I've noticed over time that my nipples have gotten bigger as LO continues nursing (not a huge deal, they were teeny before and I heard that the connective tissue breaks down as time goes on allowing your nipple to extend farther).
But I'm wondering if I need to go up to a bigger flange size. My nipples aren't touching the edges at all, but a lot more of the areola is getting sucked into the tube part these days. And I wind up breaking the section and re-placing them throughout the pumping and whenever I do that, the milk starts flowing again.