Finally, I decorate them. I dab a tiny amount of melted white chocolate candy onto the mini candy cane and gently attach it as a handle. I sprinkle mini marshmallow bits on top along with festive sprinkles. Watching these come together is almost therapeutic—they look like tiny mugs of hot chocolate, and every time I set them out at a party, people gasp before they grab one. They’re charming, delicious, and honestly one of the easiest show-stopping desserts I make during the holidays.
Pro Tips for Best Results
I tested this recipe three different ways to figure out exactly how to get the best cookie cup texture, and what really matters is how much dough you use. Too much dough and the cups expand into muffin-tops; too little dough and they crumble when you pull them out of the pan. The sweet spot for me is a tablespoon of dough per cup—firmly pressed but not overly packed. Trust me, this makes a huge difference.
Another thing I learned through trial and error is that the “re-pressing” step is essential. If you skip it, your cookie cups won’t have enough depth to hold pudding, and they’ll look more like shallow tart shells. I know it feels odd to poke freshly baked cookies, but the soft dough shapes perfectly under gentle pressure. This is one step I’ll never skip again.
When attaching the mini candy cane handles, make sure your melted white chocolate is thick enough to act as glue. The first time I made these, my chocolate was too runny and the handles kept sliding off. Now I melt the chocolate in short bursts and let it cool for about a minute so it thickens slightly. It sticks instantly this way, and you won’t have candy canes falling like dominoes on your tray.
My final tip is to chill the cookie cups for at least 20 minutes before serving. This helps the pudding set inside the cookie and keeps the candy cane handles firm. If you’re serving them outdoors or in a warm kitchen, this step becomes even more important. Cold cookie cups taste amazing anyway—the pudding firms to a perfect creamy texture that complements the soft cookie.
Common Mistakes to Avoid
I made this mistake the first time—do not overfill the mini muffin wells with cookie dough. They puff so much more than regular cookies, and without enough space to expand, they turn into rounded muffin bites instead of cups. Scrape off excess dough before baking to avoid losing that perfect shape.
Another common mistake is removing the cookies from the pan too early. Even if they look set, they’re extremely soft when hot. If you pry them out too soon, they fall apart instantly. I’ve done it, and I regretted it every single time. Letting them cool in the pan for at least 10 minutes gives them enough structure so they release cleanly.
Some people try to skip the melted white chocolate when attaching the candy cane handles, but the pudding alone won’t hold anything in place. I’ve tried it—those handles slide right off. The white chocolate acts as both glue and an extra layer of sweetness, so don’t leave it out.(See the next page below to continue…)