In a mixing bowl, pour in the heavy whipping cream. Using an electric mixer, beat on medium-high speed until stiff peaks form, about 3-5 minutes. Set aside.

In the same bowl, add softened cream cheese, canned pumpkin puree, powdered sugar, pumpkin pie spice, and vanilla extract. Beat on medium speed for about 2 minutes until fluffy and well combined.

Gently fold the whipped cream into the pumpkin mixture using a spatula, preserving airiness.

Cover the bowl with plastic wrap and refrigerate for at least 2 hours to allow flavors to meld.

Once chilled, fill a piping bag with the pumpkin mixture and pipe the filling into the cannoli shells from one end.

Dust the filled pumpkin cannoli with powdered sugar before serving, and enjoy immediately.