Wash and dry berries. Slice off stem end. Using a sharp paring knife, slice an "x" deep into berries without cutting all the way down. (depending on the size of berries). A word to the lazy: an alternate way of serving this would be to quarter or slice the strawberries and serve the filling in a small dish. The filling can be spooned over the cut strawberries. Slicing the strawberries and using them as scoops for the filling works well too.
Beat heavy whipping cream until stiff peaks form. If you are using Cool Whip you get to skip this step!
In a separate bowl, combine milk and pudding. Beat for 2 minutes. Add almond extract and whipped cream. Fit a pastry bag with a #10 or #12 round tip. I was in a hurry, so I just cut off the tip of the bag...
Fill pastry bag with pudding mixture. Pipe pudding into strawberries, spreading petals open with fingers to allow more cream to fit.