Start off by mixing everything with an electric hand mixer on low speed, then pick it up to the highest speed once you don’t see any more dry patches of powdered sugar. Beat for a total of about 4 minutes.
Use a fine-mesh sieve to sift in the flour, baking soda, and salt.
Mix on low until everything is well combined.
Now place the cookie dough onto a piece of plastic wrap. Then flatten it to a disk, wrap it, and refrigerate for about 1-2 hours.
Dust your work surface with a little bit of flour. Then use a rolling pin to roll the chilled dough to 1/2 inch thick.
Cut the cookies out using a 2-inch round cookie cutter. Then bake the cut-out cookies on a parchment-lined baking sheet at 350 degrees Fahrenheit for about 6-8 minutes. You don’t want the cookies to over-bake. These are meant to be soft.
Add the caramels and heavy cream to a bowl or saucepan and melt slowly until it’s smooth and runny. You can do this over the stove on low heat or if you’re using a bowl, just microwave it in 20-second intervals with mixing in between.
Then melt the chocolate chips in a microwave-safe bowl, also in 20-second intervals with stirring in between.
Spoon a dollop of the melted caramel over each cookies.
Then smother the tops of each cookie after the caramel has cooled. Add a sprinkle of flakey sea salt while the chocolate is still warm and enjoy!
Notes
Start by mixing on low- When creaming the butter and sugar together, start on low and go up to high once you don’t see any more dry patches of powdered sugar or it will make a mess. Same when you add the flour.
Only bake the cookies for 6-8 minutes- You don’t want the cookies to over-bake. These are meant to be soft so this is the perfect amount of time.
Let the caramel be runny- This will solidify when it cools so don't worry that it is on the runny side. This will make it easier to apply to the cookies.
Add the salt while the chocolate is melted- The flaky salt won't stick unless the chocolate is still melted, so make sure to add this before it solidifies.