In a large mixing bowl, combine heavy whipping cream and beat on medium-high speed for about 3-5 minutes until stiff peaks form.

In the same bowl you used for the cream, add softened cream cheese, canned pumpkin puree, powdered sugar, pumpkin pie spice, and vanilla extract. Beat on medium speed for approximately 2 minutes until the mixture is smooth and fluffy.

Carefully fold one-third of the whipped cream into the pumpkin mixture to lighten it. Gradually add the remaining whipped cream and continue to fold until fully integrated.

Cover the bowl with plastic wrap and refrigerate the pumpkin filling for a minimum of 2 hours.

Once chilled, fill a piping bag with the pumpkin mixture to pipe the filling into the cannoli shells.

To serve, dust each filled shell with powdered sugar and enjoy immediately.