My daughter was born the last week of May, so she's 8 weeks old now and over 12 lbs. When she was first born (at 9lbs 11 oz), the nurses at the hospital tried to help her latch and it wasn't working. She has a receding jaw (a family trait) and she was really sleepy, which made it really hard. When she would try, her latch was very painful and never correct. On the advice of a nurse, we got a nipple shield- and finally when she was about 14 hours old we got her to latch using the shield. Over the next two weeks, I used the nipple shield and was able to establish a good milk supply, in part by doing some pumping. I kept trying to wean her from the shield, but she still wouldn't/ couldn't latch correctly.
Finally, at 1 month, I was able to successfully nurse her on the left side without the shield. About two weeks later, we started to have success on the other side without the shield. She still doesn't always latch correctly without the shield at 8 weeks (it's hard to get her to open up wide enough sometimes)- but it's still getting better. I was really worried about using a nipple shield at first- afraid it would affect my supply and that I would never be able to wean her off of it. I read some old posts on these boards where mothers said they were able to wean their babies off the nipple shield at around a month old, and I found it hard to believe when she was 1, 2, or 3 weeks old that it would be possible, but it is.
For any mothers of newborns who are using a nipple shield (or considering it), I think the worst parts were always needing to clean them (I bought a second one to make it more convenient) and how messy of an eater my daughter was (I had to wash the boppy pillow, not just the cover, all of the time). The best part was that I was able to successfully get breastfeeding started, establish a good supply, and I never got cracked or sore nipples.
I get the impression that there are many reasons why my baby girl is able to latch correctly now. The biggest one is that my nipples are now stretchy. I'd look at those drawings of a proper latch with the nipple aimed back and up into the baby's mouth and wonder if they were exaggerating the nipple length to illustrate the concept... but now that my nipples are actually stretchy the drawings make much more sense. I had done the inverted/flat nipple pinch test and had concluded that my nipples were neither (which a lactation consultant agreed with) but I think they still had adhesions which loosened over a month of nursing with the nipple shield. It took a couple of weeks longer on the right than the left. Other reasons why we no longer need the shield include having a bigger, stronger baby and that we have mastered all of the other logistics of breastfeeding such as positioning and my supply is established so the only thing we needed to work on was latch.
I just wanted to write to give hope. It can and probably will improve. I did a ton of google searches at 3am while my daughter was feeding looking for advice about how to wean her off the shield- and I think the thing that really worked was to give it time and keep trying but to not let yourself or the baby get too frustrated. I think that it would have taken longer if my baby wasn't in the 90th+ percentile for size because I'm sure that it helps that her mouth is bigger.