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Step 1
Combine the cinnamon and sugar in a small shallow bowl. Rub the rims of 2 large or 4 small glases with a little water (coconut rum or tequila would work too). Dip the rims through the cinnamon sugar. Place the glasses in the freezer.
Step 2
To a blender add 2 churros (adding more if you want an extra cinnamony flavor. I used 4 churros, but it was a little intense. So good, but a little intense), ice cream, milk, vanilla extract, coconut rum or tequila if using and 2 tablespoons warm dulce de leche. Blend until your desired consistency is reached. If you do not want chunks of churros blend until completely smooth.
Step 3
Remove the glasses from the freezer and drizzle with warm dulce de leche on the insides and bottoms of the glasses. Pour in the milkshake and garnish each with a churro...or two. Bottoms up.