This is one of the more challenging breads that I've made because there are several steps involved. Instead of mixing the chocolate chips and diced prunes directly into the dough as it's being made, you prepare the dough ahead of time, chill it and roll it out like you were making a pizza, and then add your sweets. It's not difficult, per say, but any time you add more steps to a project, you increase the likelihood that one of them will go disastrously wrong, or if you are me, you will forget a step altogether.
Here's how it goes though.
Step 1: Make your challah dough. Again, I used the recipe in the book Artisian Bread in Five.
Side note: If you are at all interested in learning to make your own bread (and you really should, because it's much easier than you think!!), this is the book to get. All of their recipes are no-knead, and most of them you can make with ingredients you already have in your kitchen (except maybe the yeast, but that's cheap and easy to find).
This is not a difficult step. Follow your recipe, don't overmix, and let your dough rise for at least 2 hours. I let mine refrigerate for several days before I used it, but I would assume a few hours would be long enough- it's easier to work with when it's chilled, so I would not recommend skipping this step.
Step 2: Roll out your dough to 1/2" thick, as if you were making a pizza.
Step 4: You have to let your dough rest for an hour-twenty, then you bake it for another 45-50 minutes, but when it's done, it will look something like this:
And that's the great thing about making dough ahead of time and keeping it in your fridge. If I had to start over from scratch, I would have to wait 2 hours for the dough to rise, let it chill for at least an hour, then prepare the dough with the filling, let it rest another hour and a half, then bake it for approximately another hour. That's 5 and a half hours. Too long. I just took my dough out of the fridge and cut my wait time in half.
The verdict? This bread gets a 10/10. Two thumbs up. A gold star. It's really, really delicious. The challah dough is soft and chewy, with a nice crispy crust. Paired with chocolate, the prunes are a nice sweet touch. It's a real winner. And it looks so impressive, too. Everyone in my family should expect a loaf of this for Christmas. (spoiler alert!!)