diff --git a/lib/vagrant/action/builtin/box_check_outdated.rb b/lib/vagrant/action/builtin/box_check_outdated.rb
index 87d19a5df..135da550c 100644
--- a/lib/vagrant/action/builtin/box_check_outdated.rb
+++ b/lib/vagrant/action/builtin/box_check_outdated.rb
@@ -20,6 +20,11 @@ module Vagrant
             if !machine.config.vm.box_check_update
               return @app.call(env)
             end
+
+            if !env.has_key?(:box_outdated_refresh)
+              env[:box_outdated_refresh] = true
+              env[:box_outdated_ignore_errors] = true
+            end
           end
 
           if !machine.box
@@ -30,9 +35,17 @@ module Vagrant
           end
 
           if env[:box_outdated_refresh]
-            @logger.info(
-              "Checking if box is outdated by refreshing metadata")
-            check_outdated_refresh(env)
+            env[:ui].output(I18n.t(
+              "vagrant.box_outdated_checking_with_refresh",
+              name: machine.box.name))
+            begin
+              check_outdated_refresh(env)
+            rescue Errors::VagrantError => e
+              raise if !env[:box_outdated_ignore_errors]
+              env[:ui].detail(I18n.t(
+                "vagrant.box_outdated_metadata_error",
+                message: e.message))
+            end
           else
             @logger.info("Checking if box is outdated locally")
             check_outdated_local(env)
diff --git a/plugins/providers/virtualbox/action.rb b/plugins/providers/virtualbox/action.rb
index 34b1b08e0..5339343f1 100644
--- a/plugins/providers/virtualbox/action.rb
+++ b/plugins/providers/virtualbox/action.rb
@@ -307,6 +307,7 @@ module VagrantPlugins
           end
 
           b.use ConfigValidate
+          b.use BoxCheckOutdated
           b.use Call, Created do |env, b2|
             # If the VM is NOT created yet, then do the setup steps
             if !env[:result]
diff --git a/templates/locales/en.yml b/templates/locales/en.yml
index f41d6e559..518640c3a 100644
--- a/templates/locales/en.yml
+++ b/templates/locales/en.yml
@@ -30,11 +30,16 @@ en:
       Loading metadata for box '%{name}'
     box_outdated: |-
       * '%{name}' is outdated! Current: %{current}. Latest: %{latest}
+    box_outdated_checking_with_refresh: |-
+      Checking if box '%{name}' is up to date...
     box_outdated_local: |-
       A newer version of the box '%{name}' is available and already
       installed, but your Vagrant machine is running against
       version '%{old}'. To update to version '%{new}',
       destroy and recreate your machine.
+    box_outdated_metadata_error: |-
+      Error loading box metadata while attempting to check for
+      updates: %{message}
     box_outdated_single: |-
       A newer version of the box '%{name}' is available! You currently
       have version '%{current}'. The latest is version '%{latest}'. Run