Breastfeeding is proven to have many great health benefits for both the mother and baby which has led to national organizations like the WHO recommending that new mothers exclusively breastfeed their baby for six months. However, approximately 92% of mothers report having breastfeeding difficulties by day three post partum and only 60% of mothers breastfeed for as long as they originally intend. There is an incredibly wide range of possible issues including oral development issues, simple technique problems, or a lack of time to mature, but they are hard to diagnose. In talking with over 40 clinicians and parents, we discovered that it is nearly impossible to distinguish between these issues as the only available evidence for clinicians comes from the mothers and what they have seen in other cases. Clinicians would benefit from a way to objectively quantify a baby’s breastfeeding ability in order to determine if they have the base suction strength to breastfeed and decide if further medical intervention is required. Thus, we developed the Milk Maid - a hand-held, baby-bottle shaped screening device that outputs quantitative data regarding a baby’s ability. It functions through a small pressure sensor in the bottle that can measure negative pressures in the range of 0 - 300 mmHg. While the baby is sucking on the nipple, they generate repeated intraoral negative pressure bursts, and the Milk Maid captures this to output real time clinical data related to this suck-swallow reflex. Clinicians will now be able to more confidently decipher the extent of necessary medical intervention and give parents more concrete answers on the next steps of care for their baby. The Milk Maid serves to improve both breastfeeding outcomes and retention with the ultimate goal of helping the 1.6 million babies per year that aren’t receiving the full benefits of breastfeeding.