Preheat oven to 400 degrees F. Line muffin tin with paper liners or spray lightly with nonstick spray.
Cupcakes: In a large bowl, combine flour, flax, sugar, and baking powder. Cut in cold butter until it resembles coarse crumbs. Beat egg into half & half and creamer; stir into dry ingredients just until moistened. Fold in crushed cookies. Fill muffin cups 3/4 full.
Filling: Beat together cream cheese, sugar and egg until smooth and creamy. Make a well in center of each cupcake; fill with a spoonful of filling. (You may have some filling left over.)
Topping: Mix together flour, sugar, and crushed cookies. Cut in butter until crumbly; sprinkle evenly over top of each cupcake.
Bake in preheated oven for about 15 minutes for regular size cupcake (up to 20 minutes for jumbo size) or until cupcake tests done.
In a saucepan over low heat, melt chips and shortening until smooth. Drizzle over tops of cooled cupcakes.