Mix 2 teaspoons vanilla extract with 1 teaspoon of dry active yeast.
Cream the butter, cream cheese, vanilla with yeast, and granulated sugar with an electric mixer until light and fluffy—2-3 minutes.
Turn the mixer on low. Add the salt, then slowly add the flour. Scrape the bowl and mix until well combined.
Press the dough into a flat disk. Wrap and refrigerate the dough for (at least) 30 minutes.
Preheat the oven to 375 degrees F. Mix the brown sugar and cinnamon together in a small bowl.
Cut the dough in half and leave one half in the fridge while working with the first half.
Flour a piece of wax paper and roll the dough into a 7x13-inch rectangle that is approximately 1/4-inch thick. Then cut the dough into two sections to make the rolling easier.
Sprinkle half the cinnamon sugar over the dough leaving 1 1/2 inches bare along the long edge. Starting on the cinnamon-covered side, carefully roll the dough tightly toward the bare edge. Press the seam firmly.
Repeat with the remaining dough and cinnamon sugar. Place the rolls back in the refrigerator for at least 30 minutes to harden the dough. *At this point, you can wrap the rolls and refrigerate for 2-3 weeks if needed.
Cut the roll into 1/3- to 1/2-inch slices and lay on parchment paper lined cookie sheets.
Bake for 9-12 minutes. Cool completely. Then whisk the powdered sugar, milk and remaining vanilla extract together in a small bowl. Dip the face of each cookie into the glaze and set on a rack to dry.