In a medium bowl, whisk together 1 3/4 cups plus 2 tablespoons all-purpose flour, 1 1/2 teaspoons baking powder, and 1/2 teaspoon salt; set the dry mixture aside.
Place the 8 ounces finely chopped semi‑sweet chocolate in a microwave‑safe bowl. Microwave at 50% power for 1 minute, stir, then microwave an additional 15 seconds and stir until smooth. Set the melted chocolate aside to cool slightly.
Measure the sugar: from the 2 1/2 cups sugar (divided), set aside 1/4 cup granulated sugar for coating and use the remaining 2 1/4 cups granulated sugar in the dough.
In the bowl of a stand mixer fitted with the paddle attachment (or using a hand mixer), beat together the 2 1/4 cups granulated sugar, 1/4 cup canola oil, 2 tablespoons melted unsalted butter, and 2 tablespoons light corn syrup until combined.
Beat in 2 large eggs, 1 large egg yolk, 2 teaspoons pure vanilla extract, and 4 drops creme de menthe flavoring until fully incorporated.
With the mixer on low speed, add the cooled melted chocolate and mix until evenly distributed.
Add the reserved flour mixture to the wet ingredients and mix on low speed just until combined and no streaks of flour remain. Scrape the bowl and paddle as needed.
Shape the dough into a rough disk, wrap tightly in plastic wrap, and refrigerate for several hours or overnight until firm enough to roll.
Preheat the oven to 325°F (163°C). Line a baking sheet with parchment paper or a silicone baking mat.
Place the reserved 1/4 cup granulated sugar in one shallow bowl and the 1/2 cup confectioners’ sugar in a second shallow bowl.
Roll chilled dough into 2‑inch balls. Roll each ball lightly in the granulated sugar first, then roll generously in the confectioners’ sugar so the surface is well coated. Arrange the coated balls 2 inches apart on the prepared baking sheet (bake one sheet at a time).
Bake at 325°F: for chewier cookies, bake 10 to 12 minutes; for crisper cookies, bake 12 to 14 minutes. Remove the sheet from the oven and transfer cookies to a cooling rack to cool completely.
Store cooled cookies in an airtight container at room temperature for up to one week.