I am having this same problem. I have two Roku 3 devices, and use a USB HDD on the one Roku 3 at our summer house where we do not have Internet access for streaming 8 months per year, so I use the local HDD over USB. So I did not notice this problem until yesterday during a visit to our summer home, There was no problem a few months ago, and there was also no problem about 18 months ago with the HDD on my other Roku 3 where I set the HDD up, So a recent update seems likely as causing this problem.
The problem appears to be worked around by using WAV format for the music files. Of course that means the storage is about 10x what is needed for AAC, MP3, WMA,....
Since I am using a 4T HDD, this is not too bad except for the need to convert all the music files. Please do not break WAV formatted files!!
I had problems with at least WMA and MP3 files.
I bought the Roku 3 especially for its USB HDD support along with Netflix, Prime,.... because I want to use it sometimes with local only media, so fixing this is a priority.
The home device is 4200x-Roku3, serial # 1GN38A163811. The installed software is 9.0.0 build 4142-04.
Again, this used to work, no problem, with the exact HDD image. Nothing has changed on the HDD (no erasures and no new files when this happened).
I did not write down the serial number on my other Roku 3 at my summer home, but I bought it 2 to 3 years ago, and the installed/updated software is the same.
After I found this problem on the Roku 3 device at my summer home, I brought the HDD home and tried it on my other Roku 3. I noticed this time that the device played OK for the first 3 or 4 songs, and then the problem was duplicated. Songs will start playing OK, but at the end of each song it stops and I get the error message as discussed by the other commenters.
So, this problem seems to affect compressed music and has some intermittent behavior and it duplicated on 2 similar devices for me.
Sounds like possibly an uninitialized variable or a corrupted variable or maybe some corruption caused by decoding routines or a mismatch between variables or stack problems.
Seems like the file access, PCM rendering processes and general system processes should be fine since WAV files play fine.
I wonder if the older devices are weak on memory compared to the newer devices and perhaps there is some kind of memory overrun in older devices?
It may be nontrivial to duplicate and isolate if it depends on the state of volatile memories at power up. Modern code and code tools are supposed to eliminate such problems or at least flag such situations. You might try a few different devices as well as power ON/OFF between tests. It would be useful to know if you can duplicate this problem on a Roku 2 or Roku 3.
An option to restore/return to older versions of software (even if a bit laborious) would seem quite useful both for customers and to permit customers to provide you with clear results between versions of the software for obscure bugs. Many companies provide such options (Microsoft for example)..
Thanks & regards,