I’ve made these dulce de leche sandwich cookies a handful of times now, and daaaaang. They are really quite spectacular. They’re also a bit fussy and make a pretty big mess, so they’re definitely special occasion cookies. But still. So good!

Now that I think about it, I’m mildly appalled at how long it’s taken me to get this recipe up. I first made these cookies while I was living in the tiny house – which means it was well over a year ago now… I wonder if the 2020 time warp is ever going to end? Sigh.

Regardless of my posting negligence, these dulce de leche sandwich cookies have become my go-to, special occasion pairing for Mexican food dinners. These or my tres leches cake. But one of my besties (who makes excellent Mexican food) doesn’t like “soggy cake,” so I’m glad to have these to offer.

Like I said, though, these are messy. Like, sugar all over the place messy. Definitely worth it! But it’s important to be emotionally prepared. Perhaps there’s a way to double-coat the cookies in cinnamon sugar that doesn’t result in a mess, but I haven’t found it. I have found a new, better method for snickerdoodles thanks to this recipe. But it’s still going to make a mess since the trick is to roll the raw dough in cinnamon sugar, then after they’ve baked, toss them in cinnamon sugar a second time! (That’s where the mess really comes in). The result, however, is a very thorough coating of crystallized cinnamon sugary goodness that will end up on your counters, your fingers, and most importantly your tongue.

Again, it’s well worth it. But these aren’t really the “oh, I feel like baking some cookies right now” kind of sweets. They’re more labor intensive, but definitively impressive. Can you tell how much I love them?

They’re also easiest to make with a small cookie scoop. The 1.5 tsp scoop makes the perfect-sized cookies and works well to scoop the right amount of dulce de leche filling. 

Also of note – these bad boys are rich. Like, really rich. Like, I can usually only eat two in one sitting, which is saying something given the fierceness of my sweet tooth. But the good news is they’ll keep for several days just fine, since the dulce de leche keeps them wonderfully soft and toothsome. That’s another nice thing about them – the recipe is pretty forgiving of you accidentally over bake them a bit. The filling will soften them back up by the following day. So, they’re great make-ahead cookies, too!

Ingredients are listed in the order they appear in the recipe and anything that requires prep is in bold. Ingredients are bolded in the directions when you first encounter them, and the quantity required is included. Time estimates are bolded and italicized. I also include notes about any special equipment you’ll need.

Dulce de Leche Sandwich Cookies

Required equipment: an electric hand mixer or stand mixer. A 1.5 tsp cookie scoop (i.e. the small size) makes things a lot easier but isn’t strictly necessary. Parchment paper is semi-necessary. A silicone baking mat will work, too.

• 2 cups (300g) all-purpose flour
• 1 teaspoon baking soda
• ½ teaspoon salt
• ½ teaspoon ground anise (completely optional but does add a nice warmth)
• 2 cups (400g ) sugar, divided
• 1 tablespoon ground cinnamon
• 16 tablespoons (2 sticks, 113g) unsalted butter, softened
• 1 large egg
• 1 teaspoon vanilla extract

For the filling:

• 1 tablespoon unsalted butter
• ½ teaspoon ground cinnamon
• ½ teaspoon ground anise
• 1 can (13.4 oz) dulce de leche

Prep work: set out the butter to soften/come to room temperature. You may have to grind anise seeds if you (like me) couldn’t find ground anise. But, again, this is totally optional (and honestly not worth tracking down if you don’t already have it). The cookies are fabulous with or without it.

Preheat the oven to 350º F.  Line a cookie sheet with parchment paper.

In a small or medium bowl, whisk together 2 cups (400g) flour, 1 teaspoon baking soda, ½ teaspoon salt, and optional 1/2 teaspoon ground anise. Set aside.

In a shallow dish or bowl (I like to use a small cereal bowl), mix together 1 cup (220g) sugar with 1 tablespoon cinnamon. Set this aside to roll the dough in and then toss the baked cookies in for a second pass.

In the bowl of a stand mixer fitted with the paddle attachment (or using a hand mixer), beat 16 tablespoons butter and the other 1 cup (220g) sugar on medium-high speed until pale and fluffy, about 3 minutes. Add egg and 1 teaspoon vanilla and beat until combined.

Reduce speed to low and add flour mixture in 3 additions until just combined, scraping down bowl as needed.

Once the dough comes together and no pockets of flour remain, use the small cookie scoop to portion dough into balls. If you don’t have a cookie scoop, I recommend aiming for 1-inch balls, or a heaping teaspoonful. The cookies will spread a fair bit, so you want to start with small dough balls. Roll each dough ball in the cinnamon sugar mixture, then place 2 inches apart on the prepared cookie sheet. You want to give them a fair bit of space to expand.

Bake until the edges are firm, 10 to 12 minutes. Again, these cookies are pretty forgiving if you over bake them, so err on the side of them actually looking done.

After you pull the cookies out of the over, let them briefly cool on the sheet (maybe 1 minute – just long enough to make them a bit more tolerable to handle). Working quickly and being gentle with the hot cookies (which can be a little bit fragile while still warm) and being careful not to burn yourself, place each cookie in the cinnamon sugar and flip/wiggle around to it coat evenly. I like to sprinkle some mixture on top/bottom before/after flipping. Basically, you want to get a good ol’ coat of mixture on them. Once they’re good and coated, place cookies on wire rack and let cool completely, about 30 minutes. (This is the point that will be the messiest). 

While the cookies are cooling, make the filling. Melt 1 tablespoon butter in small saucepan over medium heat. Whisk in ½ teaspoon cinnamon and anise and cook until fragrant, about 1 minute. Remove from heat and stir in the 1 can dulce de leche.

Using the small cookie scoop again, plop a *sparing scoop of filling on the flat side of one cookie, then top with the flat side of another cookie and gently smoosh together to spread the filling. (*So, like, don’t use the *whole* bowl of the scoop but close – you’ll have pretty much exactly enough filling for each cookie if you go a little light on each scoop). 

Then clean up the mess that’ll be all over your counter, and enjoy!