Preheat oven to 350ºF. Line baking sheets with parchment paper and set aside.
In a small bowl, whisk together flour, salt, baking soda, and cinnamon. Set aside.
1 cup all-purpose flour, ¾ teaspoon salt, ½ teaspoon baking soda, ½ teaspoon ground cinnamon
Brown the butter in a medium-sized, light-colored pan, stirring it frequently as it melts and then browns to ensure that it does not burn. Once browned, immediately transfer the butter to a large, heat-safe bowl.
6 Tablespoons unsalted butter
Add both sugars and the vegetable oil to the bowl with the browned butter and whisk to combine.
¾ cup dark brown sugar, ½ cup granulated sugar, ⅜ cup vegetable oil
Add egg, egg yolk, and vanilla and whisk to combine.
1 egg plus 1 egg yolk, 1 teaspoon vanilla extract
Add the flour mixture to the butter mixture and gently stir (using a wooden spoon or rubber spatula) until combined.
Add oats one cup at a time and stir until blended.
3 cups old-fashioned oats
Scoop 1 ½ Tablespoon sized balls of dough onto prepared baking sheets, leaving 2 inches between each cookie. Flatten each cookie dough ball just slightly using the bottom of a glass.
Bake cookies one tray at a time for 11-13 minutes, or until cookies are just beginning to turn golden around the edges. Let cookies cool on the tray for 5 minutes before transferring to a wire rack to cool completely.
Make the chocolate ganache.
Place finely chopped chocolate in a heatproof bowl and set aside.
6 ounces semi-sweet chocolate baking bar
Add cream to a small saucepan and heat just until simmering. (The cream should be just beginning to bubble and should not yet be fully simmering or boiling.)
6 ounces heavy whipping cream
Pour the heated cream over the chocolate and let it sit for 2 minutes. Then stir until the chocolate is completely melted and the mixture is smooth and shiny.
Let the ganache cool completely, lightly stirring occasionally as it cools.
Once the ganache has cooled to room temperature, use an electric hand mixer or a stand mixer with the whisk attachment to whip the ganache on medium-high speed for about one to two minutes, until it becomes light and fluffy in texture and lighter in color.
Assemble the sandwich cookies.
Fit a piping bag with your desired piping tip (I used a Wilton 1M piping tip), or simply snip the corner off the bag.
Lay out the cookies, turning half of them upside-down.
Pipe the whipped ganache onto the upside-down cookies in a circular pattern beginning in the center of the cookie and working outwards towards the edges. (Alternatively, you can use a spatula or spoon to spread the whipped ganache onto the cookies.)
Once the whipped ganache has been piped onto half of the cookies, top them with the remaining cookies to create the cookie sandwiches.
Notes
Storage: Cookies without chocolate ganache can be stored in an airtight container at room temperature for up to 4 days. Cookies with ganache can be stored in an airtight container at room temperature for up to 2 days or in the fridge for up to 4 days.Be sure to use a nice quality chocolate baking bar, not chocolate chips (which will not yield the proper consistency for the ganache).