Place the dates in a medium bowl and cover with boiling water. Allow to soak for 30 minutes.

Once the dates have softened, remove them from the water. Place the dates into a blender or food processor and blend on high speed until mashed.

Add in the milk, vanilla, and salt. Blend until smooth and creamy, scraping down the sides of the blender as needed.

Once completely smooth, transfer the date caramel into an airtight container and set aside to use later or store in the fridge for up to 2 weeks.

Start by activating the yeast. Pour the warm milk into a large bowl. Add 1 tbsp of the granulated sugar and sprinkle the yeast overtop. Stir and allow to sit for 3-5 minutes, until frothy.

Then, add the egg, butter, and the rest of the sugar. Mix until combined.

Add in the flour and salt, and mix or knead with your hands until barely combined. Allow to rest for 5 minutes so the flour can soak up the liquids.

Then, pour the dough mixture onto a floured surface and knead with your hands for 5-7 minutes, until elastic and smooth.

Place the dough into a lightly greased large bowl. Cover and allow to rise in a warm environment for 30 minutes, or until doubled in size.

Grease a 9” round springform or cake pan with butter.

Once doubled, turn the dough onto a floured surface. Use a rolling pin to roll the dough out into a 15x12” rectangle. Evenly spread 1 cup of the date caramel on top. Mix together the brown sugar and cinnamon, and sprinkle it all over the date caramel.

Assemble. Using a very sharp knife or pizza cutter, cut the dough into 6, 2” wise strips. Roll up one strip and place it in the center of the pan. Coil the remaining 5 strips around the center roll, starting each strip at the end of the previous one.

Loosely cover the pan with plastic wrap and allow to proof in a warm environment for 45 minutes, until puffy and risen.

Preheat the oven to 350F.

Warm the heavy cream and pour over the cinnamon roll. Bake at 350F for 30-35 minutes, until golden brown.

Remove and cool in the pan for 10 minutes.

While cooling, make the icing by beating together all of the ingredients in a medium bowl, until smooth.

Spread the icing all over the cinnamon roll. Slice and serve warm.