Warm the milk to around 95-104°F / 35-40°C (not hotter) and pour the warm milk into a bowl of your stand mixer. Sprinkle yeast and half the sugar over the milk.
If using active dry yeast, let this sit for around 5-10 minutes until it becomes foamy; if using instant yeast, this step can be skipped.
Add flour, remaining sugar, eggs pumpkin puree, spices, and salt. Fit the stand mixer with a dough hook attachment and mix to form a thick dough.
Add in the softened butter a few cubes at a time.
Keep mixing on medium speed for around 10 minutes until the sticky dough is smooth and strong and pulls away cleanly from the sides of the bowl.
Add the raisins and mix on low speed until they are incorporated.
Once kneaded, form the soft dough into a ball. Transfer the dough to a greased large bowl and cover it.
Let the dough rise in a warm place until doubled in size, around about 1 hour. The exact time the dough rises will depend on your room temperature.
For extra flavor, the dough can undergo a slow cold rise instead. Cover it tightly with plastic wrap and place it in the refrigerator for up to 16 hours.
Shaping
After the first rise, punch down the risen dough and pull it from the bowl onto a lightly floured work surface. If the dough has come from the fridge, it will be stiff.
Mix sugar, cinnamon, and flour in a small bowl for the filling—grease, and line two 8.5 x 4.5-inch loaf pans with parchment paper. You could also use 9x5-inch pans for less high loaves.
Cut the dough into two equal pieces and shape them into balls. On a lightly floured surface, roll out one of the pieces of dough into an 8x15-inch rectangle.
Sprinkle over half the cinnamon sugar mixture. RolI the dough up tightly, jelly-roll style, into an 8-inch log. Pinch the edges to seal them and place the log onto a prepared pan. Repeat with the second piece.
Cover the loaf pans loosely and let the bread rise until doubled in size. Meanwhile, preheat the oven to 350°F (180°C).
Once risen, brush the tops of the loaves with milk and bake in the oven for approximately 35 minutes until deep golden brown (with an internal temperature of around 195°F.)
Remove from the oven and cool on a wire rack. Let the loaves cool in their pan for 5 minutes before removing and cooling to room temperature.
Notes
Both metric and US customary measurements are provided. Use the toggle on the recipe card to switch between the two. See here how to make your own pumpkin puree.