Cranberry Crinkle Tart

Arrange a rack in center of oven; preheat to 350°. Grease a 10" tart pan with cooking spray. Place on a foil-lined baking sheet.

Unwrap phyllo and stack sheets on a clean work surface. Remove 1 sheet from top of stack and drape over prepared tart pan. Press into bottom and up sides, leaving overhang. Brush phyllo with butter, then lay another sheet directly on top; brush with more butter. Arrange a third phyllo sheet perpendicular to the other 2 sheets; brush with butter. Top with a fourth phyllo sheet in line with the third; brush with butter. Using kitchen shears, trim overhang so phyllo ends at top of pan, forming a ruffled border.

Remove another phyllo sheet from stack and arrange with a long side facing you on a clean work surface. (Cover remaining phyllo with a damp towel to avoid drying out.) Fold the bottom edge up 3/4" to make a hem, then pleat the sheet upward (accordion-style), keeping the hem closest to you, until it becomes a long narrow strip.

Arrange phyllo, pleats up, along edge of tart pan. Pleat a second sheet of phyllo and arrange in pan, aligning with one end of the previous strip and tucking in any excess to form a continuous spiral. Repeat with remaining 10 phyllo sheets to fill pan with spiraled phyllo.

Bake phyllo until browned around the edges and crisp on top, 10 to 15 minutes. Brush with butter. (It will seem like a lot, but don’t worry—the pastry will absorb it.)

Continue to bake until butter is mostly absorbed, about 10 minutes more.

Meanwhile, stir cranberry sauce to loosen, if needed. Transfer sauce to piping bag fitted with medium round tip (or transfer to a resealable plastic bag, press out any air, seal tightly, and snip off a small corner).

In a large bowl, gently whisk eggs, milk, salt, 3/4 cup sugar, and zest of 1 orange to combine. (Don’t be overly vigorous; you don’t want lots of bubbles to form.)

Pipe cranberry sauce into tart folds at even intervals, targeting areas where there are gaps. Pour orange custard over.

Continue to bake tart until top is browned and slightly puffed, 30 to 40 minutes more.

Using a vegetable peeler, remove long strips of orange peel from remaining 2 oranges. Transfer orange peel to a small pot. Add water and remaining 1 cup sugar. Bring to a boil over medium-high heat and cook, stirring frequently, until thickened and an instant-read thermometer registers 220°, 5 to 6 minutes. Remove from heat, but keep syrup warm.

Brush tart all over with orange syrup and serve warm or at room temperature.