robx
    Commented Jun 8, 2011 at 4:36
  • @robx: I have removed it. And I've removed the data and installed and synced from scratch. Same problem. And no I don't think the disk is bad. Also I'm pretty certain that between all the occurrences of this problem the data has been on very different place on the disk, which exhibits no other signs of fault.
    – Caleb
    Commented Jun 8, 2011 at 7:21
  • 2
    Attention anybody with the same problem! This seems to be a common problem and besides the workaround I note below, Dropbox doesn't seem to have resolved the issue. You can help. Answering this question with "I have this problem too" doesn't help because those get deleted as non-answers on StackExchange. However you can sign up for an account and vote this post up so Dropbox can see this is a problem for more than just me and then file bug reports with that link back to it.
    – Caleb
    Commented Apr 11, 2013 at 7:33

2 Answers 2


This problem seems to be linked to "the Turkish issue" (involving both dotted and non-dotted versions of i). There is some kind of duplicate checking mechanism in Dropbox to side step problems with case insensitive file systems. In site of their claim to full UTF-8 support there is at least one bug affecting syncing of folders that contain characters that don't convert from upper to lower case and back round trip using generic algorithms.

Removing all content with the non English ı and İ characters solves this sync issue.

Once everything is in sync again across platforms, adding the content back in as find as long as there is there is not a file that would be ambiguous giving a non-case sensitive file system and a case conversion involving those letters.

  • Do you know whether they are going to fix this or not?
    – samir105
    Commented Jul 24, 2014 at 12:28
  • @samir105 I wouldn't know ;-) I don't work at Dropbox and I am no longer even using the product. This and other things went unfixed too long and I jumped ship. Feel free to bug Dropbox Inc. about this and point them to this question. It's had almost 6K views now and it has been 3 years since I reported this to Dropbox tech support. Last I checked it was still broken and eating files. Meanwhile might I recommend ownCloud? It handles this problem gracefully.
    – Caleb
    Commented Jul 24, 2014 at 12:37

I submitted this to Dropbox support and got the following answer. I have followed all the steps but the first thing it did on login and resync was delete 46 files. I am including this official answer for reference because it does include instructions on removing the extentions and meta data to do a really clean re-install of dropbox on OSX.

There appears to be a problem with the Dropbox software currently installed on your computer. I'm going to have you do a full reinstall and resync to attempt to fix the problem. Let me know if you still experience the issue after that.

First, make sure you save and quit ALL programs that access files in the Dropbox folder.

Here are the steps:

  1. Download the newest version:

  2. Stop the Dropbox desktop application (if needed)

    • Click on the Dropbox icon.
    • Choose Quit/Stop/Exit
  3. Delete Dropbox meta-data folder:

    • To delete this folder open a Terminal (Located at /Applications/Utilities/Terminal for Mac OS)
    • Copy and paste the following lines into the Terminal and press RETURN:

    mv ~/.dropbox ~/dropbox.old

    • This will make this file visible in your home folder and you can remove it by moving it to the trash.
  4. Delete the Dropbox Contextual Menu Item Plugin

    • Open the Finder and select Go to folder... from the Go menu (or press Shift-Command-G)
    • A dialog box should appear. Now copy and paste the following line into the box and press the return key:


    • Finally drag the DropboxHelperTools folder to the Trash and enter your Administrator password if prompted to complete this action.
  5. Reinstall the Dropbox desktop application

    • Open the Dropbox .dmg file and drag the new version of Dropbox to /Applications
    • Restart Dropbox from /Applications
    • Relink your account.

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