Preheat oven to 350 degrees F (175 degrees C).

Lightly grease a baking sheet.

Heat olive oil in a skillet over medium-high heat.

Cook ground beef in the skillet until browned, draining excess fat.

Add crushed tomatoes, cinnamon, cumin, paprika, and allspice to the skillet.

Reduce heat to medium and simmer the mixture until slightly reduced, about 10 minutes.

Remove one sheet of phyllo dough from the package, keeping the remaining dough covered.

On a flat surface, cut the phyllo sheet into two 14x9-inch rectangles.

Spray one rectangle with cooking spray, then layer the other rectangle on top and spray again.

Place a teaspoon of the meat mixture near the narrow end of the dough.

Fold the dough over the meat, fold in the sides, and roll into a narrow cigar shape.

Repeat the rolling process until all the meat mixture is used.

Arrange the cigars on the prepared baking sheet.

Bake in the preheated oven until lightly browned, about 25 minutes.

Let cool slightly before serving.