In a medium bowl, add the softened butter and brown sugar. Beat with a mixer until light and fluffy.
Add in the vanilla and cinnamon. Beat until well combined.
Add the flour and stir until fully incorporated.
Cover with plastic wrap and chill for at least an hour.
After the dough has chilled, preheat the oven to 350 degrees.
Line a baking sheet with parchment paper or a silicone liner.
Use a cookie scoop (or a spoon) to scoop out 2 Tb balls of dough. Use your hands to flatten the dough into a circle.
Put 5 chocolate chips into the center of the dough then roll the dough around the chips, fully closing it so no chocolate leaks out while baking.
*I used Ghirardelli baking chips, which are larger than typical chocolate chips, and used 5 chips per cookie. You may need/want to use more than 5 if you're using regular chips. Next time I may up the chip count to 7 for more chocolate.
Line up the cookie balls about 1" apart on the prepared cookie sheet.
Bake for 18-20 minutes or until just golden.
Once done, transfer to wire cooling racks.
Use a sifter (or a tea strainer, if you're me) to sprinkle the cookies with powdered sugar.
Recipe adapted from an old book my grandma gave me :)