We present an optical fiber supporting 36 information bearing orbital angular momentum (OAM) states spanning 9 OAM orders. We introduce design techniques to maximize the number of OAM modes supported in the fiber; while avoiding LP mode excitation. We fabricate such a fiber with an air core and an annular index profile using the MCVD process. We introduce a new technique for shaping OAM beams in free-space to obtain better coupling efficiency with fiber with annular index profiles. We excite 9 orders of OAM in the fiber, using interferometry to verify the OAM state on exiting the fiber. Using polarization multiplexing and both signs for the topological charge, we confirm support of 36 states, exploiting to our knowledge the highest number of OAM modes ever transmitted in optical fiber.