In a medium heavy-bottomed saucepan, combine the sugar, water, and corn syrup. Stir gently to moisten the sugar, then stop stirring completely.

Set over medium heat and cook undisturbed for 5–10 minutes, until the syrup turns a rich amber color. Meanwhile, warm the heavy cream in the microwave for 1 minute.

Once the caramel is amber (like honey or copper), remove from heat. Carefully pour in the warm cream while whisking — it will bubble up quickly.

Whisk until smooth, then stir in the vanilla and salt. If needed, return to low heat briefly to smooth everything out.

Let cool slightly, then transfer to a heat-safe jar. The caramel will thicken as it cools. Refrigerate for up to a week and warm before using.

Preheat oven to 350°F. Line a sheet pan with parchment paper.

In a medium bowl, whisk together the flour, brown sugar, granulated sugar, cinnamon, and salt.

Pour in the cooled melted butter and mix with a fork or spatula until clumps form. You want crumbly clusters, not dough. If it looks too sandy, squeeze some together with your hands.

Spread evenly on the prepared pan and bake for 8–10 minutes, until golden and set.

Let cool completely, then break into large pieces.

Preheat oven to 350°F. Line a baking sheet with parchment paper.

In a stand mixer fitted with the paddle attachment, cream the butter, granulated sugar, and brown sugar until light and fluffy, about 3 minutes.

Scrape down the bowl, then add the egg yolk and whole egg. Mix on medium speed for about 30 seconds.

Add pumpkin puree and vanilla, mixing on low just until combined.

On the lowest speed, add flour, salt, baking powder, pumpkin pie spice, and cinnamon. Mix just until no flour streaks remain.

Scoop 7 large cookie dough balls (about 6 oz each) and place on the prepared baking sheet. Bake for 14–16 minutes, until edges are set and centers look slightly soft. The cookies will continue to set on the pan as they cool — don’t wait until the centers are firm, or they’ll be overbaked.

Cool completely before frosting.

In the bowl of a stand mixer, beat butter and cream cheese on medium speed for 2 minutes. Scrape the bowl, then beat for 2 more minutes until smooth and fluffy.

With the mixer on low, add powdered sugar, then vanilla, cinnamon, and salt. Mix until combined.

Increase speed to medium-high and beat 2–3 more minutes until light and fluffy. If too soft to pipe, chill for 10–15 minutes.

Make sure cookies are completely cool before decorating.

Fill a piping bag fitted with a Wilton 8B (or another small star tip) with the cream cheese frosting. Pipe a tight swirl starting in the center of each cookie and working outward.

Fill a second piping bag or zip-top bag with salted caramel, snip the tip, and drizzle across the frosting.

Press streusel pieces into the frosting, using a mix of big and small chunks for texture.

Finish with a sprinkle of flaky sea salt.