Cream the butter, brown sugar and vanilla in a stand mixer until light and fluffy (about 2-3 minutes). Scrape the sides of the bowl to make sure all ingredients are blended.
Add in the egg and beat until combined.
Add in cocoa, flour, baking soda, and salt. Stir until all combined and the dough forms a ball. Divide the dough into two balls.
Flour your work surface and roll out the dough to 1/4 inch thickness.
Cut out cookies using a fall leaf (or pumpkin) cookie cutter and carefully transfer them to a parchment lined baking sheet or use a silicone baking mat on the sheet. Place the cookies in the freezer for 10 minutes and freeze until firm.
Preheat oven to 350 degrees. Bake the frozen cookies for 10 minutes. Remove from oven and cool on baking pan for 10 minutes and then transfer to a cooling rack and cool completely.
Make the peanut butter filling. Combine the peanut butter, powdered sugar, and vanilla in a bowl and mix until light and fluffy.
Melt the dark chocolate in the microwave 30 seconds at a time.
Dip half of the cooled cookies (leave the other half of cookies plain for the base of the cookie sandwiches) into the melted chocolate and coat about 1/3 of each cookie. Sprinkle with sea salt. Chill the chocolate dipped cookies for 10 minutes in the freezer.
Spread peanut butter filling over the bottom cookie halves (the ones NOT dipped in chocolate) and place a top cookie on top to make a cookie sandwich. Gently press down to create the sandwich.