I don't see why you couldn't go down behind the roller, under it, up over from the front then astern to come back to a cleat or wherever. If you put the line down the front of the roller, it could jump off if the sail gets ahead of the roller. It would nicely put the luff in front of the pulpit. Just watch for chafe if the pennant goes of to the side. You could always put a heavier loop of line around the roller to raise the turning point so it clears any chafing objects.... Better yet, if your roller bracket has a hole for an anchor-securing line, you could shackle a block to that hole.