They aren't easy to get down is best of situations, but a couple things to check (unfortunately both out of the water)
1. Make sure the pivot bolt on the rudder cheek isn't too tight (I use a Nylock there so I know it won't come loose when lightly tightened.
2. The routing path of the lines is going right around the roller.
3. The lines aren't too big. There's not a lot of space for them to turn up into the tube. EE had big 1/2" lines (easier to grip) and they just rubbed each other to the point they jammed up.
4. Embrace your friend the push pole. be the pole !
You will have to either tie the line to the tiller or cleat it. Force of water moving past will push it back up if you don't.