Preheat your oven to 350°F before you start mixing anything. Grease two loaf pans and line the bottoms with parchment paper for easy release later. This little step saves you from a stuck, crumbly loaf and makes cleanup faster too
In a large bowl, beat the softened butter and sugar together until the mixture turns pale and fluffy. This usually takes about two minutes with a hand mixer. Creaming properly here gives the loaf a lighter, softer crumb instead of a dense one.
Mix in the eggs one at a time, followed by the pumpkin puree, milk, and vanilla extract. Beat just until everything looks smooth and uniform. Don't worry if the batter looks slightly separated at first; it comes together once the dry ingredients go in.
In a second bowl, whisk together the flour, baking soda, baking powder, salt, cinnamon, nutmeg, and cloves. Whisking the spices into the flour first helps them distribute evenly, so you don't end up with a clove-heavy bite in one slice.
Gradually add the dry mixture into the wet ingredients, stirring gently with a spatula. Mix only until the flour disappears into the batter. Overmixing at this stage activates the gluten too much, which can make your loaf tough instead of tender.
Add the chocolate chips and fold them through the batter with a few gentle strokes. I like to save a small handful to press onto the top of the loaves before baking, purely for looks. This gives the finished bread that bakery-style, chip-studded top.
Divide the batter evenly between your prepared pans and smooth the tops with your spatula. Bake for 50-55 minutes, or until a toothpick inserted in the center comes out clean or with a few moist crumbs. If the tops brown too fast, tent them loosely with foil.
Let the loaves rest in the pan for about 10 minutes, then transfer them to a wire rack to cool completely. Slicing too early can cause the bread to crumble, since the crumb is still setting as it cools.