Satisfy your Fall cravings with these easy Pumpkin Spice Cookie Cups! Chewy chocolate cookie cups filled with pumpkin pudding and topped with whipped cream.
Seeing as how it’s officially October (crazy!!), I think it’s high time I busted out some new pumpkin recipes. I’m actually a little behind this year. Usually I get into the pumpkin spirit as soon as the calendar turns September, but we were moving at the time and I didn’t have enough foresight to fill my backlog with pumpkin recipes. Poor planning on my part, but I do have at least two pumpkin spice recipes coming at you this year. Maybe more if I can swing it.
For my first pumpkin recipe of 2016, I bring you these killer Pumpkin Spice Cookie Cups!
I’ve noticed it’s become a trend in recent years to bash all things pumpkin spice. I’m not really sure where all this hate came from, or why. There are likely more important things to focus one’s energy on than hating pumpkin spice. Maybe it’s the summer-lovers who are none too thrilled about their favourite season coming to a close, so they look for something to take out their anger on. I, on the other hand, welcome Fall and all things pumpkin with open arms. It is, after all, the best season of the entire year. Amiright?
My inspiration for these Pumpkin Spice Cookie Cups was a mini pumpkin pie, but I wanted to mix it up a bit with a rich chocolatey cookie base. The chocolate cookie cups pair surprisingly well with the pumpkin pudding filling!
You may have noticed that I have an ever-growing cookie cup collection. I am a huge fan and, judging by the response, it seems that you guys like them too! They are really fun and easy to make. Portable, bite-sized deliciousness. What’s not to love?? I’ve already got holiday themed cookie cups in mind, so watch for those in the weeks to come.
The pumpkin filling in these Pumpkin Spice Cookie Cups is not completely from scratch. I usually bake from scratch, but sometimes it’s just easier to whip out a box for something, whether it’s a cake, cookie, or the filling for these Pumpkin Spice Cookie Cups, which incorporates modified instant pudding. If you would rather not use instant mix, you can make your own pudding at home and add in the pumpkin puree and spice. Not quite as easy, but just as delicious.
Chewy chocolatey cookies paired with delicious pumpkin pudding. If you are a pumpkin spice fan like me, you will love these Pumpkin Spice Cookie Cups!
Notes & tips for these Pumpkin Spice Cookie Cups:
- If you don’t have black cocoa powder, you can use regular cocoa powder. The recipe will work fine, but it will affect the flavour and color slightly.
- These freeze very well! Store in fridge for up to 5 days or in freezer (in an airtight container) for 1-2 months.
- Serve cold or at room temperature.
- If you like these, check out some of my other other cookie cup recipes!
Pumpkin Spice Cookie Cups
INGREDIENTS
Chocolate Cookie Cups:
- 2 cups all-purpose flour
- 1/4 cup Dutch-processed cocoa powder sifted
- 1/4 cup black cocoa powder sifted
- 1 tsp baking soda
- 1/2 tsp salt
- 1 cup unsalted butter room temperature
- 1/2 cup granulated sugar
- 1 cup light-brown sugar packed
- 2 large eggs room temperature
- 1 tsp vanilla extract
Pumpkin Filling:
- 1 pkg vanilla instant pudding large, 153g, 5oz
- 12 oz can evaporated milk 354ml, chilled
- 14 oz pumpkin puree 398ml, not pumpkin pie filling
- 1 1/2 tsp pumpkin pie spice
INSTRUCTIONS
Chocolate Cookie Cups:
- Preheat oven to 350°F. Spray two regular sized muffin tins with cooking spray.
- Whisk together flour, cocoa powders, baking soda, and salt. Set aside.
- Beat butter and sugars on med-high until light and fluffy (approx. 2-3mins). Reduce speed and add eggs one at a time and vanilla. Beat until combined. Add flour mixture and mix until just combined.
- Using a large cookie scoop (3 Tbsp) scoop dough into muffin tins, press down to flatten.
- Bake for approx. 10-13mins or until mostly set, but still soft in the middle.
- Remove from oven and immediately use a small jar or container to press firmly down in the center to create a well. Cool in pans for 15mins, then place on wire rack to cool completely.
Pumpkin Filling:
- Place milk and pudding into a medium bowl and beat for 2mins (I used a hand mixer). Place in fridge to set for 5 mins. Beat in pumpkin puree and pumpkin pie spice. Pipe or spoon into cookie cups.
- Top with whipped cream if desired.
NOTES
Note: I over-baked one of my batches of cookies and they were a bit too crisp for my liking (I prefer chewy). If this happens to you, just place the unfilled cookie cups in an airtight container with a slice of bread and leave to sit overnight. They will soften right up!
The nutritional information and metric conversions are calculated automatically. I cannot guarantee the accuracy of this data. If this important to you, please verify with your favourite nutrition calculator and/or metric conversion tool.
Erica says
Can I use Regular Cocoa Powder in place of the Dutch and black cocoa powder it’s quite expensive for both where I live…?
Olivia says
Hi Erica! Regular will work fine — the color will not be as dark though.
Brenda says
Stumbled upon this blog today via Brown Eyed Baker. 😉
I plan on making this recipe as soon as I get my hands on the black chocolate.
After reading some of the comments on price, I searched around online and found…..
https://www.kingarthurflour.com/shop/items/black-cocoa-12-oz
As on commenter on King Arthur Flour suggested, transfer to an airtight stainless steel airtight canister instead of using the ziplock, to avoid the poof of lost chocolate when sealing the bag.
I have to admit, I just love it when the first cold day hits New England and I try to think of reasons to make ANYTHING with pumpkin…….however……..My second thought…….how can I convert this to a PEANUT BUTTER filling ??? !!! Hmmmmm. Any ideas? What do you think..?
Olivia says
Hi Brenda! I’m so glad you found your way to my blog 🙂 I have a couple of cookie cup recipes that have a PB filling:
https://livforcake.com/peanut-butter-jelly-cookie-cups/
https://livforcake.com/fluffernutter-cookie-cups/
I think it would go SO well with the chocolate!! I might have to add that to the list to try myself 🙂
Donna V says
Hi new to your site – wondering how to get the cookie pie crusts so even ? What did you use to create the well ? Thanks !
Olivia says
Hi Donna! Welcome 🙂 I use the rounded cap from my Pam for Baking spray (lol). Not ideal, but it’s the perfect size and works well. You could try a shot glass or the bottom of a cookie scoop too. I hope that helps!
Melissa Klotz says
My pumpkin filling never firmed up, it runs right out when you cut into them… I used the whole 15-oz can of pumpkin — the recipe says 14oz but links to a 15oz can. Maybe I used the wrong size box of instant pudding… Oh well, they still taste good.
Olivia says
Hi Melissa! Sorry these didn’t exactly work out for you. The cans available in Canada are 14oz, but 15oz in the US which is the one I linked to. That 1oz shouldn’t have made a significant difference. The pudding size very well may have though. You want to use the larger (5.1oz) boxes. Glad you still liked the flavour!
Liz says
Every time I try one of your recipes, I get requests for more. Love love love your blog and photos and creativity! You definitely have encouraged and challenged me to be a better baker through your posts! I am making this one for a little gathering we’re hosting tonight!
Olivia says
Wow, thank you Liz!! This is the nicest compliment maybe ever. Your comment totally made my morning :). I hope these live up to your expectations!
Amy says
Where did you get your teeny little stand? It’s absolutely adorable. Great photos, these cookies look stunning.
Olivia says
Thanks Amy!! My husband picked it up for me at a discount housewares store called Homesense.
Megan @ MegUnprocessed says
Awesome presentation! Love your photography!
Olivia says
Thanks so much Megan!
Rosemary says
Hi Liv, cookie cups are so cute and these look so delicious. And yes you are absolutely correct, Fall is the best season!
Olivia says
Thanks Rosemary! 😀
Elizabeth Vlug says
Thanks for your reply. Something else to add to my list when I shop in the big city or on a road trip to the USA. lol. I’m in Cobourg, Ontario.
Elizabeth Vlug says
Wow, I just checked Amazon.ca for the Black Cocoa, its expensive. $62. Not sure I can justify that price for my baking needs. 🙁
Olivia says
Whoa! It should not be that much. Where are you located??
Olivia says
I just checked around on Amazon.ca too — super overpriced there! Not surprising, sigh. It’s more reasonable on Amazon.com, but then you have to pay the exchange rate and shipping, etc. You might be able to find it in some specialty baking shops in your area, but if that fails, regular or Dutch process cocoa will be a fine substitute!
Elizabeth Vlug says
Oh I am so making these for our Thanksgiving gathering. I haven’t heard of Black cocoa before. If I can’t get it in time to make, would I just use regular cocoa? Thank you once again. (you are making me quite popular at family gatherings when I take one of your creations. I have had a few repeat request for that Key Lime Cake)
Olivia says
You can totally use regular cocoa! They just won’t be as dark :). And I’m so happy to hear that people are liking the desserts! The Key Lime Pie cake is still one of my faves 🙂