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! 

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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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