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"Upload Failed: We're sorry this didn't work"

  • April 13, 2026
  • 2 replies
  • 41 views
H

I recently migrated all of my Box folders from a university Box account to a personal Box account at the Business level. Folders are shared with maybe 30-ish other people. I use Box Drive on my Mac laptop. Since the migration, I can save new files and have them sync, but every time I try to update an existing file (ppt, word, excel), I get an error message saying “Upload failed: We’re sorry this didn’t work. Try saving again later, and if that doesn’t work, click Save a Copy” with a button for “Save a Copy”. The updates will save locally, so I don’t lose them for now, but they are not synced with Box for others. It doesn’t look like they are saved (i.e. the date last changed is not the most recent date of edits), but when I open the file, the newer version does appear, likely because a temporary file is stored. This same issue is happening with at least two other users of my Box business account.  How do I fix this, without losing all of the temporary files that I’ve created when files haven’t synced/saved properly? Thanks!

2 replies

Rona Box
  • Rona Box
  • Community Manager
  • April 14, 2026

Hi ​@haldre, 

Welcome to Box Community, and we’ll assist in making sure that all changes will update accordingly. 

 

Here are the preliminary troubleshooting steps that’ll fix this issue, 

  • Is Box Drive up to date? 
  1. To install the update, in the system notification, click Update Now. If you have closed the notification or missed it, you can navigate to the search menu by clicking the Box icon in your menu bar or by using the keyboard shortcut Ctrl + Option + Cmd + Space.
  2. From the search menu, begin the update either by clicking Update Available or by clicking the gear icon and then clicking Update. Box Drive then prompts you to close any open Box Drive files and proceed with the update.

Box Drive can also auto-update when it launches. If Drive detects that an update is available while it is starting up, it automatically applies the update without requiring any action on your part. 

 

  • If Box is up to date, please try to log out or log in. If the issue persists, kindly reset your Box Drive application manually. 

 

To manually reset Box Drive: 

  1. Quit Box Drive if it is running.
  2. Download and open the Box Reset Tool zip file.
  3. Open the Box Reset Tool from the Downloads folder.
  4. Click Reset.
    • You should see a prompt stating “Box Drive reset successfully”.
      MacOS_Box Drive_Reset Successful.png
  5. Open Box from your application folder and log back in. 

Note: The Box Reset Tool will write logs of actions performed to your Desktop folder under “Box-ResetTool-logs_(<current day>)”.

 

Once you restart Box Drive, you can review any archived unsynced files and either upload them manually or delete them to free up hard drive space.

 

Hope it helps! Let us know if you need additional assistance. 

H
  • haldre
  • Author
  • New Participant
  • April 17, 2026

Thanks for your response. I checked, and it was already updated. And then I used the Box Reset Tool, which did successfully make a folder with the current day on the label, and I can get to all of my Box folders, but whenever I open a file, it has the same “Upload Failed” error that I described before. Any other suggestions on what to do? 

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