Mix together the warm water and yeast. Let this mixture sit for about 10 minutes. You will see the yeast activate – tiny bubbles will form at the surface and the liquid will thicken slightly.
In a stand mixer mix together with a paddle attachment on medium low speed, slowly combine yeast mixture with the remaining dough ingredients. Gradually add the flour 1 cup at a time until a soft dough is formed.
Then place the dough in a well greased bowl and turn to coat the dough with the oil. Cover tightly with plastic wrap.
Allow the dough to rise until it has doubled in size (approximately 1-1 1/2 hours).
Remove dough from bowl and knead for 1-2 minutes, adding flour so it doesn’t stick to your hands or the countertop. Roll out into a large rectangle. The rectangle should be around 24”X15” but does not need to be exact.
In a small bowl mix together the filling ingredients except for the semi-sweet chocolate. Spread the butter mixture onto the dough.
Sprinkle the chopped chocolate evenly on top and gently press the chocolate down into the dough with your hands.
Roll up the dough, starting at the short end.
Slice your long roll into 12 individual cinnamon rolls using floss or a large serrated knife.
Place sliced rolls in a glass 9X13 casserole dish (sprayed with cooking spray). Make sure they are nice and snug.
Cover with plastic wrap and let rise for another 30-60 minutes, or until almost doubled in size.
Preheat the oven to 350 degrees Fahrenheit.
Bake for 25-20 minutes until the cinnamon rolls are lightly golden brown on top. Remove the rolls from the oven and let them sit for approximately 20 minutes before topping with the glaze.
Mix together the glaze ingredients with a hand held mixer until combined and creamy. Add more milk if the glaze is too thick and add more powdered sugar if the glaze is too thin based on your preference.
Spread the glaze over the warm chocolate cinnamon rolls and then they are ready to serve and enjoy!
Notes
Refrigerate the leftovers in an airtight container for up to 1 week. These are best served warmed, so microwave the leftovers for 30 seconds before enjoying them.