diff --git a/lib/vagrant/errors.rb b/lib/vagrant/errors.rb
index 5130ef177..1a4e06969 100644
--- a/lib/vagrant/errors.rb
+++ b/lib/vagrant/errors.rb
@@ -668,6 +668,10 @@ module Vagrant
       error_key(:push_strategy_not_provided)
     end
 
+    class RsyncChownCommandError < VagrantError
+      error_key(:rsync_chown_command_error)
+    end
+
     class RSyncError < VagrantError
       error_key(:rsync_error)
     end
diff --git a/plugins/synced_folders/rsync/command/rsync_auto.rb b/plugins/synced_folders/rsync/command/rsync_auto.rb
index b74abf432..9706666de 100644
--- a/plugins/synced_folders/rsync/command/rsync_auto.rb
+++ b/plugins/synced_folders/rsync/command/rsync_auto.rb
@@ -217,6 +217,10 @@ module VagrantPlugins
                 # halt is happening. Just notify the user but don't fail out.
                 opts[:machine].ui.error(I18n.t(
                   "vagrant.rsync_communicator_not_ready_callback"))
+              rescue Vagrant::Errors::RsyncChownCommandError
+                # Error executing rsync chown command
+                opts[:machine].ui.error(I18n.t(
+                  "vagrant.rsync_chown_command_error"))
               rescue Vagrant::Errors::RSyncError => e
                 # Error executing rsync, so show an error
                 opts[:machine].ui.error(I18n.t(
diff --git a/plugins/synced_folders/rsync/default_unix_cap.rb b/plugins/synced_folders/rsync/default_unix_cap.rb
index 1f4d286f7..3bf88049a 100644
--- a/plugins/synced_folders/rsync/default_unix_cap.rb
+++ b/plugins/synced_folders/rsync/default_unix_cap.rb
@@ -23,7 +23,13 @@ module VagrantPlugins
         if opts.key?(:chown) && !opts[:chown]
           return
         end
-        machine.communicate.sudo(build_rsync_chown(opts))
+
+        error_opts = {
+          error_class: Vagrant::Errors::RsyncChownCommandError,
+          error_key: :rsync_chown_command_error
+        }
+
+        machine.communicate.sudo(build_rsync_chown(opts), error_opts)
       end
 
       def build_rsync_chown(opts)
@@ -38,7 +44,7 @@ module VagrantPlugins
         "find #{guest_path} #{exclusions}" \
           "'!' -type l -a " \
           "'(' ! -user #{opts[:owner]} -or ! -group #{opts[:group]} ')' -exec " \
-          "chown #{opts[:owner]}:#{opts[:group]} '{}' + || :"
+          "chown #{opts[:owner]}:#{opts[:group]} '{}' +"
       end
     end
   end
diff --git a/templates/locales/en.yml b/templates/locales/en.yml
index 5af7bdb11..4c5c12409 100644
--- a/templates/locales/en.yml
+++ b/templates/locales/en.yml
@@ -235,6 +235,10 @@ en:
       repeats, then please fix the issue:
 
       %{message}
+    rsync_chown_command_error: |-
+      There was an error while executing find and chown command, when file missing.
+      This may not be critical since rsync chown command sometimes fails, but if this message
+      repeats, then please fix the issue.
     rsync_communicator_not_ready: |-
       The machine is reporting that it is not ready for rsync to
       communicate with it. Verify that this machine is properly running.