Purpose: The mechanism and physiology of orbital cavity remodelling after orbital fractures is not well described. This poses a challenge in the delayed operative treatment of orbital floor fractures due to variation from expected anatomy and may risk injury to critical structures during exploration as well as misguided reconstruction causing persistent orbital dystopia. Methodology: We report a case where significant orbital remodelling caused unexpected challenges to orbital floor reconstruction highlighting the need for further research in this field. Results: A 23-year-old previously well male was treated conservatively for a left orbital floor fracture sustained during a rugby match. At 4 month follow up, the patient was found to have significant orbital dystopia with vertical diplopia and cosmetically significant enophthalmos. A discrepancy of 4mm was noted on Hertel’s ophthalmometer. Intra-operatively, the neo-floor was found to have fully healed but with a significant down-sloping angulation and clinically appreciable depression. Furthermore, no fracture ledges were able to be used to guide the height of the titanium reconstruction plate posing a significant challenge. Therefore, a 3D printed model of the orbit using a recent CT scan was used to conform the plate to the required dimensions. The patient made good recovery without ocular symptoms. Conclusion: Fracture remodelling of the orbital cavity is poorly described and may not be considered in the delayed treatment of orbital fractures. Further research to describe the mechanism and pattern of how this occurs is necessary. Computer assisted design with 3D printing is a useful tool that can help overcome technical challenges in complex maxillofacial cases.