Preheat the Oven: Heat the oven to 350°F (175°C) and line baking sheets with parchment paper.
Prepare Dry Ingredients: In a bowl, mix oats, flour, baking soda, salt, and cinnamon until well combined.
Cream Butter and Sugar: Beat softened butter and brown sugar until fluffy.
Add Wet Ingredients: Mix in egg and vanilla extract until fully incorporated.
Form the Dough: Gradually add the dry mixture to the wet ingredients. Stir until a thick dough forms.
Shape the Cookies: Scoop tablespoon-sized portions onto the baking sheets, spacing them about 2 inches apart.
Bake the Cookies: Bake for 10-12 minutes or until golden around the edges. Cool completely on a rack.
Make the Ganache: Heat heavy cream and espresso in a saucepan until it just starts to simmer.
Melt Chocolate: Pour the hot cream over chocolate chips and whisk until smooth. Add vanilla extract.
Assemble the Sandwiches: Spread ganache on the flat side of half the cookies. Top with remaining cookies.
Set the Filling: Allow the ganache to set for 10-15 minutes before serving.