Ahhh okay, I think I get what you're saying now. Sounds like the stanchion pipe protrudes higher above the wire and that's why it's catching and why the tapping the lifeline won't release it?
Working on that theory, here is my modification to your roller idea, I haven't CAD'ed it up but can to give a better idea of my thoughts.
If you keep the same basic premise with the bulge on one side and lightly weighted to keep proper orientation but have the max width of the bulge part above the wire, when the sail presses into the bulge the force will create a moment between the bulge height and the wire height and this will make the fitting want to roll up and inward and flick the sail over the rail?
Anyway, it's just a theory...