Chocolate Chip Cookie Sweet Rolls (2024)

Chocolate Chip Cookie Sweet Rolls (1)

I have a sweet roll problem.

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I blame my original cinnamon rolls. For they are evil. And they must be destroyed.

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From there I made these orange marmalade rolls. A triumph.

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Then, with zero shame in my soul, I made these caramel apple rolls.

Help.

Over the weekend, I made a whole bunch of cinnamon rolls for Cookie Sunday at church. Cookie Sunday used to be called Linger Longer, and before that, I think it was happy hour, which might have inflamed the evangelicals because of its reference to discounted booze…but I’m a Presbyterian and nobody cared.

I set aside some of the cinnamon roll dough and decided to try yet another variation of sweet rolls. I steered away from anything having to do with fruit or cinnamon…and I got myself into a little trouble.

Just scroll. You’ll see what I mean.

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The whole world of my cinnamon rolls begins with this: four cups of whole milk.

This is a big moment, folks.

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Pour it into a dutch oven or other pot.

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Add a cup of sugar…

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And a cup of oil.

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Stir it together and heat it over medium heat. Don’t let it boil. Turn off the heat and allow it to cool a bit. You want it to be warm, but not too warm for the yeast.

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When it’s cooled enough, sprinkle in the yeast.

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Let it sit on the surface of the warm liquid for a couple of minutes.

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Then add eight of the nine cups of flour.

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Stir it gently to combine. It’ll be super wet and stick.

And that’s what you want.

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Then place the lid on the pot and allow to sit in a draft-free place for one hour.

I love using heavy cast iron pots for yeast doughs, as they tend to trap in the warmth and give the yeast more of a yeast-happy environment.

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Here it is an hour later!

Groovy, man.

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Time to add in an additional cup of flour…

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A good tablespoon of salt (don’t skip this!)

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A heaping teaspoon of baking powder…

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And a scant teaspoon of baking soda.

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Stir it around…

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Until it’s all combined. It’ll take a little time to get everything incorporated.

After it’s all combined, you can either proceed with the rolls OR cover the dough and keep it in the fridge for awhile. The dough really is easier to work with if it’s cooler…but I’m usually too impatient for that step.

In any event, when you’re ready to make the rolls, divide the dough in half. You can make a double batch of these rolls, OR you can make another variation: cinnamon rolls, caramel apple rolls, orange rolls. Change things up!

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Melt a stick of butter. Add in 2 teaspoons of vanilla extract.

Then roll out the dough in to a large rectangle: around 24 inches long by 10 to 12 inches deep.

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Pour the butter over the dough, then use your fingers to smear it evenly all over the surface.

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That is one big rectangle of dough.

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Sprinkle a mix of white sugar, brown sugar, and salt over the top.

Just like chocolate chip cookies!

It’s all making sense now.

Sorta.

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Grab some chocolate chips or (in my case) chocolate chunks. You can buy the chunks as is (the shortcut) or you can buy squares of semi-sweet chocolate and chunk it up yourself.

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Mmmm. This is looking very promising.

NOTE: In the recipe below, I call for chopped pecans to be added at this step. Totally optional!

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Next, begin at the side of the dough the farthest from you, and begin rolling the dough into a long log. Your fingers will act as a typewriter in a sense; you’ll go all the way down, rolling as you go, then back the other way, still rolling as you go.

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This is about 3/4 of the way done.

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When it’s totally rolled, pinch the seam to get it to seal.

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Done!

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Now use a sharp knife to cut 1/2 to 3/4-inch slices…

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Then lay them in a buttered pie pan, cake pan, or rectangular baking dish.

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Cover it with a tea towel…

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And go live the life you were born to live! Climb every mountain! Search high and low! Follow every byway—every path you know!

But only for 20 minutes or so.

(Name that movie.)

After 20 minutes, pop ’em into a 375 degree oven and bake ’em till they’re nice and golden and bubbly.

But while they bake…make the icing. You’ll want to pour it on while the rolls are still warm.

You must trust Pioneer Woman.

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Powdered sugar (sifted if you’re motivated; unsifted if you’re like me), softened butter, softened cream cheese, vanilla, salt, and milk.

Salt, because you’ll die from the sweetness otherwise.

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Mix it until it’s very pourable. Not just spreadable—pourable.

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Then as soon as the rolls are out of the oven…

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Pour it over the top.

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Mmmm. Warm rolls with cream cheese icing.

There’s nothing better. Nothing.

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Completely drown the rolls in icing—you want them positively swimming in the stuff. It’ll melt and run down into the cracks and crevices of the rolls, and your life will finally, at long, long last, make sense.

I will tell you that with this experimental batch of icing, I initially only added 3/4 cup of milk. That’s the batch you see here, and I wound up having to spread it with a knife. Ultimately, I determined that an additional 1/4 cup of milk was necessary to avoid having to spread. See the printable recipe below for the correct quantities.

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Sprinkle the tops with more chopped nuts, if you’re into that kind of thing, then remove them and serve!

Or you can let them cool, then refrigerate them till the next day. Just nuke ’em before you eat ’em.

It’s the right thing to do.

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Mmmm. Here we go.

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These were yummy. While nothing can top the original cinnamon rolls, these were a fun, chocolaty diversion.

And the more fun, chocolaty diversions in my life, I figure, the better off I’ll be.

Enjoy these!

Chocolate Chip Cookie Sweet Rolls (2024)

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