Grease a 9×13-inch baking dish and set aside. In a small bowl, mash together the filling: softened butter, brown sugar, cocoa powder, cinnamon, and instant coffee until smooth and spreadable. Cover and keep at room temp.
Make the frosting so it’s ready to go: Beat the cream cheese and marshmallow fluff until creamy. Mix in powdered sugar, vanilla, and a pinch of salt. Add 2–3 tbsp heavy cream, a little at a time, until fluffy and spreadable. Cover and refrigerate.
Bloom the yeast: In a measuring cup, stir the warm milk with the yeast and 1 teaspoon of the granulated sugar. Let stand 8–12 minutes, until foamy on top.
In the bowl of a stand mixer, whisk together flour, cocoa powder, salt, dry milk powder (if using), and the remaining granulated sugar. Add eggs, softened butter, and the foamy yeast mixture. Mix on low until a shaggy dough forms, 2–3 minutes.
Rest the dough (autolyse) for 10 minutes, then knead on medium speed until smooth, elastic, and slightly tacky, 6–8 minutes. Shape into a ball, place in a lightly oiled bowl, cover, and let rise in a warm spot until doubled, 60–75 minutes.
Turn the dough out onto a lightly floured surface. Roll into an 18×12-inch rectangle. Spread the chocolate-cinnamon filling all over, leaving a 3/4-inch clean strip along one long edge. Sprinkle on the mini chocolate chips and press them lightly to adhere.
Starting from the long edge opposite the clean strip, roll up tightly into a log and pinch the seam closed. Transfer to a sheet pan and chill in the freezer for 10 minutes to firm for cleaner slicing.
Using unflavored dental floss or a sharp knife, cut the log into 12 even rolls. Arrange cut-side up in the prepared pan with a little space between. Cover and let rise until puffy and nearly filling the pan, 35–45 minutes.
Bake at 350°F for 20–24 minutes, until the centers look set and the tops are just lightly browned. If browning quickly, tent loosely with foil for the last 5 minutes. Cool in the pan for 10 minutes.
Swirl the marshmallow cream cheese frosting over warm rolls. Top with mini marshmallows and, if desired, briefly toast with a kitchen torch or under the broiler for 20–30 seconds. Dust with cocoa powder and finish with crushed candy cane or chocolate shavings.