diff --git a/plugins/provisioners/file/provisioner.rb b/plugins/provisioners/file/provisioner.rb
index 237e32043..7b997a7dc 100644
--- a/plugins/provisioners/file/provisioner.rb
+++ b/plugins/provisioners/file/provisioner.rb
@@ -3,12 +3,25 @@ module VagrantPlugins
     class Provisioner < Vagrant.plugin("2", :provisioner)
       def provision
         @machine.communicate.tap do |comm|
+          destination = expand_guest_path(config.destination)
+
           # Make sure the remote path exists
-          command = "mkdir -p %s" % File.dirname(config.destination)
-          comm.execute(command) 
+          command = "mkdir -p %s" % File.dirname(destination)
+          comm.execute(command)
 
           # now upload the file
-          comm.upload(File.expand_path(config.source), config.destination)
+          comm.upload(File.expand_path(config.source), destination)
+        end
+      end
+
+      private
+
+      # Expand the guest path if the guest has the capability
+      def expand_guest_path(destination)
+        if machine.guest.capability?(:shell_expand_guest_path)
+          machine.guest.capability(:shell_expand_guest_path, destination)
+        else
+          destination
         end
       end
     end