In a mixing bowl, combine butter and brown sugar. Mix on high speed for at least 3 minutes with an electric mixer to "cream" them together and begin dissolving the sugar.
Add in the egg and vanilla extract and mix for 1 minute, until the egg is fully mixed in and the batter is fluffy.
In a blender, pulse the graham crackers until they become a fine powder.
Add the graham cracker powder, flour, baking soda, and salt (cinnamon optional) to the cookie dough and mix on low speed until everything is mixed in, about 1 minute.
Scoop the cookie dough onto prepared baking sheets with a large 3-4 Tablespoon cookie scoop. Smash the cookies slightly so they are about 2 inches.
Bake at 350 ℉ for 10-11 minutes, they will be starting to crack around the edges. Let cool completely before frosting.
In a mixing bowl, combine butter and cream cheese. Mix at medium/high speed with an electric mixer until fluffy, about 1 minute.
Add in the powdered sugar, cornstarch, and vanilla and mix well, until there are no sugar pockets left and frosting is smooth.
Once the cookies are completely cool, transfer the cream cheese frosting to a piping bag and pipe onto each cookie starting on the outside, frosting in a spiral to the center.
Place strawberry pie filling on each cookie, and sprinkle with graham cracker crumbs (optional). Enjoy!