2010 Tax Season Cookie Rollout – Pinwheel Cookies

Thanks, Mom, for this headline. My father’s an accountant and for a few months every year he disappears into the seemingly infinite abyss of 1040s and W2s and whatnot. I decided I wanted to make him some cookies to help him cope, and when my mother told me he was already losing weight I knew I had to take action immediately.

Though these weren’t on his list of favorites, I coyly asked him about those the other day, the man loves chocolate so he’ll deal. They also fall under the category of cookies I previously made, didn’t document, and therefore wanted to recreate. It’s a simple way to start off the rollout. If I jumped right into apricot rugelach, what would he have to look forward to?

These are great, simple cookies (semi-simple), basic flavors, and the best part is they’re slice and bake-able! The recipe makes 4 logs of dough, they freeze easily, and can be baked straight from the freezer. I only baked 2 of them, so the rest are awaiting a special occasion (Though, the coworkers have commented that my baked goods come too infrequently, so maybe tomorrow’s a special occasion? It’s a damned if you do, damned if you don’t situation – I make baked goods and get chastised because everyone’s given up sugar for the new year, and the sugar lovers say they don’t get enough.)

But this is about my dad, and the man needs to eat. If cookies will sustain him until April 15th, then I will do what I can to get him those cookies! He doesn’t know about the rollout just yet, but he’ll catch on after a few weeks.

So now, here are the chocolate/vanilla pinwheel cookies I adapted slightly from Epicurious, and have carefully selected as the first installment of the 2010 Tax Season Cookie Rollout.


  • 3 cups all-purpose flour
  • 1/2 tsp baking powder
  • 1/2 tsp salt
  • 1 cup unsalted butter, softened
  • 1 1/3 cups vanilla sugar (can use regular white sugar)
  • 2 large eggs
  • 2 tsp vanilla extract
  • 2 ounces semisweet chocolate, finely chopped
  • 1/4 cup dutch process cocoa powder

In a large bowl, sift together your dry ingredients – flour, baking powder, and salt.

Beat butter in a mixer until fluffy, then add sugar and beat some more. Add eggs one at a time, beating after each addition, then add vanilla exract. Add the flour mixture in 2 batches and beat on low until just combined.

Divide dough in half. I actually tried to put more than half the dough in the “vanilla” section, because I knew adding the cocoa powder and chocolate would give a little more mass to the chocolate half. Take the vanilla half, form it into a 4″ square, wrap in plastic and set aside.

Melt your semisweet chocolate, stir until smooth. Add it to the dough in the mixer, followed by cocoa powder, and beat until just combined. I did not have unsweetened chocolate, which this recipe called for originally, so I used the semisweet and tried to lessen the sweetness and up the chocolate factor by adding the powder. In terms of taste this was great. Dough workability was rough, man. Real rough.

I think I should have added something, tbsp of milk perhaps, to soften it a bit, but I didn’t know what. I also didn’t know how rough it would be until I tried working with it.

Anyway, mold the chocolate dough into a 4 x 4″ square, wrap in plastic, and refrigerate both squares for 30 minutes. Here, I think, is where some of my future difficulties lay. I kept the doughs in the fridge too long, and didn’t let them warm up before working with them. The chocolate dough seemed to have hardened, it was dry and crumbly. The vanilla dough was solid, but it at least started rolling out more easily after a while. I would make sure to monitor the refrigeration carefully, and not leave it in too long. (Like I did.)

Line a baking sheet with parchment paper. Cut each square of dough into four separate 4 x 1″ strips. Leave out one chocolate strip, and put the remainder on the baking sheet back in the fridge. Roll the dough out into a 6″x7″ rectangle between two sheets of parchment paper. Do not use wax paper, guess how I learned that lesson. I did not measure this, but the basic point is you want some overhang on the top and bottom when you layer the vanilla dough with the chocolate. Remove a vanilla slab from the fridge, and roll it out into a 6″x6″ square. It should be close to exact, but don’t kill yourself over it. You’ll be cutting off the ends anyway.

Place the vanilla square on top of the chocolate rectangle with about 1/2″ overhang on the top and bottom edges. Gently run a rolling pin over the doughs to make sure they stick together.

Fold one chocolate overhang onto the vanilla dough, and starting at that end, tightly roll up the rest of the dough into a log. It doesn’t have to be perfect, but it should be tight, otherwise you end up like me, with holes in the middle of some cookies.

Once you have a log, roll it out a little wider like you would clay, to make it thinner. This isn’t in the directions, but I was hoping it’d help the pattern as well as yield more cookies (albeit smaller ones.) Don’t roll it out super thin, I just did a bit because I didn’t know how my original log would split into 20 cookies. I ended up with about 25 each this way. You do the math 😉

Wrap the log in plastic wrap, I rolled mine up in parchment, and refrigerate.

Follow suit with the rest of the dough. To alternate patterns, I did 2 logs with chocolate on the bottom and 2 with vanilla. It does not affect the flavor, and if anything it’s a PITA to do because there was more chocolate dough than vanilla so I had to cut the excess and the vanilla rolls out thinner because there was less, and yadda, yadda, yadda. Anyways, they look prettier that way, but the vanilla cookies ended up smaller in this batch.

Refrigerate logs for an hour. Take them out, roll them a bit on the counter to keep them round, then refrigerate again. After another 3 hours, you can put them in the freezer (I’d put them in a freezer bag too.)

Those directions are for freezing the cookie dough to give as gifts, but I was making some of these immediately. I did leave them in the fridge for an hour, and preheated the oven to 350 while I was slicing. While you’re slicing them, rotate the log slightly so that it never gets too flat on one side. Cut the cookies about 1/4″ thick.

See the holes in the middle? Didn’t roll tight enough! Oh well, they all taste the same, and as someone once said (can’t remember who) at least in baking you get to eat your mistakes 🙂

I spaced them 4 across and 5 down on a parchment lined baking sheet.

These puff out a to be a bit larger, but you can still fit 4 of them in a row. Bake 9-11 minutes. I baked towards the lower end, rotating halfway through.

They’re simple tasting, but awesome looking. I won’t insert a joke about them being hypnotizing. (oops.)

The great thing about these too is they froze really well. I baked up the rest of them a week or so later for my coworkers. Just take them out of the freezer, slice, and pop in the oven. You’ll probably need to use the upper end of the time range for baking, but they come out as fresh and pinwheely as ever!

Also, I was just thinking you could probably mix up the flavors a bit. You’d want to keep them diverse enough so the pinwheel pattern comes out, or what’s the point? Peanut butter and chocolate are now on my “to do” list…

Hope these hit the spot for you in this early stage of Tax Season!

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