The most common cause of nipple pain is a shallow latch. This means that your baby does not have enough breast tissue in his mouth. Babies need a deep latch to get enough milk. If your baby is not latched correctly, you may notice a crease across the tip of your nipple when it comes out of your baby’s mouth. Or it may be shaped like a new lipstick, or white at the tip. If the pain doesn’t resolve or you’re having difficulty getting a deeper latch, consider having a lactation expert (A LLL Leader, International Board Certified Lactation Consultant, or knowledgeable health nurse) observe your baby at breast.