Work the cream cheese, sour cream, 1 tablespoon sugar, and vanilla together with a mixer until evenly blended. The mixture should look smooth and creamy, with no firm cream cheese pieces remaining.

Use a gentle folding motion to incorporate the 3/4 cup sliced strawberries. The fruit should remain in distinct pieces throughout the thick filling.

Portion the filling equally among the six tortillas, positioning it across the lower third, then tuck both sides inward, roll snugly, and pin each seam with a toothpick. The ends should close around the filling without stretching the tortilla or forcing cream through the seam.

Stir the 1/3 cup sugar and 1 tablespoon cinnamon together in a shallow bowl. The coating should have an even cinnamon color without concentrated patches of spice.

Cover a large plate with paper towels for draining the fried rolls. The towels should lie flat so each chimichanga can rest against an absorbent surface.

Pour vegetable oil to a depth of 2 to 2 1/2 inches in a saucepan about 5 inches deep, then bring it to 360°F over medium-high heat. Use the thermometer reading rather than the oil’s appearance to judge when it is ready.

Cook the rolls in batches for about 2 to 3 minutes, turning as needed to brown all sides. Look for a golden, blistered exterior that feels crisp rather than soft.

Move each cooked roll to the prepared plate, let it drain for 1 minute, then turn it through the cinnamon sugar. The shell should still be warm with a faint sheen of surface oil to help the coating cling.

Pull out every toothpick and check each roll before serving. No wooden points or pieces should remain in the seams.