Soft and Chewy Vanilla Cookies with Milk Chocolate Filling

I haven’t had a chance to make a lot of cookies this holiday season – the time keeps flying by, and I am struggling to keep up.  I finally decided though it was time, I had to make some cookies, and I actually had an occasion to bring them to, which forced me into it.  I wanted to find something simple that wouldn’t take very long, but that would look impressive. 

My mother who was visiting brought with her the Fine Cooking holiday issue – filled with wonderful cookies, bars, muffins, etc… and there so many incredible looking sweets, I had to go with one of their recipes.  Of course, I had to change it up just a little bit.  There were some delicious sandwich cookies filled with jam, but I had some incredible milk chocolate from the farmer’s market that was calling me from the pantry.  That was it – make the cookies, and instead of filling them with jam, I would fill them with the chocolate.  Boy were these a hit.  The cookies were very soft, and went perfectly with the delicate milk chocolate filling.  They were like a decadent yet sophisticated party in your mouth. 

I’m sure you can fill these cookies with whatever you have around – caramel, chocolate, jam, apple butters, etc…  Experiment, and have fun – but most of all, save some time to enjoy them.


  • 6-3/4 oz. (1-1/2 cups) unbleached all-purpose flour
  • 1/2 tsp. table salt
  • 1/4 tsp. baking powder
  • 6 oz. (3/4 cup) unsalted butter, softened at room temperature
  • 1-1/4 cups granulated sugar
  • Seeds scraped from 1 vanilla bean, or 1-1/2 tsp. pure vanilla extract
  • 2 large eggs
  • 1 jar of milk chocolate


Position the oven racks in the top and bottom thirds of the oven and heat the oven to 375°F. Line two cookie sheets with parchment.

In a medium bowl, whisk the flour, salt, and baking powder until well blended. In another medium bowl, beat the butter on medium-high speed with an electric mixer (a hand-held works well) until smooth. Add the sugar and vanilla bean seeds or extract and continue beating until well combined, about 2 min. Add the eggs and beat until well blended, about 1 min. longer. Add the flour mixture and mix on low speed until just blended, about 30 seconds.

Using a 1-tablespoon cookie scoop or two tablespoons, arrange heaping tablespoonfuls of the dough in mounds about 3 inches apart on the prepared cookie sheets. Bake two sheets at a time, swapping the sheets’ positions half way through baking, until the edges are golden brown, 10 to 14  min.

Set the sheets on racks and let cool for 5 min. before transferring the cookies to the racks to cool completely. Using cooled cookie sheets, bake the remaining cookie dough.

If the cookies don’t come out perfectly round, take a round biscuit cutter just smaller than the cookie and trim them up.  Once they are cooled, you can take a teaspoon of filling and carefully spread the back of one cookie.  Place another on top.

For a printer-friendly version of this recipe, please click here: Soft and Chewy Vanilla Cookies with Milk Chocolate Filling

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