2016~2021 Does the shuffle button do anything?

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Winnipeg Canada
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2017 CX-9 GT
One of the things I was looking forward to in my 2017 CX-9 was the modern audio system. Out with CDs and in with Bluetooth and mass storage USB. I created a USB drive with my favorite tracks along with a playlist in m3u8 format. It loads the playlist fine, but hitting the shuffle buttons seems to do nothing. Am I missing something? Does shuffle not work for playlists? I haven't tried shuffling a folder yet, but I can't see why that should matter.

Here's the software version:
 

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:
Winnipeg Canada
:
2017 CX-9 GT
So I see it kinda works, but I need to toggle the Shuffle feature on/off every time I start the car. Otherwise it will start playing the first song in the playlist. And sometimes, it gets into a mode where once it's done playing the first song in the playlist, it plays it again. And again. Very annoying. Really sucks if you do a lot of short trips.

Also, another really weird thing is that some songs appear to have a title of "image/jpg". That's the mime type of the cover mp3 ID3 tag. It seems this firmware version has issues with reading standard mp3 tags. I use MediaMonkey to tag my mp3s, perhaps I need to try something else? Does it not support the latest mp3 tag standards or something? It looks very amateurish to say the least. However, if someone can confirm that newer firmwares fix any of these issues, I'll be tempted to perform the update.
 
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