Step 1

Sift the flour, baking powder, and salt into a large bowl and whisk to combine.

Step 2

In a separate bowl (or in a stand mixer), add the softened butter and beat until creamy. Then, gradually add the sugar, mixing constantly, until the mixture is a pale yellow and light and fluffy, with the sugar fully incorporated.

Step 3

Add the eggs (one at a time) and the vanilla to the creamed butter, mixing well in-between each addition.

Step 4

Finally, add the flour mixture incrementally, mixing in between, until a dough forms. It shouldn’t be sticky.

Step 5

Weigh the biscuit dough and divide it into two even pieces. Wrap one in plastic wrap and return the other half to the mixer/bowl.

Step 6

Add the cacao powder, instant coffee, and cinnamon (if using) to the dough and mix well until incorporated.You can optionally chill the dough at this point for at least 30 minutes (up to a day) wrapped in plastic wrap in the refrigerator. However, I find it simpler to roll out into the rectangles first.

Step 7

Place the first dough ball between two sheets of parchment paper and roll into a rectangle that’s as close to 9x14-inches (23x35cm) and ¼-inch (0.6cm) thick. Remove the excess to make it a neat rectangle (the scraps can make spare marbled chocolate vanilla cookies).I like to measure the size on the parchment paper first, marking it with a pencil (on the side opposite the dough). That way, you can use it as a guideline while rolling.

Step 8

Repeat this step with the other dough ball - make sure the dough sheets are equal in size. Then transfer both to the fridge for at least an hour to chill (or for up to a day).

Step 9

Decide which (chocolate or vanilla dough) you want to be the outer and inner swirl in the pinwheel cookies. OR, if you can’t decide, you can even do half and half, as I did.

Step 10

Place the color you want to be the "outer" swirl on the counter first and peel away the top layer of parchment paper. Then, remove the parchment paper from the top of the other sheet and carefully flip it over, placing it on top of the first sheet. Then gently roll or press just to make sure the two adhere slightly.If you want half and half, now you can slice the sheets in half lengthwise and flip one over (so the color on the bottom is now on top).

Step 11

Now it’s time to gently roll the cookie dough into logs. You can use the parchment paper underneath to lift and help you create the first roll. Roll the first roll tightly to avoid gaps in the cookies.If the dough cracks while rolling (more likely with the drier chocolate dough), just gently pinch it together and continue rolling. If there are cracks on the outer layer, roll it on the surface a little to smooth out the cracks.TOP TIP: If you’re rolling a single log, I recommend rolling them from the longer side (for fewer swirls but a nice cookie size). If you roll from the short side, you’ll have tons of swirls and larger cookies—it’s up to you.If you’re creating two logs (As I did), I like to roll from the short side to create a nice swirl within.

Step 12

Once rolled, re-wrap the roll/s in parchment paper. Then place back in the fridge to chill for an additional hour (or overnight). Alternatively, chill it in the freezer for 20-30 minutes.

Step 13

Preheat the oven to 350ºF/175ºC.

Step 14

Remove the roll/s from the fridge. If the underside is slightly flat from resting in the fridge, lightly roll it on the surface to smooth it out. If you chilled the sugar cookie dough in the freezer, allow it a few minutes at room temperature before slicing.

Step 15

Slice the log into ¼-inch cookies and place them on a parchment-lined baking sheet, separated by around 1 inch.

Step 16

Place the baking tray on the middle shelf in the oven. Bake for between 10-12 minutes, or until the edges are just becoming golden.It's best to bake one tray of cookies at a time (so it's in the middle of the oven). While baking the first back, you can prepare and cut the cookies for the second. Alternatively, you can save the rest for later (read the storage section below for details).

Step 17

Once baked, remove the cookies from the oven. Allow them to cool on the tray for a few minutes before transferring to a rack until fully cooled.

Step 18

Make ahead: there are several ways you can make these old-fashioned pinwheel cookies ahead.The mixed dough: wrap it in plastic wrap and store in the fridge for 4-5 days or in the freezer for up to three months.The rolled cookie dough log: wrap tightly in plastic wrap and store in the freezer for up to three months. You can also gift the frozen logs to friends and family. That way, they can defrost (15-20 minutes at room temperature) and slice and bake the cookies when wanted.The sliced cookies: flash freeze the cookies spread out on a baking sheet (not touching) until solid. Then transfer to a freezer-safe container or Ziplock bag for 3 months.Store: allow the chocolate pinwheel cookies to cool and then store in an airtight container on the counter for 3-5 days. You can also freeze the baked cookies for up to 3 months. Allow them to thaw on the counter before serving.