Mandi’s Hippie Holiday Hamentashen!

So the entire reason for my previous sugarless sugar cookie experiement is that I used to use the Betty Crocker sugar cookies as the base for my very favourite cookie of all. Hamentashen!

Delicious sugar-free hamentashen!

I was brought up as more of a hippie child than a good little Jewish girl, and we hardly observed any of the Jewish holidays. However, our family just loves loves LOVES a good hamentashen. And in our family, there’s only one type of hamentashen worth mentioning. PRUNE!

Yes, the glorious prune hamentashen. Prunes get such a bad rap but they’re delicious! People are so much less squeamish about discussing fibre these days, so when is the prune stigma going to disappear?

Last year, I started a new tradition. Since I’m now married to a wonderful Christian man who actually celebrates Christmas (with a Christmas tree and church and everything) I thought it would be nice to start a new tradition: the Christmas Hamentashen!

So now I make 2 versions of my hamentashen for Christmas; traditional prune and a second version with dried pear, dried fig and cranberries and any other dried fruit I’m in the mood for.

Step #1. Make the cookie dough.

For the base of the hamentashen, follow my recent recipe for sugarless sugar cookies. I recommend making the dough one day in advance. Cookie dough is always better when chilled.

Step #2. Make the Filling.

For the prune filling: blend up a about 3 cups of pitted prunes in your food processor. Add some fresh lemon juice for a bit of liquid.

For the Christmas filling: blend approximately 3 cups worth of your favourite Christmassy dried fruit in the food processor.  I like dried pear, fresh cranberries, dried figs, cherry raisins (red raisins) and if you think it needs it, a bit of agave. I stay away from sugar now but if you like other dried fruit that has some sugar in it, go for it! Candied orange could be very delicious.

Step #3. Make & Bake.

  1. Roll out your cookie dough. I roll mine with corn stach and, conveniently, the lid to the type of cornstarch that I buy is the perfect round circle size for my hamentashen. 3 to 4 inch circles work well. You can turn some sort of other lid or glass upside down if you don’t have a good round cookie cutter.
  2. Put a tablespoon of filling in the middle of each circle.
  3. Fold up 3 sides to form a triangle. Make sure each side overlaps with the side before it. Don’t just pinch it, it has to actually overlap and stick. Leave a bit of filling showing in the middle. 
  4. Bake at 350 degrees for about 9 minutes, until golden around the edges.
  5. Let cool on a rack and enjoy!

I like to make these before the holidays and freeze them. They thaw out well so you can thaw just a few at a time. Otherwise I’ll gobble the all down too quickly! 


One thought on “Mandi’s Hippie Holiday Hamentashen!

  1. Interesting! Thank you for experimenting so we don’t have to. FYI, hamentashen is plural. Just one is a hamentash.

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