Add the whiskey, cranberry juice, lemon juice, and syrup to your shaker.
Add ice and shake vigorously.
Strain over fresh ice in your glass and dust with cinnamon. Cheers!
Cinnamon Vanilla Syrup
Add the water and sugar to a small saucepan. Bring the water to a boil and stir until the sugar is completely dissolved.
Add 4-6 cinnamon sticks. Reduce the heat and simmer for about 10 minutes.
Remove from heat then cover with a lid and let sit for a minimum of one hour before you use it. The longer you let it sit the more flavor you will get from the cinnamon.
Next, add the vanilla extract and stir to combine.
Transfer to a syrup bottle with a tight seal. Store in the refrigerator for up to 2 weeks.
Notes
For the Cinnamon Vanilla Syrup:
You can remove the cinnamon sticks if you want, but I prefer to leave them in so they continue to marinade and add more cinnamon flavor.
The quality of vanilla extract you use will make a difference in flavor. Use the best quality you can find.