Lame title probably, but whatever. I was running across a bug that if background monitoring was running and I changed an option, then background monitoring would stop but every action occurred twice. So stopping twice, JOptionPane twice, and then re-enabling of the option I just turned off or vice versa. Well, after much deliberation it was the JOption Pane warning of background monitoring being turned off because of a change in the Options object. Basically, it was just the ordering of the code. Well, rather than mess with it forever, iTunesDSM now warns of a change in the options and background monitoring in the System Tray.