"Open in iTunes" only works if iTunes is already open

When iTunes is not running and I click "sync to iTunes", it attempts to launch iTunes for me. If iTunes is not running and I click "Open in iTunes" I get a dialog that says iTunes is unresponsive. I would probably be OK with this normally but the message says to make sure no iTunes preference windows or dialog windows are open, which to me indicates thinks iTunes is running but not responding because it's blocked by a modal or something, instead iTunes simply isn't running.