Preheat oven to 375 degrees F. Line a large baking sheet with parchment paper or silpat (or grease pan well).
Place 2/3 cup milk and dark chocolate chips in a microwave-safe bowl. Microwave on high in 30-second intervals, stirring after each interval, until smooth. Stir in vanilla. Set aside to cool completely.
Meanwhile, add flour, sugar, cocoa powder, baking powder, and salt into food processor (or large bowl), and process until combined (or whisk together if not using processor). Add butter and process until just combined (or cut in with fork if not using a food processor).
While food processor is running, slowly add milk and chocolate chip mixture until just combined (or stir in until just combined if making in a bowl).
Spoon mixture into 6 large circles (or 12 small) onto prepared baking sheet. Bake for 15-20 minutes or until set (or about 8-12 minutes for small). Cool on wire racks.
Meanwhile, in large bowl mix together cream cheese and pudding mix with electric mixer on medium speed until well combined. Mix in Amaretto and milk until well combined. Fold in whipped topping. Cover and refrigerate for about 1-2 hours or until firm and thickened.
To assemble, place a chocolate shortcake on serving plate then top with cream, strawberries; repeat layers ending with a chocolate shortcake. Top with whipped topping/cream and strawberries if desired.
SNAPPY TIPS: You can make smaller shortcakes rather than the 6 large shortcakes. Adjust time as needed.SNAPPY SUBSTITUTIONS: If you don’t like dark chocolate, substitute semi-sweet chocolate chips and original unsweetened cocoa powder. Instead of Amaretto you could use any liqueur or milk. Substitute your favorite flavor of instant vanilla pudding for the vanilla such as chocolate or coconut.
Keywords: chocolate strawberry shortcake, spring dessert