It depends. If I begin using something new (say, Go) and end up using it a lot then I will install it on develop and repackage it into the "develop" box again.

It depends. If I begin using something new (say, Go) and end up using it a lot then I will install it on develop and repackage it into the "develop" box again. This takes about 5 minutes. If it's something specific for a project (i.e., a jekyll website), I just write a quick shell script to install jekyll in the Vagrantfile for that project instead of repackaging the whole box. As for your second question, yes, you would have a specific Vagrantfile/box for a project where you need a specific enviroment. My "develop" box is a general case. Here's a (slightly modified) example of a Vagrantfile that I use with a project: https://gist.github.com/taylorlapeyre/5399974 https://gist.github.com/taylorlapeyre/5399974