Combine the yeast, warm milk, vanilla extract and sugar in a mixer bowl. Allow to sit for 2-5 minutes for the yeast to dissolve. Add in 2 cups of the flour and mix to combine. Now add in the salt and egg. Mix well to combine.
With the mixer on low, begin slowly adding in the remaining flour, one cup at a time, until the dough starts to pull away from the sides of the bowl.
Slowly add in the softened butter, 1 piece at a time. Continue kneading the dough until it is fully developed and passes the windowpane test. Cover and place in a warm place for 1-2 hours, or until doubled in size.
While the dough is proofing start the jam by combining the strawberries and sugar in a small saucepan over medium heat.
Mash with a masher or spoon until the mixture begins to simmer. Once the mixture comes to a simmer whisk together the cornstarch and water them pour it into the strawberry mixture. Whisk well to fully incorporate. Continue cooking for 2-3 minutes. Stir in the cinnamon. Set aside to cool.
Remove from the heat and allow to cool completely before using. Line a 9x13 baking dish with parchment paper.
Preheat an oven to 350° F. On a lightly floured work surface, roll the dough out into a 10x15 inch rectangle. Spread the jam over the dough, reserving ½ cup for topping the rolls.
Starting with the long end, roll the dough into log. Cut into 12 equal sized rolls, place in the prepared baking dish. Spoon the remaining strawberry jam in between the layers of each roll.
Cover and place in a warm area for 30 minutes, or until puffy. Place in the preheated oven and bake for 30 minutes. Set aside to cool before frosting.
While the rolls are cooling cream together the softened butter, and cream cheese. Mix in the powdered sugar, vanilla extract and heavy cream. Mix until light and fluffy. Spread over cooled strawberry rolls. Enjoy!