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Aug 30, 2016 11:21 AM in response to Cosmos424by Kenichi Watanabe,★HelpfulA sensor tells the iPod there's a plug in the headphones jack. Maybe it's becoming faulty and sometimes not seeing that headphones are connected, so the iPod stops playing.
If it's a hardware problem, there's are accessories that connects to the dock connector, to provide a separate audio output. Here's an example
https://www.amazon.com/gp/product/B004V9CW7A
Sound quality is supposedly enhanced (compared to standard headphones output). And you get a playback remote control on the cord.