This is an odd problem, and I hope the subject header is accurate. I'm using a Sansa e280R with the latest build of Rockbox (16209-16225). It's got maybe 2000 files on it, mostly Ogg with some MP3. So far I've found two files that are very difficult to play. The first is an Amazon.com MP3, the second is an Ogg Vorbis file made from a CD.
I can't get the files to play through the normal means. Clicking on them individually, selecting the entire album, in file or database mode, all lead to the same result: the WPS appears, the metadata is loaded, then the player kicks me back to the file/db selection screen. (In both cases the song is the last one in the directory or album, so I do not know what would happen if there were more files after it.)
I've only found one way to make the files play. I start by playing some other file or album, then I go into the file or database view and open the trouble file, or use the context menu to insert it into the playlist. Then it will play fine. This only works if there are already files in the playlist; otherwise the file will appear in the playlist but won't play, it won't even go to the WPS.
I've only been using Rockbox (and my Sansa) for a couple of days. The forward and back buttons seem kind of wonky and the database does some strange things, but this is the only case I've found where it consistently fails to open a file under normal conditions. Any thoughts?
Edit: Version 15975M (soap's patched version) seems to work okay.