Step 1 of 9
Salted Caramel Thumbprint Cookies
Line two baking sheets with silicone baking mats or parchment paper. Set aside.
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Step 2 of 9
Salted Caramel Thumbprint Cookies
Place the butter, brown sugar, vanilla extract, and cinnamon into a large mixing bowl. Use a hand mixer to beat on medium speed until mixture is pale and well combined, about 1 minute.
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Step 3 of 9
Salted Caramel Thumbprint Cookies
Add the flour and salt to the bowl and beat on low speed, scraping the sides of bowl with rubber spatula as needed, until a smooth dough forms.
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Step 4 of 9
Salted Caramel Thumbprint Cookies
Divide cookie dough into 24 balls, using about 2 tablespoons for each, and arrange on the baking sheets at least 1 inch apart. Transfer the sheets to the freezer for 10-15 minutes while oven preheats. Alternately, place the dough balls on a small baking sheet or large plate to freeze, and transfer to the baking sheets for baking.
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Step 5 of 9
Salted Caramel Thumbprint Cookies
Preheat the oven to 350°F.
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Step 6 of 9
Salted Caramel Thumbprint Cookies
Remove cookies from the freezer. Bake cookies on middle rack of oven until puffy and golden brown at edges, 14-16 minutes.
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Step 7 of 9
Salted Caramel Thumbprint Cookies
Check to see that cookies are done. Remove from oven or add time as needed.
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Step 8 of 9
Salted Caramel Thumbprint Cookies
Immediately press a 1/4-inch-deep indent into the center of each cookie, using either the handle of wooden spoon or your thumb. Making deeper indents will help avoid creating cracks in the cookies.
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Step 9 of 9
Salted Caramel Thumbprint Cookies
Allow the cookies to rest and firm up on the sheets for 5-10 minutes, then transfer to a wire rack. Spoon about 3/4 teaspoon of salted caramel sauce into the indent of each cookie. Allow to cool and set completely before serving. Store leftover cookies in refrigerator.