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I get this message from a USB stick with music. Only certain songs work. The message is instant for songs that do not work. Could be a song format issue but I'll have to check.

Tesla doesn't support AAC files and can't use MP3 files with "APE" tags. Some FLAC conversions also don't work. People who tend to update their software and rip themselves with the latest and greatest settings tend to run into this more often than others. I'd keep it at standard 192kbps mp3 with no ape tags and they should all work. when you start mixing and matching things like ogg, m4a, aac, mp4, etc then of course some will have issues. Mine are only flac and mp3. I've had a few flac that didn't work and I just converted them to mp3 with no issues.
 
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Tesla doesn't support AAC files and can't use MP3 files with "APE" tags. Some FLAC conversions also don't work. People who tend to update their software and rip themselves with the latest and greatest settings tend to run into this more often than others. I'd keep it at standard 192kbps mp3 with no ape tags and they should all work. when you start mixing and matching things like ogg, m4a, aac, mp4, etc then of course some will have issues. Mine are only flac and mp3. I've had a few flac that didn't work and I just converted them to mp3 with no issues.

Thanks great info. I was just drag and dropping the music from iTunes to the USB stick.

Could you recommend a conversion tool to use to modify the files ?
 
Thanks great info. I was just drag and dropping the music from iTunes to the USB stick.

Could you recommend a conversion tool to use to modify the files ?

It totally depends on what your source file format is. I don't use iTunes for anything unless it is moving to/from my iphone itself. Even then, this is rare since I usually only use audible on my phone which gets files directly from the cloud. I've always hated itunes, but you are sort of forced to use it with apple devices. Rule of thumb is avoid it any time you can.

I keep most of my files on a NAS and have had them for a long long time. I google tools on a case by case basis. Have a flac that doesn't play? Google flac to mp3. something to that nature. (no point in converting UP, you would just re-rip from the source material) If you need to remove an APE tag, find a tool that allows mp3 tag editing and remove APE tags. (google is your friend there too)
 
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This happens to me everyday when I play a local radio station on Tunein and park my car overnight and then next morning, it would show 'Loading Error'. But after a minute, simply hit the refresh (anticlockwise arrow) and it will start streaming just fine.