iTunes headphone jack

Summary: To listen to music, I need to ensure that headphones are plugged in before starting iTunes.

My problem:

1. Start iTunes (in Windows) with nothing plugged into the headphone jack
2. Receive error message that "iTunes has detected a problem with your audio configuration. Audio/Video playback may not operate properly."
3. Click OK
4. Insert headphones (using the jack).
5. Press play to listen to music. Nothing happens.
6. Leave headphones plugged in.
7. Restart iTunes.
8. Pres play; music plays.

Similarly, if I unplug headphones while listening to music, I can't just plug them back in to listen to music again. I need to restart iTunes.

Any fix?

Thanks!