Illegal in 37 states…

If I made every recipe I ever bookmarked, printed out , or wrote down on a sticky note I would have to live to 237 years old to get them all done. I’m sure you can relate. I’m sure you have seen a recipe, got all excited about it, wanted to make it and then…shiny squirrel. The next thing you know you are distracted and the moment has passed. Last Summer I saw Cakespy add chocolate chip cookie dough into Cinnamon Rolls. And while I loved the idea of stuffing cookies into cinnamon rolls I was anti the chocolate chip cookie. Seemed weird to me. I decided that I would make them but with Oatmeal Raisin cookies because to me, those go better with cinnamon. And then…shiny squirrel.

But then the other day I was over at How Sweet It Is (fun site, she loves Funfetti and bacon) and there they were again, but again with chocolate chip cookie dough. :(  I decided before that squirrel came back I best gather up the ingredients (which yes, I had all the ingredients…go me) and get it done. One thing that I wasn’t keen on was wondering if the cookie would actually get baked, I was wondering about the whole egg thing. The pictures I saw make the insides look too gooey for my tastes. So I figured to eliminate the egg all together and go the truffle route that uses condensed milk instead of eggs. It was the right thing to do in my opinion.

Shoving cookie dough truffles into food isn’t anything new to me as I have been doing it awhile. First there was the beloved Chocolate Chip Cookie Dough Cheesecake that caused quite a stir on Stumble Upon one day that it crashed my site with more than 10,000 views in just a matter of hours. Mostly because people were shocked I could make cheesecake even worse for you…clearly these people don’t know me. :P And then I used them in cupcakes too. The oatmeal cookie truffles have been done before as well in a Cinnamon Ice Cream. My point is I am no virgin….to cookie dough truffles. ;)

In some ways I was afraid to make these. My pants were afraid for me to make these. They had been fitting nicely as of late and so my thighs quivered. Well, they always quiver…not in a good way. :P But they were quivering with both fear (of expansion) and delight (cause of expansion). Apparently I had good reason to be fearful. Topped with the caramel glaze there was so much right with these rolls that it had to be wrong. Needless to say I told my BFF if he didn’t get these out of my site that way more people were going to have to donate to the site for a new wardrobe. For in the blink of an eye two of these were gone (and these are not small…at least mine weren’t) and I could have eaten 4 more no problem. Oh, who are we kidding, 8 more, no problem. :P

So before you bookmark this and forget it….shiny squirrel.

Oatmeal Raisin Cookie Stuffed Cinnamon Rolls with Caramal Glaze

2 cups plus 3 TBSP milk
6 TBSP granulated sugar
2 tsp. salt
1/4 cup unsalted butter
1 egg, slightly beaten
2 1/2 tsp. active dry yeast
6 cups all-purpose flour

For the Filling:
16-20 1-inch oatmeal cookie dough truffles (see recipe below)
½ cup cinnamon sugar (6 ½ TBSP granulated sugar plus 1 ½ tsp. ground cinnamon)

Place 2 cups of milk in a saucepan over medium heat and bring just to a boil.
Combine 6 TBSP of the sugar, the salt, and the butter in a large bowl, pour the hot milk over it, and let cool to 110-115F.
In a small bowl, mix together the egg and yeast.
Add to the cooled milk mixture, and mix well. Add the flour and mix until the dough is soft.
Transfer the dough to a well-floured board and knead until very smooth and elastic, about 5 minutes. Yes you can do this in your mixer with the dough hook, I did. If you use the hook, add about ¼ cup flour to the mix.
Place the dough in a large, well-greased bowl, cover with plastic wrap, and let rise until doubled in volume, about 1 hour.
Lightly dust a work surface area with flour. Roll out the dough with a rolling pin, lightly dusting the top with flour to keep it from sticking to the pin. Roll it into a rectangle about 2/3 inch thick and 14 inches wide by 12 inches long.
Sprinkle the cinnamon sugar over the surface of the dough. Then scatter cookie dough truffles on to the dough. Press down slightly to make them more disc shaped.
Roll the dough up into a log, creating a cinnamon-sugar spiral as you roll. You are going to want to most likely even out the roll with your hands. It will be thick because of the cookie pieces. With the seam side down, cut the dough into pieces each about 1 3/4 inches thick. Place into a well-greased baking pan (I used a 15-x-10 inch pan you can use a cookie sheet or jelly roll pan as well). Place the buns approximately 1/2 inch apart so that they aren´t touching but are close to one another.
Proof at room temperature for 75 to 90 minutes, or until the pieces have grown into one another and have nearly doubled in size.
Preheat the oven to 350F.
When the rolls have risen, bake until golden brown, about 25-30 minutes (watch them…it’s so hard to tell with my crappy apartment oven!) Let cool for about 5 minutes. While rolls are cooling, prepare the icing (recipe follows). Drizzle the icing over the roll and enjoy.

Oatmeal Raisin Cookie Dough Truffles:

½ cup unsalted butter, at room temperature
¾ cup dark brown sugar, packed
14 oz. condensed milk
1 tsp. vanilla extract
1 cup flour
1 1/4 cup rolled oats
½ tsp. salt
½ tsp. cinnamon
¼ tsp. ginger
¼ tsp. nutmeg
½ cup raisins, chopped in half if super large variety

Using a stand mixer with a paddle attachment cream the butter and the sugar together until they are light and fluffy.

Add the condensed milk and vanilla and beat until full incorporated.

Add the flour, oats, salt, and spices and beat on low until combined.

Fold in the raisins. Make sure they are evenly distributed as much as you can.

Using a spoon try to make 1-inch balls with the dough, roll them between your palms to round them, and place them on a greased baking sheet or a large plate/platter. Cover with cling wrap, and freeze for at least 4 hours. You will have left over cookie dough truffle. Chopped those up and make this ice cream. :)

Caramel Glaze:
½ cup unsalted butter
1 cup dark brown Sugar
¼ tsp. salt
¼ cup whole milk
1 tsp. vanilla extract
2 cups powdered sugar

Place the butter and milk in a medium saucepan over low heat.
When butter has melted, add the brown sugar and salt. Cook on low for 2 minutes, stirring constantly.
Take off of heat and add the vanilla extract and powdered sugar. If you want a thicker glaze you can add more powdered sugar.
Top rolls with glaze.

Insprired by Cakespy and reminded by How Sweet It Is

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  1. yep, Peabody, you have DONE IT this time. THIS is MY shiny squirrel. I want to make these … RIGHT NOW !! I’m pretty sure I have everything, including the time, excluding the raisins, and SHINY SQUIRREL !!

    no, really. I’m making these right now!

  2. and haa haa… I totally remember when cakespy made these too… and I had grand plans to do the same back then!! :D

  3. Oh my…that looks unbelievable! I really don’t think I even have words to describe how I feel about this…AMAZING!!!

  4. You had me at caramel glaze. Oh, and anything “truffle stuffed?” I’m in.

  5. omg, you totally make me wish I was not dieting right now. These look sooooo yummy!

  6. I think this is why I was born. This will become my new favorite obsession and I will gladly eat all of these yummy rolls! Thank you for giving me the light to my mission in life :)

    ~The Newly Ordaned Oatmeal Cookie Stuffed Cinnamon Roll Eater

  7. OH.MY.GOD.

    Those looks delish.. Cant wait to see what kind of hate mail you can get out of THOSE babies :)

  8. These look insane!

  9. It’s always nice to know that I’m not the only crazy one with an attention span that has some kind of weird thing for shiny squirrels. Or cookie dough. Or making every baked good worse for me than it already is. I’m totally an oatmeal raisin girl so I totally approve of these.

  10. This WOWED me! Beautiful rolls!

  11. oh my gosh. a cookie inside of a cinnamon roll; that has got to be the best invention ever! Sadly, if i made these, I would be the only one eating them because everything I make, my family eats like one or two of then I’m left with a boat load of *insert baked good here*.

  12. Love the cookie dough truffles comment, especially :D HOLY YUM rolls!

  13. Illegal doesn’t begin to explain how amazingly bad-good these are. Excellent job!

    We invite you to share this post and some of your favorite food posts on Food Frenzy.
    Please check out our community.

  14. Oh. Ehm. Gee!!!! I can’t stop the drooling.

  15. Those look just devilishy scrummy!



  16. Oatmeal cookie, chocolate chip cookie, either way, these sound incredible!

  17. Oh my gosh, these look amazing! Awesome!

  18. Initiate salivary glands. I want one, or five!

  19. It doesn’t get much better than combining cinnamon rolls and cookies!

  20. These look sooooo good!

  21. I’ve never heard of a shiny squirrel! Can totally relate to wanting to make more than I can manage to though.

    They look good, sore of like Chelsea Buns.:)

  22. These look amazing… I might go into a coma before I even start my day if I eat these for breakfest!

    Please come and take a peek at my food blog :)

  23. You never seize to amaze me, once again taking two things I love and smashing them together. Ridiculous in a very good way. I’m actually hoping for a shiny squirrel since these would probably put me in my grave :).
    And I’m a cookie dough fiend, raw eggs be damned. Truthfully salmonella is not something you need to worry about, only 0.003% of all quality eggs carry salmonella which is 1 in every 30,000. Like many food fears, it’s a lot of scare tactic.

  24. Oh my, do you have a picture of one pulled apart? I think I would frame it.

  25. Drooling, drooling…

  26. I agree with your choice of oatmeal raisin cookie dough over the chocolate chip dough – and with the caramel glaze, they are spot on. I see shiny squirrels all the time – I have to clean out my drawer of printouts once a year before it takes over my apartment.

  27. I do that all the time! My backlog of “I really should make that someday”s is pages long by now, I swear.

    This actually reminds me of one of the things on that list: Brownie-stuffed chocolate chip cookies. Must make those at some point, when I can find gluttons willing to eat them if they come out.

  28. alas Peabody, my life is filled with shiny squirrels. I believe there is a hollow tree in my brain, and they’ve built condos. Shiny squirrel metropolis.

    however, I’ve managed to bake a few things, despite the blingy infestation. Your site allows me to dream (drool?), then the shiny squirrels take over. It might be the cause of my recent infatuation with nuts. I have a bag of pistachios, and I need to buy more bags of pecans.

    hope you have a great weekend <3

  29. Wow you’ve done it again. Taken something I already thought was decadent and made it sinfully decadent. Yikes – would love to try this.

  30. I am so glad that these are so complicated and time consuming to make because it is the only thing keeping them off of my hips!

  31. I have some challah dough sitting in the fridge which I had intended on turning into cinnamon rolls, but now I think I have to stuff them with something awesome, like cookie dough…

  32. So glad I’m not the only one who..Oh, Shiny Squirrel! And I too, need many lifetimes (and some additional talent) do make/cook/bake all the recipes in all the cookbooks, magazines, pieces of paper I’ve collected.

  33. I have all of the ingredients. Plenty of time on my hands. And need to purchase some new interview clothes anyway.

    These are going to be breakfast tomorrow.

    Hopefully NOT eight of them!

  34. I’d like to make these the night before and bake them the next morning. How should I go about doing that so they rise and bake up nicely? Thanks.

  35. Oh btw how many do these normally make?

  36. Peabody says:

    @Zoe- I have never done that so I really can’t say. I would guess that you have to get them to the rolled into rolls, and instead of letting them have the last rise put them in fridge. Then take them out of fridge in morning and let them rise. I would guess the rise will be longer as they are starting cold.
    I don’t know how many they normally make. Everyone makes their roll size different. A standard roll recipe usually makes around 12.

  37. I wish you were my real life friend and neighbor. I could totally help you prevent thigh expansion by eating these for you…


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