diff --git a/plugins/guests/windows/cap/rsync.rb b/plugins/guests/windows/cap/rsync.rb
index aa9f1bcdf..bf2456249 100644
--- a/plugins/guests/windows/cap/rsync.rb
+++ b/plugins/guests/windows/cap/rsync.rb
@@ -13,7 +13,7 @@ module VagrantPlugins
           machine.communicate.tap do |comm|
             # rsync does not construct any gaps in the path to the target directory
             # make sure that all subdirectories are created
-            comm.execute("mkdir '#{opts[:guestpath]}'")
+            comm.execute("mkdir -p '#{opts[:guestpath]}'")
           end
         end
       end
diff --git a/test/unit/plugins/guests/windows/cap/rsync_test.rb b/test/unit/plugins/guests/windows/cap/rsync_test.rb
index d32568c40..e55006512 100644
--- a/test/unit/plugins/guests/windows/cap/rsync_test.rb
+++ b/test/unit/plugins/guests/windows/cap/rsync_test.rb
@@ -19,7 +19,7 @@ describe "VagrantPlugins::GuestWindows::Cap::RSync" do
 
   describe ".rsync_pre" do
     it 'makes the guestpath directory with mkdir' do
-      communicator.expect_command("mkdir '/sync_dir'")
+      communicator.expect_command("mkdir -p '/sync_dir'")
       described_class.rsync_pre(machine, guestpath: '/sync_dir')
     end
   end