Before you start, pull out your pumpkin puree, evaporated milk, instant pudding mix, and pumpkin pie spice. Double check that your canned pumpkin is pure puree and not a pie filling blend. Having everything measured and ready makes the whole process faster and mess-free.
Add the pumpkin puree, evaporated milk, instant vanilla pudding mix, and pumpkin pie spice into your blender jar. Secure the lid tightly before starting, since this mixture can splash if it's not sealed properly. Blend on medium-high speed until the mixture looks completely smooth and has thickened up nicely.
Stop the blender and take a look at the texture. It should be thick, creamy, and free of any lumps of pudding mix. If it still looks a little thin or grainy, blend for another 15 to 20 seconds. This step only takes a moment but makes a big difference in the final texture.
Once your pudding is smooth, divide it evenly between small jars, ramekins, or dessert bowls. I like using little glass jars because they make the pudding look extra special and are easy to grab straight from the fridge. A rubber spatula helps get every bit of pudding out of the blender.
Pop the filled jars into the refrigerator for at least 15 to 20 minutes if you want a slightly firmer, chilled pudding. It's technically ready to eat right away, but I find a short chill makes the texture even better. Cover with plastic wrap if you're making it ahead of time.
Right before serving, top each jar with a generous dollop of whipped cream and a light dusting of pumpkin pie spice. This small touch makes the pudding look like it came from a bakery. Serve immediately and watch it disappear fast.