Ingredients:

  • 1 cup (225 g) unsalted butter, softened
  • 1 cup (200 g) light brown sugar, packed
  • ¾ cup (150 g) granulated white sugar
  • 1 large egg, room temperature
  • 1 tsp (5 ml) vanilla extract
  • 2 ¼ cups (270 g) all-purpose flour, spooned and leveled
  • 1 tsp (5 g) baking soda
  • ½ tsp (2.5 g) fine sea salt
  • 24 pieces Rolo Candies, unwrapped
  • ½ cup (100 g) granulated white sugar, for rolling
  • ½ tsp (2.5 g) flaky sea salt, for sprinkling

Instructions:

  1. Cream Butter and Sugars: In the bowl of a stand mixer, beat the softened butter, brown sugar, and ¾ cup of granulated sugar together on medium speed until light, fluffy, and noticeably paler in colour (approx. 3–4 minutes). Scrape down the bowl halfway through.
  2. Add Wet Ingredients: Beat in the egg and vanilla extract until just combined. Do not overmix here.
  3. Combine Dry Ingredients: In a separate bowl, whisk together the flour, baking soda, and fine sea salt.
  4. Incorporate Dry Mix: With the mixer on low speed, gradually add the flour mixture to the wet ingredients until just combined. Stop mixing the moment the last streak of flour disappears to prevent tough cookies.
  5. Chill the Dough: Wrap the dough tightly or place it in an airtight container. Refrigerate for a minimum of 45 minutes, up to 2 hours. This step is non-negotiable for thick, chewy Rolo cookies.
  6. Preheat and Prep: Preheat the oven to 375°F (190°C). Line two baking sheets with parchment paper. Place the remaining ½ cup of granulated sugar for rolling into a shallow bowl.
  7. Scoop and Roll: Use a 1.5-ounce cookie scoop to portion the dough. Roll each ball in the palm of your hand to smooth, then roll thoroughly in the granulated sugar.
  8. Arrange and Bake: Place the sugared dough balls onto the prepared baking sheets, spaced at least 2 inches apart. Bake one tray at a time for 10–12 minutes. The centers should look slightly soft and underdone.
  9. Press in Rolo: Immediately upon removing the cookies from the oven, gently press one unwrapped Rolo candy right into the center of each hot cookie. The heat will melt the chocolate and soften the caramel.
  10. Salt and Cool: Sprinkle the exposed caramel and surrounding cookie surface with a small pinch of flaky sea salt. Allow the cookies to set on the baking sheet for 5 minutes before carefully transferring them to a wire rack to cool completely.