The Hamantaschen Chronicles: 2016

Once again, we began our Hamantaschen enterprise this year full of good intention, tons of thought, and feeling ready for the challenge. And at about nine in the morning, I got a message from my friend S., who said, “I’ve never baked hamantaschen before, but I really want to do it. Can I really use whole wheat flour to make hamantaschen?”

This, friends, is not how a hamantaschen novice should start out, by worrying about whole wheat flour. As any experienced hamantaschen baker knows, one of the biggest challenges about baking these cookies is that most recipes — and I really do mean about 90% of them, in my experience —  produce a dough that bakes up into tough, tasteless things that you really have to suffer through to before you get to the good part (the filling). This is just wrong. It’s not how it’s supposed to be. In an ideal situation, both the cooky and the filling are both delicious and a pleasure to eat.


I explained to S. that the tenderness of the cooky is an Issue even under the best of circumstances, and that whole wheat flour is never, ever, going to make matters better. I then spent about an hour at the computer, sifting through recipes I’d emailed to myself, through old blog posts about hamantaschen, looking at websites, side by side with S.

“I think I’ll do the Smitten Kitchen recipe,” she said.

“Which one?” I asked. “I have three different SK tabs open now.” Proof that any hamantaschen baker worth his or her salt is always, always hunting for The One. If Deb Perelman is still looking, we’re all still looking.

S. thought that the big issue was going to be folding them so that they stay folded. I said that this is a big issue, and that failure is very frustrating, but that I’d learned that doing an egg wash on the cooky rounds before folding makes a huge difference. I emphasized that producing hamantaschen is a giant pain in the ass, and tedious, and full of tragedies. “You have to be prepared for the results to be ugly,” I said. “You have to NOT MIND THIS. You have to be ZEN AS FUCK about it. And you have to hope that the cooky part at least tastes good, not dull and floury.”

We then went to our respective kitchens and began baking. In my case, I discovered quickly that I had sorely miscalculated how much butter I had in the house. While I thought I had at least a pound stored away in the freezer, and several sticks left in the fridge, it turned out I did not, and I had to cobble together ends of various bits of butter (including using the hideously expensive Arethusa Farm Dairy butter I bought a while ago, which I was saving for Something Special) to come up with a scant pound. I got out my kitchen scale and weighed and re-weighed. No matter what I did, I had not quite a pound of butter. “No matter!” I said. “I can still do this.” I then put the butter I had into the Kitchen Aid bowl and put on the paddle attachment with the silicone edges — a handy thing because it scrapes the sides of the bowl for you as it beats the butter. I turned the machine on, and immediately heard a nasty crack. The butter was not as soft as it perhaps should have been, and I broke my paddle attachment.

I went to Facebook and typed, “This is a sign of some kind.”

Then I got out my old metal paddle attachment and started over. Cream the butter, I thought placidly. Double the recipe, cream the butter. Not quite a pound of butter, I’ll just do a little less flour, everything should be fine. The butter was creamed, and so I smoothly added sugar to the mixer bowl. I looked again at the recipe I was using, which was from a blog post I had written myself a couple of years ago. And then I caught my breath. “Double the recipe,” I’d been reciting in my head. But the recipe called for four ounces of butter, which was one stick. And it said to use a little more than a cup of sugar.

I’d managed to get myself messed up about whether a stick of butter is 4 ounces of 8 ounces. It’s four ounces, friends. Not eight.

I hadn’t doubled the recipe, I had quadrupled the recipe. If I had almost 16 ounces of butter, that meant I’d have to use significantly more than one cup of sugar. And more of…. everything.

I thanked god that I had two cans of poppyseed filling, because I was going to need them.

And then I took my own advice, and got Zen as fuck.

Because I realized that the instructions I was so carefully following were about to mess me up again, I stopped everything and tried valiantly to think hard. If I doubled the recipe, I would be using…. eight cups of flour. Which was impossible. Eight cups of flour is what I’d use to bake a couple loaves of bread, not to make hamantaschen. Not even a LOT of hamantaschen.

So I got even more zen, and I took a deep breath, and I carefully measured out three cups of flour and brought the flour canister over to the counter where I was working. “You can always add more, but you cannot take away,” was my mantra. I added the three cups of flour to the mixture and while it clearly was not enough — the dough was so soft as to be completely unworkable — I had no idea how much more I needed. I began to take flour from the canister in small quantities and work them in gently with a wooden spoon. The mixer was getting tired and the dough was crawling up the neck of the paddle. I didn’t count how many more cups I added, but it was probably a little over five cups, total, that I used. I then very smartly put the mixing bowl into the fridge to let the dough rest and chill (because it’s impossible to work at room temperature, but when it’s cold, it’s very easy) and began to prepare the baking trays. Four trays with four sheets of parchment paper were readied and stacked nearby. I floured the countertop heavily, pulled a hunk of dough out of the mixing bowl, and gingerly began to work with it.

The dough rolled out beautifully. It cut perfectly. I added the scraps back to the mixing bowl, so they could rest and re-chill, and I focused on brushing on the interior egg wash. (One jumbo egg took care of all the egg washing, inside and out, that all these cookies required.) Cut; wash; fill; fold; wash; make sure folds are sealed. The cookies — a dozen on each tray — went into the hot oven, and I let ten minutes go by before I looked nervously through the glass door to see how they were doing. This is the moment when you really have to steel yourself for disaster. There is no guarantee that what you’ve put together will, in fact, work.

To my considerable joy, the cookies looked great. A little puffier than I’d expected, somehow, but better they be puffy than that they look hard and sad. These were big, happy, fluffy kittykats of hamantaschen, and the filling was staying exactly where it was supposed to.


I let the trays bake for 25 minutes and then took them out. They were perhaps a little less golden than I might have liked, but to leave them in longer would mean risking burning; so onto the cooling racks went the cookies, and I slammed the next round in.

I spent the next few hours breathing calmly. I cut, washed, filled, folded, and washed again. And in the end I had I think 67 hamantaschen, and only two of them weren’t quite perfect little triangles. (One of them had four corners. I don’t know why it happened but when I started folding it, somehow I couldn’t get it to do what I wanted, and it turned into a square, and by then I didn’t want to fight with the dough anymore, so I let it bake as it. The other imperfect one was made with the last scrap of dough, which I pressed into a circle by hand, and since I was by then quite tired, I just curled up the edges a little and put filling on top of it and said, “Baker’s treat.”) In the end, 65 hamantaschen worthy of being served to family and given to friends. I took a picture and sent it to my husband, who was impressed. When the cookies were all on the racks and cooling, I then turned around and baked the two loaves of bread I’d been working on, which had waited with great patience in their pans on the kitchen floor right in front of the fridge (don’t ask). (One glory of the Pullman loaf is that, since it is tightly covered, you can do things like let it rise on the kitchen floor and it’s totally fine.) All of this was achieved, mind you, before I went to pick my daughter up at school at 4 p.m. (later than usual because of a special event), which is nothing short of a miracle.

That night my husband ate several cookies while my daughter and I attended services at a nearby synagogue. “They’re perfect,” he said after we got home. “It’s very impressive. Your hamantaschen success rate is about 60%, but these are perfect.” The cooky was a sweet, crumbly, soft shortbread-like cooky — it was so good that, in fact, my daughter asked if I could make the cooky again but without the poppy seeds. Could I bake it with, say, sprinkles on it instead? The filling was wonderful because, of course, it came from a can, and I had nothing to do with it. I claimed victory all over the place, and we delivered a couple dozen cookies around the neighborhood feeling triumphant.

Late that night S. checked in with me. She’d made her hamantaschen, and sent me a photo. They looked perfect, and I told her so. “The cooky is tough,” she wrote sadly. “Tough hamantaschen are endemic,” I said. “Next year, you’ll do better.” I can say this because I know from experience. I told her she did great and not to worry.

As for my perfect hamantaschen: If I can pull this off again next year, it’ll be a miracle, but on the other hand, I really think I can do it. I think I’ve got it licked. (Famous last words. Tune in, in mid-March 2017, for the next episode of the Hamantaschen Chronicles.)


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