Preheat oven to 350F and line a cookie sheet with baking paper.
In a large pot, add the oil and popcorn kernel and place it on the stove, high heat.
Shake the pot to evenly coat the kernel with oil. The kernels will pop and be ready when there is 3 seconds or less between pops.
Empty the pot and place the popped popcorn in a large bowl.
Place the sugar and butter in the pot and return to heat. Allow to melt and cook until foamy and starts to change color.
Stir with a wooden spoon and let cook for 1 minute.
Remove from heat and stir in the baking soda and salt.
Pour the mix on the popped popcorn and toss to distribute.
Spread the popcorn on the baking sheet and bake for about 15 minutes, rotating the pan midway to the baking time.
Remove from oven and let cool and crisp.
Preheat oven to 350F and line 2 baking sheet with parchment paper.
In a medium bowl, sift together the flour, baking powder, baking soda, and 1/2 tsp of the salt. Stir and set aside.
In a bowl of a standing mixer, fitted with the paddle attachment, place the butter and sugar and beat medium-high until light and fluffy. About 5 minutes.
Add the egg and vanilla into the butter and sugar mix.
Sprinkle in the flour mixture followed by the caramel popcorn and mix on low just until the popcorn is fully incorporated.
Using a cookie scooper, scoop the batter and place on the lined baking sheets leaving about 2" space for the cookies to spread.
Sprinkle the remaining of the salt on the cookies and bake for 12-15 minutes. Rotating the pan midway through the baking time.
Remove from the oven and let cool.