Arthroscopy has been increasingly used to diagnose and treat elbow pathologies. Elbow arthroscopy becomes a very difficult technique when an alteration of the anatomy can determine vessels and nerves displacement. Stiff elbow, osteoid osteoma resection, and osteochondral transplantation are complex pathologies that can be treated arthroscopically. We identify complex cases not only as failures of previous open or arthroscopic surgeries but also elbow pathologies in which severity and articular involvement cause an extensive loss of articular congruency and severe impaired loss of motion. They can be considered as a limit for arthroscopic technique. As elbow arthroscopy is becoming more popular, it is likely that the surgeon will eventually encounter an elbow that needs an arthroscopic surgery and that has been previously operated and with a previous transposition of the ulnar nerve that was previously considered a contraindication for arthroscopy procedures due to the use of the anteromedial portal. Recent literature suggests elbow arthroscopy can be performed in this situations using a standardized approach. For the same reason, surgeons will probably have to perform an arthroscopy procedure in a previous surgically treated elbow. A second arthroscopic procedure may be a joint sparing option in selective cases.