I just tried it twice and had no problems. My first attempt used a 16GB Kingston drive and Ubuntu 18.04; my second attempt used an 8GB Lexar drive and Ubuntu 19.10. (I thought there was a chance that the default ext4fs options might have changed between Ubuntu versions in a way that the Tesla might not like, but that doesn't seem to be the case, at least on my smallish partitions. That might still be a factor if your music partition is bigger, though.) My procedure, both times:
- I plugged the USB drive in and ensured that no partition from the USB drive was mounted.
- I partitioned the USB drive to have a single partition, using the MBR partition table, and set the partition's type code to 0x83.
- I created an ext4 filesystem on the drive with "sudo mkfs -t ext4 /dev/sdi1" (or "/dev/sdc1"; I used two different computers, so the USB drives showed up with different identifiers).
- I mounted the partition to /mnt.
- I typed "sudo chmod 0777 /mnt" to ensure that all users have full read/write access to the drive.
- I copied two directories with music, in MP3 format, to the drive.
- I unmounted the drive.
- I took the drive to my car and plugged it in.
- I used the Tesla's music app to look for music on the USB device. This worked both times.
- I successfully played music from the drive.
I suggest you try the above procedure as exactly as possible, using an 8-16GB USB drive, Ubuntu 18.04 or 19.10, and a small number of music files. To begin, use
one MBR partition; don't try to start with a device that's partitioned for both Sentry Mode and music use. If you can get this to work, then begin deviating in the direction of whatever did not work -- multiple partitions, a larger USB drive, GPT, more music files, or whatever. Change one variable at a time. In that way, you'll either end up with a working configuration or you'll have discovered what's causing the problem.
FWIW, my car just upgraded to 2019.36.2.1 last night.