Start by whisking together the flour and, if you’re using it, a pinch of cinnamon. This little step makes sure everything is evenly mixed, so every cookie turns out perfectly tender. Set it aside and take a moment, you’re about to get into the fun part!

In a large bowl, beat the softened butter with the powdered sugar until it’s creamy, light, and fluffy. Don’t rush this step, this is what makes the cookies melt in your mouth. Scrape down the sides a couple of times to make sure no buttery goodness is left behind.

Add the vanilla extract and freshly grated orange zest to the butter mixture and mix until fully incorporated.

Slowly fold in the flour mixture, either with a spatula or on low speed with your mixer. Mix just until combined, you want the dough soft and a little sticky, not tough or overworked.

Gather the dough into a ball, then roll it into a log about 12 inches long and 2 inches wide. Wrap it snugly in wax paper, tucking the ends under so it doesn’t dry out, and pop it in the fridge for at least 40 minutes. Chilling the dough makes it much easier to slice and helps the cookies bake evenly while intensifying the flavors.

Heat the oven to 325°F (160°C) and line a baking sheet with a sheet of parchment paper. Using two layers is a small trick that keeps the bottoms tender and lightly golden without over-browning.

When the dough is chilled, slice it into 1/4-inch rounds and arrange them on the prepared sheet, leaving a little space between each cookie. Bake for 14–16 minutes until the edges are firm but the centers are still soft and delicate. If your oven has hot spots, rotating the sheet halfway through helps everything brown evenly.

Melt the chopped dark chocolate gently, either in a double boiler or carefully in the microwave. Dip each cookie halfway, letting the excess chocolate drip off, then place them back on parchment to set. For a little extra flair, sprinkle a tiny bit of orange zest on top while the chocolate is still soft, it adds flavor, color, and that wow factor.