Preheat oven to 325 degrees F (165 degrees C). Grease cooking pan with canola oil.
Place bacon in a large skillet and cook over medium heat, turning occasionally, until bacon begins to brown but is still flexible, about 5 minutes. Mix apple butter, honey, allspice, and chili powder in a small bowl.
Wrap tenderloin in 4 slices of partially-cooked bacon and secure with toothpicks. Brush half the apple butter mixture over bacon and wrap the tenderloin with remaining slices of bacon. Brush remaining apple butter mixture over the meat. Place tenderloin on prepared broiling pan.
Bake in the preheated oven until apple butter mixture has baked into a glaze and an instant-read meat thermometer inserted into the thickest part of the tenderloin reads at least 145 degrees F (65 degrees C), about 30 minutes.