Preheat oven to 375 degrees and lightly grease a large baking sheet or line with a nonstick baking mat.
In a large bowl, cream together butter, 1/2 cup of oil, sugar, and powdered sugar.
Add egg, almond and cherry extracts, and mix well.
In a second bowl whisk together flour, baking soda, cream of tartar, and salt.
Add dry ingredients to wet ingredients and mix until just combined.
Gently stir in 1 cup of chocolate chunks and the chopped maraschino cherries.
Drop tablespoons of dough onto prepared baking sheet 2 inches apart.
Bake for 8-10 minutes until cookies look dry around the edges and edges begin to turn a lightl golden color.
Cool on pan 2-3 minutes before transferring to a cooling rack to cool completely.
While cookies are cooling, prepare the dipping chocolate. Combine remaining 1 cup chocolate chunks and 1 teaspoon oil in a medium microwave-safe bowl. Microwave on high for 45 seconds. Stir, then return to microwave for 20 seconds at a time stirring after each until completely smooth.
Dip cookies into melted chocolate and plate on wax or parchment paper to cool. (See my pro tip in the notes to speed this up!)