Rudder "Up" line getting stuck

Has anyone had their rudder lines - in this case the up line - get jammed in the pulley inside the boat?
Thats been happening to me since last season. I took it in and had it serviced but it doesn't seem to have done the trick.

I shot a video with my phone. Start it at about :08. You'll then hear some noise as I test out the other rudder controls.
Here is the moment I pull the line and the it gets jammed. You can see and hear as it pops in between the pulley and mounting hardware. No idea what to do about this. It is happening every time I pull up.

https://youtu.be/c2VPcKPzryA?t=33

Thoughts on what to do?
Thanks,
Andrew

Change the pulley?

Is it properly lined up?

Well I don't know how to change the pulley or what this part is called.

I think it's properly lined up at first, as it rolls back and forth, but when I pull hard to lift the rudder it pops off the roller.

I'll inspect it this week when I have some time I suppose.