Add milk, water, brown sugar, salt, butter, and olive oil to a medium sauce pan, and cook on medium/low until the sugar and butter is melted. (You don't want to skip this step, because cold milk will inhibit your gluten formation. Then set it aside to cool slightly.
Mill 2&1/4 cup of hard white wheat berries(465g), this should make about 3&1/2 cups of flour.(you could use other varieties if you wish)
After the milk / sugar mixture has cooled below 100 degrees F, pour it in a stand mixer bowl.
Next, put the fresh milled flour into the same bowl, and begin to mix on low until it is mostly combined.
Now crack your eggs, one at a time, into the mixture, and mix in each one to incorporate. Then add the vanilla.
Once it is all incorporated, let the dough sit for about 10 minutes.
After 10 minutes of resting, now add the instant yeast. Mix it in on low for a couple minutes.
Now, your dough is ready to knead. Knead the dough on level 2 until it passes the window pane test, which you can see in my video here or the photo below. (This could take up to 20 - 25 minutes with fresh milled flour - don't rush this process!)
After dough passes the window pane test, cover it and let it sit for 1 to 2 hours.
While the dough is rising, make the filling. Melt butter in a microwave safe bowl, then add sugar, cinnamon, a pinch of salt, cocoa powder, and crushed candy canes, mix to combine.
Once dough has risen double, on a lightly oiled work surface, press your dough out flat into a 15 x 17 rectangle.
Evenly distribute filling all over the top, and from the long side, roll the dough into a log.
Divide dough log into 12 even disks.
Place the disks on a lined 9x13 baking pan and cover. Let rise for 40 minutes (or overnight in the fridge)
Bake at 350 degrees F for 18 - 20 minutes. (If using the refrigerator method, set the shaped dough on the counter for 1-2 hours for it to come up to room temperature. Then bake.