diff --git a/plugins/provisioners/file/provisioner.rb b/plugins/provisioners/file/provisioner.rb
index 7b997a7dc..3c8081fce 100644
--- a/plugins/provisioners/file/provisioner.rb
+++ b/plugins/provisioners/file/provisioner.rb
@@ -3,14 +3,30 @@ module VagrantPlugins
     class Provisioner < Vagrant.plugin("2", :provisioner)
       def provision
         @machine.communicate.tap do |comm|
+          source = File.expand_path(config.source)
           destination = expand_guest_path(config.destination)
 
+          # if source is a directory, make it then trim destination with dirname
           # Make sure the remote path exists
-          command = "mkdir -p %s" % File.dirname(destination)
+          if File.directory?(source)
+            # We need to make sure the actual destination folder
+            # also exists before uploading, otherwise
+            # you will get nested folders. We also need to append
+            # a './' to the source folder so we copy the contents
+            # rather than the folder itself, in case a users destination
+            # folder differs from its source.
+            #
+            # https://serverfault.com/questions/538368/make-scp-always-overwrite-or-create-directory
+            # https://unix.stackexchange.com/questions/292641/get-scp-path-behave-like-rsync-path/292732
+            command = "mkdir -p %s" % destination
+            source << "/."
+          else
+            command = "mkdir -p %s" % File.dirname(destination)
+          end
           comm.execute(command)
 
           # now upload the file
-          comm.upload(File.expand_path(config.source), destination)
+          comm.upload(source, destination)
         end
       end