As recommended on kvz.io I have been using vagrant-vbguest to automatically update my Virtual Box Guest Additions.

I installed LMDE 2 (Linux Mint Debian Edition) on my laptop today and tried to install the plug-in but I run into some problems and wanted to document my solution. Really all that was required was installing two extra packages:

sudo aptitude update
sudo aptitude install ruby-dev zlib1g-dev
sudo vagrant plugin install vagrant-vbguest