custom song play length

I have several live songs that I set to play a custom length to trim clapping and cheering off of the beginning and end of the songs. This used to work great but one day (over a year ago) I walked away from my macBook while I was setting a new album and the battery died. It has never worked since and when I sync to my iPhone to play in the car some songs work and others don't. I can see that the trimmed song lengths are saved in Music, the play status bar is shortened to the correct time, but when the indicator reaches the end, the status indicator stops and the song continues to play until it reaches the original song end. macOS and Music have been updated and are current, iOS and Music have been updated on the phone, and all devices have been restarted and cold booted with no changes.