Cinnamon Roll Pie With Vanilla Glaze

Quick Recipe Version (TL;DR)

• Yield: 10 slices (1 nine-inch pie)
• Prep Time: 35 minutes
• Cook Time: 65 minutes
• Total Time: 4 hours 0 minutes

Quick Ingredients

• All-purpose flour, sugar, salt, unsalted butter, ice water, apple cider vinegar
• Brown sugar, granulated sugar, ground cinnamon
• Eggs, heavy cream, whole milk, cornmeal, vanilla extract
• Powdered sugar (confectioners’ sugar)

Do This

• 1) Make pie dough; chill 30 minutes.
• 2) Roll into a 9-inch pie plate; crimp and freeze 10 minutes; par-bake at 375°F for 15 minutes.
• 3) Stir cinnamon-sugar swirl mixture.
• 4) Whisk gooey “chess-pie-style” filling.
• 5) Pour filling into crust; dot and swirl cinnamon mixture through.
• 6) Bake at 350°F for 45–50 minutes until edges are set and center gently jiggles; cool 2 hours.
• 7) Drizzle vanilla glaze over the cooled pie; slice and serve.

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Why You’ll Love This Recipe

• It tastes like a cinnamon roll and a gooey custard pie had the best possible mash-up.
• Buttery, flaky crust plus cinnamon-sugar swirls in a soft, gooey center.
• Simple vanilla glaze gives you that classic cinnamon-roll finish without extra fuss.
• Great make-ahead dessert: it slices best after it cools and sets.

Grocery List

• Produce: None (optional: 1 lemon for zest if you want a brighter glaze)
• Dairy: Unsalted butter, heavy cream, whole milk, large eggs
• Pantry: All-purpose flour, granulated sugar, light brown sugar, ground cinnamon, cornmeal, powdered sugar, vanilla extract, apple cider vinegar, fine salt

Full Ingredients

Buttery Pie Crust (9-inch)

• 1 1/4 cups (150 g) all-purpose flour
• 1 tablespoon (12 g) granulated sugar
• 1/2 teaspoon fine salt
• 1/2 cup (113 g) unsalted butter, cold and cubed
• 3 tablespoons (45 ml) ice water, plus 1–2 tablespoons (15–30 ml) more if needed
• 1 teaspoon (5 ml) apple cider vinegar

Cinnamon-Sugar Swirl

• 1/2 cup (100 g) packed light brown sugar
• 2 tablespoons (25 g) granulated sugar
• 1 1/2 tablespoons ground cinnamon
• 3 tablespoons (43 g) unsalted butter, melted
• 1 tablespoon (8 g) all-purpose flour
• 1/8 teaspoon fine salt

Gooey Cinnamon Roll Pie Filling

• 4 large eggs, room temperature
• 3/4 cup (150 g) packed light brown sugar
• 1/2 cup (100 g) granulated sugar
• 1/2 cup (113 g) unsalted butter, melted and cooled to warm (not hot)
• 1/2 cup (120 ml) heavy cream
• 1/4 cup (60 ml) whole milk
• 2 tablespoons (18 g) yellow cornmeal
• 1 tablespoon (8 g) all-purpose flour
• 1 tablespoon (15 ml) apple cider vinegar
• 2 teaspoons vanilla extract
• 1/2 teaspoon ground cinnamon
• 1/2 teaspoon fine salt

Simple Vanilla Glaze

• 1 cup (120 g) powdered sugar (confectioners’ sugar)
• 2 tablespoons (30 ml) whole milk, plus 1–2 teaspoons (5–10 ml) more as needed
• 1 teaspoon vanilla extract
• Pinch of fine salt

Step-by-Step Instructions

Step 1: Make the pie dough

In a medium bowl, whisk together the flour, sugar, and salt. Add the cold cubed butter and cut it in with a pastry cutter (or rub it in with your fingertips) until the mixture looks like coarse crumbs with some pea-size butter pieces remaining.

In a small cup, stir together 3 tablespoons (45 ml) ice water and the apple cider vinegar. Drizzle it over the flour mixture and gently toss with a fork until the dough starts to clump. If it still looks very dry, add 1 more tablespoon (15 ml) ice water; add the final tablespoon only if needed.

Turn the dough onto the counter and press it together into a disk (don’t knead). Wrap tightly and refrigerate for 30 minutes.

Step 2: Roll, shape, and par-bake the crust

Preheat the oven to 375°F (190°C). Place a rack in the lower third of the oven.

On a lightly floured surface, roll the dough into a 12-inch circle. Transfer to a 9-inch pie plate, ease it into the corners without stretching, and trim to a 1-inch overhang. Fold the overhang under and crimp.

Freeze the shaped crust for 10 minutes (this helps it hold its shape). Line the crust with parchment paper and fill with pie weights or dried beans. Par-bake for 15 minutes. Carefully lift out the parchment and weights, then bake 5 minutes more to dry the bottom slightly.

Reduce the oven temperature to 350°F (175°C). Let the crust cool while you make the swirl and filling (about 10 minutes is fine).

Step 3: Mix the cinnamon-sugar swirl

In a small bowl, stir together the brown sugar, granulated sugar, cinnamon, flour, and salt. Add the melted butter and mix until it forms a thick, spoonable paste.

Set aside. If it firms up while it sits, warm it for 5–10 seconds in the microwave and stir again.

Step 4: Whisk the gooey filling until smooth

In a large bowl, whisk the eggs until the yolks and whites are fully blended. Add the brown sugar and granulated sugar and whisk for about 30 seconds until glossy.

Whisk in the melted butter (make sure it’s warm, not hot), then whisk in the heavy cream, milk, cornmeal, flour, apple cider vinegar, vanilla, cinnamon, and salt. Whisk until you don’t see dry pockets of cornmeal or flour.

This filling is designed to bake up soft and gooey in the center, like cinnamon-roll-meets-chess-pie energy, while still slicing clean once cooled.

Step 5: Fill the crust and create cinnamon swirls

Place the par-baked crust on a rimmed baking sheet (easier to move, and it catches drips). Pour the filling into the crust.

Drop small spoonfuls of the cinnamon-sugar swirl all over the top (aim for 12–16 small dollops). Use a butter knife or skewer to gently drag through the dollops in loose S-shapes. Keep your swirls near the surface; you want visible cinnamon ribbons, not a fully blended filling.

Step 6: Bake until set at the edges with a gentle center jiggle

Bake at 350°F (175°C) for 45–50 minutes, rotating the pan at the 30-minute mark for even browning. The pie is done when the edges are set and slightly puffed, the top looks dry (not wet), and the center still has a small, gentle jiggle when you nudge the pan.

If the crust edges brown too quickly, shield them with foil after about 35 minutes. For extra precision, you can check an internal temperature: aim for 175°F–180°F (79°C–82°C) in the center.

Step 7: Cool completely, glaze, and slice

Cool the pie on a rack for 2 hours before glazing and slicing. This cooling time is essential: it lets the custardy center finish setting so you get clean slices with gooey softness.

For the glaze, whisk powdered sugar, milk, vanilla, and salt until smooth. Start with 2 tablespoons (30 ml) milk and add an additional 1–2 teaspoons (5–10 ml) only if needed to reach a thick, drizzleable consistency.

Drizzle the glaze over the cooled pie in ribbons. Let the glaze set for 10 minutes, then slice and serve.

Pro Tips

• Don’t skip the par-bake. It keeps the crust flaky instead of turning soggy under the gooey filling.
• Cool fully for best slices. The pie will look tempting early, but the texture is best (and less runny) after the full 2-hour cool.
• Swirl gently near the surface. If you swirl too deep, the cinnamon mixture can disappear into the custard instead of making pretty ribbons.
• Use room-temp eggs. They mix more smoothly and help the filling bake evenly.
• Shield the crust when needed. A foil ring at minute 35–40 prevents over-browning while the center finishes baking.

Variations

• Pecan Cinnamon Roll Pie: Sprinkle 1/2 cup (60 g) chopped pecans over the filling before swirling.
• Cream Cheese Glaze: Replace the vanilla glaze with a quick cream cheese glaze: whisk 2 oz (57 g) softened cream cheese with 1 cup (120 g) powdered sugar, 2 tablespoons (30 ml) milk, 1 teaspoon vanilla, and a pinch of salt.
• Extra-spiced: Add 1/4 teaspoon ground nutmeg and/or 1/8 teaspoon ground cloves to the filling for a deeper cinnamon-roll vibe.

Storage & Make-Ahead

Store leftover pie loosely covered in the refrigerator for up to 4 days. For the best texture, let slices sit at room temperature for 15–20 minutes before eating, or warm in the microwave for 10–15 seconds (just enough to soften the gooey center). To make ahead, bake the pie up to 1 day in advance, cool completely, and refrigerate; glaze shortly before serving for the prettiest finish. You can also freeze individual slices (well wrapped) for up to 2 months; thaw overnight in the refrigerator.

Nutrition (per serving)

Approximate per 1/10 pie: Calories: 430; Fat: 23 g; Saturated Fat: 13 g; Carbohydrates: 52 g; Sugar: 34 g; Protein: 6 g; Fiber: 1 g; Sodium: 220 mg.