Trailer roller advice

With out seeing it in person I would say the roller pivot stop has worn enough to allow over pivoting of that roller .

Remove the roller assembly and turn 180 degrees and re-install and test the angle.

Before I rebuilt my Sparton trailer I had the same issue,sometimes loading boat with the trailer in to far will cause the same issue, but suspect a wore pivot stop.

JMHO Jeff

Bring fairly new to trailers, that was my first thought is getting some kind of wedge in there. The boat doesn’t have that much of a v bow, not needing that great of angle. I’ll have to check it out in the light again.