Place the dates in a medium bowl & cover with boiling water. Allow to soak for 30 mins.
Once softened, remove from the water. Place into a blender or food processor and blend. Add in the milk, vanilla, and salt. Blend until smooth & creamy.
Once completely smooth, set aside to use later or store in the fridge for up to 2 weeks.
Pour the warm milk into a large bowl. Add 1 tbsp of the sugar & sprinkle the yeast on top. Stir & allow to sit for 3-5 mins, until frothy.
Add the egg, butter, and the rest of the sugar. Mix until combined.
Add the flour & salt, and mix until barely combined. Rest for 5 mins.
Pour the mixture onto a floured surface & knead with your hands for 5-7 mins, until elastic & smooth.
Place the dough into a lightly greased large bowl. Cover & rise in a warm environment for 30 mins, or until doubled in size.
Grease a 9" round springform or cake pan w/ butter.
Once doubled, turn the dough onto a floured surface. Roll the dough into a 15x12" rectangle. Evenly spread 1 cup of the date caramel on top, then sprinkle the brown sugar and cinnamon all over.
Cut the dough into 6, 2" wide strips. Roll up one strip & place in the center of the pan. Coil the remaining 5 strips around the center roll.
Loosely cover the pan & allow to proof in a warm environment for 45 mins, until puffy.
Preheat the oven to 350F.
Warm the heavy cream & pour over the cinnamon roll. Bake at 350F for 30-35 mins, until golden brown. Remove & cool in the pan for 10 mins.
Spread the icing all over the cinnamon roll. Slice & serve warm.
