diff --git a/plugins/providers/virtualbox/action/customize.rb b/plugins/providers/virtualbox/action/customize.rb
index 0bcb84a6d..f2bfda255 100644
--- a/plugins/providers/virtualbox/action/customize.rb
+++ b/plugins/providers/virtualbox/action/customize.rb
@@ -25,11 +25,12 @@ module VagrantPlugins
                 arg.to_s
               end
 
-              result = env[:machine].provider.driver.execute_command(processed_command)
-              if result.exit_code != 0
+              begin
+                env[:machine].provider.driver.execute_command(processed_command + [:retryable => true])
+              rescue Vagrant::Errors::VBoxManageError => e
                 raise Vagrant::Errors::VMCustomizationFailed, {
-                  :command => processed_command.inspect,
-                  :error   => result.stderr
+                  :command => command,
+                  :error   => e.inspect
                 }
               end
             end
diff --git a/plugins/providers/virtualbox/action/sane_defaults.rb b/plugins/providers/virtualbox/action/sane_defaults.rb
index fc3f66ead..1dcac0a74 100644
--- a/plugins/providers/virtualbox/action/sane_defaults.rb
+++ b/plugins/providers/virtualbox/action/sane_defaults.rb
@@ -55,11 +55,19 @@ module VagrantPlugins
         # the given string to the log, and also includes the exit status in
         # the log message.
         #
+        # We assume every command is idempotent and pass along the `retryable`
+        # flag. This is because VBoxManage is janky about running simultaneously
+        # on the same box, and if we up multiple boxes at the same time, a bunch
+        # of modifyvm commands get fired
+        #
         # @param [Array] command Command to run
         # @param [String] log Log message to write.
         def attempt_and_log(command, log)
-          result = @env[:machine].provider.driver.execute_command(command)
-          @logger.info("#{log} (exit status = #{result.exit_code})")
+          begin
+            @env[:machine].provider.driver.execute_command(command + [:retryable => true])
+          rescue Vagrant::Errors::VBoxManageError => e
+            @logger.info("#{log} (error = #{e.inspect})")
+          end
         end
 
         # This uses some heuristics to determine if the NAT DNS proxy should
diff --git a/plugins/providers/virtualbox/driver/base.rb b/plugins/providers/virtualbox/driver/base.rb
index d06898b2d..1e0795739 100644
--- a/plugins/providers/virtualbox/driver/base.rb
+++ b/plugins/providers/virtualbox/driver/base.rb
@@ -108,6 +108,11 @@ module VagrantPlugins
 
         # Execute a raw command straight through to VBoxManage.
         #
+        # Accepts a :retryable => true option if the command should be retried
+        # upon failure.
+        #
+        # Raises a VBoxManage error if it fails.
+        #
         # @param [Array] command Command to execute.
         def execute_command(command)
         end
diff --git a/plugins/providers/virtualbox/driver/version_4_0.rb b/plugins/providers/virtualbox/driver/version_4_0.rb
index 9341a0362..e0ce73cac 100644
--- a/plugins/providers/virtualbox/driver/version_4_0.rb
+++ b/plugins/providers/virtualbox/driver/version_4_0.rb
@@ -129,7 +129,7 @@ module VagrantPlugins
         end
 
         def execute_command(command)
-          raw(*command)
+          execute(*command)
         end
 
         def export(path)
diff --git a/plugins/providers/virtualbox/driver/version_4_1.rb b/plugins/providers/virtualbox/driver/version_4_1.rb
index 6d56c851c..1f80965d2 100644
--- a/plugins/providers/virtualbox/driver/version_4_1.rb
+++ b/plugins/providers/virtualbox/driver/version_4_1.rb
@@ -129,7 +129,7 @@ module VagrantPlugins
         end
 
         def execute_command(command)
-          raw(*command)
+          execute(*command)
         end
 
         def export(path)
diff --git a/plugins/providers/virtualbox/driver/version_4_2.rb b/plugins/providers/virtualbox/driver/version_4_2.rb
index 75f9a664e..d9d3f86f1 100644
--- a/plugins/providers/virtualbox/driver/version_4_2.rb
+++ b/plugins/providers/virtualbox/driver/version_4_2.rb
@@ -127,7 +127,7 @@ module VagrantPlugins
         end
 
         def execute_command(command)
-          raw(*command)
+          execute(*command)
         end
 
         def export(path)
diff --git a/plugins/providers/virtualbox/driver/version_4_3.rb b/plugins/providers/virtualbox/driver/version_4_3.rb
index 306328cb5..5685c0ada 100644
--- a/plugins/providers/virtualbox/driver/version_4_3.rb
+++ b/plugins/providers/virtualbox/driver/version_4_3.rb
@@ -127,7 +127,7 @@ module VagrantPlugins
         end
 
         def execute_command(command)
-          raw(*command)
+          execute(*command)
         end
 
         def export(path)