Context: Lesser metatarsophalangeal (MTP) instability is a common condition that can become debilitating and require surgery. Evidence Acquisition: An extensive literature review was performed through MEDLINE and Google Scholar for publications relating to the etiology, diagnosis, and treatment of lesser MTP instability using the keywords metatarsophalangeal instability, athlete, forefoot pain, and metatarsalgia from database inception to 2019. Study Design: Clinical review. Level of Evidence: Level 4. Results: Lesser MTP instability is a common condition, especially in the active and aging populations. It is frequently misdiagnosed, causing delays in treatment that allow for progressive pain and deformity, which prevents an active lifestyle. Fortunately, MTP instability can be diagnosed easily with the drawer test. Magnetic resonance imaging is helpful when still in doubt. Conservative treatment entails joint immobilization and gradual return to play with taping and offloading metatarsal pads. Conclusion: Lesser MTP instability is a common diagnosis. Its early detection and conservative treatment can help the patient regain their previous level of activity and avoid surgery.