Preheat oven to 350℉. Line a baking sheet with parchment paper and set aside.
In a large bowl, add butter, brown sugar, and granulated sugar. Using a hand mixer or stand mixer, beat until fluffy, about a minute. Add eggs and vanilla extract. Beat until fluffy, about a minute.
In a separate bowl, sift together the flour, chai spices, baking soda, and salt. Gradually stir dry ingredients into butter mixture until just combined. Add old fashioned oats and stir until just combined. Dough will feel sticky.
Scoop dough using a 1.5 tablespoon (medium) scoop or shape by hand into 1.5 inch balls. Place cookie dough balls 2 inches apart onto a prepared baking sheet.
Bake for about 11-13 minutes, or until lightly browned around edges and across the tops. Allow to cool for 5 minutes before removing to a wire rack to cool completely.
Filling
In a bowl, add room temperature butter. Beat with a hand mixer until creamy.
Add confectioner's sugar gradually and mix on low speed until ingredients are fully combined. Then, whip at high speed for 2-3 minutes, or until light and fluffy.
Add milk, maple syrup, and salt, then whip for an additional about 2-3 minutes, or until light and fluffy.
Pipe frosting with a piping bag or spread frosting generously with a knife onto the bottoms of half of the cookies. Top with remaining unfrosted cookies to make sandwiches.
Notes
Oat variations: Quick cook oats can be substituted with old fashioned oats for a chewier, more substantial cookie texture. Steel-cut oats do not work well in this recipe.
Storage: Cookies will keep for 5-7 days at room temperature in a sealed container. Add a slice of bread to the container to help keep your cookies soft for longer, replacing the bread slice as needed.
Freezing: Leftover dough and baked cookies can both be frozen for up to 3 months. To thaw, place on the counter for 1-2 hours.