diff --git a/plugins/communicators/ssh/communicator.rb b/plugins/communicators/ssh/communicator.rb
index da43cb23e..b009cb5ca 100644
--- a/plugins/communicators/ssh/communicator.rb
+++ b/plugins/communicators/ssh/communicator.rb
@@ -307,10 +307,11 @@ module VagrantPlugins
         scp_connect do |scp|
           uploader = lambda do |path, remote_dest=nil|
             if File.directory?(path)
+              dest = File.join(to, path.sub(/^#{Regexp.escape(from)}/, ""))
+              create_remote_directory(dest)
               Dir.new(path).each do |entry|
                 next if entry == "." || entry == ".."
                 full_path = File.join(path, entry)
-                dest = File.join(to, path.sub(/^#{Regexp.escape(from)}/, ""))
                 create_remote_directory(dest)
                 uploader.call(full_path, dest)
               end
diff --git a/test/unit/plugins/communicators/ssh/communicator_test.rb b/test/unit/plugins/communicators/ssh/communicator_test.rb
index d6e9d2b85..9139f0439 100644
--- a/test/unit/plugins/communicators/ssh/communicator_test.rb
+++ b/test/unit/plugins/communicators/ssh/communicator_test.rb
@@ -565,6 +565,16 @@ describe VagrantPlugins::CommunicatorSSH::Communicator do
       end
     end
 
+    it "creates remote directory given an empty directory" do
+      file = Dir.mktmpdir
+      begin
+        expect(communicator).to receive(:create_remote_directory).with("/destination/dir/#{ File.basename(file)}/")
+        communicator.upload(file, "/destination/dir")
+      ensure
+        FileUtils.rm_rf(file)
+      end
+    end
+
     it "raises custom error on permission errors" do
       file = Tempfile.new('vagrant-test')
       begin