In a large bowl, add the flour, sugar, seasonings and oatmeal.
1/2 Cup Flour, 3/4 Cup Old Fashioned Oatmeal, 3/4 Cup Brown Sugar, 1/2 teaspoon Cinnamon, Dash of Salt
Stir everything together.
Add the butter cubes and using a pastry cutter begin to cut in the butter. As the butter begins to be incorporated into the mixture, switch to using your hands and squeeze and mix everything together until it is like a very thick dough and no flour remains.
6 Tablespoons Unsalted Butter
Spread onto a parchment lined baking sheet and bake at 350 for 8 minutes. Set aside to cool then crumble in small chunks.
Apple Filling
Peel, core, and dice the apples.
3 Granny Smith or Honeycrisp Apples
Over medium heat, stir in apples, sugar, salt and cinnamon.
1/3 Cup Sugar, 1 teaspoon Ground Cinnamon, Pinch of Salt
Cover and cook stirring occasionally for 4-6 minutes or until very slightly softened.
In a small dish combine cornstarch and 2 tablespoons water. Add to the pan while stirring and continue to cook until apples are soft and filling is thickened. Set aside to cool.
1-2 Tablespoons Water, 2 Tablespoons Cornstarch
Cookie
Preheat oven to 350 and line 2 baking sheets with parchment.
Cream the butter until smooth then add in the cream cheese and cream again.
1/2 Cup Unsalted Butter, 2 Tablespoons Cream Cheese
Add in sugars and beat until smooth, about 1 minute.
1/2 Cup Brown Sugar, 1/3 Cup White Sugar
Scrape the sides of the bowl down and mix in the vanilla and egg.
1 Large Egg, 1 teaspoon Vanilla
In a bowl, whisk together the dry ingredients. Pour the dry ingredients into the mixer and mix until 1/2 the flour is incorporated then switch to a wooden spoon and gently fold together.
Using a large cookie scoop, scoop out 8-10 large cookies then roll into a ball.
Roll the dough in cinnamon sugar then place 4 at a time on a baking sheet. We like to refrigerate covered with plastic wrap at this point so they will spread as little as possible but it is not necessary. The dough not being baked should, however be refrigerated until use.
Make a well using a tablespoon in the center of each ball.
Bake 10 minutes.
Remove from oven and immediately press using a small glass or measuring cup to indent the center for the filling one more time.
Bake an additional minute or two or until the center does not appear shiny and doughy.
Set aside to cool completely, pressing with the glass a final time if needed.
Once everything is cool, add the filling, top with a little crumble and a drizzle of glaze if desired.
Glaze
In a saucepan, brown the butter over medium heat then pour off into a bowl. Whisk in powdered sugar and vanilla, adding a little milk if needed.