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Preheat oven to 350 F (177 C) and line a baking sheet with parchment paper.
Make the streusel by mixing together the flour, brown sugar, cinnamon and salt. Add the cubed, soft butter and use your fingers to work into the dry ingredients to form clumps (similar to wet sand texture). Chill in the fridge until ready to use.
Make the dough by stirring together the softened butter and sugars until combined. Mix in the egg yolk and vanilla extract until well combined.
Add the flour, cornstarch, cinnamon, baking soda/powder, and salt. Mix until combined.
Scoop the dough onto the parchment lined baking sheet into two large balls. Use your thumbs, or the bottom of a ½ tablespoon measuring spoon to make a large indent in each ball. Spoon in the streusel filling to fill each cavity.
Pop in the fridge to chill while the oven finishes preheating (about 5-10 minutes).
Bake for 8-11 minutes until the edges are set and just getting golden brown. Allow to cool on the baking sheet for 10 minutes then transfer to a wire rack.
In a small bowl, microwave the butter, brown sugar, and 1 tsp heavy cream for just 20-30 seconds until melted and bubbly. Mix in the vanilla and powdered sugar - you can add a little more cream if needed to thin to desired thickness. Pipe over the cookies and enjoy!