diff --git a/plugins/communicators/ssh/communicator.rb b/plugins/communicators/ssh/communicator.rb
index 373db189a..47d7b9e84 100644
--- a/plugins/communicators/ssh/communicator.rb
+++ b/plugins/communicators/ssh/communicator.rb
@@ -317,10 +317,11 @@ module VagrantPlugins
               else
                 dest = to
                 if to.end_with?(File::SEPARATOR)
-                  create_remote_directory(dest)
                   dest = File.join(to, File.basename(path))
                 end
               end
+              @logger.debug("Ensuring remote directory exists for destination upload")
+              create_remote_directory(File.dirname(dest))
               @logger.debug("Uploading file #{path} to remote #{dest}")
               upload_file = File.open(path, "rb")
               begin
diff --git a/test/unit/plugins/communicators/ssh/communicator_test.rb b/test/unit/plugins/communicators/ssh/communicator_test.rb
index 0cde8b32d..f1c8df03b 100644
--- a/test/unit/plugins/communicators/ssh/communicator_test.rb
+++ b/test/unit/plugins/communicators/ssh/communicator_test.rb
@@ -547,13 +547,24 @@ describe VagrantPlugins::CommunicatorSSH::Communicator do
       file = Tempfile.new('vagrant-test')
       begin
         expect(scp).to receive(:upload!).with(instance_of(File), "/destination/dir/#{File.basename(file.path)}")
-        expect(communicator).to receive(:create_remote_directory).with("/destination/dir/")
+        expect(communicator).to receive(:create_remote_directory).with("/destination/dir")
         communicator.upload(file.path, "/destination/dir/")
       ensure
         file.delete
       end
     end
 
+    it "creates remote directory path to destination on upload" do
+      file = Tempfile.new('vagrant-test')
+      begin
+        expect(scp).to receive(:upload!).with(instance_of(File), "/destination/dir/file.txt")
+        expect(communicator).to receive(:create_remote_directory).with("/destination/dir")
+        communicator.upload(file.path, "/destination/dir/file.txt")
+      ensure
+        file.delete
+      end
+    end
+
     it "raises custom error on permission errors" do
       file = Tempfile.new('vagrant-test')
       begin