Start by making the pumpkin caramel.  Put sugar, water, and corn syrup in a medium saucepan over medium heat.  Bring to a gentle boil, swirling the pan around to stir.  Bring the syrup to a medium amber color (this will take 5-8 minutes).  Remove pan from heat and immediately add the cream and butter.  Stir well, the mixture will foam up.  Mix in the pumpkin spice and pumpkin, until completely incorporated.  Pour into a heat-proof bowl and cover.  Chill in refrigerator for 4 hours.

While the pumpkin caramel is chilling, make the cookies.  Beat the butter in a large mixing bowl with an electric mixer on medium-high speed for 30 seconds.  Beat in the brown sugar and 1/4 teaspoon salt.  Once combined, scrape the sides of the bowl and add in the egg and vanilla; mix until combined.  Carefully mix in the flour until combined.  Cover and chill dough for 1 hour.

Preheat oven to 375 F.  Roll out chilled dough into 1-inch balls.  On ungreased cookie sheets, place the dough balls 2-inches apart.  Press your thumb into the center of each dough ball.  Bake for 8-10 minutes, until the bottoms of the thumbprints are lightly browned.  Remove from oven & press down the centers of any puffed up cookies with the back of a spoon.  Cool completely on a wire cooling rack.  Once cooled, spoon the chilled pumpkin caramel into the centers of the thumbprints.  Sprinkle each cookie with flaked sea salt.  Enjoy!

Bring sugar, water, and corn syrup to a boil over medium-high heat in a medium saucepan.

Gently boil until the caramel turns golden amber, about 5-8 minutes.

Remove from heat and add in the butter and cream. It will foam up, so don’t be alarmed. Stir until combined & butter is melted.

Stir in the pumpkin and pumpkin pie spice.

Stir until combined and move to a heat-proof bowl.

Cover and refrigerate for 4 hours. I thought this was the perfect time to use my silicone pumpkin lid to cover the bowl 🙂

Time to make the cookies.  Start by beating the butter for 30 seconds with an electric mixer (either a hand mixer or stand mixer will work)

Beat in the brown sugar and salt.

Scrape the sides of the bowl and add in the egg and vanilla. Beat until combined.

Mix in the flour until incorporated.

Cover dough and refrigerate for 1 hour.

Roll chilled dough into 1-inch balls. Place 2-inches apart on ungreased cookie sheets.

Press thumb into the center of each cookie.

Bake for 8-10 minutes until the bottoms of cookies are turning golden brown. If the cookies have puffed up, press down the centers with the back of a spoon to get your thumbprint back. Cool completely on wire cooling racks.

Spoon the chilled pumpkin caramel into the center of each cooled thumbprint.

Sprinkle on the flaked salt. I didn’t have flaked salt, so I just used kosher salt. Enjoy!