Preheat and prep: Heat the oven to 350°F (175°C). Line two baking sheets with parchment paper for easy cleanup.

Cream the butter and sugar: In a large bowl, beat the softened butter and sugar until light and creamy, about 2–3 minutes. This creates a tender, slightly fluffy cookie.

Add egg and extracts: Mix in the egg, vanilla, and almond extract (if using) until combined. Scrape the bowl so everything blends evenly.

Whisk dry ingredients: In a separate bowl, whisk together the flour, cocoa powder, baking powder, and salt to break up any cocoa lumps.

Combine the dough: Add the dry ingredients to the butter mixture. Mix on low just until the dough comes together. It should be soft but not sticky.

Shape the cookies: Scoop about 1 tablespoon of dough and roll into smooth balls. Place 2 inches apart on the prepared baking sheets.

Make the thumbprints: Use your thumb or the back of a 1/2-teaspoon measuring spoon to press a shallow well in the center of each ball. If the edges crack, gently nudge them back together.

Fill with cherry preserves: Stir the preserves to loosen. Spoon about 1/2 teaspoon into each well, filling nearly to the top but not overflowing.

Bake: Bake for 10–12 minutes, until the edges look set and the bottoms are slightly firm. The centers should remain soft.

Cool completely: Let cookies cool on the sheet for 5 minutes, then transfer to a wire rack. Cool completely before drizzling.

Melt the chocolate: Microwave the chocolate and oil in 20-second bursts, stirring between each, until smooth and glossy.

Drizzle and set: Use a spoon or piping bag to drizzle over the cooled cookies. Let the chocolate set at room temperature or chill for 10 minutes to speed it up.