Unwrap the Rolo candies. Arrange in a single layer on a tray or small plate. Freeze at least 1 hour, or overnight.

In a large bowl, whisk together all purpose flour, baking soda, baking powder, and kosher salt. Set aside.

In a separate bowl or the bowl of a stand mixer, mix the softened butter on high speed until light and fluffy, about 30 seconds.

Add the dark brown sugar and granulated sugar and mix on medium-high speed until well combined, about 30 seconds more.

Mix in the egg and vanilla bean paste.

Add the dry ingredients and mix until just combined. Mix in the milk.

With a wooden spoon, stir in the chopped milk chocolate and the frozen Rolo candies.

Cover bowl with plastic wrap/clingfilm and refrigerate at least 1 hour, or overnight.

Meanwhile, preheat oven to 350° F  (176° C). Line a half-sheet rimmed baking tray with parchment or a silicone mat.

With your hands, portion the chilled dough into 1 1/2 – 2-inch balls. You should have about 18 total. Arrange half of the balls* on prepared tray, allowing space for the cookies to spread as they bake.

Bake in preheated oven for 14-17 minutes, or until gooey and lightly golden brown.

For perfectly round cookies, quickly reshape with a greased round metal cutter.

Cool on tray for 10 minutes, then arrange on a parchment-lined wire rack to cool completely.

Repeat with remaining cookie dough.

Store Rolo cookies in an airtight container at room temperature for up to 5 days.