Dumb question from an old man regarding Bluetooth audio

[Varilux]

I would encourage you to visit your dealer. My radio had a number of glitches from day one.
One of them was the issue you mention (I would have to unplug/plug in my iPod for it to be recognized.
Another was it would create a "new" Bluetooth connection each time I started the vehicle (i.e., if I named the Bluetooth connection, it would overwrite it and default it back to UConnect).
When using Android Autoplay, it would do screwy things with my location after I returned from a trip.
And so on...

I visited the UConnect website, which informed me there was no update for my radio. However, when I visited the dealer (to have glitches in the gauge cluster sorted), they also reflashed my radio (the paperwork indicates 18-60-02-Y8 was the flash), and that pretty much sorted all the issues.

I've found it still occasionally doesn't see my iPod when I start the vehicle, but it's only maybe 2% of the time (vs. the 100% of the time in the past).

Anyway, it might be worth a visit to the dealer- I'm much happier with the functionality of my radio now (and it's good to be able to name the Bluetooth connection, because I rent a lot of Jeeps when traveling, and end up with a bunch of connections I need to unpair from time to time).

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[ToddEichel]

I get the suggestions to go to a USB drive, but if you already have an iPod and I'm assuming you use iTunes for managing albums and playlists and whatnot. Switching to a "simpler" solution of a USB drive can be a lot more work, especially if you use playlists and things as opposed to just a folder full of songs. I've spent a lot of frustrating time tweaking ID3 tags and messing with things just to get it to work the way I want. For instance, often a track number isn't included and you end up with albums playing songs in alphabetical order instead of the order it was intended, and don't even get me started on double albums. It was unmanageable with a large library.

The other issue is if you're using a subscription service, i.e. Apple Music right now, as opposed to purchasing MP3's or ripping CD's, there's no way to get that music onto a USB drive. So a lot of it depends on how you currently consume your music and where you get it from.

The simplest (though probably most expensive, but you were talking about doing this anyway) is to just purchase a new iPod Touch and plug it in. No need to use Bluetooth, just use the lightning cable plugged into a USB port. If you're having to unplug and replug every time, it could either be the old iPod, or an issue with your uConnect software, as others have said.