In a large bowl, with a hand mixer or use a stand mixer fitted with the whisk attachment, cream room temperature butter, granulated sugar, and brown sugar until light and fluffy. The mixture should resemble peanut butter. Beat in egg, sour cream, almond extract, and vanilla extract.
In a separate bowl combine the flour, unsweetened cocoa powder, Dutch-process cocoa powder, baking powder, baking soda, and salt. Stir to combine. Add in both kinds of chocolate chips and stir once more.
Combine wet and dry and mix until just combined. Be careful not to overmix the dough. The dough is very thick and moist. Cover the dough and chill for 1–4 hours. Preheat the oven to 350℉ (or 325℉ for convection oven).
Line a large sheet pan with parchment paper or a silicone baking mat. Measure 1-1/2 tablespoonfuls of dough for each cookie and then roll an unwrapped Rolo into the center of the dough. Make sure the Rolo is completely encapsulated by the dough. The dough is very wet and sticky, so this party is tricky and messy. If the dough is too wet, put it back in the fridge for 20–30 minutes and try again. Place the cookies 2–3 inches apart on the sheet pan. I only bake 6 cookies at a time because they spread a lot. Chill dough balls on sheet pan for 20 minutes before baking.
Bake for 8–14 minutes or until set, just until the top is no longer glossy. Be careful not to over bake. A soft, very slightly underbaked cookie is the best for a delicious fudgy texture! Remove from the oven and let cookies stand on sheet pan for 5 minutes before removing to a wire cooling rack.
While the cookies are just out of the oven and still on the sheet pan, press a few more chocolate chips into the tops of the cookies. Let stand for a few minutes and then sprinkle some salt onto the melty chocolate chips on top of the cookies. Let cool for 15–20 minutes. Repeat to bake the rest of the cookies.
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Notes
Note 1: For this recipe, use both regular unsweetened cocoa powder and Dutch-process cocoa powder. Substituting one for the other can significantly affect the flavor and texture of the cookies. Dutch-process cocoa has the acid removed, so it requires an additional acid in the recipe, while using only natural cocoa can result in cookies that lack richness and depth.Storage: Store cookies in an airtight container at room temperature for best enjoyment within 3–4 days. For freezing, drop cookie dough balls onto a large sheet pan and freeze until solid. Once frozen, transfer them to an airtight container or bag and freeze for up to 3 months. You can bake the cookies straight from the freezer without thawing, though you may need to add a few extra minutes to the baking time. Bake until the tops are no longer glossy, and the centers remain soft.