In 2005, Scotland became the first nation to make breastfeeding in public a legal right, but current breastfeeding targets and maternity leave allowance do not acknowledge the conflicting demands women face when juggling employment and motherhood. This paper explores how employment and maternity leave relate to breastfeeding duration among mothers in Scotland. The Growing Up in Scotland national longitudinal cohort study of 5,217 babies born in 2004-2005 was used. Multivariate proportional hazards regression models were specified using one cross-sectional wave of data to predict breastfeeding duration. Mothers working as employees, full-time (Hazard Ratio 1.6) or part-time (HR1.3), had a higher risk of earlier breastfeeding cessation than non-working mothers. However, self-employed mothers did not differ significantly from non-working mothers in their breastfeeding patterns. Mothers who took longer maternity leave breastfed for longer. The relationships between employment, maternity leave and breastfeeding duration were significant when controlling for known predictors of breastfeeding. Younger mothers, those with less formal education, single mothers, those of white ethnic background, and first-time mothers were more likely to stop breastfeeding sooner, as has been noted in previous research. Employment and early return to work are both factors associated with a shorter duration of breastfeeding. More flexible working conditions and more generous employment leave could help to prolong breastfeeding among working mothers. Current health and employment policy in Scotland and the UK could be better coordinated so that working mothers have the adequate support to meet the conflicting demands of employment and motherhood.