Jul 12

Fresh Pineapple & Caramel Stuffed Cookies

I’m passionate about stuffing things inside cookies.

pineapple-caramel stuffed cookies-1

Like seriously, there are few things that bring me more joy.  Except maybe this.  And snacks.  I love snacks.  One of my very favorite snacks is Chobani Pineapple Greek Yogurt with some dark chocolate chips added in.  It’s perfect.  And then Chobani has a Caramel with Pineapple Chunks flavor which it also…pur-fect. 

So my thought process for these cookies was…I like caramel (duh), I like pineapple, I like chocolate (goes without saying) and I looove eating cookies.  Almost as much as Barb Killner loooves eating pizza.  Almost.

pineapple-caramel stuffed cookies-7

Along with stuffing cookies with thing, I’ve also become obsessed with Excel.  I blame wedding planning.  Like I have spreadsheets for everything now.  Okay, only like 3 spreadsheets but still that’s borderline obsessive for me.  

Wanna know our daily budget breakdown for our honeymoon? There’s a spreadsheet for that.  Wanna know 8 wedding catering options in Houston?  There’s a spreadsheet for that too.

Pineapple-caramel stuffed cookies

When I was talking to my Dad about catering options I was like, “well, we can’t go with this caterer because they only have plastic plates.”  To which he said, “HUH?!” To which I said, “Mom, says we can’t have plastic plates.”  To which he says, “HUH?!”

I’m really fine with having plastic plates (and so is my mom).  But it’s fun to see my dad freakout just a little.  Kinda like how he freaks out when I try to convince him that the Kardashians really do have some redeeming qualities.  And kinda like how I freakout when I’m looking at my phone in bed at night and I accidentally hit the camera ON and I’m so scared (even though it’s pitch black) that a face is gonna appear on my screen.  Seriously, every time that happens (read: every night) I jump up and turn on the light as fast as I can.  I’m not alone though.  Because I saw this on Insta the other day…tru dat.

pineapple-caramel stuffed cookies-6

Okay, now on to important things.  The winner of the WTFlavor Chobani Giveaway is…Liz @ I Heart Vegetables.  Congratulations Liz!! Send an email with your address to and I’ll send your information on to Chobani.

Thank you again, Chobani, for allowing me to host this giveaway!!!

And now onto some other important things…these caramel stuffed cookies.  Make them.  And confuse your family as to why there are yellow things in their cookies that aren’t M&M’s.

pineapple-caramel stuffed cookies-9

Fresh Pineapple & Caramel Cookies

Yield: 16 cookies



13 dates, pitted (or scant 1 cup)

1 Tbsp peanut butter

1 Tbsp milk (I used almond milk)

1 pinch salt


1 1/4 cup oat flour

1 cup almond flour

1/2 tsp baking powder

1/4 tsp salt

1/2 cup dark chocolate chips

1/2 cup fresh pineapple, cut into small cubes

1/3 cup honey

1/4 cup coconut oil

1 egg

1/2 tsp vanilla extract



Add dates, peanut butter, almond milk and salt into a food processor/high powered blender. Process until smooth and no date pieces are remaining. Caramel filling will be super sticky. Wetting your hands frequently, roll caramel filling into 16 balls. Place onto a foil-lined baking sheet and place in the freezer to allow them to harden.


In a bowl, combine the oat flour, almond flour, baking powder, salt, chocolate chips and pineapple chunks. In a separate, microwavable-safe bowl, add honey and coconut oil. Heat 15 seconds or until honey and oil are thin. Allow to cool slightly. Whisk in egg and vanilla extract into the thinned honey/coconut oil. If honey/coconut oil mixture is still warm, allow it to cool for another 5 minutes before adding it to your dry ingredients (otherwise your chocolate chips will melt).

Once cool, pour your wet ingredients into your dry ingredients and combine until a dough is formed. Cover bowl of dough and place in the freezer for 20-25 minutes.

Preheat oven to 375F. Spray 2 baking sheet with non-stick cooking spray. Remove dough and caramel filling balls from the freezer. Use a spoon to scoop out some dough. Roll dough into a ball and then flatten. Place caramel ball into the center of the flattened cookie and wrap dough up around the caramel filling to completely hide the caramel within the cookie. Roll the cookie ball between your hands until smooth. Repeat with remaining dough/caramel filling to make 16 cookies total.

Bake for 11-13 minutes. Allow cookies to cool on baking sheet for 10 minutes and then move to a cooling rack to continue cooling. Store in the FRIDGE for up to 4 day. Makes 16 cookies.

12 comments on “Fresh Pineapple & Caramel Stuffed Cookies”

  1. I think you like stuffing food into cookies about as much as I like seeing said pictures of stuffed cookies ;) Do you normally make caramel with peanut butter? I can imagine it tasting really good I just never knew that was one of the ingredients.

    Also, I really like the new formatting for your recipes. At least I think it’s new… Now I have to go back and check your past few posts because I feel like something looks different than normal.

    • I have no idea how you make caramel…but the PB addition tasted caramel-y to me so I went with it haha:))

      Thanks for noticing the new recipe formatting! It’s just a plug-in for wordpress!

  2. Gahhh stuffed cookies! Amazing.

  3. I saw this post on the train to work this morning and all I could think was “I WANT THIS FOR BREAKFAST!!” These are an acceptable breakfast food, correct?

  4. I just so happen to have all these ingredients in my kitchen at the moment! :) May sub the pineapple for some cherries though!

  5. Pineapple is my absolute favorite fruit! I love cookies and this recipe sounds soo interesting and looks great in the photos! I definitely have to try it out. =)

    • I LOVE pineapple too:) For this recipe I debated for like a day about just using dried pineapple but I’m glad I went with the fresh pineapple instead!

  6. Pingback: MIMM #13 – Hooray for Music and Beer | foodiEcology

  7. Pingback: Pineapple-Caramel Stuffed Cookies | IMG Recipes| Discover Recipes, Cooking Tips & Food Images

Leave a Reply

Your email address will not be published. Required fields are marked *

Back to Top