In recognition of the irrefutable disadvantages of not breastfeeding to the mother, baby, society and the environment, increasing the duration of breastfeeding has become a focus of national and international health objectives. However, many mothers experience such painful sore nipples that they stop breastfeeding before they intended. The purpose of this study is to examine the relationship between various aspects of optimal breastfeeding (e.g. the positioning of the baby at the mother's breast, the positioning of the baby's head and mouth, the breastfeeding dynamic and the latching process) using a guided assessment and documentation tool and the breastfeeding mother's level of reported pain on a five-point verbal descriptor scale. Ninety-five healthy postpartum breastfeeding mothers who sequentially reported sore nipples within ten days of giving birth to healthy, term babies in a hospital in Latvia participated in the study. Each mother's midwife observed, assessed and documented a breastfeed using a guidance assessment form, the Lactation Assessment Tool (LAT). Each mother scored her own pain during breastfeeding. Four attribute categories were scored and examined as related to the pain levels of the mother: the baby's face position (chin and nose and head position, cheekline, lip flange and angle of mouth opening); the baby's body position (height at the breast, body rotation and body in relation to mother's body); the breastfeeding dynamic (change in breastfeeding pattern (suck vs swallow) and movement of mother's breast) and the latching process of the baby (root, gape, seal and suck). No significant difference was found between the mother's level of reported pain and the assessed head position, body position or breastfeeding dynamic attributes of the baby. However, more optimal latching process behaviour of the baby (rooting, gaping, sealing, and sucking behaviour) are slightly related to lower levels of reported pain (r(88) = -0.09, p > 0.05). This should serve to remind clinicians that no one aspect of positioning may be more critical than another. Assessment of breastfeeding should be comprehensive and should begin before the infant is at the breast. Early stages of the infant's breast seeking behaviours should be observed as well as the actual feeding.