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Challah is a bread badass. It looks all shiny and put together on the outside, braided into fancy styles of the kind my 6th grade self would have only dreamed of sporting. The inside is soft and pillowy, with a rich, eggy flavor and a hint of sweetness. It's not satisfied just gracing your bread basket or toaster, either. Challah is the comeback kid, making bread pudding, French toast, and stuffing more than an afterthought.
I was a little nervous to make my first loaf because I grew up in New York City, where not only can you always get challah—scarcity being a problem I've encountered here in San Francisco—but you can get really awesome challah. But with Thanksgivingukkah fast approaching, there was no time for self-doubt. So I got out the stand mixer, rolled up my sleeves, ran across the street because I forgot to buy eggs, and finally got cracking.
What differentiates this recipe from other breads is the inclusion of eggs (making it similar to a brioche), a bit of sugar, and vegetable oil. About that sugar; this bread isn't sweet, it's just not savory or even plain. The cranberries push it more towards sweet territory, though, so if you like your challah more neutral, feel free to leave them out.
While plain challah exists, for me, the braid is de rigeur. I decided to go all out and make a 6-strand braid, and thanks to instructions from The Shiksa in the Kitchen, it was easy. However if it's your first go-around or you're not particularly dexterous, a regular three strand braid works just as well. Maybe your Thanksgivingukkah table won't even notice.*
This bread does have three rises, which means about 2 1/2 hours of rising time in total, so plan accordingly. Definitely double the batch so that you can use one bread for eating out of hand and other for one of those delights I mentioned above.