diff --git a/lib/vagrant/action/vm/customize.rb b/lib/vagrant/action/vm/customize.rb
index 5469fb576..715dedfd5 100644
--- a/lib/vagrant/action/vm/customize.rb
+++ b/lib/vagrant/action/vm/customize.rb
@@ -18,7 +18,13 @@ module Vagrant
                 arg
               end
 
-              env[:vm].driver.execute_command(processed_command)
+              result = env[:vm].driver.execute_command(processed_command)
+              if result.exit_code != 0
+                raise Errors::VMCustomizationFailed, {
+                  :command => processed_command.inspect,
+                  :error   => result.stderr
+                }
+              end
             end
           end
 
diff --git a/lib/vagrant/driver/virtualbox.rb b/lib/vagrant/driver/virtualbox.rb
index 6d43bdffc..deb17daa0 100644
--- a/lib/vagrant/driver/virtualbox.rb
+++ b/lib/vagrant/driver/virtualbox.rb
@@ -76,7 +76,7 @@ module Vagrant
 
       # Executes a raw command.
       def execute_command(command)
-        execute(*command)
+        raw(*command)
       end
 
       # Forwards a set of ports for a VM.
diff --git a/lib/vagrant/errors.rb b/lib/vagrant/errors.rb
index 0fad2ec7f..7d1b099cc 100644
--- a/lib/vagrant/errors.rb
+++ b/lib/vagrant/errors.rb
@@ -334,6 +334,11 @@ module Vagrant
       error_key(:no_base_mac, "vagrant.actions.vm.match_mac")
     end
 
+    class VMCustomizationFailed < VagrantError
+      status_code(61)
+      error_key(:failure, "vagrant.actions.vm.customize")
+    end
+
     class VMFailedToBoot < VagrantError
       status_code(21)
       error_key(:failed_to_boot, "vagrant.actions.vm.boot")
diff --git a/templates/locales/en.yml b/templates/locales/en.yml
index abfce1148..0e9550bc5 100644
--- a/templates/locales/en.yml
+++ b/templates/locales/en.yml
@@ -313,6 +313,16 @@ en:
         clear_shared_folders:
           deleting: Cleaning previously set shared folders...
         customize:
+          failure: |-
+            A customization command failed:
+
+            %{command}
+
+            The following error was experienced:
+
+            %{error}
+
+            Please fix this customization and try again.
           running: Running any VM customizations...
         destroy:
           destroying: Destroying VM and associated drives...