Cook the bacon in a dry skillet over medium heat until browned and crispy, turning occasionally, 5 - 10 minutes. Drain on paper towels, then crumble into 1/2 pieces when cool.
Place the maple sugar and 2/3 of the bacon in a coffee grinder, and grind finely. In the bowl of a stand mixer fitted with the paddle, cream the butter, maple-bacon sugar, salt and paprika together on medium-low speed until just combined, 2 - 3 minutes. (You don't want to incorporate much air into this batter, it will make the cookies harder to form and they won't hold their shape as well.) Add the flour, mixing on low to combine, scraping down the sides of the bowl as necessary. Remove the bowl and give the dough a final fold with a rubber spatula to make sure it's well combined. Flatten the dough into a disc, wrap and chill until mostly firm, about 30 minutes.
Make the topping:
In a mortar and pestle, pound the remaining 1/3 of the bacon with the flaky salt, coarse sugar, and a couple pinches of smoked paprika until it's the texture of coarsely cracked pepper. Set aside.
Bake the cookies:
Position two racks in the upper and lower thirds of the oven and preheat to 350º. Line two cookie sheets with parchment paper.
Roll the dough out on a lightly floured surface to 1/8" thick. If the dough cracks, it may be too cold - let it sit for a few minutes to soften a bit. Cut out shapes as close together as possible, spacing the cut cookies on the lined sheets 1 - 2" apart. Gather up the dough scraps and reroll. Cut out more shapes. Sprinkle the cut cookies with the topping and bake, rotating once or twice, until golden, 15 - 20 minutes. Cool completely. The cookies will keep at room temperature for up to a week.
Nutritional values are based on one of twenty four cookies.