Chill 4 glasses in the freezer while you prep. Let the cream cheese sit at room temperature for about 30 minutes (or microwave the cubed cream cheese for 10 to 15 seconds) so it's soft enough to blend smoothly.

Add the vanilla ice cream, milk, softened cream cheese, pumpkin puree, sugar and pumpkin pie spice to a blender.

Blend on low speed to break everything up, then increase to high and blend just until completely smooth, about 45 to 60 seconds total. Scrape down the sides once if needed. Don't over-blend, or the shake will get thin.

Check the consistency. Add a splash more milk if it's too thick, or another scoop of ice cream if it's too thin, and pulse briefly to combine.

Pour into the chilled glasses. Top each with whipped cream, chopped pecans, a pinch of pumpkin pie spice and a cinnamon stick. Serve immediately.