In a medium size bowl, whisk together flour and baking soda. Set aside.
In a large bowl using an electric mixer, beat together butter and sugars on medium speed until light and fluffy. Add eggs and vanilla extract; mix until combined.
Scrape down the sides of the bowl, add cocoa and pudding mix; mix on low speed until combined. Add flour mixture; mix on low speed until combined.
Cover cookie dough with plastic wrap and refrigerate for at least 3 hours. Do not bake cookies without chilling as they are prone to spreading.
Preheat oven to 350F degrees.
Scoop dough into 2 teaspoon rounds, or use a #60 disher to scoop balls of dough. Sandwich a Rolo between two balls of dough, covering the Rolo completely and forming a ball. Lightly sprinkle the top with sea salt.
Place rounds of dough, sea salt side up, on a silicone mat/parchment paper-lined baking sheet 2" apart. Cookies will spread.
Bake 9-11 minutes or until edges have set. Do not overbake, which is easy to do with chocolate cookies.
Cool cookies on baking sheet on a wire rack for 8 minutes; transfer to a wire rack to cool completely. Eat & Enjoy!
Notes
Double Chocolate Salted Caramel Cookies should be stored in an airtight container and will keep 4+ days.¹ You want a 3.7-3.9 ounce package of instant pudding mix, NOT sugar-free or cook & serve. You're also NOT making the pudding, just using the mix in the batter.