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To keep brown sugar soft and make measuring easier, store it in a large zippered heavy duty plastic bag. You can easily place a measuring cup inside the bag, and use the bag itself to press the sugar into the cup.
I thought you might like to hear about a new kitchen product that keeps brown sugar (among other food items) soft and fresh for months on end with very little effort. The SugarBaby brown sugar saver can be found at www.sugarbabyproducts.com They also have some great recipes!!!