IPod no longer disconnects

My iPod used to automatically disconnect after it updated. I transfered a file from my MacBook, which I manually added to my iPod. The manual update to the iPod on the MacBook requires that I manually disconnect the iPod from the MacBook. Fine. On my main Mac, the iPod should sync when connected and disconnect when finished. When I synced the iPod with my main Mac, it no longer disconnects automatically. Any thoughts?

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