Make sure you are using
Windows, and are running spigot's run.bat in
NOGUI mode
Make sure your server has ran, and stopped using the stop command, at least once.
Then drag and drop the plugin into your server's plugin folder.
Now, the important bit: Navigate to your server's log file, at
Server\logs\latest.log
Set this file to
READ ONLY (Right click->Properties->Tick "Read Only"), to prevent the server from updating the log file. This will produce a big error in the console when starting the server, ignore it, the server will still launch.
You can disable this, but then all your players will be notified that the log updated.