VirtualBox Randomly Stopped Working

Written on February 23, 2018

[ virtual-environments wwe ]

I have no idea why, but yesterday when I tried opening VirtualBox to play around, my MacBook Pro told me that it failed to open. Huh? Whatever, let me reboot and try again… Failed to open! Ok, ok – let me google it this. What do I write? “VirtualBox won’t open.” Too general… Oh, I know! Try opening it in Terminal.

cd /Applications/
open VirtualBox.app/
  LSOpenURLsWithRole() failed with error -10810 for the file /Applications/VirtualBox.app.

Sweet, at least it gave me something specific to google.

Hmm, seems like everyone thinks things like this could be a permissions problem. I will check to make sure my Mac’s security settings allow apps from sources other than Apple. Yes, it does. Well, let’s look in Terminal:

ls -l | grep VirtualBox
  drwxr-xr-x   3 krbn  someNumber  102 Feb 13 13:19 VirtualBox.app

Looks like everyone has permission to read and execute… That group looks a little weird, so maybe that’s the problem.

# Attempt 1: there is an admin group; try that
sudo chgrp -R admin VirtualBox.app/
open VirtualBox.app/
  LSOpenURLsWithRole() failed with error -10810 for the file /Applications/VirtualBox.app.
  
# Attempt 2: wheel
sudo chgrp -R wheel VirtualBox.app/
open VirtualBox.app/
  LSOpenURLsWithRole() failed with error -10810 for the file /Applications/VirtualBox.app.
  
# Ok... Change it back and try something else
sudo chgrp -R someNumber VirtualBox.app/

The other solution to similar issues was to reinstall VirtualBox. The first time I installed VirtualBox, I did so manually…but I wonder if you could just use HomeBrew? One quick google later: yes, you can.

brew cask install virtualbox
  ==> Satisfying dependencies
  ==> Downloading http://download.virtualbox.org/virtualbox/5.2.6/VirtualBox-5.2.6-120293-OSX.dmg
  ######################################################################## 100.0%
  ==> Verifying checksum for Cask virtualbox
  ==> Installing Cask virtualbox
  ==> Running installer for virtualbox; your password may be necessary.
  ==> Package installers may write to any location; options such as --appdir are ignored.
  ==> installer: Package name is Oracle VM VirtualBox
  ==> installer: Upgrading at base path /
  ==> installer: The upgrade was successful.
  🍺  virtualbox was successfully installed!

Nice! Let’s take a look.

open VirtualBox.app

Success! And my Ubuntu VirtualBox is still there: double win!

Side Note: I noticed that the user and group are different when installing with HomeBrew.

ls -l | grep VirtualBox
  drwxr-xr-x   3 root    admin                 102 Feb 23 09:48 VirtualBox.app