1) In a mixing bowl, combine the mascarpone cheese, only 3 tablespoons of the Marsala wine, heavy whipping cream and 2 tablespoons of sugar.
2) In another bowl, combine the strawberries, the remaining marsala wine and sugar. Cover both bowls and refrigerate.
3) Place tablespoons of crumbled cookies into 6 wine glasses. Divide the strawberry mixture with the juices to each of the wine glasses. Top each glass with the Mascarpone mixture and then the remaining cookies.