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Mar 24, 2016 8:26 PM in response to zombi85by Kenichi Watanabe,If you have not already, do a Reset (restart) on the iPod
Learn how to reset your iPod - Apple Support
If that does not help... Since all songs stop playing at the same time, your iPod may be "timing out" for some reason. In case the reason is your headphones not being recognized (as plugged in), first make sure the plug is fully inserted. If that's not the problem, the headphones jack can receive remote control signals from buttons on the cord. Even if your headphones do not have buttons on the cord, the iPod may be getting false signals (in this case to pause). Try different headphones to rule out faulty headphones as the cause.
You can also do a Restore on the iPod using iTunes, in case the iPod has data corruption affecting its onboard software. This erases the iPod, reinstalls it software, and set it to default settings.