Rheumatologists have long considered OA and PsA as two completely distinct arthropathies. This review highlights how some forms of generalized OA and PsA may afflict the same entheseal-associated anatomical territories. While degeneration or inflammation may be clearly discernible at the two extremes, there may be a group of patients where differentiation is impossible. Misdiagnosis of a primary degeneration-related pathology as being part of the PsA spectrum could lead to apparent failure of disease-modifying agents, including apparent anti-TNF and apparent IL23/17 axis therapy failure. This is not a reflection of poor clinical acumen, but rather a failure to appreciate that the pathological process overlaps in the two diseases. Whether the category of OA-PsA overlap disease exists or whether it represents the co-occurrence of two common arthropathies that afflict the same anatomical territories has implications for the optimal diagnosis and management of both OA and PsA.