Preheat the oven to 350° F (180°C). Line a cookie sheet with parchment paper or a silicone baking mat. Set aside.
In the bowl of a stand mixer, cream the softened butter, brown sugar, and granulated sugar until light in color and fluffy in texture.
1 cup salted butter, softened, 1 cup brown sugar, ½ cup granulated sugar
Scrape the sides of the bowl and add in the mashed banana, egg, and vanilla. Mix until combined.
1/3 cup mashed overripe banana, 1 egg, 1 tsp vanilla
Add in the flour, cornstarch, and salt. Mix until a soft dough forms.
3 ¼ cups all-purpose flour, ½ Tbsp corn starch, ½ tsp salt
Scoop the cookies using a #24 cookie scoop (about 2.5 Tbsp) and roll into balls.
Roll each ball in the chopped pecans, then gently roll the coated ball in your hands to push the pecan pieces into the dough slightly.
2 cups chopped pecans, for rolling
Arrange on your prepared cookie sheet. Use the back of a tablespoon spoon to press down in the center of each dough ball to create your thumbprint crater. Do not wait until after baking to create this crater, the cookies will crack and fall apart.
Bake at 350° for 10 mins.
As soon as they come out of the oven use the same tablespoon spoon to define your thumbprint.
Allow to cool for 10 mins on the cookie sheet before transferring to a wire rack to cool completely.
Once cool, melt the caramels and heavy cream in the microwave in 30 second increments until smooth, stirring in between.
40 soft caramels, 2 ½ Tbsp heavy cream
Carefully spoon caramel into the center of each cookie. Allow the caramel to set up, the cookies can be placed in the fridge to help speed up this process.
Once the caramel has set up, drizzle melted milk chocolate onto the tops of the cookies. Top with flake salt, if desired. Let the chocolate set up.
1/2 cup semi-sweet chocolate chips, melted, flakey sea salt, for topping
Store at room temperature or in the fridge for up to 4 days. Enjoy!