diff --git a/Vagrantfile b/Vagrantfile
index 2bc61a5a8..909bebf66 100644
--- a/Vagrantfile
+++ b/Vagrantfile
@@ -25,9 +25,11 @@ Vagrant.configure("2") do |config|
   end
 end
 
-$shell = <<-CONTENTS
+$shell = <<-'CONTENTS'
 export DEBIAN_FRONTEND=noninteractive
 MARKER_FILE="/usr/local/etc/vagrant_provision_marker"
+RUBY_VER_REQ=$(awk '$1 == "s.required_ruby_version" { print $4 }' /vagrant/vagrant.gemspec | tr -d '"')
+BUNDLER_VER_REQ=$(awk '/s.add_dependency "bundler"/ { print $4 }' /vagrant/vagrant.gemspec | tr -d '"')
 
 # Only provision once
 if [ -f "${MARKER_FILE}" ]; then
@@ -35,13 +37,13 @@ if [ -f "${MARKER_FILE}" ]; then
 fi
 
 # Update apt
-apt-get update
+apt-get update --quiet
 
 # Install basic dependencies
-apt-get install -y build-essential bsdtar curl
+apt-get install -qy build-essential bsdtar curl
 
 # Import the mpapis public key to verify downloaded releases
-su -l -c 'curl -sSL https://rvm.io/mpapis.asc | gpg -q --import -' vagrant
+su -l -c 'gpg --keyserver hkp://keys.gnupg.net --recv-keys 409B6B1796C275462A1703113804BB82D39DC0E3' vagrant
 
 # Install RVM
 su -l -c 'curl -sL https://get.rvm.io | bash -s stable' vagrant
@@ -49,19 +51,23 @@ su -l -c 'curl -sL https://get.rvm.io | bash -s stable' vagrant
 # Add the vagrant user to the RVM group
 #usermod -a -G rvm vagrant
 
-# Install some Rubies
-su -l -c 'rvm install 2.2.3' vagrant
-su -l -c 'rvm --default use 2.2.3' vagrant
+# Install latest Ruby that complies with Vagrant's version constraint
+RUBY_VER_LATEST=$(su -l -c 'rvm list known' vagrant | tr '[]-' ' ' | awk "/^ ruby  ${RUBY_VER_REQ:0:1}\./ { print \$2 }" | sort | tail -n1)
+su -l -c "rvm install ${RUBY_VER_LATEST}" vagrant
+su -l -c "rvm --default use ${RUBY_VER_LATEST}" vagrant
 
 # Output the Ruby version (for sanity)
 su -l -c 'ruby --version' vagrant
 
 # Install Git
-apt-get install -y git
+apt-get install -qy git
 
-# Prepare to run unit tests
-su -l vagrant -c 'gem install bundler -v 1.12.5'
-su -l vagrant -c 'cd /vagrant; bundle install'
+# Upgrade Rubygems
+su -l -c "rvm ${RUBY_VER_LATEST} do gem update --system" vagrant
+
+# Install bundler and prepare to run unit tests
+su -l -c "gem install bundler -v ${BUNDLER_VER_REQ}" vagrant
+su -l -c 'cd /vagrant; bundle install' vagrant
 
 # Automatically move into the shared folder, but only add the command
 # if it's not already there.