Preheat your oven to 350°F (175°C) and position a rack in the center.

Line a baking sheet with parchment paper or a silicone baking mat.

Measure your ingredients (especially flour and cocoa) so you’re ready to go.

Pro tip: Spoon the flour into your measuring cup and level it off with the back of a knife—packing flour can make cookies dense.

In a medium bowl, whisk together 1 ½ cups all-purpose flour, ½ cup unsweetened cocoa powder, and ¼ teaspoon salt. If your cocoa has lumps, sift it or press through a fine mesh.

In a large bowl (or the bowl of a stand mixer), beat 1 cup softened unsalted butter and ¾ cup granulated sugar on medium-high until pale and fluffy, about 2–3 minutes.

Add 1 large egg yolk and 1 teaspoon vanilla extract, beating until combined.

Lower the speed and add the dry ingredients in two additions, mixing just until no streaks of flour remain. Scrape the bowl and finish folding the last bit by hand if needed — don’t overmix.

Pro tip: Creaming the butter and sugar until light and fluffy traps tiny air bubbles that give the cookies lift and a tender crumb — don’t rush this step.

Use a small cookie scoop or a tablespoon to portion the dough (about 1 tbsp per cookie). Roll each portion into a smooth ball.

Place the balls on the prepared baking sheet about 1½–2 inches apart.

Using the back of a teaspoon or your thumb, press a shallow indentation (about ½ inch deep) into the center of each ball. If the dough cracks around the edges, chill the tray for 10–15 minutes and try again, or gently press the edges to smooth them.

Pro tip: Using the back of a slightly wet teaspoon helps make a smooth, even well without sticking.

Bake one tray at a time in the preheated oven for 10–12 minutes, until the edges are set but the centers still look a touch soft.

If the indentations puff up while baking, press them gently again with the back of the teaspoon as soon as the cookies come out of the oven.

Transfer the cookies to a cooling rack and let them cool completely before filling (about 20–30 minutes).

Pro tip: The cookies will firm up as they cool — pull them when the edges are set but the center still jiggles slightly for that soft, fudgy texture.

In a small saucepan over low heat, combine 20 soft caramels (unwrapped) and 2 tablespoons heavy cream. Stir constantly until the caramels melt into a smooth, glossy sauce.

OR microwave in a microwave-safe bowl in 20–30 second bursts, stirring between bursts, until smooth.

If the caramel is too thick to pipe or spoon, stir in an extra teaspoon of cream at a time until it reaches a thick but pourable consistency.

Pro tip: Whisk or stir continuously and keep the heat low — caramels scorch quickly and can become grainy if overheated.

Spoon or pipe a small amount of warm caramel into each cooled cookie indentation. Don’t overfill — leave a little room if you plan to drizzle chocolate.

Optional: Melt a small handful (about ¼ cup) of chocolate chips in the microwave in 15–20 second bursts and drizzle over the caramel-filled cookies.

While the caramel is still warm, sprinkle a pinch of flaky sea salt on top for a delicious sweet-salty pop.

Let the cookies sit at room temperature until the caramel sets (about 30 minutes). To speed this up, place the tray in the fridge for 10–15 minutes.

Pro tip: Add the sea salt while the caramel is warm so it adheres and dissolves slightly into the caramel for maximum flavor.

Store cookies in an airtight container at room temperature for up to 4 days. Layer with parchment paper to prevent sticking.

For longer storage, freeze baked unfilled cookies in a single layer on a tray until solid, then transfer to a freezer bag for up to 3 months. Thaw, then warm and fill with caramel just before serving.

To revive slightly firm caramel, microwave an individual cookie for 6–8 seconds to soften the center before serving.