For the Maple Shortbread Cookies
Use a paddle attachment in a bowl with a stand or hand-held mixer, and beat the butter with the maple sugar for 60 seconds. You will still see the maple sugar crystals because it takes longer to break them down. Add the powdered sugar and beat until the mixture is light and fluffy about 2 minutes.
Add the maple sryup and maple extract and beat together until combined.
In a separate bowl, whisk the all-purpose flour, cornstarch, and salt together. Add into the mixing bowl and beat until the dough comes together.
Wrap the dough in plastic and chill in the refrigerator for 30 minutes. If you chill the dough for over an hour, let the dough sit at room temperature for about 15 minutes to soften and roll out.
Preheat the oven to 350°F. Line two cookie sheets with parchment paper.
On a lightly floured surface, roll the dough about 1/8" thick. It also helps to sprinkle flour on the top of the dough and the rolling pin. If the dough sticks to the rolling pin, add more flour to the dough and rolling pin.
Using a maple leaf cookie cutter, press the cutter into the dough to cut out maple leaf-shaped cookies. To keep the cookie cutter from sticking to the dough, place the cutter into a bowl of flour to lightly dust it. Carefully place the cookies onto the cookie sheets lined with parchment paper. The cookies do not spread, so you can utilize plenty of space on the cookie sheet. Repeat this process until you have cut out as many cookies as possible. (My rule of thumb is only to form the dough of scraps and roll out two times. So, there are three total rolls. After that, the dough will be overworked and lose its texture).
Bake the Maple Leaf Cookies for 8 - 10 minutes until they are barely lightly golden brown on the edges. Remove from the oven and allow to cool completely on wire racks.
For the Maple Cream Filling
Use a paddle attachment in a bowl with a stand or hand-held mixer, and beat the butter, powdered sugar, maple syrup, vanilla extract, maple extract, and salt together until smooth and creamy.
Assemble Maple Leaf Cream Cookies
Spread a small portion of filling on one Maple Leaf Cookie, then cover with a second cookie. Repeat until there are no more cookies to assemble.
Enjoy immediately or store in an airtight container for up to one week. These cookies soften and taste better the next day!