I have to take back my previous commit that the Empire loves me again. After receiving an in game ascension from Outsider to Serf, Serf to Master broke again and my ascension wasn't awarded.
I filed a ticket with the Ministry of Frontier Developments that included screenshots of me accepting the mission, completing the mission and receiving a pat on the back for completing. It only took 24 hours for an resolvement advisement to come through the deep space relay and the Imperial Navy to recognize me as a Master. One step closer to an Imperial Clipper!