Place the softened butter and brown sugar in a stand mixer with the paddle attachment or a large mixing bowl and beat with an electric mixer on medium-high speed until combined.
1/2 cup + 1 Tablespoon salted butter, softened, 1/2 cup light brown sugar
Add the egg yolk, molasses, vinegar and vanilla extract and beat on medium-high speed until smooth and fully combined, scraping the sides of the bowl as needed.
1 large egg yolk, 1/2 cup molasses, 1/2 Tablespoon apple cider vinegar, 1 teaspoon vanilla extract
Pour the flour over the molasses mixture. Then evenly distribute the baking soda, ginger, cinnamon, allspice, and cloves over the flour.
Mix on low speed just until combined into a thick and sticky cookie dough, scraping the sides of the bowl as needed. Do not overmix as it can contribute to dry cookies.
Place two sheets of 2 feet long pieces of plastic wrap on the countertop. Pour half of the dough on each piece of plastic wrap. With the help of the plastic wrap and your hands, press and form the dough into a disc shape (see notes) and wrap the plastic wrap around it tightly. Place the dough discs in the fridge for 2 hours or overnight. If chilling overnight, the dough will need to rest at room temperature for 20 minutes so it's easier to roll.
Once ready to bake, preheat the oven to 350°F. Line baking sheets with Silpat liners or parchment paper.
On a lightly floured surface, roll each dough disc to ¼ inch thick. It is also helpful to flour your rolling pin and sprinkle some flour on the top of the dough. The dough should be at least ¼ inch thick or the cookies will be too thin. If you roll the dough thicker (½ inch), the cookies will need to bake longer. (See "Prep Tips" in the Notes below.)
Using cookie cutters, cut out the cookies and place them on the prepared baking sheets about 1 inch apart (the cookies don’t spread much). Reroll the scraps, as needed, throughout this process until all the dough is used.
Bake smaller cookies for 6-8 minutes and medium-sized cookies for 8-10 minutes. The cookies should spring back when slightly touched and be puffed and rounded on the edges. Do not overbake.
Cool the baked cookies on the baking sheet for 5 minutes, then remove them and transfer to a cooling rack to cool completely before decorating.
Decorate with icing, if desired.
Decorated or undecorated cookies can be stored at room temperature for up to 1 week.
Video
Notes
Ingredients Tips - We prefer to use Grandma’s or Brer Rabbit brand of molasses versus blackstrap in these cookies. Blackstrap molasses is more bitter and thicker than regular molasses which is usually a touch sweeter and less concentrated.Prep Tips - It’s easier to roll out the chilled cookie dough when it is in a disc shape. The dough may crack and be crumbly as you roll. The first few rolls are always the hardest since the dough is stiff. Re-rolling the scraps is much easier. You can use your fingers to help meld the cracking edges back together. Baking Tips - Bake the same sizes of cookies together so the bake times are similar. Decorating Tips - We usually purchase a premade frosting in a pouch that we cut off the tip to decorate the cookies.Storage Tips - Undecorated cookies can be frozen in an airtight container for up to 3 months. We haven’t tried freezing decorated cookies, but royal icing usually freezes best. The dough discs may be frozen for up to 3 months. We recommend placing the plastic covered dough discs in a freezer bag. Thaw in the fridge overnight before rolling out.