In the past decade, biological nurturing and activation of maternal and infant instincts after birth have constituted a major advance in clinical breastfeeding support. Yet, physiologic breastfeeding initiation is not enough to ensure ongoing pain-free and effective breastfeeding for many pairs. Current interventions, including “hands-off” mammalian approaches, do not improve breastfeeding outcomes, including in randomized controlled trials. Back-arching, difficulty latching or staying on the breast, and fussing at the breast are common signs of infant positional instability during breastfeeding. These cues are, however, often misdiagnosed as signs of medical conditions or oral connective tissue abnormalities, and underlying positional instability is not addressed. New clinical approaches are urgently required. This article offers a clinical approach to fit and hold (or latch and positioning)—gestalt breastfeeding, which aims to optimize positional stability and intraoral breast tissue volumes for pain-free effective breastfeeding. The word gestalt (pronounced “ger-shtolt”) means a whole that is more than the sum of its parts. Gestalt breastfeeding builds on the theoretical foundations of complexity science, physiologic breastfeeding initiation, and new understandings of the biomechanics of infant suck elucidated in ultrasound studies. It also integrates simple psychological strategies from applied functional contextualism, popularly known as Acceptance and Commitment Therapy, empowering women to attend mindfully to breast sensations and their infant’s cues. Gestalt breastfeeding can be reproduced for research purposes, including in comparison studies with oral surgery, and has the potential to improve breastfeeding outcomes.