This has been an issue I've had recently, but a Google search shows it's been around with others since 2002. Searched in this community and couldn't find anything.
When playing songs in a playlist, Winamp randomly and abruptly ends songs and advances to the next. Watching the timer, the title flips to the next song, the current song plays for a few more seconds, and then the next song starts. No rhyme nor reason to the song type, other than the fact that the 6:00 minute seems to be a popular trigger.
I suspect it has something to do with the crossfade, but I've used both the internal crossfade and SQRSoft Crossfade and haven't been able to determine if either of those are the cause. I'm happy to assist in some more in-depth troubleshooting if it turns out to be something that the needs to be fixed in the code. But I'm posting this here in case someone has had this problem and figured out that it's a setting problem that can be fixed.
TIA