Preheat the oven to 375 degrees F. (see note) Line baking sheets with parchment paper or lightly grease with cooking spray. Set aside.
For the browned butter, cut the butter into pieces and add to a stainless skillet or saucepan. Heat on medium-low until the butter melts. Continue cooking, swirling or stirring occasionally; the butter will foam and sizzle as it cooks and golden bits (the butter solids) will settle to the bottom. Cook until the butter has a nutty fragrance and the solids are golden brown. Watch closely; it can burn quickly.
Remove from the heat and scrape the butter and all the browned bits into a large bowl. Cool the butter until the texture is thick and sludgy – or at the very least, no longer warm. This cooling step is important so the cookies don’t spread while baking!
Add the brown sugar, granulated sugar, eggs and vanilla and mix until well combined.
Add the flour, cream of tartar, baking soda, cinnamon and salt, and stir until evenly mixed.
In a bowl or shallow dish, whisk together the 1/4 cup sugar and 1 teaspoon cinnamon.
Scoop out two tablespoons of dough (I use a #40 cookie scoop) for each cookie, flatten into discs, place half a caramel in the center of each, roll up the dough around the caramel and roll the balls until smooth.
Roll in the cinnamon and sugar mixture and place the cookie dough balls a couple inches apart on the prepared baking sheets.
Bake for 9-11 minutes until flattened and a few cracks form in the top (see note if your cookies are flattening or NOT flattening while baking).
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