With an electric mixer using a paddle attachment, combine the butter and brown sugar and beat on high speed until mixture is light and fluffy, approximately 3 minutes, scraping the sides of the bowl occasionally.Add in egg and vanilla extract and mix on medium speed until fluffy and mixed well.
Add salt, baking soda, and graham cracker crumbs and mix until just combined. Add flour one cup at a time and mix on low speed about 1 minute until flour is completely mixed in.
Preheat oven to 350° F. Line 2 cookie or baking sheets with parchment paper or a silicone baking mat.
Using ⅓ cup scoop, measure out 12 balls of dough, and optionally roll in graham cracker crumbs, then place evenly on baking sheets. Bake for 10-11 minutes when cookies begin to crack. Cool completely.
For the Frosting:
With an electric mixer mix cream cheese and butter together on medium/high speed until smooth and creamy. Add powdered sugar 1 cup at a time mixing on low speed until powdered sugar is completely mixed in between additions. Add vanilla extract and mix well. Add cornstarch 1 Tb at a time as needed for desired thickness.
Spoon frosting into a piping bag and using a large round tip, frost each cookie in a spiral pattern.
For Streusel:
Mix together graham cracker crumbs and melted butter, then sprinkle onto frosted cookies generously. Spoon cherry pie filling over cookies 3-5 cherries or as preferred. Serve within 2 hours of making or refrigerate for up to 3 days.