Name: Sugar Free Boston Cream Cookies Recipe
Prep time: 25 min
Cook time: 12 min
Total time: 37 min
Cuisine: No Added Sugar
Ingredients: 2 cups Flour; 1 tbsp Cornstarch; 1 tsp Baking Powder; ½ cup Butter, softened to room temperature; ¾ cup Sugar Alternative (granular sugar alternative that measures like sugar and can be baked with); 1 tsp Vanilla Extract; ¼ cup Milk; 1 Sugar Free Pudding Mix; 1 cup Milk; 4 oz Whipped Topping (no added sugar or low sugar Cool Whip); 1 Sugar Free Chocolate Frosting, softened to room temperature

If you’ve ever wished the classic dessert could be portable, get excited: Sugar Free Boston Cream Cookies take all the rich, dreamy flavor of Boston cream pie and tuck it into a hand-held, no added sugar treat! These cookies balance a buttery soft base with a luscious layer of vanilla cream and a smooth, glossy cap of chocolate frosting, making them irresistible to kids and adults alike. Whether you’re baking for a special occasion or just feel like treating yourself without the sugar rush, this recipe promises delicious satisfaction, one nostalgic bite at a time.

Sugar Free Boston Cream Cookies Recipe - Recipe Image

Ingredients You’ll Need

The beauty of Sugar Free Boston Cream Cookies is how a few familiar pantry staples combine to create a show-stopping cookie. Each ingredient plays a key role in achieving the soft crumb, rich cream, and signature chocolate finish that makes this treat unforgettable!

Flour: Provides the essential structure that keeps your cookies soft but sturdy enough to hold the cream and chocolate.
Cornstarch: Adds tenderness to the cookies and helps create that classic bakery-style softness.
Baking Powder: Ensures your cookies puff up slightly, giving them a light, cake-like texture that’s hard to resist.
Butter (softened): Lends rich flavor and a melt-in-your-mouth quality to every bite.
Sugar Alternative: Go for a granular sweetener that bakes like regular sugar for the perfect sweetness—without the extra carbs!
Vanilla Extract: Enhances the subtle flavors of both the cookie and cream layers, infusing your cookies with a warm, inviting aroma.
Milk: Keeps the cookie dough moist and helps bring everything together effortlessly.
Sugar Free Pudding Mix: The secret to an absurdly good vanilla cream filling in a fraction of the time.
Milk (for cream): Blends with the pudding mix to create a silky-smooth filling—use what you have on hand, dairy or unsweetened non-dairy works too.
Whipped Topping (sugar free or low sugar): Folds into the cream filling, creating that fluffy, spoonable perfection you’ll want to lick from the bowl.
Sugar Free Chocolate Frosting (softened): Crowns each cookie with rich, decadent chocolate that ties everything together.

How to Make Sugar Free Boston Cream Cookies

Step 1: Preheat and Prepare Your Baking Gear

First things first: set your oven to 350°F. Prep your baking sheets by lining them with parchment paper or a silicone baking mat. This simple step keeps your cookies from sticking and makes cleanup a breeze, so you can focus on the fun part—assembling and enjoying!

Step 2: Mix Your Dry Ingredients

In a medium bowl, whisk together the flour, cornstarch, and baking powder. This quick mix distributes the leavening evenly, helping your cookies rise perfectly and develop that soft, cloud-like texture the Sugar Free Boston Cream Cookies are known for.

Step 3: Cream Butter and Sugar Alternative

Grab a large mixing bowl and blend your softened butter with your sugar substitute until the mixture is light and somewhat fluffy. Stir in the vanilla extract and milk. This creates a gorgeous base that’ll make your cookies tender and full of flavor, even without traditional sugar.

Step 4: Combine to Form Dough

Add the flour mixture to your wet ingredients and gently mix until a dough forms. Don’t overwork it—stop as soon as everything’s combined to keep your cookies soft and tender.

Step 5: Scoop and Bake

Use a medium cookie scoop to portion the dough onto your prepared baking sheets, spacing them 1.5 to 2 inches apart. Bake for about 12 minutes, or until the edges just begin turning golden. The cookies will look slightly underdone in the center, but that’s exactly what you want for that signature Boston cream texture.

Step 6: Create an Indent & Cool

Straight out of the oven, press a small measuring cup or another flat-bottomed tool gently into each cookie’s center to create a well for the cream. Let the cookies cool completely on the baking sheet—this helps the base set and makes assembly easier.

Step 7: Prepare the Vanilla Cream

While your cookies are baking or cooling, whisk together the sugar free pudding mix and 1 cup of milk. Once smooth, fold in the whipped topping gently. Pop it in the fridge for at least 30 minutes so the cream thickens to the perfect spoonable consistency.

Step 8: Assemble Your Sugar Free Boston Cream Cookies

Once the cookies and cream are both ready, fill each cookie’s indent with a generous tablespoon of vanilla cream. Next, add a dollop of softened sugar free chocolate frosting right on top—just a teaspoon or two creates a luxurious finish worthy of the real deal!

How to Serve Sugar Free Boston Cream Cookies

Garnishes

While these cookies have all the drama they need thanks to the glossy chocolate topping, a sprinkle of finely chopped nuts or a few curls of sugar free chocolate can make each one pop for special occasions. Even a dusting of cocoa powder adds a sophisticated touch!

Side Dishes

The richness of Sugar Free Boston Cream Cookies pairs beautifully with a tall glass of unsweetened almond or oat milk, or even a hot mug of coffee or tea. For a dessert platter, serve alongside a crisp fruit salad or some fresh berries for a balanced treat.

Creative Ways to Present

Stack these cookies on a tiered cake stand for a wow-worthy dessert centerpiece, or box them up in bakery-style parchment for heartfelt edible gifts. They’re also great for cookie swaps, after-school snacks, or mini desserts with a little homemade flair.

Make Ahead and Storage

Storing Leftovers

Keep leftover Sugar Free Boston Cream Cookies in an airtight container in the refrigerator. The cream and frosting need to be chilled to keep their texture and ensure food safety. They’ll stay fresh for up to 3 days, which makes them awesome for prepping ahead for events or packed lunches.

Freezing

If you want to freeze these cookies, it’s best to freeze the bases alone and assemble with cream and frosting after thawing for the best texture. Store the plain baked cookies in an airtight bag or container for up to 2 months. Thaw at room temperature, then finish them with fresh cream and chocolate before serving.

Reheating

These cookies are actually best served cold or at room temperature, but if you’ve refrigerated them and want to take the chill off, a few minutes on the counter will do the trick. Avoid microwaving assembled cookies as the frosting and cream will melt.

FAQs

Can I make Sugar Free Boston Cream Cookies with gluten free flour?

Absolutely! Use your favorite cup-for-cup gluten free blend—it may require a touch more moisture if the dough feels dry, but the result should still be soft and delicious.

What’s the best sugar alternative for these cookies?

Go for a granular sweetener that measures like sugar and is specifically formulated for baking. Brands like Swerve, Lakanto, or Monk Fruit sweeteners all work well here.

Can I use a homemade pudding or custard for the cream layer?

Yes, you can swap in your favorite homemade sugar free vanilla custard if you want a more old-fashioned filling. Just make sure it’s thick enough to hold its shape on the cookie!

Do Sugar Free Boston Cream Cookies need to be refrigerated?

Yes, thanks to the cream and chocolate layers, these cookies stay freshest when stored in the refrigerator. Just let them sit out a few minutes before serving for the best texture and flavor.

How can I prevent the cookie base from getting soggy?

Allow the cookies to cool completely before adding the cream and frosting, and if you’re making them ahead, assemble just before serving or store them in a single layer separated by parchment paper.

Final Thoughts

Whether you’re sharing them at a family get-together or keeping them tucked away as your personal sweet escape, Sugar Free Boston Cream Cookies are a smile-inducing treat you’ll want to make again and again. There’s just something magical about that classic combination of creamy vanilla and chocolate on a soft cookie base. If you make these, don’t forget to savor every bite—you deserve it!