There are actually quite a few reasons why you can struggle with early breastfeeding.  Here are some possible scenarios that you might find yourself dealing with a baby who is not breastfeeding well:    Probably the most common reason for a hard start is a premature birth.  When babies are born early it can make it more difficult for them to breastfeed. The reasons can be numerous so it is not helpful at this point to conjecture.  What we really want to do is say.. okay, this is the situation, now what do we do about it. Ohhh, I love this question because it is probably one of the most easiest questions I get to answer.