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Rosh Hashanah Caramel Apple & Pomegranate Challah Pudding


a New Challah Recipe from

rebbetzin Rochie's Kitchen!

We’re back at pre-Tishrei, and while many things in the world feel crazy and different now, this at least is something we’ve done before.

We know what’s ahead, and part of that is the sheer quantity of cooking and baking that will happen in our kitchen between now and Shmini Atzeres.


As you may know from my cookbook, RISING - I’m all about the serving of the food, and not so much the spending all day cooking it.

So, I love myself a hack that allows one recipe to do double (or even triple!) duty.


A note about making challah!

While making challah can feel like a big deal to many people, I hope that many of you have tried it and realized that it’s not that big a deal, (especially if you’ve taken a challah class with me!) and even more importantly, it’s the most rewarding to serve, and also - it’s a mitzvah! So, I hope you don’t need more convincing that challah is a worthwhile endeavor this Tishrei.


It is also a minhag that the most important time to separate challah with a bracha is in the Aseres Yemei teshuva. So if you’ve been holding off until now, go ahead and put up a full batch of dough and get in your challah mitzvah now!

This recipe assumes that you, like myself and so many others, are putting up big batches of challah. My classic recipe (using a 5 lb bag of flour) makes 8 challahs, and very often a few of those find their home in my freezer to patiently await their turn. Pre-Rosh Hashanah I like to take them all out and restock the freezer with round Tishrei challahs. But what to do with all those lovely challahs?

They can get new life as incredible Rosh Hashanah desserts, perfectly themed and extremely delicious. You can make these desserts with spelt challah, whole wheat challah, or any challah you may have on hand (even store bought challah!)

What I love about these is there’s basically one recipe, and it can be used 3 different ways. Rosh Hashanah dessert? Done and Done.

May your new year be as sweet and rewarding as these desserts, and may we celebrate this Tishrei with Moshiach.

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Upside down Caramel Apple and Pomegranate Pudding Cake


This recipe is the basis for all 3 recipes below. The texture of the cake is really special, something of a cross between a pudding and a cake. Don’t tell anyone that it’s made of leftover challah, and watch their expression as they take their first bite. This is a truly unusual and beautiful dessert. Instead of using a parve milk, you can use the Califia Farm creamer (which is a combination of almond and coconut cream) It’s supremely rich, and they come in many flavor combinations which adds to this already delicious recipe. I tried it using the Pecan Caramel flavor, and it was incredible. Enjoy!

8” or 9” springform pan (or round baking pan)

Small saucepan

Medium mixing bowl

2 whole Granny Smith Apples, peeled, quartered and cut into 1/4” thick slices

For Caramel:
3/4 cup Brоwn Sugar
1/4 сup Unsalted Margarine
(I used Earth Balance with very good results)
1/ 2 tsp cinnamon
1 tsp vanilla
1/4 tsp salt

For the pudding cake:
1 loaf Challah, diced into 1/2” cubes.

(If you have challah in your freezer, it slices the easiest when slightly frozen) The drier the challah the better! So use leftover challah, or leave the challah out a while after dicing.
2 cups Pareve Milk (Soy, Almond or coconut whatever your preference, or see recipe description for cream option!)
4 large Eggs
1 cup Granulated Sugar (if using a sweetened creamer, reduce sugar by 1/4 cup)
1 teaspoon Vanilla Extract
1 teaspoon Ground Cinnamon

For Garnish:
1 cup Pomegranate Arils, for garnish
Powdered Sugar, for garnish
Serve with Vanilla Ice Cream, or whipped cream


  1. Preheat your oven to 350 degrees F.

  2. Spray your springform or round cake pans with nonstick cooking spray. Place springform or round baking pan in a larger pan, like a 9X13 or a baking tray. Just in case there is any leakage, this will protect your oven.

  3. In a medium bowl, whisk together milk, eggs, sugar, vanilla extract, and cinnamon until combined. Place the challah cubes in the custard mixture. Gently press the challah down to fully submerge in the custard. Allow to soak while preparing the caramel and apples.

  4. Prepare the caramel:
    In a ѕmаll ѕаuсераn оvеr medium hеаt, mеlt all caramel ingredients together. As it begins to melt, stir constantly to prevent it sticking, and cook until slightly bubbling. About 2 minutes in total.

  5. Slice the Apples

    Pоur саrаmеl ѕаuсе into the bottom of the рrераrеd round pan. Layer sliced apples on tор in a single circular layer. Add the soaked challah, pouring in the last of the liquid at the end.

  7. Bake in the preheated oven for 1 hour until the pudding cake is puffed and golden. A toothpick inserted in the center should come out clean.

  8. Cool for a few minutes before running a knife along the edges (if not using a springform) and inverting the cake onto a serving platter.

  9. Garnish with pomegranates and powdered sugar. Serve warm (if possible!) with a scoop of vanilla ice cream. Enjoy!

Mini Caramel Apple Puddings:


This recipe should make at least 8-12 ramekins depending on the size

  1. Follow instructions as above.

  2. Double the Caramel Recipe.
Using half of the caramel, divide evenly into greased ramekins.

  3. Add 1/2 cup parve cream (like Califia farms, or coconut cream) to the reserved caramel, and warm through, to make it more liquid and easier to pour.

  4. Bake for 30-35 minutes.

  5. Serve (warm if possible) with a scoop of ice cream on top and top with the reserved caramel sauce


Challah pudding stuffed apples:


8-12 Large Cortland Apples
Pecans, roughly chopped (only use if not making this for Rosh Hashanah)



  1. Preheat oven to 325 F

  2. Using a corer, melon baller or cookie scooper, scoop out a nice sized cavity in each apple. Leaving at least 1/2” of apple all around. Be careful not to go through to the bottom of the apple, but be sure to remove the core and seeds. If the apple seems like it might tip over, you can trim a little off the bottom to help it stay upright.

  3. Prepare the challah custard mixture as above.

  4. If using pecans, stir in the pecans.

  5. Generously stuff apples with bread mixture, mounding it on top. This top will get all crispy and delicious, so be generous!

  6. Set in 9- by 13-in. baking pans, you will need 2 or 3, or use a larger roasting pan.

  7. Bake until each apple is very tender when pierced, about 1 hour; check after 40 minutes and tent loosely with foil if they're getting dark.

  8. Serve (warm if possible) with ice cream and the caramel sauce.


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