Breastfeeding is optimal for infant health, but more than 66% of mothers cease exclusive breastfeeding within three months after giving birth. Evaluating infants’ sucking effort provides valuable diagnosis to mothers encountering barriers with breastfeeding. Sucking microstructure is defined as an array of metrics that comprehensively capture infants’ ability to create a sealed latch onto mother’s nipple and regulate feeding, including number of sucks, sucks per burst, number of bursts, intra suck interval, and maximal sucking pressure. In this paper, we proposed a breastfeeding diagnostic device (BDD) which allows convenient and objective measurement of infants’ sucking microstructure in both home and clinical settings. BDD utilizes an air-based pressure transducer to measure infants’ sucking behavior. We conducted pilot clinical studies on six dyads of mother and infant to test the feasibility of the BDD system. To facilitate comparison, both breastfeeding and bottle-feeding were conducted on the six dyads using the BDD in home settings, and the outcomes are comparable with prior recordings in research or clinical settings. By offering a convenient and objective measurement of the sucking microstructure, the BDD will provide clinically meaningful guidance and diagnosis to mothers struggling with breastfeeding. BDD will also serve as an objective metric useful in research areas relevant to infant behaviors, assessment of neurodevelopment, and potentially a screening tool for developmental disabilities.