What is it so painful to breastfeed?

Help with latching: If it feels like a terrible nipple pinch, you need to try a new latching position. Your baby may not be getting enough breast/nipple into her mouth. Stop and try again. A certain soreness will occur in most cases but it should get easier and resolve within a few weeks.

Inappropriate latch?: Oftentimes, if your baby is not latching well onto the areola (but instead right onto the nipple), you will experience pain. Break the latch, make sure your baby's mouth is wide open and reposition higher up. If you have cracked nipples, that may cause discomfort (try lanolin and acetaminophen/ibuprofen). Also, a breast infection (mastitis) may cause you to experience sharp stabbing pains/fever.