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Need help diagnosing problem with USB Flash drive for audio

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I thought I was doing it right....I just got a 128GB Patriot drive (same unit used by some other folks), formatted FAT32, I dragged and dropped about 75GB of mostly AAC, some MP3 music from iTunes on my Mac over to the drive, successfully copied (although it seems to have skipped some of what I dragged over, can't tell what).

It shows up when I plug it into the car, but hangs on the "Preparing to copy" step - I waited over 10 minutes.

What did I do wrong? Where should I look? Is it a naming thing? I used no folders, just dragged over the tracks...

Thanks!
 
I would think it would ignore DRM music, as it won't even appear to be music to anything that isn't aware of it. (DRM stuff from iTunes uses a different file extension, for example.)

Your symptoms sound to me like there may be filesystem corruption. That can cause all sorts of weird failures, and hanging while trying to chase down some bad data in the structure of the filesystem wouldn't be surprising. You might try reformatting the drive on your computer and then copying everything over again, just to rule that out.

If it still fails, I'd say one of your music files disagrees with the music player for some reason. I'd go for a binary search there: remove half the files from the drive, try again. If it still fails, the bad file is in the half that remains. If it works, the bad file is in the half you took out. Do it again with the half you isolated it into. Repeat until you find the file that causes the problem. A bit laborious, but not too bad, especially if you can haul a laptop into the car so you can make quick turnarounds on each try.
 
OK...it was the odd file types...the Tesla simply went into limbo, not sure which one did it. And then when I put the drive back with just MP3 and AAC files, it took about 15 minutes to index it all, not the 30 seconds that some folks have seen....of course, I don't have lossless files, so I have a lot more of them...about 14,000 songs....I guess it took a while to go out and get album art for all of those...

It sounds great! Much better than bluetooth, I think....I'll do some comparing with the same file sent from my phone and from the USB drive just to see....
 
OK...it was the odd file types...the Tesla simply went into limbo, not sure which one did it. And then when I put the drive back with just MP3 and AAC files, it took about 15 minutes to index it all, not the 30 seconds that some folks have seen....of course, I don't have lossless files, so I have a lot more of them...about 14,000 songs....I guess it took a while to go out and get album art for all of those...

It sounds great! Much better than bluetooth, I think....I'll do some comparing with the same file sent from my phone and from the USB drive just to see....

That still seems like an oddly long time. I have a 2 TB hard drive attached with just over 14,000 songs too (mostly lossless, but hundreds of aac, and a smattering of mp3). I think it takes at most a minute or two when I plug it in, sometimes faster. Does seem like the amount of time it takes varies some, not sure why it would. I'd have expected a fairly new, non-slow flash drive to be faster than the hard drive.