Start by placing vegetable oil in a 2 to 3-quart saucepan over medium heat. You want the oil to reach a temperature of about 340 to 350°F. Using a candy thermometer is a great idea here; I find it helps maintain that perfect frying temperature. Make sure the oil is about 1 inch deep.
While the oil is heating, whisk together the pudding mix, milk, and vanilla in a medium-sized bowl for about 2 minutes. This process is crucial as it helps the pudding set properly. After this, let it sit for a bit.
Next, unwrap the Taco Boats and set up your frying station. Layer two paper towels on a cookie sheet; this will help absorb excess oil once the pies are fried. In a small bowl, combine the granulated sugar and cinnamon, and keep it nearby.
Once the oil is hot, carefully add the Taco Boats to the oil in batches. I like to fry one or two at a time, gently pressing them down with a slotted spoon to keep them submerged. They should fry for about 1 to 2 minutes until they turn golden brown. Flip them as needed to achieve even cooking.
After frying, remove each pie from the oil and let it drain on the paper towels. Allow them to cool just enough to handle. While they’re still warm, roll them in the cinnamon and sugar mixture to coat them completely. This adds that signature churro flavor.
If you desire, you can give your pies a second coating of the cinnamon sugar mixture once they've cooled completely. This step is optional but absolutely delicious!
Finally, fill each cooled shell with the prepared pudding mixture. Feel free to top it with fresh strawberries for an added burst of flavor. These Chocolate Churro Pies are best served the day they are made for maximum freshness and flavor.