I first made these in 2016 using a cookie press. This year (2022) we’ve added embossed rolling pins, and one of the first recipes I converted for pins was the pumpkin spice! These cookies are delicious all on their own, but become downright decadent when you add the caramel pecan (nuts optional) sandwich cookie stuffing.

Real pumpkin, pecans, caramel frosting, and all the right “pumpkin spice” spices combine in these gooey, nutty, spicy, pumpkiny bites of fall flavor heaven. This recipe is made with pumpkin pie filling for a rich flavor.

🍎Apple Pie recipe variation included in this post!🍏 It uses pureed apple pie filling instead of pumpkin. The caramel pecan stuffing is equally fabulous in the apple cookies.

Making embossed cookies is such an easy way to wow your thanksgiving guests! Start a new dessert tradition for Thanksgiving with our embossed rolling pins. They also make thoughtful gifts for bakers. 🙂

Here’s Apple Pie and Pumpkin Spice shown together. I used the leaves pin for the apple cookies. The pie fillings make such different colors! The caramel pecan stuffing on the left has nuts, right does not.

Our website has all of our 200+ disk shapes, cookie press, embossed rolling pins, baking accessories plus more about our Women/Family Owned company! impressbakeware.com

All products are on our Etsy shop.

Our cookie press and disks and embossed rolling pins are also available on Amazon.

Pumpkin Spice Rolled Cookies

1 cup (2 sticks) butter, softened
2/3 cup granulated sugar
1/2 cup light brown sugar
1/3 cup canned pumpkin pie filling
1 teaspoon vanilla extract
1 egg
3 3/4 cups all-purpose flour
1/4 teaspoon salt
1 teaspoon cinnamon
1/2 teaspoon cloves
1/4 teaspoon nutmeg

Apple Pie Rolled Cookies

1 cup (2 sticks) butter, softened
2/3 cup granulated sugar
1/2 cup light brown sugar
1/3 cup canned apple pie filling, pureed
1/4 teaspoon LorAnn Apple Flavor Super Concentrate
1 teaspoon vanilla extract
1 egg
3 3/4 cups all-purpose flour
1/4 teaspoon salt
1 teaspoon cinnamon
1/2 teaspoon cloves
1/4 teaspoon nutmeg

Preheat oven to 400°F.

Recipe makes about 52 1 1/2″ sandwich cookies (or 104 individual cookies).

These directions are for pumpkin, apple variation explained below!

In a large bowl, combine flour, spices, and salt. Set aside. Using an electric mixer, cream the butter. Add the sugars and cream together very well, until it is light and fluffy. Add the pumpkin, then the vanilla, and the egg, re-creaming the mixture after each addition. Add the flour mixture slowly, mixing on a slow speed until it comes together. Make sure all of the flour is incorporated evenly. It may seem very crumbly so knead it by hand to make sure it is uniformly smooth and mixed.

Perfect rolling dough has a clay-like, workable texture that is not too sticky or too stiff. If it feels difficult to knead, it is probably too stiff. Add a little water or vanilla extract a teaspoon at a time until you achieve a workable texture. If it is too easy to knead or is sticking to your fingers, it is probably too soft. Add flour a tablespoon at a time until it is workable like clay.

Apple Pie variation: Follow the same instructions as the pumpkin spice recipe, substituting the apple pie filling, pureed until smooth and creamy, for the pumpkin, adding the LorAnn flavor when you add the vanilla, AND using a shorter baking time. The apple cookies should appear set and dry but do not let them brown much or they will be overdone! Remaining instructions are the same.

You can also refrigerate the dough for 10 to 15 minutes if you’re working in warm conditions. This dough does not generally require any refrigerating. You should only need to on a hot day or in a particularly hot kitchen. Re-knead the dough making sure the temperature is even throughout so that it rolls and impresses evenly.

Divide your dough into balls a little bigger than your fist. Work with one portion at a time to keep it manageable. Cover the unused portion to keep it from drying out.

Use a regular rolling pin (preferably one with thickness spacer rings to make a perfect thickness, picture of ours at bottom of post) to roll your dough on to a silicone baking mat, parchment paper, glass cooktop, or lightly floured surface. Oil the pin and roll to a 1/4” thickness, and wide enough to accommodate the designed pin. Create a long rectangular slab of dough. The patterns on the embossed pins are designed to repeat, so you will be rolling a long rectangle of patterned dough.

Oil your embossed pin with canola (or similar) oil before rolling. Make sure to get it down into the engraved areas. Wipe off any excess with a paper towel. Oil should be down in the patterns, but not pooling in them! You can use a pastry brush or apply by hand, gently squeezing the pin to get oil into the shapes, and rubbing the surface to coat.

Roll with your embossed pin, pressing down with a steady pressure that leaves a deep impression in the dough. The designs should be as raised up on the dough as deep as they are in the pin. If the pattern is not deep enough it will disappear as the cookies bake and puff. As this dough is not cold or stiff, you do not have to press terribly hard! Just an even pressure.

Here is a quick video of me oiling the pin, embossing this dough, cutting shapes with cookie cutters, and getting them off to parchment paper.

Once rolled, use cookie cutters to cut out shapes. Remove any excess dough around the edges. Keep your spatula/lifter flat, dust the end with a little flour, and lift the shapes, beginning by lifting one edge slightly first, then sliding the spatula/scraper under the whole shape. Transfer them to a cookie sheet lined with parchment paper, spacing them at least an inch apart. The rolling pin with thickness rings, bench/dough scraper and cookie cutters I’m using here are available at our website and Etsy shops. Links at bottom.

If you are making sandwich cookies, make sure to roll out some dough without embossing, as bottom cookies don’t need to be fancy. Cut them out in even numbers of sizes and shapes as your patterned cookies so you can match them up.

Bake at 400°F for 6-10 minutes, checking at 6 minutes and every minute after as cookies brown quickly. They are done when the edges are slightly brown. Remember for apple variation don’t let them brown or they’ll get crunchy!

NOTE: With all of the recipes here, the cookies harden the longer they bake, so bake only a few cookies first to test timing for desired doneness and hardness.

Move to a cooling rack after 5 minutes. Once cooled, cover them loosely if you like them semi-soft, or completely (like sealed in a zip bag) if you like them very soft. The flavor of these enhances as they cool.

Now to make them into sandwiches. First, grind up your pecans into sizes that are small enough to stuff between two cookies. You don’t want little boulders in there or you’ll have terribly lopsided sandwiches! But you don’t have to be overly picky, either. I used a Magic Bullet to grind mine. A blender or food processor would work well too.

Caramel Pecan Filling/Stuffing

6 Tablespoons butter
½ cup heavy cream
1 cup brown sugar
1 teaspoon vanilla
1 ¼ cups powdered sugar
¾ cup finely ground pecans (use a food processor or blender)

This filling is a boiled caramel icing recipe. Place the butter, heavy cream and brown sugar in a medium saucepan and cook over medium heat. Stir often, warming the mixture till it just begins to boil. It will have a nice, smooth sheen. Remove from heat and let cool a bit. Add the vanilla. Pour into a medium bowl and refrigerate until fairly set or firm. Stir occasionally to set evenly.

When firm but still stirrable, slowly add the powdered sugar. Let it set for a few minutes, then add the pecans.

Feel free to add more or less pecans if you like. This is just the ratio that was tastiest to me. Heck, if you don’t like nuts, leave them out. The caramel frosting is equally awesome without the pecans. And if you should find a big pecan chunk as you’re mixing them in? Do yourself a favor, for Pete’s sake pick that thing out and eat it! Oh, the yummy heaven. This stuff is addictive.

You can spread this on with a knife or use a decorating bag and tips. If needed you can stiffen the mixture by refrigerating until desired firmness, or adding more powdered sugar as needed. Piping with a decorating bag and tip makes a nice clean edge to your sandwich cookies. Make sure your pecans are ground VERY fine or they will clog up the hole! When choosing a tip, the larger the hole the better. I used a Wilton #8 round.

Match up your blank bottom and embossed top cookies. Apply the stuffing whichever way you choose. Here’s how they look with the filling piped on. That’s apple cookies on the left and pumpkin cookies on the right.

Stack the embossed cookies on top and you’re done!

🙏 We have a request: If you are enjoying our recipes (ads free!) please consider supporting our Women/Family-owned USA Small Business! We sell over 300 shapes of cookie press disks, beautiful embossed rolling pins, & more. We make no money from ads on this blog. I create these recipes to give our customers a wide variety of creative ideas. The 2022 holiday season is off to a difficult start for many small businesses. If you like what we do, every disk and pin purchased helps us stay in business and keep bringing you our totally unique recipes, disks, and pins. THANK YOU for helping our families through this tough year! ~Susie & Jill & our Families

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I hope you all truly enjoy these and they bring something new and wonderful to your holiday celebrations or cozy fall weekends.

As always, Happy Baking from our families to yours!

~Susie

Disk Designer/Co-Owner at Impress! Bakeware, LLC

Our website has all of our 200+ disk shapes, cookie press, embossed rolling pins, baking accessories plus more about our Women/Family Owned company! impressbakeware.com

All products are on our Etsy shop.

Our cookie press, disks, and embossed rolling pins are also available on Amazon

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If you’re not familiar with rolling pins with thickness rings, here’s ours: