I asked this very same question several times in the past, and no fix was ever put forward. I have never used gapless, I have not upgraded iTunes to the 'gapless' version, crossfade is disabled, and yet both my iTunes and my iPod (Nano) run songs together! It is very annoying, and I never remember having this with other mp3 players. Both my iPod and iTunes have been relegated to mostly unused mainly because of this.