Preheat the oven to 350°F (convection). Line a baking sheet with parchment paper and set aside.

In a medium bowl, mix together the room-temperature cream cheese, powdered sugar, cocoa powder, and vanilla until smooth. Scoop 1-tablespoon portions onto a parchment-lined plate or tray and freeze until firm.

In a large bowl or stand mixer fitted with the whisk or paddle attachment, beat the room-temperature butter, granulated sugar, and brown sugar until light and off-white in color, about 1–2 minutes.

Add the egg, molasses, and vanilla extract, mixing until fully combined.

Add the all-purpose flour, cocoa powder, espresso powder, baking powder, and baking soda. Gently fold the dry ingredients into the dough until no dry spots remain.

Bake one test cookie to check spread and ensure no ingredients were missed.

Scoop ⅓ cup of cookie dough and flatten it in your palm. Place a chilled cream cheese ball in the center, then fold the dough around the filling to seal completely. Roll each cookie dough ball in a mixture of granulated sugar and color-coated chocolate chips.

Place the filled cookie dough balls onto the prepared baking sheet, spacing evenly apart.

Bake for 12–13 minutes, until the edges are set and the centers look slightly underbaked.

For perfectly round cookies, use a round bowl, cup, or cookie cutter to gently swirl around the cookies immediately after removing them from the oven.

Let the cookies rest on the baking sheet for about 10 minutes before transferring.

Enjoy fresh, or store cookies in an airtight container in the refrigerator for up to 8 days.