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. You may decide to take baby off the breast to try to reposition and fix baby's latch, but you should break the suction first to avoid causing further pain to yourself. You can break the suction by pressing down on your breast near baby’s mouth, pulling down on baby’s chin, or inserting your finger into the corner of baby’s mouth. 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.