Put the yeast and one teaspoon sugar into the warm water. Mix it briefly to combine and set to the side.
Whisk together eggs, pumpkin, butter, vanilla brown sugar, salt, sugar, cinnamon and pumpkin spice into a large bowl. If using a stand mixer or bread maker, transfer the wet mixture into the bowl.
Add the flour then yeast mixture and begin mixing.
Once mixed, knead for 20 minutes or until bread dough is ready. It will be smooth and elastic-y and spring back gently when pressed on with a finger. Let the dough rise until doubled, about one hour.
Don't let it rise too long or it will get sticky and be hard to work with.
As soon as the dough starts rising, make the filling so it has plenty of time to cool. Put the butter and milk in a saucepan over medium heat, just until the butter is melted, no longer.
Add the egg yolk, cocoa, sugar and flour and mix.
Set aside to cool while the bread rises.
When the dough is done rising, flour a flat work surface.
If making 2 loaves in loaf pans, divide into 2 sections. For one large loaf on a sheet pan, don't divide.
Roll each piece out into a large rectangle, or one very large rectangle, about ⅛" thick.
Spread chocolate mixture across the dough evenly.
Roll up from one of the shorter ends.
Gently press down a little, then cut in half length wise. Fold the ends over and under to create a twist, and tuck the ends in. See this video for an example.
After shaping, allow to rise another 20 minutes.
Preheat the oven to 350* F and bake for 30-40 minutes until golden brown.
Allow to cool for 20 minutes before serving.
Notes
Make sure the eggs and pumpkin are at room temperature. If they are cold, the bread dough will be sticky and difficult to work with.This stores great in an airtight container for up to 4 days. Reheat individual slices in the microwave for 8-12 seconds.