Make the rolls: In the bowl of a large stand mixer fitted with a dough hook attachment, dissolve yeast in warm milk. Let stand 5 minutes until foamy. Mix in sugar, oil, eggs, and salt until combined. Add 4 cups flour to mixture and mix on medium speed until dough pulls away from sides of bowl and forms a soft dough, adding additional flour by the tablespoon if needed.
Turn dough onto a floured surface and knead until smooth and elastic. Place in a greased bowl, turning once to grease top. Let rise in a warm place until doubled, about 1 hour.
Punch risen dough down and on a floured surface, roll into a 12x18 rectangle. In a small bowl, lightly mash sugar, cinnamon, raspberries, and orange zest until spreadable. Spread raspberry filling to within 1-in of dough edges. Starting at the long end, roll dough up tightly, pinching edges to seal. Cut rolls into 1/2 to 1-in rolls and place swirl side-up in a greased 9x13 baking pan or a 9-in pie pan. Cover pan with plastic wrap and let rise 30 minutes or until doubled.
Remove plastic wrap from rolls. Bake rolls at 375F 20-25 minutes or until a light golden brown. Let cool slightly on a wire cooling rack.
Make the glaze: In a small bowl, whisk sugar, vanilla, and just enough milk to achieve a thick glaze consistency.
Drizzle glaze over slightly-cooled rolls and let stand 5 minutes to let glaze set. Enjoy cinnamon rolls warm!