Combine apples, sugar, butter, cornstarch, and cinnamon in a medium sized skillet over medium-low heat. Stir frequently until butter is melted and sugar is dissolved.

Increase heat to medium and bring to a simmer. Simmer for 5 minutes, stirring occasionally, until apples are tender when pierced with a fork.

Remove from heat and pour into a heatproof bowl. Place in the refrigerator while you prepare the dough.

Preheat oven to 350F (175C) and line a baking sheet with parchment paper. Set aside.

Combine softened butter and sugars in a large bowl and use an electric mixer (or a stand mixer with paddle attachment) to beat until light and fluffy.

Add eggs and vanilla and stir until combined.

In a separate, medium-sized bowl whisk together flour, cornstarch, baking powder, baking soda, and salt.

Gradually add dry ingredients to wet, stirring until completely combined.

Cover bowl with plastic wrap and place in the refrigerator to chill slightly while you prepare the streusel.

Melt butter in a small bowl and allow to cool until no longer warm to the touch.

Combine flour, sugars, salt and cinnamon in medium-sized bowl and stir until combined.

Drizzle cooled butter into flour mixture and claw together with a fork until you have a clumpy streusel.

Remove apple filling and cookie dough from refrigerator.

Scoop dough by 2 Tablespoon-sized balls and roll until smooth. Place on baking sheet and make an indent in the cookie (I used the back of the cookie scoop to make indent – do not push too deep or make the cookie too thin or the cookie won’t be able to support the weight of it after baking)).

Scoop a level Tablespoon of filling into the indent you just created

Take a small handful of streusel (about 1 Tablespoon) and nestle gently into the filling. Use enough to completely cover the filling.

Transfer to center rack of 350F (175C) oven for 13-14 minutes or until edges begin to turn a light golden brown. Allow to cool completely before decorating with glaze and “ice cream” (below, if using).

Beat butter, salt, and vanilla in large bowl using an electric mixer until butter is smooth.

Add powdered sugar ½ cup at a time, waiting until each cup is completely mixed before adding more. Once finished, the buttercream should be very stiff, almost a play-dough like consistency. It should be easy to roll into a ball. Add more powdered sugar, if needed, to reach proper consistency.

Set aside while you prepare the vanilla bean glaze.

Whisk together powdered sugar with 1 Tablespoon of milk and vanilla bean paste until completely combined. Add additional milk, a splash at a time, until glaze is smooth and ribbons off of your whisk.

Drizzle glaze on cookie. Scoop buttercream by one Tablespoon sized scoop and place on cookie, gently nestling onto the glaze (which will help “cement” it).

Allow glaze to harden before enjoying.