Quoted from mrboboto:
I think you just solved my problem- I either have the wrong pulley or its very worn as it’s more like an “O” shaped hole.
Definitely need to fix that. Top pulley looks very similar but has three small holes around the middle to where the reel slides in. If you reel does not have those prongs to fit in those holes that's another issue.
Top pulley (need to check manual to verify but this looks like it):