Pumpkin Pudding Cookies – 3 Ways

These pudding cookies are hands down the best pumpkin cookies we’ve ever had! THIS. IS. IT! It’s got the texture of a fluffy chocolate chip cookie but tastes like pumpkin. And best of all, we’re including three different ways to make it!

Years ago, my friend Krysta introduced me to a pudding in chocolate chip cookies recipe which we still obsess over to this day. When I saw pumpkin spice pudding mix hit the shelves of Walmart and Harmons this fall, I just knew I had to make a new version. The only problem was, which do I make?! I would normally shoot all three and do three different posts over the years, but this time I decided that since you all went nuts about it on instagram, I’d just get the recipe up ASAP!

You all know I can’t help myself when it comes to cookies! I have to try all kinds of different add-ins (kitchen sink cookies), toppings (peanut butter blossoms), stuffings (s’mores stuffed chocolate chip cookies) and techniques (lemon crinkle cookies).

We found 3 ways that we love these pumpkin pudding cookies – coated in cinnamon and sugar, loaded with chocolate chips, or stuffed with Rolos! We will detail each of those versions below.

Tips for the Best Pumpkin Pudding Cookies

Here are a few tips for the best pumpkin pudding cookies:

• You need 5.1 ounces of pudding but the pudding is only sold as 3.4 ounce boxes, so you’ll need to use 2 boxes and either weigh the powder into a bowl with a food scale, or just use about 1 1/2 boxes.
• If you go with the Rolos options, make sure there is a lot of dough on the bottom because the Rolos will seep out if there isn’t enough dough on the bottoms.
• If you make the chocolate chip version, save a few chocolate chips to place on top of each cookie. It makes them look so pretty and appetizing!

Ingredients for Pumpkin Pudding Cookies

These will just be your standard cookie ingredients here with the

Paula Deen Banana Pudding

Not Yo Momma’s Paula Deen Banana Pudding is a fluffy mixture of creamy pudding and whipped cream with cream cheese and sweetened condensed milk. Plus it’s served with Chessman Cookies on the bottom and on top!

I loved banana pudding anything as a little girl. If lip smackers had been smart when I was entering jr high they would have made bank off of a lip gloss for banana pudding anything. 

Did you buy Lip Smackers as well? Something like, white cake batter, or Dr Pepper? Those were the good ol’ days. 

Paula Deen’s Not Yo Mama’s Banana Pudding 

Paula Deen Banana Pudding, or the full name, Paula Deen’s Not Yo Momma’s (or Mama’s) Banana Pudding is a little bit deceiving so I just want to get this out of the way first, it’s not a banana pudding recipe. 

I mean, it is. There are banana slices under the pudding. But the actual pudding is a french vanilla pudding whipped up with sweetened condensed milk and cream cheese. 

That’s a legit pudding dessert. 

Ingredients for Not Yo Momma’s Banana Pudding

Here’s your quick grocery list to make your banana pudding with Chessman Cookies. 

• Chessman Cookies: traditionally used in a classic recipe for banana pudding and can be found on the cookie aisle
  • Fun Fact: This recipe is sometimes known as Chessman banana pudding!
• French Vanilla Instant Pudding Box: make sure it is instant pudding and not cook & serve pudding
• Cool Whip: if you can’t find a 12oz tub of Cool Whip, use 1 and half of the 8oz tubs
• Cream Cheese: make sure it is room temperature so that it doesn’t get lumpy
• Sweetened Condensed Milk: adds sweetness and creaminess to the dessert
• Milk: combines with the pudding mix the create the pudding
• Bananas: ripe bananas are the best for their sweetness and bold banana flavor

The measurements for each ingredient can be found in the recipe card at the end of this post.

Substitute for Chessman Cookies

Vanilla Wafers are the best substitute for Chessman cookies if you can’t find them. Chessman Cookies are usually by the Pepperidge Farm brand so look by the Mint Milano cookies.

How to Make Paula Deen Banana Pudding  

1. Set the Cool Whip in the fridge or on the counter for a faster thaw.
2. Whisk milk and the instant pudding mix together in a small bowl. 
3. In another bowl, blend the cream cheese and sweetened condensed milk with a handheld electric mixer.
4. Fold the Cool Whip into the cream cheese mixture. 
5. Stir together the vanilla pudding mixture and cream cheese mixture. 
6. Layer 1 bagof cookies on the bottom of a 9×13 dish, top the cookies with a layer of bananas. 
7. Pile on the pudding.