Heat milk to 110F, then combine milk, brown sugar, and yeast in a bowl or measuring glass. Let sit for ten minutes, until foamy.
Pour the yeast mixture into the bowl of a stand mixer, and oil and eggs. Whisk to combine wet ingredients, then add flour and salt. Use the dough hook or a spatula to roughly combine the ingredients into a shaggy dough. Add the raisins and knead on medium low speed for ten minutes.
Cover the mixing bowl with plastic wrap and let rise for an hour, or until doubled in size.
Flour the counter top as lightly as possible and spread/stretch the dough into a rectangle that is the length of your loaf pan, about 9 inches by 18 for a 9x5 bread pan.
Make the cinnamon filling by stirring together brown sugar, cinnamon, and melted butter/warmed oil. Evenly spread over the top of the dough rectange, then roll the dough up as tightly as possible. Place the roll seam side down into a greased loaf pan, cover with plastic wrap and let rise for 30 minutes.
Preheat oven to 375F, and bake bread for 40-50 minutes.
The 2 Tbsp of sugar in the dough won't make the bread very sweet, you may want to double for a sweeter loaf.