Upgrading Homestead to VirtualBox 5

As with everything, we need to make a consious decision when we do things. In this case a VirtualBox Guest Additions mismatch has severe performance implications and in my case has halted the synchronizing between Vagrant and OS/X.

_Note on conventions used in this article:

  • console commands are bold and italic:_ which php5-fpm


  • Homestead 2
  • VirtualBox 5 (5.0.0 or greater)
  • Vagrant 1.7.4 (or greater)


  1. Let’s start off by halting Homestead: homestead halt
  2. And next Vagrant: make sure you download the latest version (1.7.4 as of this writing) and install as usual.
  3. Download and install the latest version of VirtualBox (5.0.0 as of this writing).
  4. Now for the tricky bit: upgrading VirtualBox Guest Additions. Let’s bring Homestead back up: homestead up Notice now how it says the Guest Addition version does not match the VirtualBox version?
  5. SSH into Homestead: homestead ssh
  6. Remove any existing packages that we need to build the Guest Additions. (We will install the new versions next.) sudo apt-get remove dkms build-essential linux-headers-*
  7. Remove any remnants of the old Guest Additions: sudo rm -rf VBoxGuestAdditions-*
  8. Now lets install the new replacements for them: sudo apt-get install dkms build-essential linux-headers-$(uname -r)
  9. Great! We have the system prepped, and ready to install the new Guest Additions. In my example I am using the 5.0.0 version, but make sure you use the version that matches your VirtualBox (one command, please excuse the inappropriate line breaks — wish Medium had propper code snippet support, the code blocks they do have break the lists): wget http://download.virtualbox.org/virtualbox/5.0.0/VBoxGuestAdditions_5.0.0.iso
  10. Create a mount point for the ISO: sudo mkdir /media/VBoxGuestAdditions
  11. And mount the ISO (again, this is a single command on one line): sudo mount -o loop,ro VBoxGuestAdditions_5.0.0.iso /media/VBoxGuestAdditions
  12. Now we can finally install the Guest Additions: sudo sh /media/VBoxGuestAdditions/VBoxLinuxAdditions.run
  13. Once this completes successfully, we can clean up: sudo umount /media/VBoxGuestAdditions sudo rm -rf /media/VBoxGuestAdditions rm VBoxGuestAdditions.iso sudo rm -rf /opt/VBoxGuestAdditions-4_
  14. Exit out of Homestead, and restart it: exit homestead halt
  15. Let’s bring it back up: homestead up

And we can rejoice not seeing a Guest Addition version warning! Mission accomplished. Now pat yourself on the back, and get back to work already! 😄


This process also fixes instances of the following error that may be encountered while running homestead up:

==> default: Mounting shared folders…
default: /vagrant => /Users/mike/.composer/vendor/laravel/homestead
Failed to mount folders in Linux guest. This is usually because
the “vboxsf” file system is not available. Please verify that
the guest additions are properly installed in the guest and
can work properly. The command attempted was:
mount -t vboxsf -o uid=`id -u vagrant`,gid=`getent group vagrant | cut -d: -f3` vagrant /vagrant
mount -t vboxsf -o uid=`id -u vagrant`,gid=`id -g vagrant` vagrant /vagrant

The error output from the last command was:

mount: wrong fs type, bad option, bad superblock on vagrant,
missing codepage or helper program, or other error

In some cases useful info is found in syslog — try dmesg | tail or so.