Prepare the base of your crockpot by greasing a 6-quart crock with butter. Pour the cherry pie filling into the crock, then stir in the vanilla extract, 1 teaspoon of ground cinnamon, and the nutmeg to ensure even flavor distribution.

Combine the all-purpose flour, granulated sugar, baking powder, salt, and the remaining ¼ teaspoon of ground cinnamon in a food processor. Add the cold, cubed butter and pulse until the mixture becomes crumbly. Gradually stream in the milk while pulsing, stopping as soon as the batter comes together. Avoid overmixing to maintain the ideal texture.

Drop spoonfuls of the batter over the cherry filling, spacing them evenly to cover most of the surface. Gaps are acceptable, as the batter will expand during cooking.

For crispier results, you may place several layers of paper towels over the crockpot opening before covering it with the lid. This optional step helps reduce excess moisture. If your crockpot tends to run hot, you can skip this to avoid overheating.

Secure the lid and cook on High for 2 to 2.5 hours. Monitor closely, as cooking times may vary depending on the appliance's settings.

To prepare the brown sugar crumble, combine the light brown sugar, all-purpose flour, and cubed butter in a food processor. Pulse until the mixture resembles coarse crumbs. Store this topping in the refrigerator until ready to use.

Approximately 90 minutes into the cooking process, remove the crumble from the refrigerator and sprinkle it evenly over the cobbler. Break up any large clumps for a uniform topping. Replace the lid and continue cooking.

When the cobbler is fully cooked, allow it to rest for 10–15 minutes before serving.

Serve warm with a scoop of vanilla ice cream or a dollop of whipped cream, and enjoy this comforting dessert.