Keep the unsalted butter around 68°F to 72°F, then beat it with the granulated cane sugar for 2 to 3 minutes. Scrape the bowl halfway through and keep beating until the mixture looks pale and slightly fluffy. Add the large egg and 1 1/2 teaspoons vanilla, then beat for another 30 seconds. The mixture should lose its grainy look and cling smoothly to the sides without appearing oily. Stop when you can still see a little structure from the butter. If you beat past 5 minutes the butter warms too much and the cookies can spread. Keep the butter cool because trapped air helps the cookies stay tender.

Whisk the all-purpose flour with baking powder and kosher salt for 20 seconds, then add it to the butter mixture in three additions. Mix on low for about 60 to 90 seconds total and stop as soon as no dry flour remains. Press the dough into a thick disk and chill it at about 38°F for 30 minutes. The finished dough should feel smooth and firm enough to lift without sticking heavily to your fingers. A few tiny flour streaks can disappear as you press the disk together. Mix too long and the cookies get tough. Chill the dough because firm butter prevents excessive spreading during baking.

Roll the chilled dough to an even 1/4-inch thickness, then cut exactly 12 pumpkin shapes with a 3-inch cutter. Press scraps together only once and reroll gently so the second batch doesn't become dense. Arrange all 12 shapes with about 2 inches between them and chill at 38°F for 10 minutes. The Halloween Pumpkin Designs should look clean around the stems but not factory perfect. Small differences around the curves are fine. If the dough turns shiny while you're cutting, the butter is warming and the shapes will spread. Chill the cutouts because cold edges hold their pumpkin outline in the oven.

Bake the 12 chilled cookies at 350°F for 10 to 12 minutes and rotate the tray once at minute 6. Pull them when the outer curves turn light golden but the centers still look pale and matte. Leave them on the tray for 5 minutes, then cool them completely for about 25 minutes before glazing. You'll notice a buttery vanilla smell right as the edges start coloring. The Halloween Pumpkin Designs should remain mostly flat with only slight puffing through the centers. (I tried 375°F first and the stems browned too quickly. 350°F kept the shapes cleaner.) Go past 12 minutes and the edges turn hard. Cool completely because warm cookies make the glaze run thin.

Whisk the powdered cane sugar with 3 tablespoons whole milk, the remaining 1/2 teaspoon vanilla and orange gel food coloring for 60 to 90 seconds at 68°F to 72°F. The glaze should fall in a thick ribbon and disappear back into itself in about 8 seconds. Spread a thin orange layer over each cooled cookie and leave the stem exposed if you like. The surface should settle smooth but still show a few handmade ripples near the edges. Let all 12 cookies stand for 20 to 25 minutes until the glaze feels dry when lightly touched. If the glaze disappears instantly during mixing it's too thin and can slide off the cookies. Keep the glaze thick because a slow-set coating preserves clean pumpkin shapes.

Melt the semisweet chocolate chips in 20-second bursts until the chocolate reaches about 95°F to 105°F, stirring between each burst. Pipe different eyes and mouths onto all 12 glazed cookies and keep the lines slightly uneven. Let the chocolate stand for 15 minutes at room temperature, then arrange the cookies on one serving plate. The final Halloween Pumpkin Designs should have glossy dark faces over dry orange glaze with crisp golden cookie edges peeking around the sides. Some smiles can tilt and some eyes can differ in size. That's the fun part. Overheated chocolate turns thick and grainy, so stop heating once it's fluid. Gentle heat keeps cocoa butter smooth enough for clean lines.