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When you are single pumping or hand expressing, plan on spending around 20 to 30 minutes (total per session). Switch sides when your milk stops spraying and slows to a trickle. Breast compression (massage from outer quadrants toward the nipple) can also encourage your milk to flow. You will probably find that double pumping is quicker and easier, and often results in a greater quantity of expressed milk in less than 15 minutes.