Unwrap the Rolo candies. Place in a bowl or plastic bag and freeze for one hour.

In a large bowl, whisk together 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.

Add the dark brown sugar and granulated sugar and mix on medium-high speed until well combined.

Mix in the egg and vanilla bean paste.

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

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

Cover bowl with plastic wrap/clingfilm and transfer to the refrigerator to chill, at least one hour.

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 balls total. Transfer half to prepared tray, allowing space for the cookies to spread as they bake.

Bake in preheated oven for 12-14 minutes, or until caramel is gooey and cookies are golden brown.

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

Cool on tray for 10 minutes, then transfer parchment sheet* to a wire rack to cool completely.

Repeat with remaining cookie dough.

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