Hi Kristi,
Linda Pohl's method for applying a nipple shield might help here, as 
well as using the largest shield possible (Medela's 24mm or Ameda's only 
size). Place the shield on your finger pads from both hands, teat up. 
Use your thumbs on the center of the teat to push down to turn the 
shield teat half way inside out - like a turtle drawing his head into 
his shell by folding his neck skin. Leave a little bit of teat right 
side out at the end. Place this over mom's nipple. Then press on the 
depression around the folded area with 2 fingers from each hand, 
straight in to the breast and then slightly outward. The teat everts and 
draws some breast into it. If the nipples are very flat, they might not 
come in well, but some areola around them does, and that takes care of 
the problem.
If Linda is on Lactnet right now, I'm sure she can explain it better.
Catherine Watson Genna, IBCLC  NYC

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