Hamantaschen Challah and Chocolate French Toast Casserole

I am a bit late posting this. The Shabbos before Purim I made Hamantaschen Challah: egg rich, vanilla scented dough surrounding a dark chocolate filling.

Slices show an oval of chocolate bread floating in the center of the challah.

I used leftovers to make decadently rich baked French toast (a kind of bread pudding, topped with a toffee sauce and milk chocolate chips).

The inspiration for the chocolate filling is this recipe for chocolate cherry bread from the Metropolitan Bakery in Philadelphia (and here is the video of the chef making this bread). To make things easier, instead of making two doughs,  I just added cocoa powder plus a little more water and sugar to half a batch of regular challah.

Hamantaschen Challah

21 ounces bread flour (plus another 1.5 ounces, held in reserve)
1 Tbl. yeast
1 cup water
4 ounces oil
3 eggs
3.5 ounces sugar
1 Tbl. kosher salt (or 2 1/4 tsp. table salt)

for chocolate dough: add another 5 Tbl sugar, 8 Tbl. cocoa, and another 2-4 Tbl. water to half of the plain dough
can also add chocolate chips and dried cherries

egg glaze: 1 egg, beaten

Mix together the flour, yeast, egg, oil, and water. Mix the dough, rest 15 minutes, and then mix the dough more until the gluten is developed. Add the sugar and salt and mix more. The dough will get wet and sticky after you add the sugar and salt. Don’t add the extra 1.5 ounces of flour yet. Mix some more and dump the dough onto a well floured baking sheet (use the extra flour for very generously flouring the sheet). Divide the dough in half. Add the extra water and sugar, plus the cocoa powder to half of the dough.  You could also add chocolate chips or dried cherries, if you like.  Add the chocolate dough to the sheet with the plain dough (make sure the surface is well floured).

Let the two doughs rise, covered, for about two hours. Divide the each dough in half to make two chocolate balls and two plain dough balls. Flatten the plain dough to make a large circle, place over a chocolate ball, and pinch the sides to make a hamantaschen shape.

Let the shaped loaves rise for another hour and a half. Glaze towards the end of rising, and when the glaze dries, add a second coat of egg glaze.

Bake the loaves at 350 degrees for 35 minutes.

Chocolate French Toast Casserole
8 slices chocolate challah
5 eggs
1 1/2 cups milk
1/2 cup brown sugar
1 cup cream or half-n-half
1 tsp. vanilla
1/2 tsp. cinnamon

Toffee Milk Chocolate Chip Topping
1/2 cup melted butter
1/2 cup brown sugar
1 cup (or more) milk chocolate chips

Lay the slices of challah in a 9″x13″ pan. Mix together the eggs, milk, cream, sugar, cinnamon and vanilla. Pour egg mixture over the challah. Combine the topping ingredients (except the chocolate chips) and spread over the top. Sprinkle over the chocolate chips.

Let the casserole sit overnight in the refrigerator. Bake the next morning at 350 degrees for 40-50 minutes.


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11 Responses to “Hamantaschen Challah and Chocolate French Toast Casserole”

  1. Shoshana Ohriner Says:

    You are so creative! These look great.

  2. Chavi Samet Says:

    Now that’s creative! How did they come out?
    It’s so funny, I made bread pudding yesterday, and I just noticed that my sister posted a Strawberry Shortcake Bread Pudding on her blog… I guess we’re all thinking in the same vein- get rid of chametz!! I’m sure with the twist of chocolate challah, it was extra decadent.

    • pragmaticattic Says:

      The challah was great, but here is the thing: the challah with chocolate added is a bit slower rising than the vanilla (partly because you need to add more sugar so that it won’t be bitter). Next time I would add lots of chocolate chunks to add more sweetness without adding even more sugar to the dough. Maybe also a pinch more more yeast to the chocolate dough?

      And, yes, we are all thinking: get rid of chometz!! It was super decadent with the chocolate chips and toffee sauce.

      BTW, your sister’s blog is great–you both are so talented in the kitchen. Did she really work for Shallots in NYC? That is so cool.

  3. Chavi Samet Says:

    Adding the chunks sounds like a great idea— I would probably add more yeast as insurance, or even if you could find the Osmotolerant stuff, but I havent seen it here at all.

    Thanks so much for the compliments on her blog and both of our abilities in the kitchen- I wish I could cook as well as she could! And yes, she really did work in Shallots, way back when.

    Any interesting spelt recipes up your sleeve? I have flour to be rid of…

    • pragmaticattic Says:

      Oh, right! The osmotolerant yeast . . . I have always wanted to try that kind of yeast with a sweet challah recipe.

      Wow, I would have loved to have worked at Shallots . . . I took a class with Laura Frankel at the restaurant once.

      Spelt . .. I have never baked with spelt. You are more adventurous that way. But, there is a recipe on LevanaCooks for Spelt Challah that uses up 12 cups of spelt flour. And Tamar Ansh has a challah recipe that uses 5 lbs. of spelt flour.

  4. Schlissel Challah « Pragmatic Attic Says:

    […] my schlissel challah, I used this recipe, scaled up to use 5 lbs. of […]

  5. Paula Says:

    So how do you keep the hamantaschen shape without it opening up.? It was fine till it went into the oven. .. then it magically had to be renamed into Esther’s crown!

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