1. In a small skillet under medium heat, lightly toast whole raw almonds until fragrant (about 2-3 minutes). Transfer toasted almonds to a chopping broad, roughly chop and place in a small bowl.
2. Finely chop dried cranberries and place in bowl with chopped toasted almonds.
3. In a medium mixing bowl, add flour, powdered sugar, cornstarch, and salt. Lightly whisk to combine.
4. In the bowl of a stand mixer fitted with a paddle attachment, add the butter and mix at medium speed (4 on stand mixer) until light and fluffy, about (1) minute.
5. Reduce mixer speed to low (2 on stand mixer) and add all of the flour mixture at once followed by the vanilla and almond extracts. Continue to mix at low speed until dough starts to form into a ball shape.
6. Mix in the chopped almonds and dried cranberries until incorporated into dough. Turn off mixer.
7. Transfer cranberry almond shortbread cookie dough onto a lightly floured surface. With a bench scrapper, divide dough in half. Use hands to gently form each half of dough in a small rectangle and individually wrap with plastic wrap.
8. Refrigerate cookie doughs for at least (1) hour or overnight.
9. Line a large baking sheet with parchment paper and preheat over 350F. Roll out first half of cranberry almond shortbread cookie dough into roughly an 8” x 4.5” rectangle. Use a sharp knife/bench scrapper to cut dough into 15 equal square pieces.
10. Transfer cut cookie dough onto prepared baking sheet. Repeat process with second half of cookie dough.
11. Place cut cookie dough pieces in the freezer for at least 15 minutes before baking at 350F for 10-12 minutes rotating the pan (s) halfway through bake time.
12. Allow cranberry almond shortbread cookies to rest in baking pan for at least 5 minutes before transferring to a cooling rack to cool to room temperature.

Assembly (Optional)

1. In a double boiler, melt chocolate chips and oil until smooth. Allow melted chocolate to cool to room temperature before transferring to a pastry bag.
2. Make a small cut at the tip of pastry bag and drizzle melted chocolate over cooled cranberry almond shortbread cookies.
3. Allow chocolate to set before serving cookies.